Basic information
- CAS
17299-00-2- Standard SMILES
CN(CCCCCCN(C)C(=O)Oc1ccc[n+](C)c1)C(=O)Oc1ccc[n+](C)c1- InChIKey
AHZBEVXBKNYXPU-UHFFFAOYSA-N- Molecular formula
- C22H32N4O4+2
- Average molar mass
- 416.5 g/mol
- Monoisotopic mass
- 416.24235551
Overview
Distigmine is a carbamate ester resulting from the formal condensation of both carboxy groups of hexane-1,6-diylbis(methylcarbamic acid) with the hydroxy group of 3-hydroxy-1-methylpyridinium. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and a muscarinic agonist. It is a carbamate ester and a pyridinium ion.
Names & identifiers
- Preferred name
- Distigmine
- IUPAC
- (1-methylpyridin-1-ium-3-yl) N-methyl-N-[6-[methyl-(1-methylpyridin-1-ium-3-yl)oxycarbonylamino]hexyl]carbamate
Names & synonyms
DistigmineDistigmine ionDistigmine cation17299-00-2HexamariumT940307O7BPyridinium, 3,3'-(1,6-hexanediylbis((methylimino)carbonyloxy))bis(1-methyl-CHEBI:80756DTXSID00169484Pyridinium, 3,3'-[1,6-hexanediylbis[(methylimino)carbonyloxy]]bis[1-methyl-RefChem:135137DTXCID1091975
Show more names
1-methyl-3-((methyl((6-(methyl((((1-methylpyridin-1-ium-3-yl)oxy)carbonyl))amino)hexyl))carbamoyl)oxy)pyridin-1-iumDistigmine [WHO-DD]UNII-T940307O7B(1-methylpyridin-1-ium-3-yl) N-methyl-N-[6-[methyl-(1-methylpyridin-1-ium-3-yl)oxycarbonylamino]hexyl]carbamate3,3'-{hexane-1,6-diylbis[(methylcarbamoyl)oxy]}bis(1-methylpyridin-1-ium)Distigmine - API StandardsCHEMBL1199307SCHEMBL16674116
Database identifiers
- CAS
17299-00-2- PubChem CID
- 3116
- DTXSID
DTXSID00169484- ChEMBL
CHEMBL1199307- ChEBI
CHEBI:80756- UNII
- T940307O7B
- Nikkaji
- J221.234J
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 30
- Formal charge
- 2
- Complexity
- 487
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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