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Substance Name: Tretinoin [USAN:USP:INN:BAN]
RN: 302-79-4
UNII: 5688UTC01R
InChIKey: SHGAZHPCJJPHSC-YCNIQYBTSA-N

Note

  • An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).

Molecular Formula

  • C20-H28-O2

Molecular Weight

  • 300.439
 

Classification Codes

  • Antineoplastic Agents
  • Dermatologic Agents
  • Drug / Therapeutic Agent
  • Keratolytic
  • Keratolytic Agents
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Names and Synonyms

Name of Substance

  • Retinoic acid
  • trans-Retinoic acid
  • Tretinoin
  • Tretinoin [USAN:USP:INN:BAN]

MeSH Heading

  • Tretinoin

Synonyms

  • 15-Apo-beta-caroten-15-oic acid
  • 2,4,6,8-Nonatetraenoic acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-
  • 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid
  • 3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid
  • 4-09-00-02387 (Beilstein Handbook Reference)
  • A-Acido (Argentina)
  • A-Vitaminsyre
  • A-Vitaminsyre [Denmark]
  • Aberel
  • Aberela
  • Aberela [Norway]
  • Acid A Vit (Belgium, Netherlands)
  • Acnavit
  • Acnavit [Denmark]
  • Airol
  • Aknefug
  • Aknoten
  • all-trans Retinoic acid
  • all-trans-Retinoic acid
  • all-trans-Vitamin A acid
  • all-trans-Vitamin A1 acid
  • Alltrans-retinoic acid
  • ATRA
  • Atralin
  • Avita
  • Avitoin
  • Avitoin [Norway]
  • beta-RA
  • Betarretin
  • BRN 2057223
  • CCRIS 3294
  • Cordes vas
  • Cordes VAS [Germany]
  • Dermairol
  • Effederm
  • Effederm [France]
  • EINECS 206-129-0
  • Epi-aberel
  • Eudyna
  • HSDB 2169
  • NSC 122758
  • NSC-122758
  • Refissa
  • Renova
  • Retin-A
  • Retin-A Micro
  • Retinoic acid
  • Retinoic acid, all-trans-
  • Ro 1-5488
  • Tretinoin
  • Tretinoina
  • Tretinoina [INN-Spanish]
  • Tretinoine
  • Tretinoine [INN-French]
  • Tretinoino
  • Tretinoino [INN-Spanish]
  • Tretinoinum
  • Tretinoinum [INN-Latin]
  • UNII-5688UTC01R
  • Vesanoid
  • Vitamin A acid
  • Vitamin A acid, all-trans-
  • Vitamin a acid, trans-
  • Vitamin A1 acid, all-trans-

Systematic Names

  • Retinoic acid
  • Retinoic acid, all-trans-
  • Tretinoin

Superlist Name

  • all-trans-Retinoic acid

Mixture Name

  • Solage

Registry Numbers

CAS Registry Number

  • 302-79-4

FDA UNII

  • 5688UTC01R

Other Registry Numbers

  • 187175-63-9
  • 56573-65-0
  • 7005-78-9

Related Registry Number

  • 13497-05-7 (hydrochloride salt)

System Generated Number

  • 0000302794

Structure Descriptors

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-YCNIQYBTSA-N

Smiles

C=1(C(CCCC1C)(C)C)\C=C\C(=C\C=C\C(=C\C(O)=O)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 208mg/kg (208mg/kg)   Drugs in Japan Vol. -, Pg. 886, 1995.
mouse LD50 intravenous 92mg/kg (92mg/kg)   United States Patent Document. Vol. #3878202,
mouse LD50 oral 1100mg/kg (1100mg/kg)   American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
mouse LD50 subcutaneous 253mg/kg (253mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
mouse LD50 subcutaneous 253mg/kg (253mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SLEEP
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat LD50 intraperitoneal 96mg/kg (96mg/kg) BLOOD: NORMOCYTIC ANEMIA

BEHAVIORAL: ATAXIA

SPINAL CORD: OTHER DEGENERATIVE CHANGES
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat LD50 intravenous 75mg/kg (75mg/kg)   Drugs in Japan Vol. -, Pg. 886, 1995.
rat LD50 oral 2gm/kg (2000mg/kg)   American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
rat LD50 subcutaneous 53mg/kg (53mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 181 deg C   EXP
log P (octanol-water) 6.3 (none)   EXP
Water Solubility 0.126 mg/L 25 EST
Vapor Pressure 2.42E-07 mm Hg 25 EST
Henry's Law Constant 9.50E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.93E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.