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Home> Encyclopedia >Antineoplastic Agents>Pharmaceutical Intermediates>Organic Intermediates


CAS No.: 865-21-4
Molecular Weight:810.989
Modify Date.: 2023-02-28 08:42
Introduction: Vinblastine is a cytotoxic alkaloid used against various cancer types. Vinblastine inhibits the formation of microtubule and suppresses nAChR with an IC50 of 8.9 μM. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

(3aR-(3aα,4Β,5Β,5aΒ,9(3R*,5S*,7R*,9S*),10bR*,13aα))-methyl 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino(8,1-cd)carbazole-5-carboxylate [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-Methyl 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino[8,1-cd]carbazole-5-carboxylate 1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-(5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino(5,4-b)indol-9-yl)-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, (3aR-(3aα,4Β,5Β,5aΒ,9(3R*,5S*,7R*,9S*),10bR*,13aα))- 1H-Indolizino[8,1-cd]carbazole, vincaleukoblastine deriv. 1H-Indolizino[8,1-cd]carbazole-5-carboxylic acid, 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-, methyl ester, [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]- 2H-3,7-Methanoazacycloundecino[5,4-b]indole, vincaleukoblastine deriv. EINECS 212-734-0 Methyl 11-acetyloxy-12-ethyl-4-(17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl)-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate Rozevin UNII-5V9KLZ54CY VINBLASTINE SULFATE(RG) vinblastine sulfuric acid salt Vinblastine sulphate Vinblastine,Vincaleukoblastine Vincaleucoblastin Vincaleucoblastine Vincaleukoblastine Vincoblastine Vincristine EP Impurity H

