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

General Information of Drug (ID: DR5937)
Drug Name
Neostigmine
Synonyms
Eustigmin; Eustigmine; Intrastigmina; Juvastigmin; Neostigmin; Neostigminum; Prostigmin; Prostigmine; Prozerin; Sulfonatooxymethane; Synstigmin; Syntostigmine; Vagostigmin; Vagostigmine; Neostigmine [BAN]; Neostigmine omega; M-Trimethylammoniumphenyldimethylcarbamate; Neostigmine (BAN); Prostigmin (TN); Vagostigmin (TN); [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium; [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium bromide; Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester); Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-(9CI); (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate; (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate (ester); 3-Trimethylammoniumphenyl N,N-dimethylcarbamate; 3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium; 3-{[(dimethylamino)carbonyl]oxy}-N,N,N-trimethylanilinium
Indication Myasthenia gravis [ICD11: 8C6Y] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 223.29 Topological Polar Surface Area 29.5
Heavy Atom Count 16 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4456
ChEBI ID
CHEBI:7514
CAS Number
59-99-4
TTD Drug ID
D08USJ
Formula
C12H19N2O2+
Canonical SMILES
CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C
InChI
InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
InChIKey
ALWKGYPQUAPLQC-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
Neostigmine metabolite M2 DM017563 N. A. Conjugation - Monoglucosidation 1 [2]
PTMA DM014964
15384
Unclear - Unclear 1 [3] , [2]
3-OH PDMA DM003654 N. A. Oxidation - N-demethylation 2 [2]
Neostigmine metabolite M1 DM017562 N. A. Conjugation - Monoglucosidation 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008945 Neostigmine PTMA Unclear - Unclear Unclear [3], [2]
MR008948 Neostigmine Neostigmine metabolite M2 Conjugation - Monoglucosidation Unclear [2]
MR008946 PTMA 3-OH PDMA Oxidation - N-demethylation Unclear [2]
MR008947 3-OH PDMA Neostigmine metabolite M1 Conjugation - Monoglucosidation Unclear [2]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Isolation and characterisation of metabolites of neostigmine from rat urine
3 Metabolites of neostigmine and pyridostigmine do not contribute to antagonism of neuromuscular blockade in the dog

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