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

General Information of Drug (ID: DR0070)
Drug Name
Almotriptan malate
Synonyms
Almotriptan; Almotriptan (malate); Almotriptan malate; Almotriptan malate (USAN); Almotriptan malate [USAN]; Almotriptan maleate; CHEBI:53781; LAS 31416; LAS 31416 D,L-malate acid; PNU 180638E; PNU-180638E; Almogran; Almotriptan [USAN:INN:BAN]; Axert; CHEBI:520985; DSSTox_CID_24289; DSSTox_GSID_44289; DSSTox_RID_80142; LAS-31416; N,N-dimethyl-2-(5-((pyrrolidin-1-ylsulfonyl)methyl)-1H-indol-3-yl)ethanamine; N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine; N,N-dimethyl-2-{5-[(pyrrolidin-1-ylsulfonyl)methyl]-1H-indol-3-yl}ethanamine; NCGC00095135-01; UNII-1O4XL5SN61; WKEMJKQOLOHJLZ-UHFFFAOYSA-N; 1-(((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine; 154323-57-6; 1O4XL5SN61; 1-(((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)sulfonyl)pyrrolidine, hydroxybutanedionate (1:1); 1-(((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidine malate (1:1); 1-[[[2-(Dimethyl-amino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidine Malate; 181183-52-8; AK110510
Indication Migraine [ICD11: 8A80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 469.6 Topological Polar Surface Area 160
Heavy Atom Count 32 Rotatable Bond Count 9
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
123607
ChEBI ID
CHEBI:53781
CAS Number
181183-52-8
Formula
C21H31N3O7S
Canonical SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)CS(=O)(=O)N3CCCC3.C(C(C(=O)O)O)C(=O)O
InChI
1S/C17H25N3O2S.C4H6O5/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20;5-2(4(8)9)1-3(6)7/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3;2,5H,1H2,(H,6,7)(H,8,9)
InChIKey
QHATUKWEVNMHRY-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-OH-almotriptan DM000052
154700009
Oxidation - Pyrrolidine Oxidation 1 [5]
Almotriptan malate metabolite M1 DM000049 N. A. Oxidation - Oxidative Deamination 1 [5]
Almotriptan malate metabolite M7 DM000061 N. A. Oxidation - Deamination 1 [4]
LAS 32195 DM000059 N. A. Oxidation - N-Oxidation 1 [5]
N-desmethylalmotriptan DM000060
71315712
Oxidation - N-Demethylation 1 [4] , [5]
2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}acetic acid DM000050
59581892
Other reaction - Dehydration 2 [5]
ACP-5461 DM000053 N. A. Other reaction - Tautomerisation 2 [5]
Almotriptan malate metabolite M8 DM000051 N. A. Conjugation - Conjugation 3 [5]
LAS 31911 DM000054 N. A. Other reaction - Dehydration 3 [5]
Almotriptan malate metabolite P13 DM000058 N. A. Oxidation - N-Demethylation 4 [6]
Almotriptan malate metabolite P5 DM000057 N. A. Oxidation - Hydroxylation 4 [6]
Almotriptan malate metabolite P6 DM000056 N. A. Oxidation - N-Dealkylation 4 [6]
Almotriptan malate metabolite P9 DM000055 N. A. Oxidation - Hydroxylation 4 [6]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000152 Almotriptan malate Almotriptan malate metabolite M1 Oxidation - Oxidative Deamination MAOA [5]
MR000153 Almotriptan malate Almotriptan malate metabolite M3 Oxidation - Pyrrolidine Oxidation CYP3A4 ... [5]
MR000154 Almotriptan malate LAS 32195 Oxidation - N-Oxidation FMO3 [5]
MR000155 Almotriptan malate LAS 31612 Oxidation - N-Demethylation CYP1A2 ... [4], [5]
MR000156 Almotriptan malate Almotriptan malate metabolite M7 Oxidation - Deamination MAOA [4]
MR000144 Almotriptan malate metabolite M1 EX01-008 Other reaction - Dehydration ALDH1A1A1 [5]
MR000146 Almotriptan malate metabolite M3 ACP-5461 Other reaction - Tautomerisation Unclear [5]
MR000147 ACP-5461 LAS 31911 Other reaction - Dehydration ALDH1A1A1 [5]
MR000145 EX01-008 Almotriptan malate metabolite M8 Conjugation - Conjugation Unclear [5]
MR000148 LAS 31911 Almotriptan malate metabolite P9 Oxidation - Hydroxylation Unclear [6]
MR000149 LAS 31911 Almotriptan malate metabolite P6 Oxidation - N-Dealkylation Unclear [6]
MR000150 LAS 31911 Almotriptan malate metabolite P5 Oxidation - Hydroxylation Unclear [6]
MR000151 LAS 31911 Almotriptan malate metabolite P13 Oxidation - N-Demethylation Unclear [6]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde dehydrogenase 1 (ALDH1) DME0286 Homo sapiens
AL1A1_HUMAN
1.2.1.36
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[5]
⏷ Show the Full List of 9  DME(s)
References
1 Almotriptan Malate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine Clin Pharmacokinet. 2005;44(3):237-46. doi: 10.2165/00003088-200544030-00002.
3 Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan Drug Metab Dispos. 2003 Apr;31(4):404-11. doi: 10.1124/dmd.31.4.404.
4 Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11.
5 Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine. Clin Pharmacokinet. 2005;44(3):237-46.
6 Disposition and metabolism of almotriptan in rats, dogs and monkeys Xenobiotica. 2006 Sep;36(9):807-23. doi: 10.1080/00498250600802508.

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