1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C46H58N4O9 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
211 - 216 oC
2.1 Boiling point
755.65°C (rough estimate)
2.1 Refractive index
1.6000 (estimate)
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 AnalyticLaboratory Methods
Analyte: vinblastine sulfate;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /vinblastine sulfate;/
2.2 Appearance
2.3 Color/Form
2.4 Decomposition
When heated to decomposition it emits toxic fumes of oxides of nitrogen.
2.5 pKa
5.4, 7.4(at 25℃)
2.6 Water Solubility
Practically insoluble in water, petroleum ether; soluble in alcohols, acetone, ethyl acetate, chloroform
In water, 4.46X10-2 mg/L at 25 deg C (est)
2.7 Spectral Properties
Specific optical rotation: -32 deg at 23 deg C/D ( c = 0.88 in methanol)
MAX ABSORPTION (ETHANOL): 214, 259 NM (LOG E= 4.73, 4.21)
2.8 Stability
2.9 StorageTemp
Sealed in dry,Store in freezer, under -20°C
3. Use and Manufacturing
3.1 Methods of Manufacturing
... Isolated from periwinkle, Vinca rosea Linn, Apocynaceae.
4. Safety and Handling
4.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl vinblastine sulfate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /Vinblastine sulfate/
4.2 Packing Group
4.2 Octanol/Water Partition Coefficient
log Kow = 3.70
4.3 Other Preventative Measures
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Accidental contamination of the health-care environment, resulting in exposure of personnel, patients, visitors, and family members to hazardous substances, is prevented by maintaining the physical integrity and security of packages of hazardous drugs. 1. Access to all areas where hazardous drugs are stored is limited to specified authorized staff. 2. A method should be present for identifying to personnel those drugs that require special precautions (eg, cytotoxics). One way to accomplish this is to apply appropriate warning labels to all hazardous drug containers, shelves, and bins where the drug products are stored. ... 3. A method of identifying, for patients and family members, those drugs that require special precautions in the home should be in place. This may be accomplished in the health-care setting, by providing specific labeling for discharge medications, along with written instructions. 4. Methods for identifying shipping cartons of hazardous drugs should be required from manufacturers and distributors of these drugs. 5. Written procedures for handling damaged packages of hazardous drugs should be maintained. Personnel involved in shipping and receiving hazardous drugs should be trained in these procedures, including the proper use of protective garments and equipment. Damaged shipping cartons of hazardous drugs should be received and opened in an isolated area (eg, in a laboratory fume hood, if available, not in a vertical laminar airflow biological safety cabinet used for preparing sterile products). /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Facilities (eg, shelves, carts, counters, and trays) for storing hazardous drugs are designed to prevent breakage and to limit contamination in the event of leakage. Bins, shelves with barriers at the front, or other design features that reduce the chance of drug containers falling to the floor should be used. Hazardous drugs requiring refrigeration should be stored separately from nonhazardous drugs in individual bins designed to prevent breakage and to contain leakage. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Until the reproductive risks (or lack thereof) associated with handling hazardous drugs within a safety program have been substantiated, staff who are pregnant or breast-feeding should be allowed to avoid contact with these drugs. Policies should be in effect that provide these individuals with alternative tasks or responsibilities if they so desire. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The pharmacy should provide access to information on toxicity, treatment of acute exposure (if available), chemical inactivators, solubility and stability of hazardous drugs (including investigational agents) used in the workplace. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Appropriate engineering controls should be in place to protect the drug product from microbial contamination and to protect personnel and the environment from the potential hazards of the product. These engineering controls should be maintained according to applicable regulations and standards. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Biological safety cabinets should be cleaned and disinfected regularly to ensure a proper environment for preparation of sterile products. For routine cleanups of surfaces between decontaminations, water should be used (for injection or irrigation) with or without a small amount of cleaner. If the contamination is soluble only in alcohol, then 70% isopropyl or ethyl alcohol may be used in addition to the cleaner. In general, alcohol is not a good cleaner, only a disinfectant, and its use in a biohazard cabinet should be limited. The biohazard cabinet should be disinfected with 70% alcohol before any aseptic manipulation is begun. The excessive use of alcohol should be avoided in biohazard cabinets where air is recirculated ... because alcohol vapors may build up in the cabinet. A lint-free, plastic-backed disposable liner may be used in the biological safety cabinet to facilitate spill cleanup. ... If used, the liner should be changed frequently ... /or/ whenever it is overtly contaminated. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The biological safety cabinets should be decontaminated on a regular basis (ideally at least weekly) and whenever there is a spill or the biological safety cabinet is moved or serviced, including for certification. ... Currently, no single reagent will deactivate all known hazardous drugs; therefore, decontamination of a biological safety cabinet used for such drugs is limited to removal of contamination from a nondisposable surface (the cabinet) to a disposable surface (eg, gauze or towels) by use of a good cleaning agent that removes chemicals from stainless steel. The cleaning agent selected should have a pH approximating that of soap and be appropriate for stainless steel. Cleaners containing chemicals such as quaternary ammonium compounds should be used with caution, because they may be hazardous to humans and their vapors may build up in any biological safety cabinet where air is recirculated. Similar caution should be used with any pressurized aerosol cleaner; spraying a pressurized aerosol into a biological safety cabinet may disrupt the protective containment airflow, damage the high efficiency particulate air filter, and cause an accumulation of the propellant within a biological safety cabinet where air is recirculated, resulting in a fire and explosion hazard. During decontamination, the operator should wear a disposable closed front gown, disposable latex gloves covered by disposable utility gloves, safety glasses or goggles, a hair covering, and a disposable respirator, because the glass shield of the biological safety cabinet occasionally must be lifted. The blower must be left on, and only heavy toweling or gauze should be used in the biological safety cabinet to prevent it from being "sucked" up the plenum and into the high efficiency particulate air filter. Decontamination should be done from top to bottom (areas of lesser contamination to greater) by applying the cleaner, scrubbing, and rinsing thoroughly with distilled or deionized water. