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55079-83-9 molecular structure
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(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

ChemBase ID: 342
Molecular Formular: C21H26O3
Molecular Mass: 326.42934
Monoisotopic Mass: 326.18819469
SMILES and InChIs

SMILES:
O(c1c(c(c(c(c1)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C)C)C
Canonical SMILES:
COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
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-UGOGCBOOSA-N

Cite this record

CBID:342 http://www.chembase.cn/molecule-342.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
IUPAC Traditional name
acetretin
Brand Name
Acetretin
Soriatane
Synonyms
Acitretin
9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid, 13-cis-Etretin, Isoacitretin, Isoetretin, Ro 13-7652
13-cis Acitretin
CAS Number
55079-83-9
69427-46-9
PubChem SID
160963805
PubChem CID
6437841

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
A189925 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.011076  H Acceptors
H Donor LogD (pH = 5.5) 4.976502 
LogD (pH = 7.4) 3.2266924  Log P 5.5870485 
Molar Refractivity 104.1665 cm3 Polarizability 38.030373 Å3
Polar Surface Area 46.53 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 5.2  LOG S -5.83 
Solubility (Water) 4.78e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.0729 mg/L expand Show data source
Acetone expand Show data source
Chloroform expand Show data source
Dichloromethane expand Show data source
Ethyl Acetate, expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
190-193°C expand Show data source
Hydrophobicity(logP)
5.7 expand Show data source
Storage Condition
Amber Vial, -80°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00459 external link
Item Information
Drug Groups approved
Description An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of etretinate with the advantage of a much shorter half-life when compared with etretinate. [PubChem]
Indication For the treatment of severe psoriasis in adults.
Pharmacology Acitretin is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.
Toxicity Oral, rat: LD50 = >4000 mg/kg. Symptoms of overdose include headache and vertigo.
Affected Organisms
Humans and other mammals
Biotransformation Following oral absorption, acitretin undergoes extensive metabolism and interconversion by simple isomerization to its 13-cis form (cis-acitretin). Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted.
Absorption Oral absorption of acitretin is optimal when given with food, and is linear and proportional with increasing doses from 25 to 100 mg. Approximately 72% (range 47% to 109%) of the administered dose was absorbed after a single 50 mg dose of acitretin was given to 12 healthy subjects.
Half Life 49 hours (range 33 to 96 hours)
Protein Binding Over 99.9% bound to plasma proteins, primarily albumin.
Elimination Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted. The chain-shortened metabolites and conjugates of acitretin and cis-acitretin are ultimately excreted in the feces (34% to 54%) and urine (16% to 53%).
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - A189925 external link
A synthetic retinoid which is the major metabolite of etretinate (E938000).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
  • • Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)
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PATENTS

PATENTS

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INTERNET

INTERNET

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