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13-cis-Vitamin A acid(CAS No. 4759-48-2)

13-cis-Vitamin A acid C20H28O2 (cas 4759-48-2) Molecular Structure

4759-48-2 Structure

Identification and Related Records

【Name】
13-cis-Vitamin A acid
【CAS Registry number】
4759-48-2
【Synonyms】
Isotretinoin [USAN:BAN:INN]
(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoate
Retinoic acid, (13cis)-
13-cis-Retinoic acid
Isotretinoin Retinoic acid
Prestwick_642
Neovitamin A acid
Claravis
Teriosal
Roaccutan
Isotretion
Isotretinoin?
Isotretinoine [INN-French]
isoretinoin
4-09-00-02388 (Beilstein Handbook Reference)
【EINECS(EC#)】
225-296-0
【Molecular Formula】
C20H28O2 (Products with the same molecular formula)
【Molecular Weight】
300.44
【Inchi】
InChI=1/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-
【Canonical SMILES】
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
【Isomers smiles】
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
【MOL File】
4759-48-2.mol

Chemical and Physical Properties

【Appearance】
yellowish crystalline powder
【Density】
1.011 g/cm3
【Melting Point】
174-177℃
【Boiling Point】
462.8 °C at 760 mmHg
【Flash Point】
350.6 °C
【Water】
insoluble
【Solubilities】
insoluble in water
【Color/Form】
Reddish-orange plates from isopropyl alcohol
Yellowish to orange crystalline powder
【Stability】
Stable, but probably air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
【Storage temp】
?20°C
【Spectral properties】
Max absorption: 354 nm (Epsilon=39,800)
【Computed Properties】
Molecular Weight:300.43512 [g/mol]
Molecular Formula:C20H28O2
XLogP3:6.3
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:5
Exact Mass:300.20893
MonoIsotopic Mass:300.20893
Topological Polar Surface Area:37.3
Heavy Atom Count:22
Formal Charge:0
Complexity:567
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:4
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:3
Feature 3D Ring Count:1
Effective Rotor Count:5.8
Conformer Sampling RMSD:0.8
CID Conformer Count:37

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R36/37/38;R61
【Safety Statements 】
S26;S37/39;S45;S53
【Safety】

Hazard Codes:?ToxicT
Risk Codes:?61-36/37/38-20/21/22
R61:May cause harm to the unborn child.?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety?Codes:?53-26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical
advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the
label whenever possible.)
S53: Avoid exposure - obtain special instructions before use.
WGK Germany: 3
RTECS: VH6440000
Poison by intraperitoneal route. Moderately toxic by ingestion. A human teratogen by ingestion with fetal developmental abnormalities of the skin and appendages and other postnatal effects. Human reproductive effects. Human systemic effects: decreased immune response, diarrhea, hypermotility, irritative dermatitis, sweating. Human mutation data reported. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