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The high efficiency particulate air filters /or other exhaust scrubbing system/ of the biohazard cabinet must be replaced whenever they restrict required airflow velocity or if they are overtly contaminated (eg, by a breach in technique that causes hazardous drug to be introduced onto the clean side of the supply high efficiency particulate air filter). Personnel and environmental protection must be maintained during replacement of a contaminated high efficiency particulate air filter. Because replacement of a high efficiency particulate air filter generally requires breaking the integrity of the containment aspect of the cabinet, this procedure may release contamination from the filter into the pharmacy or intravenous preparation area if carried out in an inappropriate manner. Before replacement of a high efficiency particulate air filter contaminated with hazardous drugs, the biological safety cabinet service agent should be consulted for a mutually acceptable procedure for replacing and subsequently disposing of a contaminated high efficiency particulate air filter. One procedure would include moving the biological safety cabinet to a secluded area or using plastic barriers to segregate the contaminated area. Protective clothing and equipment must be used by the servicer. The biological safety cabinet should be decontaminated before filter replacement. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ During removal of gloves, ... avoid touching the inside of the glove or the skin with the contaminated glove fingers. ... The worker should wear a protective disposable gown made of lint free, low-permeability fabric with a solid front, long sleeves, and tight-fitting elastic or knit cuffs when preparing hazardous drugs. Washable garments are immediately penetrated by liquids and therefore provide little, if any protection. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ When double gloving, one glove should be placed under the gown cuff and one over. The glove-gown interface should be such that no skin on the arm or wrist is exposed. Gloves and gowns should not be worn outside the immediate preparation area. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Eyewash fountains should be available in areas where hazardous drugs are routinely handled. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Although noninjectable dosage forms of hazardous drugs contain varying proportions of drug to nondrug (nonhazardous) components, there is potential for personnel exposure and environmental contamination with the hazardous components. Procedures should be developed to avoid the release of aerosolized powder or liquid into the environment during manipulation of these drugs. Drugs designated as hazardous should be labeled or otherwise identified as such to prevent their improper handling. Tablet and capsule forms of these drugs should not be placed in automated counting machines, which subject them to stress and may introduce powdered contaminants into the work area. During routine handling of hazardous drugs and contaminated equipment, workers should wear one pair of gloves of good quality and thickness. The counting and pouring of hazardous drugs should be done carefully, and clean equipment dedicated for use with these drugs should be used. ... When hazardous drug tablets in unit-of-use packaging are being crushed, the package should be placed in a small sealable plastic bag and crushed with a spoon or pestle; caution should be used not to break the plastic bag. Disposal of unused or unusable oral or topical dosage forms of hazardous drugs should be performed in the same manner as for hazardous injectable dosage forms and waste. ... Hazardous drug work areas should have a sink (preferably with an eyewash fountain) and appropriate first aid equipment to treat accidental skin or eye contact according to the protocol. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ A distinctive warning label with an appropriate CAUTION statement should be attached to all hazardous drug materials, consistent with state laws and regulations. This would include, for example, syringes, IV containers, containers of unit-dose tablets and liquids, prescription vials and bottles, waste containers, and patient specimens that contain hazardous drugs. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Supplies of disposable gloves and gowns, safety glasses, disposable plastic-backed absorbent liners, gauze pads, hazardous waste disposal bags, hazardous drug warning labels, and puncture-resistant containers for disposal of needles and ampuls should be conveniently located for all areas where hazardous drugs are handled. Assembling a "hazardous drug preparation and administration kit" is one way to furnish nursing and medical personnel with the materials needed to reduce the risk of preparing and administering a hazardous drug. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Prospective temporary and permanent employees who may be required to work with hazardous drugs should be so notified and should receive adequate information about the policies and procedures pertaining to their use. This notification should be documented during the interview process and retained as part of the employment record for all employees. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All personnel involved with the transportation, preparation, administration, and disposal of cytotoxic and hazardous substances should continually be updated on new or revised information on safe handling of cytotoxic and hazardous substances. Policies and procedures should be updated accordingly. