Mr. Ibrahem/Isotretinoin
Clinical data
PronunciationSee note at tretinoin
Trade namesAccutane, Roaccutane, others[1]
Other names13-cis-retinoic acid
AHFS/Drugs.comMonograph
MedlinePlusa681043
License data
Pregnancy
category
  • AU: X (High risk)
Routes of
administration
By mouth, topical
Drug classRetinoid[2]
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVariable
Protein binding99.9%
MetabolismLiver
Elimination half-life10–20 hours
ExcretionKidney and fecal
Identifiers
  • (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
  • O=C(O)\C=C(/C=C/C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C
  • 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- checkY
  • Key:SHGAZHPCJJPHSC-XFYACQKRSA-N checkY
  (verify)

Isotretinoin, sold under the brand name Accutane among others, is a medication primarily used to treat severe acne.[2] Specifically it is used for acne that is nodular and has not improved with other treatments.[2] Other uses include psoriasis, ichthyosis, and certain cancers.[2] It is taken by mouth or applied to the skin.[2][3]

Common side effects include inflammed lips, high blood triglycerides, joint pain, and muscle pain.[2] Other side effects may include sexual problems, increased susceptibility to sunburn, hair loss, and mental health problems.[3] Isotretinoin is known to cause birth defects and effective birth control is required starting a month before beginning treatment.[3] It is a retinoid, meaning it is related to vitamin A and tretinoin.[2] It is believed to work via altering sebaceous gland function.[2]

It was patented in 1969 and approved for medical use in 1982.[4] While it remains avaliable under a number of generic names the original brand name was discontinued in 2009 due to a combination of low sales and multiple lawsuits over side effects.[5] In the United States and United Kingdom special programs are in place to decrease the risk of women becoming pregnant while using the medication.[2][3] In the United Kingdom 20 mg per day for a month costs the NHS about 17 pounds.[3]

References edit

  1. ^ "Isotretinoin international brands". Drugs.com. Retrieved 1 June 2017.
  2. ^ a b c d e f g h i j k "Isotretinoin Monograph for Professionals". Drugs.com. Retrieved 5 October 2020.
  3. ^ a b c d e BNF 79. London: Pharmaceutical Press. March 2020. p. 1308. ISBN 978-0857113658.
  4. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 476. ISBN 978-3-527-60749-5.
  5. ^ DeNoon, Daniel J. "Acne Drug Accutane No Longer Sold". WebMD. Retrieved 5 October 2020.