Acitretin

HCID 5284513CAS 54757-46-9

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Basic information

Standard SMILES
COc1cc(C)c(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)c(C)c1C
InChIKey
IHUNBGSDBOWDMA-AQFIFDHZSA-N
Molecular formula
C21H26O3
Average molar mass
326.436 g/mol
Monoisotopic mass
326.18819469

Names & identifiers

Preferred name
Acitretin
IUPAC
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
English name
Acitretin
Molecular formula
C21H26O3
Molecular weight
326.43

Names & synonyms

AcetretinetretinAcitrenAcitretiSORIATANEACITRETINro10-1670NEOTIGASONAcritretinAcitretin A

Database identifiers

CAS
54757-46-9、55079-83-9
PubChem CID
5284513
DTXSID
DTXSID6022553
ChEMBL
CHEMBL1131
ChEBI
CHEBI:50173
UNII
LCH760E9T7
EC Number
259-474-4
Nikkaji
J23.289K

Properties

Physicochemical properties

Melting point
228 · 228-230°C
Boiling point
404.46 °C · 404.46°C (rough estimate)
Density
1.1348 · 1.1348 (rough estimate)
refractive index
1.47 · 1.4700 (estimate)
storage temp.
-20 °C · -20°C
solubility
Practically insoluble in water, sparingly soluble in tetrahydrofuran, slightly soluble in acetone and in ethanol (96 per cent), very slightly soluble in cyclohexane.

Safety & regulation

Safety data

F
8-10-21
PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
RA8460000
ridadr
UN 3077 9/PG 3
hs_code
2918992090

Chemistry & industry

Applications · 5 items

DescriptionAcitretin is the free acid form of etretinate useful in the treatment of severe psoriasis and other disorders of keratinization. Although the two compounds have virtually the same efficacy and teratogenic side-effects, acitretin is advantageous for child-bearing women, as its shorter half-life reduces the necessary contraception period from two years to only one month after treatment ceases.

UsesA synthetic retinoid which is the major metabolite of etretinate (E938000).

Usesantipsoriatic;binds to nuclear receptors that regulate gene transcription

UsesAcitretin, a retinoid that binds to nuclear receptors and regulates gene expression, is a potent activator of the α-secretase ADAM10 gene expression and apoptosis inducer via the CD95 signalling pathway. Acitretin is a systemic retinoid drug used in the treatment of severe psoriasis.

General DescriptionPharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Acitretin is a major metabolite of etretinate and belongs to the class of retinoid and is typically used for treating psoriasis. Acitretin inhibits excessive cell growth and keratinisation which are the major symptoms of psoriasis, therefore reducing plaque formation and scaling.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]

Additional notes

DefinitionChEBI: All-trans-acitretin is an acitretin, a retinoid and an alpha,beta-unsaturated monocarboxylic acid. It has a role as a keratolytic drug.

Related reactions

4 records

Linked notes

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