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The work area should be designed to provide easy access to those items necessary to prepare, label, and transport final products; contain all related waste; and avoid inadvertent contamination of the work area. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Each health-care setting should have an established first aid protocol for treating cases of direct contact with hazardous drugs, many of which are irritating or caustic and can cause tissue destruction. Medical care providers in each setting should be contacted for input into this protocol. The protocol should include immediate treatment measures and should specify the type and location of medical follow-up and work-injury reporting. Copies of the protocol, highlighting emergency measures, should be posted wherever hazardous drugs are routinely handled. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Only individuals trained to administer hazardous drugs should be allowed to perform this function. Training programs should contain information on the therapeutic and adverse effects of these drugs and the potential, long term health risk to personnel handling these drugs. Each individual's knowledge and technique should be evaluated before administration of these drugs. This should be done by written examination and direct observation of the individual's performance. /Antineoplastic agents/
4.4 Hazard Class
4.4 Cleanup Methods
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Spill kits containing all materials needed to clean up spills of hazardous drugs should be assembled or purchased. These kits should be readily available in all areas where hazardous drugs are routinely handled. If hazardous drugs are being prepared or administered in a nonroutine area (home setting or unusual patient-care area), a spill kit should be obtained by the drug handler. The kit should include two pairs of disposable gloves (one outer pair of utility gloves and one inner latex pair); low-permeability, disposable protective garments (coveralls or gown and shoe covers); safety glasses or splash goggles; respirator; absorbent, plastic-backed sheets or spill pads; disposable toweling; at least 2 sealable thick plastic hazardous waste disposal bags (prelabeled with an appropriate warning label); a disposable scoop for collecting glass fragments; and a puncture-resistant container for glass fragments. All individuals who routinely handle hazardous drugs must be trained in proper spill management and cleanup procedures. Spills and breakages must be cleaned up immediately according to the following procedures. If the spill is not located in a confined space, the spill area should be identified and other people should be prevented from approaching and spreading the contamination. Wearing protective apparel from the spill kit, workers should remove any broken glass fragments and place them in the puncture-resistant container. Liquids should be absorbed with a spill pad; powder should be removed with damp disposable gauze pads or soft toweling. The hazardous material should be completely removed and the area rinsed with water and then cleaned with detergent. The spill cleanup should proceed progressively from areas of lesser to greater contamination. The detergent should be thoroughly rinsed and removed. All contaminated materials should be placed in the disposal bags provided and sealed and transported to a designated containment receptacle. Spills occurring in the biohazard cabinet should be cleaned up immediately; a spill kit should be used if the volume exceeds 150 ml or the contents of one drug vial or ampule. If there is broken glass, utility gloves should be worn to remove it and place it in the puncture-resistant container located in the biohazard cabinet. The biological safety cabinet, including the drain spillage trough, should be thoroughly cleaned. If the spill is not easily and thoroughly contained, the biological safety cabinet should be decontaminated after cleanup. If the spill contaminates the high efficiency particulate air filter, use of the biological safety cabinet should be suspended until the cabinet has been decontaminated and the high efficiency particulate air filter replaced. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ If hazardous drugs are routinely prepared or administered in carpeted areas, special equipment is necessary to remove the spill. Absorbent powder should be substituted for pads or sheets and left in place on the spill for the time recommended by the manufacturer. The powder should then be picked up with a small vacuum unit reserved for hazardous drug cleanup. The carpet should then be cleaned according to usual procedures. The vacuum bag should be removed and discarded or cleaned, and the exterior of the vacuum cleaner should be washed with detergent and rinsed before being covered and stored. The contaminated powder should be discarded into a sealable plastic bag and segregated with other contaminated waste materials. Alternatively, inexpensive wet or dry vacuum units may be purchased for this express use and used with appropriate cleaners. All such units are contaminated, once used, and must be cleaned, stored, and ultimately discarded /properly/ ... The circumstances and handling of spills should be documented. Health-care personnel exposed during spill management should also complete an incident report or exposure form. /Antineoplastic agents/
4.5 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All contaminated disposables should be contained in sealable bags for transfer to larger waste containers. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ All bottles must be discarded as contaminated waste after decontamination of the biohazard cabinet. All protective apparel (gown, gloves, goggles, and respirator) should be discarded as contaminated waste. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The contaminated filters must be removed, bagged in thick plastic and prepared for disposal in a hazardous waste dump site or incinerator licensed by the Environmental Protection Agency (EPA). /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ The gown should be removed and placed in a sealable container before removal of the inner gloves. The inner gloves should be removed last and placed in the container with the gown. