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

General Information of Drug (ID: DR0147)
Drug Name
Astemizole
Synonyms
Alermizol; Astemisan; Astemison; Astemizol; Astemizol [German]; Astemizol [INN-Spanish]; Astemizolum; Astemizolum [INN-Latin]; GNF-PF-2461; Hestazol; Hismanal; Histamen; Histaminos; Histazol; Laridal; Metodih; Metodik; Novo-mastizol A; Paralergin; R 42512; R-43512; Retolen; Wareezol; Waruzol; astemizole; 1-[(4-Fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; 68844-77-9; BRN 4830190; C28H31FN4O; CCRIS 7595; EINECS 272-441-9; HSDB 6799; Kelp; UNII-7HU6337315
Indication Allergic rhinitis [ICD11: CA08] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 458.6 Topological Polar Surface Area 42.3
Heavy Atom Count 34 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
2247
PubChem SID
9050 ; 459037 ; 855746 ; 4266413 ; 5313663 ; 7847301 ; 7978732 ; 8150150 ; 8151518 ; 10321136 ; 11112828 ; 11335214 ; 11360453 ; 11363342 ; 11365904 ; 11368466 ; 11372003 ; 11374824 ; 11376628 ; 11461425 ; 11466164 ; 11467284 ; 11485540 ; 11485887 ; 11489548 ; 11490887 ; 11493037 ; 11494262 ; 11528621 ; 11538010 ; 12013338 ; 14760289 ; 22391432 ; 26613163 ; 26680817 ; 26746979 ; 26746980 ; 26751496 ; 26751497 ; 29221421 ; 46487928 ; 46508569 ; 47216611 ; 47440072 ; 47515146 ; 47736292 ; 47810587 ; 47885241 ; 48034934 ; 48259050
ChEBI ID
CHEBI:2896
CAS Number
68844-77-9
TTD Drug ID
D0Y2HR
Formula
C28H31FN4O
Canonical SMILES
COC1=CC=C(C=C1)CCN2CCC(CC2)NC3=NC4=CC=CC=C4N3CC5=CC=C(C=C5)F
InChI
1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15-24(16-19-32)30-28-31-26-4-2-3-5-27(26)33(28)20-22-6-10-23(29)11-7-22/h2-13,24H,14-20H2,1H3,(H,30,31)
InChIKey
GXDALQBWZGODGZ-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
2-(4-hydroxyphenyl)acetaldehyde DM001604
440113
Oxidation - N-Dealkylation 1 [2]
6-hydroxyastemizole DM001603
10027871
Oxidation - Hydroxylation 1 [2]
Desmethylastemizole DM003090
155805
Oxidation - O-Demethylation 1 [6]
6-hydroxydesmethylastemizole DM001601
11754001
Oxidation - O-Demethylation 2 [2]
6-hydroxydesmethylastemizole DM001601
11754001
Oxidation - 6-Hydroxylation 2 [2]
Norastemizole DM001602
123618
Oxidation - N-Dealkylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000331 Astemizole 6-hydroxyastemizole Oxidation - Hydroxylation CYP2D6 ... [2]
MR000332 Astemizole 2-(4-hydroxyphenyl)acetaldehyde Oxidation - N-Dealkylation Unclear [2]
MR000333 Astemizole Desmethylastemizole Oxidation - O-Demethylation CYP2J2 ... [6]
MR000330 6-hydroxyastemizole 6-hydroxydesmethylastemizole Oxidation - O-Demethylation CYP3A43 [2]
MR000334 Desmethylastemizole 6-hydroxydesmethylastemizole Oxidation - 6-Hydroxylation Unclear [2]
MR000335 Desmethylastemizole Tecastemizole Oxidation - N-Dealkylation Unclear [2]
⏷ Show the Full List of 6 MR(s)
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
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
References
1 Comparative tolerability of second generation antihistamines. Drug Saf. 1999 May;20(5):385-401.
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 Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity. Drug Metab Dispos. 2012 May;40(5):943-51.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Drug Interactions Flockhart Table
6 DrugBank(Pharmacology-Metabolism)Astemizole

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