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Isotretinoin Basic information |
Product Name: | Isotretinoin |
Synonyms: | RETINOIC ACID, 13-CIS-;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid;3,7-DIMETHYL-9-(2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-2Z,4E,6E,8E-NONATETRANENOIC ACID;13-CIS-RETINOIC ACID;13-cis-vitamin a acid;(L)-ISOTRETINOIN;ISOTRETINOIN;Lsotretinoin |
CAS: | 4759-48-2 |
MF: | C20H28O2 |
MW: | 300.44 |
EINECS: | 225-296-0 |
Product Categories: | Antibiotics;Organic acids;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;-;API;BUSPAR;Other APIs;intermediates |
Mol File: | 4759-48-2.mol |
|
Isotretinoin Chemical Properties |
Melting point | 172-175 °C(lit.) |
Boiling point | 381.66°C (rough estimate) |
density | 1.0597 (rough estimate) |
refractive index | 1.4800 (estimate) |
storage temp. | −20°C |
solubility | Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent). It is sensitive to air, heat and light, especially in solution. Carry out all operations as rapidly as possible and avoid exposure to actinic light; use freshly prepared solutions. |
form | Fine Crystalline Powder |
color | Yellow-orange to orange |
Water Solubility | insoluble |
λmax | 354nm(EtOH)(lit.) |
Merck | 14,5228 |
Stability: | Stable, but probably air and light sensitive. Combustible. Incompatible with strong oxidizing agents. |
CAS DataBase Reference | 4759-48-2(CAS DataBase Reference) |
EPA Substance Registry System | Retinoic acid, 13-cis-(4759-48-2) |
Safety Information |
Hazard Codes | T |
Risk Statements | 61-36/37/38-20/21/22 |
Safety Statements | 53-26-36/37/39-45-37/39 |
WGK Germany | 3 |
RTECS | VH6440000 |
TSCA | Yes |
HS Code | 29362100 |
Hazardous Substances Data | 4759-48-2(Hazardous Substances Data) |
Toxicity | LD50 (20 day) in mice, rats (mg/kg): 904, 901 i.p.; 3389, >4000 orally (Kamm) |
Uses | Vitamin A class drugs. It can rapidly and strongly inhibit the cell proliferation and differentiation process of skin glands cells. It has a high effect on severe nodular cystic acne. This product has a high gastrointestinal absorption, but invalid for topical administration. It is used for treating severe acnes which cannot be treated by other drugs. It also has some effects on treating cystic acne, the party of acne, rosacea, ichthyosis, follicular keratosis and pityriasis red hair and other skin diseases. |
Production methods |
β-ionone and ethyl chloride are first reacted together after which the product is further reacted with triphenylphosphine to obtain Triphenyl salt. The Triphenyl salt is further reacted with cyclopentenone derivative to produce isotretinoin and its 8Z isomer. Separate out the 8Z isomer and convert it to isotretinoin through isomerization with the help of nitric acid. |
Chemical Properties | Yellow-Orange Crystalline Powder |
Uses | 5HT1a receptor agonist, anxiolytic |
Uses | isotretinoin is a retinoid derivative with improved bioavailability and percutaneous absorption for acne treatment products. |
Uses | Used as a treatment for severe acne. Presently being studied in conjuction with the treatment of photoaged skin. |
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