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Hazardous drug waste should be placed in specially marked (specifically labeled CAUTION: HAZARDOUS CHEMICAL WASTE) thick plastic bags or leakproof containers. These receptacles should be kept in all areas where the drugs are commonly used. All and only hazardous drug waste should be placed in them. Receptacles used for glass fragments, needles, and syringes should be puncture resistant. Hazardous drug waste should not be mixed with any other waste. Waste containers should be handled with uncontaminated gloves. ... Gloves, gowns, drug vials, etc, should be sealed in specially labeled (CAUTION: HAZARDOUS CHEMICAL WASTE) thick plastic bags or leakproof containers. ... All hazardous waste collected from drug preparation and patient-care areas should be held in a secure place in labeled, leakproof drums or cartons (as required by state or local regulation or disposal contractor) until disposal. This waste should be disposed of as hazardous or toxic waste in an EPA-permitted state-licensed hazardous waste incinerator. Transport to an offsite incinerator should be done by a contractor licensed to handle and transport hazardous waste. ... If access to an appropriately licensed incinerator is not available, transport to and burial in an EPA-licensed hazardous waste dump site is an acceptable alternative. While there are concerns that destruction of carcinogens by incineration may be incomplete, newer technologies and stringent licensing criteria have improved this disposal method. ... Chemical deactivation of hazardous drugs should be undertaken only by individuals who are thoroughly familiar with the chemicals and the procedures required to complete such a task. The IARC recently published a monograph describing methods for chemical destruction of some cytotoxic (antineoplastic) drugs in the laboratory setting. The chemicals and equipment described, however, are not generally found in the clinical setting, and many of the deactivating chemicals are toxic and hazardous. Most procedures require the use of a chemical fume hood. The procedures are generally difficult, and the deactivation is not always complete. Serious consideration should be given to the negative aspects of chemical deactivation before one commits to such a course of action. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Regulatory agencies such as the EPA and state solid and hazardous waste agencies and local air and water quality control boards must be consulted regarding the classification and appropriate disposal of drugs that are defined as hazardous or toxic chemicals. EPA categorizes several of the antineoplastic agents as toxic wastes, while many states are more stringent and include as carcinogens certain cytotoxic drugs and hormonal preparations. EPA also allows exemptions from toxic waste regulations for small quantity generators, whereas certain states do not. It is critical to research these regulations when disposal procedures are being established. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ If the biological safety cabinet is equipped with a drainpipe and valve, it may be used to collect rinse water. The collection vessel used must fit well around the drain valve and not allow splashing. Gauze may be used around the connection to prevent aerosol from escaping. The collection vessel must have a tight fitting cover, and all rinse water (gauze, if used) must be disposed of as contaminated waste. /Antineoplastic agents/
4.6 Formulations/Preparations
Parenteral Injection, for IV use only 1 mg/mL, Vinblastine Sulfate Injection (with benzyl alcohol 0.9%), Abraxis; Sterile, for IV use only 10 mg, Bedford
Vials, 10 mg /Vinblastine sulfate/
4.7 Protective Equipment and Clothing
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Protective apparel: Disposable closed-front gown or coveralls, disposable utility gloves over disposable latex gloves, NIOSH-approved air-purifying half-mask respirator equipped with a high efficiency filter, and eye protection should be worn. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Class 100 clean-air work stations, both horizontal and vertical airflow (with no containment characteristics), are inappropriate engineering controls for handling hazardous drugs because they provide no personnel protection and permit environmental contamination. Although there are no engineering controls designed specifically for the safe handling of hazardous chemicals as sterile products, Class II contained vertical-flow biological safety cabinets (biohazard cabinets) have been adopted for this use. Biohazard cabinetry is, however, designed for the handling of infectious agents, not hazardous chemicals. ... Based on design, ease of use, and cost considerations, Class II contained-vertical-flow biohazard cabinetry is currently recommended for use in preparing sterile doses of hazardous drugs. Class II cabinetry design and performance specifications are defined in NSF Standard 49. Biological safety cabinets selected for use with hazardous drugs should meet NSF Standard 49 specifications to ensure the maximum protection from these engineering controls. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers should wear powder free, disposable surgical latex gloves of good quality when preparing hazardous drugs. Selection criteria for gloves should include thickness (especially at the fingertips where stress is the greatest), fit, length, and tactile sensation. ... The practice of double gloving is supported by research that indicates that many glove materials vary in drug permeability even within lots; therefore, double gloving is recommended. ... In general, surgical latex gloves fit better, have appropriate elasticity for double gloving and maintaining the integrity of the glove-gown interface, and have sufficient tactile sensation (even during double gloving) for stringent aseptic procedures. ... Powdered gloves should be avoided. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ Workers who are not protected by the containment environment of a biohazard cabinet should use respiratory protection when handling hazardous drugs. Respiratory protection should be an adjunct to and not a substitute for engineering controls. Surgical masks of all types provide no respiratory protection against powdered or liquid aerosols of hazardous drugs. In situations where workers may be exposed to potential eye contact with hazardous drugs, an appropriate plastic face shield or splash goggles should be worn. /Antineoplastic agents/
/PRECAUTIONS FOR ANTINEOPLASTIC AGENTS:/ During compounding of hazardous drugs (eg, crushing, dissolving, and preparing an ointment), workers should wear low permeability gowns and double gloves. Compounding should take place in a protective area such as a disposable glove box. If compounding must be done in the open, an area away from drafts and traffic must be selected, and the worker should use appropriate respiratory protection. /Antineoplastic agents/
4.8 Report

