isotretinoin
Also known as Ro-43780, 13-RA, cis-RA, (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid, 13-cis-vitamin A acid, (7e,9e,11e,13Z)-retinoic acid, 13-cis-retinoic acid, cis-retinoic acid
Isotretinoin, also known as '13-cis-retinoic acid and sold under the brand name Accutane' among others, is a medication used to treat skin diseases like harlequin-type ichthyosis, lamellar ichthyosis, and severe cystic acne or moderate acne that is unresponsive to antibiotics. Isotretinoin is used off-label to treat basal cell carcinoma and squamous cell carcinoma, although clinical evidence suggests it is not effective in this setting. 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. In i
Chemical data
- Formula
- C20H28O2
- Molecular weight
- 300.4 g/mol
- IUPAC name
- (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
- SMILES
- CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
- InChIKey
- SHGAZHPCJJPHSC-XFYACQKRSA-N
- XLogP
- 6.3
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Article
20 sectionsContents
- Medical uses
- Prescribing restrictions
- Adverse effects
- Possible permanent effects
- Sexual
- Skin
- Teratogenicity
- Psychological effects
- Depression and suicidality
- Psychosis
- Musculoskeletal
- Gastrointestinal
- Eyes
- Pharmacology
- Mechanism of action
- CNS activities
- Pharmacokinetics and pharmacodynamics
- History
- Brands
- References
Isotretinoin, also known as '13-cis-retinoic acid and sold under the brand name Accutane' among others, is a medication used to treat skin diseases like harlequin-type ichthyosis, lamellar ichthyosis, and severe cystic acne or moderate acne that is unresponsive to antibiotics. Isotretinoin is used off-label to treat basal cell carcinoma and squamous cell carcinoma, although clinical evidence suggests it is not effective in this setting. 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. In its pure form, isotretinoin is an orange powder.
The most common adverse effects are dry lips (cheilitis), dry and fragile skin (xeroderma), dry eyes and an increased susceptibility to sunburn. Uncommon and rare side effects include muscle aches and pains (myalgias), and headaches, the drug is known to cause depression in some users. Some of those side effects can persist long after the discontinuation of the use of the drug. Isotretinoin may cause liver failure, therefore the patient's blood levels should be regularly tested. It 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 associated with psychiatric side effects, most commonly depression, and more rarely, psychosis and unusual behaviors. Other rare side effects include hyperostosis and premature epiphyseal closure, which have been reported to be persistent.