3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium

• ChemBase ID: 1211
• Molecular Formular: C12H19N2O2+
• Molecular Mass: 223.29146
• Monoisotopic Mass: 223.14465286
• SMILES: c1(cc(ccc1)[N+](C)(C)C)OC(=O)N(C)C
• Canonical SMILES: O=C(N(C)C)Oc1cccc(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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium
• IUPAC Traditional name: neostigmine
• Brand Name: Neostigmine omega; Prostigmin
• Synonyms: Neostigmine

Database IDs

• CAS Number: 59-99-4
• PubChem SID: 46509161; 160964672
• PubChem CID: 4456

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -2.2459824
• LogD (pH = 7.4): -2.2459824
• Log P: -2.2459824
• Molar Refractivity: 75.2818 cm^3
• Polarizability: 24.687561 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.65
• LOG S: -3.58
• Solubility (Water): 6.77e-02 g/l

DETAILS

DrugBank - DB01400

• Drug Groups: approved
• Description: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. [PubChem]
• Indication: Neostigmine is used for the symptomatic treatment of myasthenia gravis by improving muscle tone.
• Pharmacology: Neostigmine is a cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. By inhibiting acetylcholinesterase, more acetylcholine is available in the synapse, therefore, more of it can bind to the fewer receptors present in myasthenia gravis and can better trigger muscular contraction.
• Toxicity: Overdosage of Neostigmine can cause cholinergic crisis, which is characterized by increasing muscle weakness, and through involvement of the muscles of respiration, may result in death. The LD 50 of neostigmine methylsulfate in mice is 0.3 ± 0.02 mg/kg intravenously, 0.54 ± 0.03 mg/kg subcutaneously, and 0.395 ± 0.025 mg/kg intramuscularly; in rats the LD 50 is 0.315 ± 0.019 mg/kg intravenously, 0.445 ± 0.032 mg/kg subcutaneously, and 0.423 ± 0.032 mg/kg intramuscularly.
• Affected Organisms: Humans and other mammals
• Biotransformation: Neostigmine undergoes hydrolysis by cholinesterase and is also metabolized by microsomal enzymes in the liver.
• Absorption: Neostigmine bromide is poorly absorbed from the gastrointestinal tract following oral administration
• Half Life: The half-life ranged from 42 to 60 minutes with a mean half-life of 52 minutes.
• Protein Binding: Protein binding to human serum albumin ranges from 15 to 25 percent.
• External Links: Wikipedia; RxList; Drugs.com