Accutane

Isotretinoin

Clinical data
Pronunciation	See note at tretinoin
Trade names	Various
AHFS/Drugs.com	Monograph
MedlinePlus	a681043
License data	US FDA: Isotretinoin
Pregnancy category	AU: X (High risk) US: X (Contraindicated)
Routes of administration	By mouth, topical
ATC code	D10AD04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Variable
Protein binding	99.9%
Metabolism	Hepatic
Biological half-life	10–20 hours
Excretion	Renal and fecal
Identifiers
IUPAC name (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
CAS Number	4759-48-2 Y
PubChem CID	5282379
IUPHAR/BPS	7600
DrugBank	DB00982 Y
ChemSpider	4445539 Y
UNII	EH28UP18IF
KEGG	D00348 Y
ChEBI	CHEBI:6067 Y
ChEMBL	CHEMBL547 Y
ECHA InfoCard	100.022.996
Chemical and physical data
Formula	C20H28O2
Molar mass	300.44 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)\C=C(/C=C/C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C
InChI InChI=1S/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- Y Key:SHGAZHPCJJPHSC-XFYACQKRSA-N Y

Isotretinoin (INN), also known as 13-cis-retinoic acid, is an oral pharmaceutical drug primarily used to treat severe nodular acne. Rarely, 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.

Isotretinoin is primarily used as a treatment for severe acne. The most common adverse effects are a transient worsening of acne (lasting 2–3 weeks), 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 which controls normal embryonic development.

In the United States, a special procedure is required to obtain the pharmaceutical. In most other countries, a consent form is required which explains these risks. Women taking isotretinoin must not get pregnant during and for 1 month after isotretinoin therapy. Sexual abstinence or effective contraception is mandatory during this period. Barrier methods by themselves (e.g., condoms) are not considered adequate due to the unacceptable failure rates of approximately 3%. Women who fall pregnant whilst on isotretinoin therapy are generally counselled to have a termination. Isotretinoin has no effect on male reproduction.