Related Searches: Cytidine,5'-deoxy-5-fluoro-, 2',3'-diacetate, 5-Fluoro-2-oxindole, 5-Fluoro-1-indanone, 5-Fluoro Cytosine, b-D-Ribofuranose, 5-deoxy-,1,2,3-triacetate, View all

Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-(CAS No. 154361-50-9)

Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]- C15H22FN3O6 (cas 154361-50-9) Molecular Structure

154361-50-9 Structure

Identification and Related Records

Cytidine, 5'-deoxy-5-fluoro-N-[(pentyloxy)carbonyl]-
【CAS Registry number】
Xeloda (TN)
Cytidine,5'-deoxy-5-fluoro-N-[(pentyloxy)- carbonyl]-
Pentyl [1-(3,4-dihydroxy-5-methyl-oxolan-2-yl)-5-fluoro-2-oxo-pyrimidin-4-yl]aminoformate;Capecitabine
pentyl (1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate
【Molecular Formula】
C15H22FN3O6 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

Colourless solid
1.49 g/cm3
【Melting Point】
Slightly soluble
White to off-white crystalline powder
Crystals from ethyl acetate
【Storage temp】
Store in original container in a cool dark place.
【Computed Properties】
Molecular Weight:359.350083 [g/mol]
Molecular Formula:C15H22FN3O6
H-Bond Donor:3
H-Bond Acceptor:7
Rotatable Bond Count:7
Tautomer Count:4
Exact Mass:359.149264
MonoIsotopic Mass:359.149264
Topological Polar Surface Area:121
Heavy Atom Count:25
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:4
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:9
Conformer Sampling RMSD:1
CID Conformer Count:87

Safety and Handling

【Skin, Eye, and Respiratory Irritations】
Ocular irritation occurred in 5-15% of patients receiving capecitabine for metastatic breast cancer or metastatic colorectal cancer. Abnormal vision occurred in 5% of patients receiving capecitabine monotherapy for metastatic colorectal cancer. Severe ocular irritation and corneal deposits were reported in 2 patients with a history of keratoconjunctivitis sicca who received higher doses of capecitabine for metastatic breast cancer or metastatic colon cancer. Ophthalmic examination is recommended for patients receiving capecitabine who experience severe ocular symptoms or decreased visual acuity. Increased lacrimation was reported in 12% of patients receiving capecitabine and docetaxel and in 7% of those receiving docetaxel alone for metastatic breast cancer. Among patients receiving capecitabine alone as adjuvant therapy for stage III colon cancer, conjunctivitis occurred in 5% of patients. Conjunctivitis and lacrimal duct stenosis each occurred in less than 5% of patients receiving capecitabine monotherapy for metastatic breast cancer or metastatic colorectal cancer in clinical trials.
【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/
Formulations: Oral tablets, 150 mg and 500 mg Capecitabine (Xeloda) /by/ Roche
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl capecitabine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【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/
【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/

? Capecitabine , with CAS number of 154361-50-9, can be called Cytidine,5'-deoxy-5-fluoro-N-[(pentyloxy)- carbonyl]- ; (1-(5-Deoxy-beta-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl)-carbamic acid pentyl ester ; pentyl N-[1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methyl-oxolan-2-yl]-5-fluoro-2-oxo-pyrimidin-4-yl]carbamate ; Capecitabine (JAN/USAN) ; Pentyl [1-(3,4-dihydroxy-5-methyl-oxolan-2-yl)-5-fluoro-2-oxo-pyrimidin-4-yl]aminoformate;Capecitabine ; Pentyl [1-(3,4-dihydroxy-5-methyl-oxolan-2-yl)-5-fluoro-2-oxo-pyrimidin-4-yl]aminoformate ; Capecitabine and its intermediates ; Capecitabine 99% . It is a?colourless solid,?Capecitabine (CAS NO.154361-50-9) can be used as an antineoplastic agent, a prodrug of doxifluridine.? Capecitabine (CAS NO.154361-50-9) is an orally-administered chemotherapeutic agent used in the treatment of metastatic breast and colorectal cancers. Capecitabine (CAS NO.154361-50-9) is a prodrug, that is enzymatically converted to 5-fluorouracil in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue.

【Octanol/Water Partition Coefficient】
log Kow = 0.56 (est)
【Disposal Methods】
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/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: M. Arasaki et al., EP 602454; eidem, US 5472949 (1994, 1995 both to Hoffmann-La Roche)

