Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1859)
Drug Name
Desmethylastemizole
Synonyms
Demethylastemizole; Desmethylasteizole; Desmethylastemizole; L460QHM1YN; LAGYWHSFHIMTPE-UHFFFAOYSA-N; O-Demethylastemizole; O-Desmethyl Astemizole; R 44 271; R 44271; R-44-271; SCHEMBL1152697; ZINC13537287; 4-[2-[4-[[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]phenol; 73736-50-2; AC1L4F06; AKOS030240026; BDBM50131433; CHEMBL60796; CTK8G2140; DTXSID10224058; FT-0666079; Phenol, 4-(2-(4-((1-((4-fluorophenyl)methyl)-1H-benzimidazol-2-yl)amino)-1-piperidinyl)ethyl)-; UNII-L460QHM1YN
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 444.5 Topological Polar Surface Area 53.3
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
155805
PubChem SID
10252754 ; 11538011 ; 15379663 ; 46231728 ; 50164560 ; 57348207 ; 96099814 ; 103247839 ; 104022591 ; 104442275 ; 126443278 ; 128460301 ; 134339942 ; 134341608 ; 135111389 ; 137606696 ; 162260518 ; 163137036 ; 164839349 ; 179323459 ; 198977263 ; 224821588 ; 227390776
CAS Number
73736-50-2
TTD Drug ID
D0C9UF
Formula
C27H29FN4O
Canonical SMILES
C1CN(CCC1NC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)F)CCC5=CC=C(C=C5)O
InChI
1S/C27H29FN4O/c28-22-9-5-21(6-10-22)19-32-26-4-2-1-3-25(26)30-27(32)29-23-14-17-31(18-15-23)16-13-20-7-11-24(33)12-8-20/h1-12,23,33H,13-19H2,(H,29,30)
InChIKey
LAGYWHSFHIMTPE-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6-hydroxydesmethylastemizole DM001601
11754001
Oxidation - 6-Hydrolyzationn 1 [2]
CO-glucuronide DM005855 N. A. Conjugation - Glucuronidation 1 [2]
Norastemizole DM001602
123618
Oxidation - N-Dealkylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006260 Desmethylastemizole 6-Hydroxydesmethylastemizole Oxidation - 6-Hydrolyzationn CYP2D6 [2]
MR006261 Desmethylastemizole Norastemizole Oxidation - N-Dealkylation CYP3A4 [2]
MR006262 Desmethylastemizole CO-glucuronide Conjugation - Glucuronidation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2J2 (CYP2J2) DME0031 Homo sapiens
CP2J2_HUMAN
1.14.14.24
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Pharmacokinetics of astemizole in children. Rhinol Suppl. 1992 Sep;13:21-5.
2 Involvement of multiple human cytochromes P450 in the liver microsomal metabolism of astemizole and a comparison with terfenadine. Br J Clin Pharmacol. 2001 Feb;51(2):133-42.
3 Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole. Drug Metab Dispos. 2002 Nov;30(11):1240-5.

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