Details of the Drug

General Information of Drug (ID: DM2CZFA)

Drug Name
Etretinate
Synonyms
etretinate; 54350-48-0; Tegison; Ethyl etrinoate; Retinoid; Etretinatum; Etretinato; Ro 10-9359; Etretinatum [INN-Latin]; Etretinato [INN-Spanish]; UNII-65M2UDR9AG; CCRIS 3615; HSDB 7185; EINECS 259-119-3; NSC 297936; 65M2UDR9AG; Ro-10-9359; Tigason; CHEBI:4913; C23H30O3; Ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate; Ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate; 3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonanetetraenoic acid ethy
Indication
Disease Entry ICD 11 Status REF
Keratosis ED56 Approved [1]
Affected Organisms
Humans and other mammals
ATC Code
D05BB01: Etretinate
D05BB: Retinoids for treatment of psoriasis
D05B: ANTIPSORIATICS FOR SYSTEMIC USE
D05: ANTIPSORIATICS
D: DERMATOLOGICALS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 354.5
Logarithm of the Partition Coefficient (xlogp) 6.8
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 120 days [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 4.23139 micromolar/kg/day [3]
Chemical Identifiers
Formula
C23H30O3
IUPAC Name
ethyl (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
Canonical SMILES
CCOC(=O)/C=C(\\C)/C=C/C=C(\\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
InChI
InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
InChIKey
HQMNCQVAMBCHCO-DJRRULDNSA-N
Cross-matching ID
PubChem CID
5282375
ChEBI ID
CHEMBL464
CAS Number
54350-48-0
UNII
65M2UDR9AG
DrugBank ID
DB00926
TTD ID
D0B1IP
INTEDE ID
DR0672
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Retinoic acid 4-hydroxylase 26B1 (CYP26B1)
Main DME 		DEZT8FM CP26B_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [5]
14-3-3 protein theta OTWG7F3H 1433T_HUMAN Gene/Protein Processing [5]
14-3-3 protein zeta/delta OT2TKG9P 1433Z_HUMAN Gene/Protein Processing [5]
17-beta-hydroxysteroid dehydrogenase type 2 (HSD17B2) OT3K7HY5 DHB2_HUMAN Regulation of Drug Effects [6]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [5]
Actin, cytoplasmic 1 (ACTB) OT1MCP2F ACTB_HUMAN Gene/Protein Processing [5]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Gene/Protein Processing [5]
ATP synthase subunit beta, mitochondrial (ATP5F1B) OTLFZUQK ATPB_HUMAN Gene/Protein Processing [5]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [7]
Beta-actin-like protein 2 (ACTBL2) OTD6B81U ACTBL_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7599).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Lipopolysaccharide opposes the induction of CYP26A1 and CYP26B1 gene expression by retinoic acid in the rat liver in vivo. Am J Physiol Gastrointest Liver Physiol. 2007 Apr;292(4):G1029-36.
5 Consequences of the natural retinoid/retinoid X receptor ligands action in human breast cancer MDA-MB-231 cell line: Focus on functional proteomics. Toxicol Lett. 2017 Nov 5;281:26-34. doi: 10.1016/j.toxlet.2017.09.001. Epub 2017 Sep 5.
6 Transgenic male mice expressing human hydroxysteroid dehydrogenase 2 indicate a role for the enzyme independent of its action on sex steroids. Endocrinology. 2007 Aug;148(8):3827-36. doi: 10.1210/en.2007-0365. Epub 2007 May 17.
7 Bexarotene activates the p53/p73 pathway in human cutaneous T-cell lymphoma. Br J Dermatol. 2009 Mar;160(3):519-26. doi: 10.1111/j.1365-2133.2008.08931.x. Epub 2008 Nov 25.