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

General Information of Drug (ID: DR3087)
Drug Name
Arecoline
Synonyms
arecoline; Arecholine; Arecaline; 63-75-2; Methylarecaiden; Methylarecaidin; Arecolin; Arekolin; Arecoline base; Arecaidine methyl ester; Arecholin; methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate; 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester; Methyl N-methyltetrahydronicotinate; C8H13NO2; N-Methyltetrahydronicotinic acid, methyl ester; Methyl 1,2,5,6-tetrahydro-1-methylnicotinate; UNII-4ALN5933BH; NSC 56321; Methyl N-methyl-1,2,5,6-tetrahydronicotinate; CCRIS 7688
Indication Parkinsonism [ICD11: 8A00] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 155.19 Topological Polar Surface Area 29.5
Heavy Atom Count 11 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2230
ChEBI ID
CHEBI:2814
CAS Number
63-75-2
TTD Drug ID
D07EFM
Formula
C8H13NO2
Canonical SMILES
CN1CCC=C(C1)C(=O)OC
InChI
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChIKey
HJJPJSXJAXAIPN-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
1-Methyl-3,4- dehydropiperidine-3- carboxaldehyde DM015919
15428061
Unclear - Unclear 1 [2]
Arecaidine DM014934
10355
Unclear - Unclear 1 [2]
Arecoline mercapturic acid DM019828 N. A. Unclear - Unclear 1 [2]
1-Methyl-3,4- dehydropiperidine-3- carboxaldehyde DM015919
15428061
Unclear - Unclear 2 [2]
4-Mercapto-1- methylnipecotic acid methyl ester diastereomers DM016372
85859971
Unclear - Unclear 2 [2]
Arecaidine mercapturic acid DM019831 N. A. Unclear - Unclear 2 [2]
Arecaidine N-oxide DM019830 N. A. Unclear - Unclear 2 [2]
Arecaidinylglycine DM019829 N. A. Unclear - Unclear 2 [2]
Arecoline mercapturic acid DM019828 N. A. Unclear - Unclear 2 [2]
N-methylnipecotic acid DM015367
2736937
Unclear - Unclear 2 [2]
N-methylnipecotylglycine DM016232
61158014
Unclear - Unclear 3 [2]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012559 Arecoline Arecaidine Unclear - Unclear ES [2]
MR012567 Arecoline 1-Methyl-3,4- dehydropiperidine-3- carboxaldehyde Unclear - Unclear FMO1 [2]
MR012569 Arecoline Arecoline mercapturic acid Unclear - Unclear Unclear [2]
MR012568 1-Methyl-3,4- dehydropiperidine-3- carboxaldehyde 4-Mercapto-1- methylnipecotic acid methyl ester diastereomers Unclear - Unclear FMO3 [2]
MR012560 Arecaidine N-methylnipecotic acid Unclear - Unclear CYP3A4 ... [2]
MR012561 Arecaidine 1-Methyl-3,4- dehydropiperidine-3- carboxaldehyde Unclear - Unclear Unclear [2]
MR012562 Arecaidine Arecoline mercapturic acid Unclear - Unclear Unclear [2]
MR012563 Arecaidine Arecaidinylglycine Unclear - Unclear Unclear [2]
MR012564 Arecaidine Arecaidine N-oxide Unclear - Unclear Unclear [2]
MR012565 Arecaidine Arecaidine mercapturic acid Unclear - Unclear Unclear [2]
MR012570 Arecoline mercapturic acid 4-Mercapto-1- methylnipecotic acid methyl ester diastereomers Unclear - Unclear Unclear [2]
MR012566 N-methylnipecotic acid N-methylnipecotylglycine Unclear - Unclear Unclear [2]
⏷ Show the Full List of 12 MR(s)
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: 296).
2 Genetic toxicology and toxicokinetics of arecoline and related areca nut compounds: an updated review

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