NCI Carcinogenesis Studies (ipr); No Evidence: mouse CANCAR    Cancer. 40 (1977),1935. ; (ipr); Clear Evidence: rat CANCAR    Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.

4.9 Skin, Eye, and Respiratory Irritations
Care must be taken to avoid contact of vinblastine sulfate solutions with the eyes as severe irritation and possibly corneal ulceration can result.
... A nurse who sought attention 6 days after squirting vinblastine solution in one eye, having developed by this time photophobia, pain, tearing, and redness of the eye, with vision reduced to 1/10 /is described/. Microcystic edema involved the entire corneal epithelium, and in the following days the epithelium ulcerated and came off in small sheets. Healing from the periphery toward the center began 2 wk after the accident, and in 3.5 wk the eye returned to normal.
4.10 Safety

Human poison by intravenous route. Experimental poison by intraperitoneal route. Human systemic effects by intravenous and ocular routes: visual field changes, conjunctiva irritation and other eye effects, cardiomyopathy including infarction, and changes in bone marrow. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as an antineoplastic agent. See also VINCALEUKOBLASTINE SULFATE (1:1) (SALT).
RIDADR: 1544
HazardClass: 6.1(a)
PackingGroup: II

4.11 Specification

 Vinblastine (865-21-4) is a vinca alkaloid and a chemical analogue of vincristine. It binds tubulin, thereby inhibiting the assembly of microtubules. It is M phase cell cycle specific since microtubules are a component of the mitotic spindle and the kinetochore which are necessary for the separation of chromosomes during anaphase of mitosis.

4.12 Toxicity

dni-hmn:oth 200 µg/L

    26QZAP    Advances in Antimicrobial and Antineoplastic Chemotherapy, Progress in Research and Clinical Application. 2 (1972),377.

cyt-mus-ipr 900 µg/kg

    ENMUDM    Environmental Mutagenesis. 8 (1986),273.

ivn-man LDLo:2319 µg/kg/38W-I:CVS

    LANCAO    Lancet. 2 (1980),692.

ocu-hmn TDLo:14 µg/kg:EYE

    BJOPAL    British Journal of Ophthalmology. 62 (1978),97.

unr-man TDLo:80 µg/kg:BLD

    CCROBU    Cancer Chemotherapy Reports, Part 1. 50 (1966),219.

ipr-rat LD50:1 mg/kg

    VINIT*    Vsesoyuznyi Institut Nauchnoi i Tekhnicheskoi Informatsii (VINITI). All-Union Institute of Scientific and Technical Information. (Moscow, USSR) #3713-83 .

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)

