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

General Information of Drug (ID: DR5139)
Drug Name
Sumatriptan
Synonyms
Sumatran; Sumatriptanum; Sumax; GR 43175; GR 43175X; NP101; GR-43175; Imigran (TN); Imitrex (TN); KS-1116; Sumatriptanum [INN-Latin]; Sumatriptan (JAN/USP/INN); (3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide; 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide; 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide; 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; 3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide; 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide; 3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide
Indication Migraine [ICD11: 8A80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 295.4 Topological Polar Surface Area 73.6
Heavy Atom Count 20 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5358
ChEBI ID
CHEBI:10650
CAS Number
103628-46-2
TTD Drug ID
D0Z6UC
Formula
C14H21N3O2S
Canonical SMILES
CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN(C)C
InChI
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
InChIKey
KQKPFRSPSRPDEB-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
Cinnarizine metabolite M1 DM003163
70048
Unclear - Unclear 1 [2]
N-Desmethyl sumatriptan DM015721
10826690
Unclear - Unclear 1 [2]
Sumatriptan N-oxide DM018560 N. A. Unclear - Unclear 1 [2]
Cinnarizine metabolite M1 DM003163
70048
Unclear - Unclear 2 [2]
Indo-3-yl-acetic acid derivative DM015787
11778526
Unclear - Unclear 2 [2]
N-Desmethyl sumatriptan DM015721
10826690
Unclear - Unclear 2 [2]
Cinnarizine metabolite M1 DM003163
70048
Unclear - Unclear 3 [2]
Glucuronide of Indo-3-yl-acetic acid derivative DM018559 N. A. Unclear - Unclear 3 [2]
Indo-3-yl-acetic acid derivative DM015787
11778526
Unclear - Unclear 3 [2]
Glucuronide of Indo-3-yl-acetic acid derivative DM018559 N. A. Unclear - Unclear 4 [2]
Indo-3-yl-acetic acid derivative DM015787
11778526
Unclear - Unclear 4 [2]
Indo-3-yl-acetic acid derivative DM015787
11778526
Unclear - Unclear 5 [2]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010640 Sumatriptan N-Desmethyl sumatriptan Unclear - Unclear CYP2D6 ... [2]
MR010646 Sumatriptan Indo-3-yl-acetaldehyde derivative Unclear - Unclear MAO-A [2]
MR010647 Sumatriptan Sumatriptan N-oxide Unclear - Unclear CYP2D6 ... [2]
MR010641 N-Desmethyl sumatriptan N-Desmethyl sumatriptan Unclear - Unclear CYP2D6 ... [2]
MR010642 N-Desmethyl sumatriptan Indo-3-yl-acetaldehyde derivative Unclear - Unclear MAO-A [2]
MR010643 Indo-3-yl-acetaldehyde derivative Indo-3-yl-acetic acid derivative Unclear - Unclear Unclear [2]
MR010645 Indo-3-yl-acetic acid derivative Glucuronide of Indo-3-yl-acetic acid derivative Unclear - Unclear Unclear [2]
MR010644 Indo-3-yl-acetic acid derivative Indo-3-yl-acetic acid derivative Unclear - Unclear Unclear [2]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[2]
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: 54).
2 Metabolism of sumatriptan revisited

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