【Cleanup Methods】
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Spills. Emergency procedures to cover spills or inadvertent release of hazardous drugs should be included in the facility's overall heath and safety program. Incidental spills and breakages should be cleaned up immediately by a properly protected person trained in the appropriate procedures.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Spills: ... Personnel Contamination. Contamination of protective equipment or clothing, or direct skin or eye contact should be treated by: immediately removing the gloves or gown; immediate cleansing of the affected skin with soap and water; flooding of an affected eye at an eyewash fountain or with water or isotonic eyewash designated for that purpose for at least 15 minutes; obtaining medical attention; documenting the exposure in the employee's medical record.
【Formulations/Preparations】
Oral: Capsules, liquid-filled: 10 mg Accutane (with Parabens) (Roche), Amnesteem (Bertek), Claravis (Barr), Sotret (with parabens) (Ranbaxy); 20 mg Accutane (with Parabens) (Roche), Amnesteem (Bertek), Claravis (Barr), Sotret (with parabens) (Ranbaxy); 30 mg Sotret (with parabens) (Ranbaxy); 40 mg Accutane (with Parabens) (Roche), Amnesteem (Bertek), Claravis (Barr), Sotret (with parabens) (Ranbaxy).
IN CREAMS AND ... IN GEL FORMULATIONS. [DEPAOLIS AM; J CHROMATOGR 258: 314-19 (1983)] PubMed Abstract
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl isotretinoin, 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 CYTOTOXIC AND HAZARDOUS DRUGS:/ The equipment and procedures for protection of workers in this record are primarily intended to protect the health of workers involved in: (1) the bulk production/manufacture or packaging of the material (2) transport, delivery and storage of the bulk material (3) the formulation of the individual drug at the health care facility to be administered to the patient. Once the drug is prepared for individual administration to the patient, health care workers handling the drug in that form and concentration may follow precautions consistent with handling any other drug similarly prepared /SRP/.
All provisions of the OSHA Hazard Communication Standard are in effect in all industries, including employers whose employees are exposed to Food and Drug Administration (FDA) regulated drugs that pose a hazard. If hazardous FDA-regulated drugs are administered by injection or orally, they would be covered by the HCS. ...The scope and application of HCS exempts drugs that are in solid final form, as per 29 CFR 1910.1200(b)(6)(viii). The final form exemption would also apply to tablets or pills that are occasionally crushed, if the pill or tablet is not designed to be dissolved or crushed prior to administration.
The OSHA Hazard Communication Standard only applies to pharmaceuticals that the drug manufacturer has determined to be hazardous and that are known to be present in the workplace in such a manner that employees are exposed under normal conditions of use or in a foreseeable emergency. The pharmaceutical manufacturer and the importer have the primary duty for the evaluation of chemical hazards. The employer may rely upon the hazard determination performed by the pharmaceutical manufacturer or importer.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ 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 ? . 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. /Cytotoxic and hazardous drugs/
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ The American Society of Hospital Pharmacists recommends that hazardous drug preparation be performed in a restricted, preferably, centralized area. Signs restricting the access of unauthorized personnel are to be prominently displayed. Eating, drinking, smoking, chewing gum, applying cosmetics, and storing food in the preparation area should be prohibited.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Horizontal airflow work benches provide an aseptic environment for the preparation of injectable drugs. However, these units provide a flow of filtered air originating at the back of the work space and exiting toward the employee using the unit. Thus, they increase the likelihood of drug exposure to both the preparer and other personnel in the room. As a result, the use of horizontal Biological Safety Cabinets is contra-indicated in the preparation of hazardous drugs. Smoking, drinking, applying cosmetics, and eating where these drugs are prepared, stored, or used also increase the chance of exposure /and should be prohibited/.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Contaminated materials used in the preparation and administration of hazardous drugs, such as gloves, gowns, syringes and vials, present a hazard to support and housekeeping staff. The use of properly labeled, sealed and covered disposal containers, handled by trained and protected personnel, should be routine, and is required under the Bloodborne Pathogens Standard if such items are contaminated with blood or other potentially infectious materials. Hazardous drugs and contaminated materials should be disposed of in accordance with federal, state, and local laws. Disposal of some of these drugs is regulated by the EPA. Drugs that are unused commercial chemical products and are considered by the EPA to be toxic wastes must be disposed of in accordance with 40 CFR part 261. Spills can also represent a hazard; the employer should ensure that all employees are familiar with appropriate spill procedures.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Where hazardous drugs ... are used in the workplace, sound practice dictates that a written Hazardous Drug Safety and Health Plan be developed ... should be readily available and accessible to all employees, including temporary employees, contractors, and trainees. ...The American Society of Hospital Pharmacists recommends that the Hazardous Drug Safety and Health Plan be reviewed and its effectiveness reevaluated at least annually and updated as necessary.