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

General Information of Drug (ID: DR2436)
Drug Name
Rizatriptan benzoate
Synonyms
Rizatriptan (benzoate); Rizatriptan Benzoate (Maxalt); Rizatriptan benzoate; Rizatriptan benzoate [USAN:USP]; WR978S7QHH; 145202-66-0; 2-(5-((1H-1,2,4-TRIAZOL-1-YL)METHYL)-1H-INDOL-3-YL)-N,N-DIMETHYLETHANAMINE BENZOATE; 3-(2-(Dimethylamino)ethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)indole monobenzoate; L 705,126; L 705126; L-705,126; L-705126; MK 0462; MK 462; MK-0462; MK-462; Maxalt; Maxalt-MLT; AK163196; N,N-Dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine benzoate; UNII-WR978S7QHH
Indication Migraine [ICD11: 8A80] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 391.5 Topological Polar Surface Area 87
Heavy Atom Count 29 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
77997
ChEBI ID
CHEBI:8875
CAS Number
145202-66-0
Formula
C22H25N5O2
Canonical SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)CN3C=NC=N3.C1=CC=C(C=C1)C(=O)O
InChI
1S/C15H19N5.C7H6O2/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20;8-7(9)6-4-2-1-3-5-6/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3;1-5H,(H,8,9)
InChIKey
JPRXYLQNJJVCMZ-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-Hydroxy rizatriptan DM015782
11742124
Oxidation - Demethylation 1 [4]
6-Hydroxy rizatriptan DM015782
11742124
Oxidation - Hydroxylation 1 [4]
Rizatriptan N10-oxide DM015611
10069964
Oxidation - N-oxidation 1 [4]
Triazolomethyl-indole-3-acetic acid DM015636
10244117
Oxidation - Oxidative deamination 1 [4]
6-Hydroxy rizatriptan sulfate DM015586
9976084
Conjugation - Sulfation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009689 Rizatriptan benzoate 6-Hydroxy rizatriptan Oxidation - Hydroxylation Unclear [4]
MR009691 Rizatriptan benzoate Triazolomethyl-indole-3-acetic acid Oxidation - Oxidative deamination MAOA [4]
MR009692 Rizatriptan benzoate Rizatriptan N10-oxide Oxidation - N-oxidation Unclear [4]
MR009690 6-Hydroxy rizatriptan 6-Hydroxy rizatriptan sulfate Conjugation - Sulfation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[2]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
References
1 Rizatriptan benzoate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 LABEL:Rizatriptan benzoate
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Disposition and pharmacokinetics of the antimigraine drug, rizatriptan, in humans

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