CAS 55079-83-9|CAS 54757-46-9|acitretin|Soriatane|Acitretin|(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid|Acitretin|9-(4-methoxy-2,3,6-trimethylphenyl)-3...

General Information

Structure

Molecular Formula

C₂₁H₂₆O₃

Molecular Mass

326.42934

Exact Mass

326.18819469

Charge

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

Canonic Smiles

COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C

Isomeric Smiles

c1c(c(c(c(c1C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC

Calculated Properties

JChem

LogD (pH = 7.4)

3.01

LogD (pH = 5.5)

4.78

Log P

5.59

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

4.77

Polar Surface Area

46.53

Polarizability

38.57

Molar Refractivity

104.17

LOG S

-6.88

Data Source

Names and Identifiers

IUPAC Traditional name

acitretin (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Synonyms

SoriataneAcitretinAcitretin9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acidNeotigason, Soriatane(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic AcidEtretinNeotigasonall-trans-acitretinAcitretinaAcitretineAcitretinumall-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acidacitretinEtretin(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid

IUPAC name

(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

API Name

Acitretin

Brand Name

NeotigasonSoriatane

International Nonproprietary Name (INN)

acitretin

Names and Identifiers

Registration numbers

MDL Number

MFCD00866632

EC Number

259-474-4

CAS Number

55079-83-954757-46-9

PubChem SID

2486831816203756613561028449836682

PubChem CID

5284513

DrugBank ID

DB00459

BKMS React Database

31766145043145956

BRENDA Ligand Database

31766145956145043

Wikipedia Title

Acitretin

MetaboLights Database

MTBLS2406MTBLS2145MTBLS1693

Reaxys Registry

15057225

ACToR Database

54757-46-955079-83-9

Beilstein Number

2458933

CHEBI ID

CHEBI:50173CHEBI:50172

CHEMBL

CHEMBL1131CHEMBL3186098

Reactom Database

Patent number

SureChEMBL Database

BRENDA Database

KEGG DRUG Database

LINCS Database

BindingDB Database

Drug Central Database

CompTox Database

DTXSID6022553

Registration numbers

Properties

Pharmacology Properties

Second generation retinoid

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1368

Research Area: Inflammation
Biological Activity:
Acitretin is a second generation retinoid. It is taken orally, and is typically used for psoriasis. It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t1/2=120 days), making dosing difficult. In contrast, acitretin’s half-life is approximately 2 days. [1]

Sigma Aldrich

44707

Biochem/physiol Actions
Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).

TRC

A189900

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

ChEBI

CHEBI:50172

A retinoid that consists of 3,7-dimethylnona-2,4,6,8-tetraenoic acid having a 4-methoxy-2,3,6-trimethylphenyl group attached at position 9.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Acitretin

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)

• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)

• Pilkington, T. et al., Drugs, 1992, 43, 597, (rev)

• Haenni, R. et al., Helv. Chim. Acta, 1977, 60, 2309, (synth, pmr, ms, metab)

• Coffey, J.W. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 705, (rev, isomers)

• Jakobsen, P. et al., J. Chromatogr., 1987, 415, 413, (hplc)

• Mayer, H. et al., Experientia, 1978, 34, 1105, (rev, pharmacol)

• Ward, A. et al., Drugs, 1983, 26, 9, (rev)

• Bestmann, H.J. et al., Annalen, 1984, 1740, (isoetretin)

• Paravicini, U. et al., Ann. N.Y. Acad. Sci., 1981, 359, 54, (rev, metab)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EMJ500; REP400

• Cunliffe, W.J., Biochem. Soc. Trans., 1986, 14, 943, (props)

• Bouvy, M.L. et al., Pharm. Weekbl., Sci. Ed., 1992, 14, 33, (Acitretin, rev, pharmacokinet)

• Ger. Pat., 1977, 2 636 879; CA, 87, 23565y, (synth, deriv)

• Englert, G. et al., Helv. Chim. Acta, 1978, 61, 2697, (pmr, isom)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 758

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

acitretin (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Synonyms

IUPAC name

(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

API Name

Acitretin

Brand Name

NeotigasonSoriatane

International Nonproprietary Name (INN)

acitretin

Registration numbers

MDL Number

MFCD00866632

EC Number

259-474-4

CAS Number

55079-83-954757-46-9

PubChem SID

2486831816203756613561028449836682

PubChem CID

5284513

DrugBank ID

DB00459

BKMS React Database

31766145043145956

BRENDA Ligand Database

31766145956145043

Wikipedia Title

Acitretin

MetaboLights Database

MTBLS2406MTBLS2145MTBLS1693

Reaxys Registry

15057225

ACToR Database

54757-46-955079-83-9

Beilstein Number

2458933

CHEBI ID

CHEBI:50173CHEBI:50172

CHEMBL

CHEMBL1131CHEMBL3186098

Reactom Database

Patent number

SureChEMBL Database

BRENDA Database

KEGG DRUG Database

LINCS Database

BindingDB Database

Drug Central Database

CompTox Database

DTXSID6022553

Molecule Details

Selleck Chemicals

S1368

Sigma Aldrich

44707

Biochem/physiol Actions
Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs).

TRC

A189900

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

ChEBI

CHEBI:50172

A retinoid that consists of 3,7-dimethylnona-2,4,6,8-tetraenoic acid having a 4-methoxy-2,3,6-trimethylphenyl group attached at position 9.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Acitretin

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)

• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)

• Pilkington, T. et al., Drugs, 1992, 43, 597, (rev)

• Haenni, R. et al., Helv. Chim. Acta, 1977, 60, 2309, (synth, pmr, ms, metab)

• Coffey, J.W. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 705, (rev, isomers)

• Jakobsen, P. et al., J. Chromatogr., 1987, 415, 413, (hplc)

• Mayer, H. et al., Experientia, 1978, 34, 1105, (rev, pharmacol)

• Ward, A. et al., Drugs, 1983, 26, 9, (rev)

• Bestmann, H.J. et al., Annalen, 1984, 1740, (isoetretin)

• Paravicini, U. et al., Ann. N.Y. Acad. Sci., 1981, 359, 54, (rev, metab)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EMJ500; REP400

• Cunliffe, W.J., Biochem. Soc. Trans., 1986, 14, 943, (props)

• Bouvy, M.L. et al., Pharm. Weekbl., Sci. Ed., 1992, 14, 33, (Acitretin, rev, pharmacokinet)

• Ger. Pat., 1977, 2 636 879; CA, 87, 23565y, (synth, deriv)

• Englert, G. et al., Helv. Chim. Acta, 1978, 61, 2697, (pmr, isom)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 758

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Second generation retinoid

Molecule

ID:72641