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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
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.
- pka
- 4.72 · 4.72±0.33(Predicted)
- form
- powder
- color
- Light yellow to yellow
- λmax
- 352 nm · 352nm(MeOH)(lit.)
- Merck
- 14 · 14,112
- Stability
- LIGHT SENSITIVE
- InChI
- InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
- InChIKey
- IHUNBGSDBOWDMA-AQFIFDHZSA-N
- SMILES
- C(O)(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C=C(OC)C(C)=C1C
- CAS DataBase Reference
- 55079 · 55079-83-9(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- acitretin
- FDA UNII
- 760 E9T7 · LCH760E9T7
- NCI Drug Dictionary
- acitretin
- ATC code
- 5 BB02 · D05BB02
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
- Protein binding
- 99 · >99 (< 0.1% present as unbound drug in pooled human plasma)
- Excreted unchanged in urine
- Excreted as metabolites.%
- Volume of distribution
- 9 · 9(L/kg)
- Biological half-life
- 50 · 50 / -
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 315 · H315-H319-H360-H410
- Precautionary statements
- 201 · P201-P273-P302+P352-P305+P351+P338-P308+P313
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T,N
- Risk Statements
- 61 · 61-36/38-50/53
- Safety Statements
- 53 · 53-26-45-60-61-37/39
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 8460000 · RA8460000
- F
- 8 · 8-10-21
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 2918992090 · 2918992090
- Storage Class
- 6.1 C · 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Repr. 1BSkin Irrit. 2
- Hazardous Substances Data
- 55079 · 55079-83-9(Hazardous Substances Data)
- Toxicity
- 50 i.p · LD50 i.p. in mice (mg/kg): >4000 (1 day), 700 (10 days), 700 (20 days) (Bollag, 1978)
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
- Toxicity
- LD50 i.p. in mice (mg/kg): >4000 (1 day), 700 (10 days), 700 (20 days) (Bollag, 1978)
- risk_code
- 61-36/38-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- T,N
- safety_code
- 53-26-45-60-61-37/39
- hazard_class
- 9
- Storage Class
- 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H315-H319-H360-H410
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Repr. 1BSkin Irrit. 2
- Precautionary statements
- P201-P273-P302+P352-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 55079-83-9(Hazardous Substances Data)
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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
Linked notes
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