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

General Information of Drug (ID: DR0761)
Drug Name
Galantamine hydrobromide
Synonyms
Galantamin; Galantamina; Galantamina [INN-Spanish]; Galantamine; Galantamine [USAN:INN]; Galantaminum; Galantaminum [INN-Latin]; Galanthamine base; Galanthaminum; Jilkon; Lycoremin; Lycoremine; Razadyne ER; galanthamine; (-)-Galantamine; (-)-Galanthamine; (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol; 0D3Q044KCA; 357-70-0; BRN 0093736; CHEBI:42944; CHEMBL659; GNT; HSDB 7361; NCGC00017256-04; NSC 100058; UNII-0D3Q044KCA; Galantamine hydrobromide; Galanthamine (hydrobromide); Galanthamine hydrobromide; Lycoremine hydrobromide; MJ4PTD2VVW; Nivaline (pharmaceutical); Reminyl; (4aS,6R,8aS)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol hydrobromide; (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide; C17H22BrNO3; EINECS 217-780-5; MFCD00067672; SMR000449267; UNII-MJ4PTD2VVW
Indication Alzheimer disease [ICD11: 8A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 368.3 Topological Polar Surface Area 41.9
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
121587
CAS Number
1953-04-4
TTD Drug ID
D0R9VR
Formula
C17H22BrNO3
Canonical SMILES
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O.Br
InChI
1S/C17H21NO3.BrH/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17;/h3-6,12,14,19H,7-10H2,1-2H3;1H/t12-,14-,17-;/m0./s1
InChIKey
QORVDGQLPPAFRS-XPSHAMGMSA-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
Galantamine glucuronide metabolite DM002105 N. A. Conjugation - Glucuronidation 1 [4]
Galantamine N-oxide metabolite DM002104
11748698
Oxidation - N-Oxidation 1 [4] , [2]
Galantaminone DM002093
625124
Oxidation - Oxidation 1 [4]
N-desmethyl-galantamine DM002106
9838394
Unclear 1 [4]
O-desmethyl-galantamine DM002101
443722
Oxidation - O-Demethylation 1 [4] , [2]
Sulfate conjugate of galantamine DM002107 N. A. Conjugation - Sulfation 1 [4]
Epigalantamine DM002094
676392
Reduction - Reduction 2 [5]
O-desmethyl-galantamine glucuronide metabolite DM002103 N. A. Conjugation - Glucuronidation 2 [5]
O-desmethyl-galantaminone DM002100 N. A. Oxidation - O-Demethylation 2 [5]
Sulfate conjugate of O-desmethyl-galantamine DM002102
154699493
Conjugation - Sulfation 2 [5]
Epigalantamine N-oxide metabolite DM002097 N. A. Oxidation - N-Oxidation 3 [5]
N-desmethyl-epigalantamine DM002099
443721
Oxidation - N-Demethylation 3 [5]
O-desmethylepigalantamine DM002095
11012328
Oxidation - O-Demethylation 3 [5]
Sulfate conjugate of epigalantamine DM002098 N. A. Conjugation - Sulfation 3 [5]
O-desmethyl-epigalantamine glucuronide metabolite DM002096 N. A. Conjugation - Glucuronidation 4 [5]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001109 Galantamine hydrobromide Galantaminone Oxidation - Oxidation Unclear [4]
MR001110 Galantamine hydrobromide O-desmethyl-galantamine Oxidation - O-Demethylation CYP2D6 [4], [2]
MR001111 Galantamine hydrobromide Galantamine N-oxide metabolite Oxidation - N-Oxidation CYP3A4 [4], [2]
MR001112 Galantamine hydrobromide Galantamine glucuronide metabolite Conjugation - Glucuronidation Unclear [4]
MR001113 Galantamine hydrobromide N-desmethyl-galantamine Unclear Unclear [4]
MR001114 Galantamine hydrobromide Sulfate conjugate of galantamine Conjugation - Sulfation Unclear [4]
MR001100 Galantaminone Epigalantamine Reduction - Reduction Unclear [5]
MR001101 Galantaminone O-desmethyl-galantaminone Oxidation - O-Demethylation Unclear [5]
MR001107 O-desmethyl-galantamine Sulfate conjugate of O-desmethyl-galantamine Conjugation - Sulfation Unclear [5]
MR001108 O-desmethyl-galantamine O-desmethyl-galantamine glucuronide metabolite Conjugation - Glucuronidation Unclear [5]
MR001102 Epigalantamine O-desmethylepigalantamine Oxidation - O-Demethylation Unclear [5]
MR001103 Epigalantamine Epigalantamine N-oxide metabolite Oxidation - N-Oxidation Unclear [5]
MR001104 Epigalantamine Sulfate conjugate of epigalantamine Conjugation - Sulfation Unclear [5]
MR001105 Epigalantamine N-desmethyl-epigalantamine Oxidation - N-Demethylation Unclear [5]
MR001106 O-desmethylepigalantamine O-desmethyl-epigalantamine glucuronide metabolite Conjugation - Glucuronidation Unclear [5]
⏷ Show the Full List of 15 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
⏷ Show the Full List of 7  DME(s)
References
1 Galantamine Hydrobromide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics of galantamine. Clin Pharmacokinet. 2003;42(15):1383-92.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 The metabolism and excretion of galantamine in rats, dogs, and humans Drug Metab Dispos. 2002 May;30(5):553-63. doi: 10.1124/dmd.30.5.553.
5 DrugBank(Pharmacology-Metabolism)Galantamine hydrobromide

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