no data available


no data available


no data available


no data available

2.3 Other hazards which do not result in classification

no data available

6. Other Information
6.0 Uses
6.1 Brand name
Velban (Lilly).
6.2 Description
An alkaloid derived from the periwinkle, Catharanthus roseus (formerly Vinca rosea) used as an antitumor drug in the treatment of Hodgkins lymphoma and other cancers. It binds to the microtubule subunit, tubulin, at a site distinct from that of colchicine and podophyllotoxin. This binding is reversible, temperature dependent and rapid, and results in large tubulin aggregates of highly ordered structure (vinblastine paracrystals).
6.3 Physical properties
Appearance: needlelike crystals were produced when recrystallized by methanol. Solubility: soluble in chloroform, acetone, and ethanol. Melting point: 211– 216?°C.?Sulfate melting point of vinblastine is 284–285?°C; hydrochloric acid melting point of vinblastine is 244–246?°C (decomposes). Specific optical rotation: +42°.
6.4 Originator
Velban ,Lilly ,US ,1961
6.5 Uses
Vinblastine is used for severe lymphoblastic leukemia, Hodgkin’s disease, nonHodgkin’s lymphoma, neuroblastoma, sarcoma, and other cancerous diseases.
6.6 Uses
Labelled Vinblastine (V314000). Antitumor alkaloid isolated from periwinkle, Vinca rosea Linn., Apocynaceae; inhibits microtubule assembly. An antineoplastic.
6.7 Indications
It was recorded in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the European Pharmacopoeia (9th ed.), and The International Pharmacopoeia (5th ed.).
Vinblastine sulfate injection is used as the first-line therapy to treat Hodgkin lymphoma, lymphocytic leukemia, testis tumor, and choriocarcinoma intravenously in clinical practice generally according to ABVD methods (Adriamycin, bleomycin, vinblastine, and dacarbazine).
6.8 Manufacturing Process
According to US Patent 3,225,030, 1,500 grams of dried ground plant of Vinca rosea were intimately mixed with 1,000 ml of a 2% tartaric acid solution, and the mixture was extracted with three 9-liter portions of benzene. The benzene extracts were combined and were concentrated in vacuo to about 1,500 ml. The concentrate was mixed with 1 liter of 2% tartaric acid and the mixture was steam-distilled under reduced pressure until all of the benzene had distilled over. The insoluble residue was dissolved in hot methanol, a second 1-liter portion of 2% tartaric acid solution was added, and the mixture was steam-distilled under reduced pressure until all of the methanol had distilled.
The undistilled aqueous tartaric acid solution was extracted with three 1-liter portions of ethylene dichloride, and was then brought to a pH of about 8.5 to 9.5 by the addition of 28% aqueous ammonium hydroxide. The ammoniacal solution was extracted with three 1-liter portions of ethylene dichloride; the ethylene dichloride extracts were combined, were dried, and were evaporated in vacuo, yielding a residue of 3.35 grams of a light-brown powder.
1 1/2 grams of the residue were dissolved in 10 ml of benzene, and the solution was passed over a chromatographic adsorption column containing 50 grams of alumina (Alcoa activated alumina, Grade F-20) which had previously been shaken for about 20 minutes with a mixture of 100 ml of benzene containing 1.5 ml of 10% acetic acid.
The column was developed by washing it with 2,100 ml of benzene. The column was then washed sequentially with 300 ml of benzene-chloroform solvent (95:5 by volume) and 800 milliliters of benzene-chloroform solvent (75:25) to remove indeterminate impurities. The leurosine was eluted from the alumina by passing over the column 900 ml of benzene chloroform solvent (50:50).
The eluate was evaporated to dryness in vacuo, leaving an amorphous residue of 113 mg of leurosine. The residue was treated with a few ml of methanol in which it quickly dissolved, but from which leurosine quickly precipitated in crystalline form. Because of the affinity of leurosine for water, and the presence of traces of water in the solvents, the leurosine was obtained in the form of its octahydrate. Although the material as obtained was substantially pure, it was further purified by recrystallizing it from hot methanol solution. The hydrated leurosine obtained decomposed at about 200° to 205°C.
Further elution of the above chromatographic column with a 50:50 benzene- chloroform solvent mixture or with a 25:75 benzene-chloroform solvent mixture serves to elute vincaleukoblastine. Vincaleukoblastine also occurs in the latter fractions containing leurosine. Vincaleukoblastine is obtained from vincaleukoblastine-containing fractions by evaporation to dryness, either of a filtrate from which leurosine has previously been isolated, or from a chromatographic eluate fraction. The resulting residue is dissolved in ethanol and 286 ethanolic sulfuric acid is added until the pH is lowered to about 4. The solution is seeded with crystals of vincaleukoblastine sulfate and is chilled for about 24 hours. Vincaleukoblastine sulfate, if present, precipitates during this period and can be separated by filtration. Vincaleukoblastine sulfate melts at about 284° to 285°C.
6.9 Therapeutic Function
Cancer chemotherapy
6.10 Mechanism of action
Vinblastine suppresses cell growth during metaphase, affects amino acid metabolism, in particular at the level of including glutamine acid into the citric acid cycle and preventing it from transformation into urea, and it also inhibits protein and nucleic acid synthesis.
6.11 Pharmacokinetics
Leukopenia is the dose-limiting side effect, and dose reductions are warranted in patients with serum bilirubin levels greater than 3 mg/dL. The drug-related impact on erythrocyte and thrombocyte levels usually is insignificant. Like vincristine, it is administered as an IV bolus or infusion. The initial elimination half-life of 3.7 minutes is similar to vincristine, but the 24.8-hour terminal half-life is significantly shorter.
6.12 Clinical Use
In addition to the hematologic indications that it shares with vincristine, vinblastine sulfate has found utility in the treatment of advanced testicular carcinoma (often in combination with bleomycin), advanced mycosis fungoides, Kaposi's sarcoma, and histiocytosis X.
7. Computational chemical data
  • Molecular Weight: 810.989g/mol
  • Molecular Formula: C46H58N4O9
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 810.42037944
  • Monoisotopic Mass: 810.42037944
  • Complexity: 1700
  • Rotatable Bond Count: 10
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 12
  • Topological Polar Surface Area: 154
  • Heavy Atom Count: 59
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
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