3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium

• ChemBase ID: 427
• Molecular Formular: C9H13N2O2+
• Molecular Mass: 181.21172
• Monoisotopic Mass: 181.09770267
• SMILES: O(c1c[n+](ccc1)C)C(=O)N(C)C
• Canonical SMILES: C[n+]1cccc(c1)OC(=O)N(C)C
• InChI: InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
• InChIKey: RVOLLAQWKVFTGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium
• IUPAC Traditional name: pyridostigmine
• Brand Name: Mestinon; Regonol; Mestinon-SR
• Synonyms: Pyridostigmine Bromide; Pyridostigmine Bromine; Pyridostigminum; Pyridine N-Oxide; Pyridostigmine

Database IDs

• CAS Number: 155-97-5
• PubChem SID: 46506129; 160963890
• PubChem CID: 4991
• ATC CODE: N07AA02
• CHEMBL: 1115
• Chemspider ID: 4817
• DrugBank ID: DB00545
• KEGG ID: D00487
• Unique Ingredient Identifier: 19QM69HH21
• Wikipedia Title: Pyridostigmine
• Medline Plus: a682229

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.526827
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -3.4667275
• LogD (pH = 7.4): -3.4667275
• Log P: -3.4667275
• Molar Refractivity: 49.659 cm^3
• Polarizability: 18.862652 Å^3
• Polar Surface Area: 33.42 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.13
• LOG S: -2.32
• Solubility (Water): 1.04e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.04 mg/mL [Predicted by ALOGPS]
• Hydrophobicity(logP): 1.554

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: 7.6 +/- 2.4%
• Excretion: Renal
• Half Life: 1.78 +/- 0.24hrs
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C (Australia); C (US)

DETAILS

DrugBank - DB00545

• Drug Groups: approved
• Description: A cholinesterase inhibitor with a slightly longer duration of action than neostigmine. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants. [PubChem]
• Indication: For the treatment of myasthenia gravis.
• Pharmacology: Pyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. Since it is a quaternary amine, it is poorly absorbed in the gut and doesn't cross the blood-brain barrier. Pyridostigmine has a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hydrolysis by cholinesterases and by liver.
• Absorption: Poorly absorbed from the GI tract with an oral bioavailability of 7.6 +/- 2.4%.
• Half Life: 3 hours following oral administration.
• References: Singer W, Opfer-Gehrking TL, McPhee BR, Hilz MJ, Bharucha AE, Low PA: Acetylcholinesterase inhibition: a novel approach in the treatment of neurogenic orthostatic hypotension. J Neurol Neurosurg Psychiatry. 2003 Sep;74(9):1294-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Singer W, Opfer-Gehrking TL, McPhee BR, Hilz MJ, Bharucha AE, Low PA: Acetylcholinesterase inhibition: a novel approach in the treatment of neurogenic orthostatic hypotension. J Neurol Neurosurg Psychiatry. 2003 Sep;74(9):1294-8. Pubmed