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]
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]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Hypertriglyceridaemia Not Available RARA OT192V9V [4]
Hypertriglyceridaemia Not Available RXRA OTP1TBDM [4]
Lipid metabolism disorders Not Available PRDX4 OTT4OR8G [4]
Lipid metabolism disorders Not Available LPL OTTW0267 [4]
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
CHEBI:4913
CAS Number
54350-48-0
DrugBank ID
DB00926
TTD ID
D0B1IP
INTEDE ID
DR0672

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 [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [6]
14-3-3 protein theta OTWG7F3H 1433T_HUMAN Gene/Protein Processing [6]
14-3-3 protein zeta/delta OT2TKG9P 1433Z_HUMAN Gene/Protein Processing [6]
17-beta-hydroxysteroid dehydrogenase type 2 (HSD17B2) OT3K7HY5 DHB2_HUMAN Regulation of Drug Effects [7]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [6]
Actin, cytoplasmic 1 (ACTB) OT1MCP2F ACTB_HUMAN Gene/Protein Processing [6]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Gene/Protein Processing [6]
ATP synthase subunit beta, mitochondrial (ATP5F1B) OTLFZUQK ATPB_HUMAN Gene/Protein Processing [6]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [8]
Beta-actin-like protein 2 (ACTBL2) OTD6B81U ACTBL_HUMAN Gene/Protein Processing [6]
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 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5 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.
6 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.
7 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.
8 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.