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Class II or III Biological Safety Cabinets (BSC) that meet the current National Sanitation Foundation Standard should minimize exposure to hazardous drugs during preparation. ... Use of a dedicated BSC, where only hazardous drugs are prepared, is prudent practice. ... The cabinet should be cleaned according to the manufacturer's instructions. ? Decontamination should consist of surface cleaning with water and detergent followed by thorough rinsing. ... The ASHP recommends that BSCs be serviced and certified by a qualified technician every six months or any time the cabinet is moved or repaired.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Work equipment. NIH has recommended that work with hazardous drugs be carried out in a Biological Safety Cabinet on a disposable, plastic-backed paper liner. The liner should be changed after preparation is completed for the day or after a shift, whichever comes first. Liners should also be changed after a spill. Syringes and IV sets with Luer-lock fittings should be used for hazardous drugs. Syringe size should be large enough so that they are not full when the entire drug dose is present. A covered disposable container should be used to contain excess solution. A covered sharps container should be in the Biological Safety Cabinet. The ASHP recommends that hazardous drug-labeled plastic bags be available for all contaminated materials (including gloves, gowns, and paper liners), so that contaminated material can be immediately placed in them and disposed of in accordance with ASHP recommendations.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Labeling. In addition to standard pharmacy labeling practices, all syringes and IV bags containing hazardous drugs should be labeled with a distinctive warning label, such as: SPECIAL HANDLING/DISPOSAL PRECAUTIONS. Those hazardous drugs covered under OSHA's Hazard Communication Standard must also have labels in accordance with section (f) of the standard to warn employees handling the drug(s) of the hazards.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Waste Disposal. Equipment. Thick, leak-proof plastic bags, colored differently from other hospital trash bags, should be used for routine accumulation and collection of used containers, discarded gloves, gowns, and any other disposable material. Bags containing hazardous chemicals (as defined by Section C of OSHA's Hazard Communication Standard), shall be labeled in accordance with Section F of the Hazard Communication Standard where appropriate. Where the Hazard Communication Standard does not apply, labels should indicate that bags contain hazardous drug-related wastes. Needles, syringes, and breakable items not contaminated with blood or other potentially infectious materials should be placed in a "sharps" container before they are stored in the waste bag. Such items that are contaminated with blood or other potentially infectious material must be placed in a "sharps" container. ... Handling. Prudent practice dictates that every precaution be taken to prevent contamination of the exterior of the container. Personnel disposing of hazardous drug waste should wear gowns and protective gloves when handling waste containers with contaminated exteriors. Prudent practice further dictates that such a container with a contaminated exterior be placed in a second container in a manner that eliminates contamination of the second container. Disposal. Hazardous drug-related wastes should be handled separately from other hospital trash and disposed of in accordance with applicable EPA, state, and local regulations for hazardous waste.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ Transport. Hazardous drugs should be securely capped or sealed, placed in sealed clear plastic bags, and transported in containers designed to avoid breakage. Personnel involved in transporting hazardous drugs should be trained in spill procedures, including sealing off the contaminated area and calling for appropriate assistance.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ 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.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ 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.
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ 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.
【Protective Equipment and Clothing】
Gloves:/ latex gloves should be used for the preparation of hazardous drugs unless the drug-product manufacturer specifically stipulates that some other glove provides better protection. Thicker, longer latex gloves that cover the gown cuff are recommended for use with hazardous drugs. Gloves with minimal or no powder are preferred?double gloving is recommended if it does not interfere with an individual's technique. /Hazardous drugs not in solid final form/
A protective disposable gown made of lint-free, low-permeability fabric with a closed front, long sleeves, and elastic or knit closed cuffs should be worn /during preparation of hazardous drugs/. The cuffs should be tucked under the gloves. If double gloves are worn, the outer glove should be over the gown cuff and the inner glove should be under the gown cuff. /Hazardous drugs not in solid final form/
Where a biological safety cabinet is not currently available, a NIOSH-approved respirator appropriate for the hazard must be worn /during preparation of hazardous drugs/. /Hazardous drugs not in solid final form/
Whenever splashes, sprays, or aerosols of hazardous drugs may be generated that can result in eye, nose, or mouth contamination, chemical-barrier face and eye protection must be provided and used in accordance with 29 CFR 1910.133. /Hazardous drugs/
【Specification】