An antineoplastic agent. A prodrug of doxifluridine.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Antimetabolites that are useful in cancer chemotherapy.
【Therapeutic Uses】
Antimetabolites, Antineoplastic Agent
【Biomedical Effects and Toxicity】
Capecitabine is readily absorbed from the GI tract; on average, at least 70% of an oral dose of the drug is absorbed. Although in vitro studies have shown that capecitabine is unstable under highly acidic conditions, the drug appears to be absorbed intact immediately upon dissolution without degradation secondary to the acidic pH of the stomach.
According to the manufacturer, peak plasma concentrations of capecitabine occur in about 1.5 hours, and peak plasma concentrations of fluorouracil, its active drug, occur slightly later at 2 hours.
In adults with cancer who received a capecitabine dosage of 2510 mg/sq m daily in 2 divided doses, administered approximately 12 hours apart within 30 minutes following the end of a meal, blood samples drawn on day 1 of the treatment cycle showed that peak plasma concentrations of 3.93 and 0.66 ug/mL for capecitabine and fluorouracil, respectively, were achieved in about 2 hours.
Considerable interindividual variations (ie, exceeding 85%) in peak plasma concentrations and areas under the concentration-time curves (AUCs) have been reported following oral administration of capecitabine.
Presence of food in the GI tract decreases the rate and extent of absorption of capecitabine and, to a lesser extent, decreases the peak plasma concentration and AUC of its metabolites. Peak plasma concentrations and AUC were decreased by 60 and 35%, respectively, for capecitabine and by 43 and 21%, respectively, for fluorouracil when the drug was administered with food. Times to peak plasma concentration for both capecitabine and fluorouracil were delayed by 1.5 hours when capecitabine was administered with food.
Distribution of capecitabine and its metabolites into body tissues and fluids has not been fully characterized. Capecitabine or its metabolites are distributed into tumors, intestinal mucosa, plasma, liver, and other tissues. Animal studies show that capecitabine and its metabolites do not readily penetrate the blood-brain barrier; it is not known whether capecitabine or its metabolites distribute into CSF and brain tissue in humans.
Plasma protein binding (mainly to albumin) of capecitabine and its metabolites is less than 60% and is not concentration dependent.
It is not known whether capecitabine or its metabolites cross the placenta. It is not known whether capecitabine or its metabolites are distributed into milk.
Capecitabine and its metabolites are excreted predominantly in urine (95.5%); fecal excretion is minimal (2.6%). Greater than 70% of a dose of capecitabine is excreted in urine within 24 hours. Most of the capecitabine dose is excreted in urine as metabolites, principally FBAL, a catabolite of fluorouracil (57% of an administered dose); about 3% of an administered dose is excreted in urine as unchanged drug.
The effect of dialysis on the elimination of capecitabine has not been determined; however, the manufacturer reports that dialysis may reduce circulating concentrations of 5'-DFUR, a low molecular weight metabolite of the drug.
Capecitabine is a novel oral fluoropyrimidine carbamate that is preferentially converted to the cytotoxic moiety fluorouracil (5-fluorouracil; 5-FU) in target tumor tissue through a series of 3 metabolic steps. After oral administration of 1250 mg/sq m, capecitabine is rapidly and extensively absorbed from the gastrointestinal tract [with a time to reach peak concentration (tmax) of 2 hours and peak plasma drug concentration (Cmax) of 3 to 4 mg/L] and has a relatively short elimination half-life (t(1/2)) [0.55 to 0.89 hr]. Recovery of drug-related material in urine and feces is nearly 100%. Plasma concentrations of the cytotoxic moiety fluorouracil are very low [with a Cmax of 0.22 to 0.31 mg/L and area under the concentration-time curve (AUC) of 0.461 to 0.698 mg x hr/L]. The apparent t(1/2) of fluorouracil after capecitabine administration is similar to that of the parent compound. Comparison of fluorouracil concentrations in primary colorectal tumor and adjacent healthy tissues after capecitabine administration demonstrates that capecitabine is preferentially activated to fluorouracil in colorectal tumor, with the average concentration of fluorouracil being 3.2-fold higher than in adjacent healthy tissue (p = 0.002). This tissue concentration differential does not hold for liver metastasis, although concentrations of fluorouracil in liver metastases are sufficient for antitumor activity to occur. The tumor-preferential activation of capecitabine to fluorouracil is explained by tissue differences in the activity of cytidine deaminase and thymidine phosphorylase, key enzymes in the conversion process. As with other cytotoxic drugs, the interpatient variability of the pharmacokinetic parameters of capecitabine and its metabolites, 5'-deoxy-5-fluorocytidine and fluorouracil, is high (27 to 89%) and is likely to be primarily due to variability in the activity of the enzymes involved in capecitabine metabolism. Capecitabine and the fluorouracil precursors 5'-deoxy-5-fluorocytidine and 5'-deoxy-5-fluorouridine do not accumulate significantly in plasma after repeated administration. Plasma concentrations of fluorouracil increase by 10 to 60% during long term administration, but this time-dependency is assumed to be not clinically relevant. ... [Reigner B et al; Clin Pharmacokinet 40 (2): 85-104 (2001)] PubMed Abstract
An excretion balance and pharmacokinetic study was conducted in cancer patients with solid tumors who received a single oral dose of capecitabine of 2000 mg including 50 microCi of 14C-radiolabelled capecitabine. Blood, urine and fecal samples were collected until radioactive counts had fallen to below 50 dpm/mL in urine, and levels of intact drug and its metabolites were measured in plasma and urine by LC/MS-MS (mass spectrometry) and 19F-NMR (nuclear magnetic resonance) respectively. Based on the results of the 6 eligible patients enrolled, the dose was almost completely recovered in the urine (mean 95.5%, range 86-104% based on radioactivity measurements) over a period of 7 days after drug administration. Of this, 84% (range 71-95) was recovered in the first 12 hours. Over this time period, 2.64% (0.69-7.0) was collected in the feces. Over a collection period of 24-48 hr, a total of 84.2% (range 80-95) was recovered in the urine as the sum of the parent drug and measured metabolites (5'-DFCR, 5'-DFUR, 5-FU, FUH2, FUPA, FBAL). Based on the radioactivity measurements of drug-related material, absorption is rapid (tmax 0.25-1.5 hours) followed by a rapid biphasic decline. The parent drug is rapidly converted to 5-FU, which is present in low levels due to the rapid metabolism to FBAL, which has the longest half-life. There is a good correlation between the levels of radioactivity in the plasma and the levels of intact drug and the metabolites, suggesting that these represent the most abundant metabolites of capecitabine. The absorption of capecitabine is rapid and almost complete. The excretion of the intact drug and its metabolites is rapid and almost exclusively in the urine. [Judson IR et al; Invest New Drugs 17 (1): 49-56 (1999)] PubMed Abstract

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