Isotretinoin
Isotretinoin, also known as 13-cis-retinoic acid and sold under the brand name Accutane among others, is a medication primarily used to treat severe acne. It is also used to prevent certain skin cancers (squamous-cell carcinoma), and in the treatment of other cancers. It is used to treat harlequin-type ichthyosis, a usually lethal skin disease, and lamellar ichthyosis. It is a retinoid, meaning it is related to vitamin A, and is found in small quantities naturally in the body. Its isomer, tretinoin, is also an acne drug.
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Pronunciation | See note at tretinoin |
Trade names | Accutane, Roaccutane, others |
AHFS/Drugs.com | Monograph |
MedlinePlus | a681043 |
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Routes of administration | By mouth, topical |
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Bioavailability | Variable |
Protein binding | 99.9% |
Metabolism | Liver |
Elimination half-life | 10–20 hours |
Excretion | Kidney and feces |
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ECHA InfoCard | 100.022.996 |
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Formula | C20H28O2 |
Molar mass | 300.442 g·mol−1 |
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The most common adverse effects are dry lips (cheilitis), dry and fragile skin, and an increased susceptibility to sunburn. Uncommon and rare side effects include muscle aches and pains (myalgias), and headaches. Isotretinoin is known to cause birth defects due to in-utero exposure because of the molecule's close resemblance to retinoic acid, a natural vitamin A derivative that controls normal embryonic development. It is also associated with psychiatric side effects, most commonly depression but also, more rarely, psychosis and unusual behaviours. Other rare side effects include hyperostosis and premature epiphyseal closure, which have been reported to be persistent.
Isotretinoin was patented in 1969 and approved for medical use in 1982. In 2021, it was the 264th most commonly prescribed medication in the United States, with more than 1 million prescriptions.