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Isotretinoin information


Isotretinoin
Clinical data
PronunciationSee note at tretinoin
Trade namesAccutane, Roaccutane, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa681043
License data
  • US DailyMed: Isotretinoin
Pregnancy
category
  • AU: X (High risk)
Routes of
administration
By mouth, topical
ATC code
  • D10AD04 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • BR: Class C2 (Retinoids)[4]
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only
  • EU: Rx-only[5]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVariable
Protein binding99.9%
MetabolismLiver
Elimination half-life10–20 hours
ExcretionKidney and feces
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 checkY
PubChem CID
  • 5282379
IUPHAR/BPS
  • 7600
DrugBank
  • DB00982 checkY
ChemSpider
  • 4445539 checkY
UNII
  • EH28UP18IF
KEGG
  • D00348 checkY
ChEBI
  • CHEBI:6067 checkY
ChEMBL
  • ChEMBL547 checkY
CompTox Dashboard (EPA)
  • DTXSID4023177 Edit this at Wikidata
ECHA InfoCard100.022.996 Edit this at Wikidata
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
  • 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- checkY
  • Key:SHGAZHPCJJPHSC-XFYACQKRSA-N checkY
  (verify)

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.

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.[6] In 2021, it was the 264th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7][8]

  1. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ "Product. Roaccutane PI". guildlink.com.au.
  4. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  5. ^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. 1 December 2022. Retrieved 25 December 2022.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 476. ISBN 978-3-527-60749-5.
  7. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  8. ^ "Isotretinoin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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help prevent acne in women. Medical professionals typically reserve isotretinoin pills for severe acne, due to greater potential side effects. Early and...

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months. Isotretinoin is a known teratogen, with an estimated 20‑35% risk of physical birth defects to infants that are exposed to isotretinoin in utero...

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pimples. Prescription medications used to treat acne and pimples include isotretinoin, which is a retinoid, anti-seborrheic medications, anti-androgen medications...

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Rosacea

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with tentative benefit include brimonidine cream, ivermectin cream, and isotretinoin. Dermabrasion or laser surgery may also be used. The use of sunscreen...

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mediates the high teratogenicity of retinoid pharmaceuticals, such as isotretinoin (13-cis-retinoic acid) used for treatment of cancer and acne. Oral megadoses...

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absolutely contraindicated in pregnancy; examples include thalidomide and isotretinoin. Relative contraindications are contraindications for circumstances in...

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Acne miliaris necrotica

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Erythromycin 2% gel 1% hydrocortisone cream Doxycycline 50 mg twice daily Isotretinoin 0.5 mg/kg daily The condition affects all ages.[citation needed] The...

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IPLEDGE program

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dispense isotretinoin. Isotretinoin carries a high risk of causing severe birth defects if taken during pregnancy (see Teratogenicity of isotretinoin) and...

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D10AD04 Isotretinoin D10AD05 Motretinide D10AD06 Trifarotene D10AD51 Tretinoin, combinations D10AD53 Adapalene, combinations D10AD54 Isotretinoin, combinations...

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desloratadine is in the treatment of acne, as an inexpensive adjuvant to isotretinoin and possibly as maintenance therapy or monotherapy. The most common side-effects...

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2002 Tampa Cessna 172 crash

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claiming that psychological side effects from isotretinoin caused the incident. Bishop used isotretinoin, which is known to induce depression and rarely...

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Photophobia

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optic nerve hypoplasia Hydrophthalmos, or congenital glaucoma Iritis Isotretinoin has been associated with photophobia Optic neuritis Pigment dispersion...

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Tretinoin

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given that tretinoin is the all-trans isomer of retinoic acid. The name isotretinoin is the same root tretinoin plus the prefix iso-. Regarding pronunciation...

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liver failure. Isotretinoin — when all topical treatments or antibiotics against acne have failed, many dermatologists resort to isotretinoin, which is an...

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Hidradenitis suppurativa

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medication approved by the FDA for the treatment of HS as of 2021. Topical isotretinoin is usually ineffective in people with HS, and is more commonly known...

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Photodermatitis

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tetracycline, doxycycline, minocycline) Benzoyl peroxide Retinoids (e.g., isotretinoin) Some NSAIDs (e.g., ibuprofen, naproxen sodium) Fluoroquinolone antibiotic:...

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instruments or cauterized with a device that uses light. The acne drug isotretinoin can cause severe flare-ups of macrocomedones, so dermatologists recommend...

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ciclosporin, azathioprine or mycophenolate mofetil, cyclophosphamide, Isotretinoin and steroids in these patients. There are persisting uncertainties, due...

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Tazarotene

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Meibomian gland

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dysfunction may be caused by some prescription medications, notably isotretinoin. A blocked meibomian gland can cause a chalazion (or "meibomian cyst")...

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