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.?
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Do not store in direct sunlight. Store in a tightly closed container. Store in a dry area. Store in freezer.

【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
/PRECAUTIONS FOR CYTOTOXIC AND HAZARDOUS DRUGS:/ 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.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Usage】
Used as a treatment for severe acne. Presently being studied in conjuction with the treatment of photoaged skin.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs used to treat or prevent skin disorders or for the routine care of skin.
- An agent that causes the production of physical defects in the developing embryo.
【Therapeutic Uses】
Keratolytic Agents; Teratogens
Isotretinoin is indicated in the treatment of severe, recalcitrant nodular acne, where severe is defined as numerous lesions of at least 5 mm in diameter that may be suppurative or hemorrhagic. (Isotretinoin is also indicated for severe, inflammatory acne and acne conglobata. Taking into consideration its potential adverse effects, isotretinoin may be considered in patients with moderately severe acne who are prone to scarring or dyspigmentation. /NOT included in US product labeling/) Because of its potential adverse effects, isotretinoin should be reserved for patients who are unresponsive to or intolerant of conventional therapy, including systemic antibiotics. /Included in US product labeling/
Isotretinoin is used in the treatment of gram-negative folliculitis and severe rosacea. /NOT included in US product labeling/
Isotretinoin is used in the treatment of hidradenitis suppurative and is more effective for less established conditions and for those mild in severity (less scarring). Complete suppression or prolonged remission is uncommon. Using isotretinoin as adjunctive therapy to intralesional steroids, systemic antibiotics, or local surgery has proved beneficial for some patients with hidradenitis suppurative. /NOT included in US product labeling/
Isotretinoin has been used for severe keratinization disorders, such as lamellar ichthyosis, keratosis follicularis (Darier's disease), palmoplantar keratoderma (keratosis palmaris et plantaris), and pityriasis rubra pilaris (PRP). Longer periods of isotretinoin therapy are usually required for keratinization disorders than for acne vulgaris, thus increasing the risk of side effects, including skeletal changes. /NOT included in US product labeling/
Oral administration of 13-cis-retinoic acid (40 or 160 mg/kg bw daily) significantly reduced the inflammation associated with developing and established adjuvant arthritis, an experimentally induced arthritis in rats that resembles human rheumatoid arthritis. [Brinckerhoff CR et al; Science 221 (AUG 19): 756 (1983)]
【Biomedical Effects and Toxicity】
The drug readily crosses the placenta in animals. It is not known if isotretinoin is distributed into milk.
Radiolabeled doses administered to rats showed high concentrations of radioactivity in many tissues after 15 minutes, maximizing at 1 hour and declining to non detectable concentrations in most tissues after 24 hours. Low radioactive concentrations in rats were still detectable in the liver, ureter, ovary, and adrenal and lacrimal glands after 7 days.
Rapidly absorbed from the gastrointestinal tract; amount absorbed increase when isotretinoin is taken with food. Data suggest that isotretinoin and 4-oxo-isotretinoin may be reabsorbed from the bile.
The harmonic mean elimination for the simultaneous iv and oral administration of isotretinoin was approx 5.5 hr. The mean blood clearance, following iv admin, and the intrinsic clearance, following oral administration, were 5.19 and 6.63 ml/min/kg, respectively. The average abs bioavailability was approx 21% indicating an overall 1st-pass effect of approx 80%. Analysis of gut contents for total (14)-C activity suggested that a fraction of the isotretinoin dose was biologically or chemically degraded in the gut lumen prior to absorption. [Cotler S et al; DRUG METAB DISPOS 11 (5): 458-62 (1983)] PubMed Abstract
Clinical doses of isotretinoin range from 0.5 to 8 mg/kg/day, with acute side effects appearing following doses of 1 mg/kg/day or greater. Plasma concn of isotretinoin following single and multiple doses peak between 2 to 4 hr and exhibit elimination half-lives of 10 to 20 hr. Isotretinoin blood concn-time curves following a single- or multiple-dose regimen are well described by a linear model with biphasic disposition characteristics. ... In most conditions, the retinoids produce a maximal effect in about 8 weeks (at the highest tolerated dose), with a slow recurrence of symptoms usually occurring within several weeks following cessation of treatment - except in the treatment of cystic acne with isotretinoin. Maintenance or intermittent dosing usually results in a prolongation of remission. [Lucek RW, Colburn WA; Clin Pharmacokinet 10 (1): 38-62 (1985)] PubMed Abstract
A case study involving the disposition of 13-cis retinoic acid in embryonic tissues from a woman who unintentionally took 40 mg/day of isotretinoin from day 8-28 of gestation was discussed. When the pregnancy was terminated on day 31, between 72 and 80 hr after the last dose of isotretinoin, maternal serum samples were obtained. Retinoid concn in the maternal serum, embryonic tissue, and 6 samples of placental tissue were later measured by high performance liquid chromatography. The results showed that in humans, the intake of isotretinoin during pregnancy results in high placental and embryonic concn of all-trans-retoinic acid, in contrast to what was previously discovered in mice experiments. It was concluded that the metabolic activation of isotretinoin to the all-trans isomer could be responsible for the teratogenicity of isotretinoin.
Elimination: Biliary or feces: 83%; Renal: 65%.
Distribution of isotretinoin into human body tissues and fluids has not been fully characterized. Following oral administration of isotretinoin in animals, the drug is distributed into many tissues including liver, ureters, adrenals, ovaries, and lacrimal glands. Isotretinoin and its metabolites are distributed into bile in humans, principally as glucuronide conjugates; biliary concentration of the drug is proportional to hepatobiliary function and may be negligible in the presence of obstructive biliary disease. The drug has also been detected in synovial fluid. Unlike vitamin A, isotretinoin is not stored in the liver.
Isotretinoin and its metabolites are conjugated, possibly with glucuronic acid, before being excreted in urine and feces. Excretion of unchanged isotretinoin in urine appears to be negligible. Isotretinoin appears to be excreted in feces, mainly as unchanged drug. Limited data suggest that isotretinoin and its metabolites are excreted in feces via biliary elimination and that the drug and its metabolites also undergo enterohepatic circulation. In adults with normal renal and hepatic function, 65-85% of a single, radiolabeled 80 mg oral dose of isotretinoin is excreted in urine and feces in approximately equal proportions.

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