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Substance Name: Isotretinoin [USAN:USP:INN:BAN]
RN: 4759-48-2
UNII: EH28UP18IF
InChIKey: SHGAZHPCJJPHSC-XFYACQKRSA-N

Note

  • A topical dermatologic agent that is used in the treatment of ACNE VULGARIS and several other skin diseases. The drug has teratogenic and other adverse effects.

Molecular Formula

  • C20-H28-O2

Molecular Weight

  • 300.439
 

Classification Codes

  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Keratolytic
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Teratogens

Names and Synonyms

Name of Substance

  • 13-cis-Retinoic acid
  • Isotretinoin
  • Isotretinoin [USAN:USP:INN:BAN]

MeSH Heading

  • Isotretinoin

Synonyms

  • 13-cis-Retinoic acid
  • 13-cis-Vitamin A acid
  • 13-RA
  • 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid
  • 4-09-00-02388 (Beilstein Handbook Reference)
  • Absorica
  • Accutane
  • Amnesteem
  • BRN 1885770
  • CCRIS 4286
  • Claravis
  • EINECS 225-296-0
  • HSDB 3929
  • Isosuprea Lidose
  • Isotane
  • Isotretinoin
  • Isotretinoine
  • Isotretinoine [INN-French]
  • Isotretinoino
  • Isotretinoino [INN-Spanish]
  • Isotretinoinum
  • Isotretinoinum [INN-Latin]
  • Isotrex
  • Myorisan
  • Neovitamin A acid
  • Ro 4-3780
  • Ro-4-3780
  • Roaccutane
  • Sotret
  • Teriosal
  • UNII-EH28UP18IF
  • Zenatane

Systematic Names

  • Isotretinoin
  • Retinoic acid, 13-cis-

Superlist Names

  • Isotretinoin
  • Retinoic acid

Registry Numbers

CAS Registry Number

  • 4759-48-2

FDA UNII

  • EH28UP18IF

System Generated Number

  • 0004759482

Structure Descriptors

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-

InChIKey

SHGAZHPCJJPHSC-XFYACQKRSA-N

Smiles

C\C(=C\C(=O)O)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 30mg/kg/21W (30mg/kg) MUSCULOSKELETAL: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): NAILS: OTHER		 American Journal of Diseases of Children. Vol. 142, Pg. 316, 1988.
child TDLo oral 360mg/kg/26W- (360mg/kg) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER CUTIS; Cutaneous Medicine for the Practitioner. Vol. 38, Pg. 275, 1986.
man TDLo oral 24mg/kg/4W-I (24mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: OTHER CHANGES		 Gastroenterology. Vol. 93, Pg. 606, 1987.
man TDLo oral 37mg/kg/5W-I (37mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE"

IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE		 Archives of Dermatology. Vol. 122, Pg. 815, 1986.
man TDLo unreported 21mg/kg/3W-I (21mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 290, Pg. 820, 1985.
mouse LD50 intraperitoneal 138mg/kg (138mg/kg)   "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984.
mouse LD50 oral 3389mg/kg (3389mg/kg)   "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984.
rabbit LD50 oral 1960mg/kg (1960mg/kg)   "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984.
rat LD50 intraperitoneal 901mg/kg (901mg/kg)   Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.
rat LD50 oral > 4gm/kg (4000mg/kg)   Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.
women TDLo oral 56mg/kg/8W-I (56mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" CUTIS; Cutaneous Medicine for the Practitioner. Vol. 37, Pg. 115, 1986.