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

General Information of Drug (ID: DR2305)
Drug Name
Rimantadine
Synonyms
Remantadine; Riamantadine; Rimant; Rimant & .alpha. IFN; Rimantadina; Rimantadina [INN-Spanish]; Rimantadine (INN); Rimantadine [INN:BAN]; Rimantadinum; Rimantadinum [INN-Latin]; Rimantidine & .alpha.IFN; 1-(1-Adamantyl)ethanamine; Alpha-Methyladamantanemethylamine; Enamine_005755; Flumadine (TN); 1-(1-Adamantyl)ethylamin; 1-(1-adamantyl)-ethylamine; 1-(1-adamantyl)ethylamine; 1-(adamantan-1-yl)ethan-1-amine; 1-(tricyclo[3.3.1.1~3,7~]dec-1-yl)ethanamine; 1-Adamantan-1-yl-ethylamine; 1-Adamantan-1-ylethylamine; 1-tricyclo[3.3.1.1~3,7~]dec-1-ylethanamine; Alpha-Methyl-1-adamantanemethylamine; Tricyclo(3.3.1.1^3,7)decane-1-methanamine, .alpha.-methyl-& IFN.alpha
Indication Influenza virus infection [ICD11: 1E30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 179.3 Topological Polar Surface Area 26
Heavy Atom Count 13 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
5071
PubChem SID
9445 ; 626310 ; 643525 ; 3722269 ; 3722270 ; 7379880 ; 7980519 ; 8153120 ; 10506879 ; 11347986 ; 11380337 ; 15120598 ; 15219656 ; 16214800 ; 29215454 ; 29215455 ; 29224140 ; 46505973 ; 47589624 ; 47589625 ; 48416520 ; 49864987 ; 57322594 ; 57820265 ; 78405535 ; 92250339 ; 92309235 ; 93625279 ; 96025169 ; 103250293 ; 104308193 ; 104812960 ; 117395770 ; 117395954 ; 117665755 ; 119525101 ; 125327867 ; 125412242 ; 125539014 ; 129343015 ; 132521219 ; 134224207 ; 134338344 ; 134989610 ; 135692348 ; 137038244 ; 139157511 ; 144021575 ; 160839516 ; 160963824
ChEBI ID
CHEBI:94440
CAS Number
13392-28-4
TTD Drug ID
D0TQ1G
Formula
C12H21N
Canonical SMILES
CC(C12CC3CC(C1)CC(C3)C2)N
InChI
1S/C12H21N/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H3
InChIKey
UBCHPRBFMUDMNC-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
Equatorial epimers of p-hydroxyrimantadine DM015710
10726524
Oxidation - Hydroxylation 1 [3] , [4]
m-Hydroxyrimantadine DM015371
2769978
Oxidation - Hydroxylation 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009683 Rimantadine m-Hydroxyrimantadine Oxidation - Hydroxylation Unclear [3], [4]
MR009684 Rimantadine Equatorial epimers of p-hydroxyrimantadine Oxidation - Hydroxylation Unclear [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [2]
References
1 Rimantadine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 Determination of rimantadine and its hydroxylated metabolites in human plasma and urine
4 Quantitation of the enantiomers of rimantadine and its hydroxylated metabolites in human plasma by gas chromatography/mass spectrometry

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