Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H19N2O2.CH3O4S |
| Molecular Weight | 334.389 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COS([O-])(=O)=O.CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C
InChI
InChIKey=OSZNNLWOYWAHSS-UHFFFAOYSA-M
InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
| Molecular Formula | C12H19N2O2 |
| Molecular Weight | 223.2915 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | CH3O4S |
| Molecular Weight | 111.097 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01400Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/neostigmine-methylsulfate-injection.html
Sources: http://www.drugbank.ca/drugs/DB01400
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/neostigmine-methylsulfate-injection.html
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. Neostigmine is used for the symptomatic treatment of myasthenia gravis by improving muscle tone.
CNS Activity
Sources: http://www.drugbank.ca/drugs/DB01400
Curator's Comment: Neostigmine, unlike physostigmine, does not cross the blood-brain barrier.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
300 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/382915/ |
0.07 mg/kg single, intravenous dose: 0.07 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEOSTIGMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
69.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/382915/ |
0.07 mg/kg single, intravenous dose: 0.07 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEOSTIGMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
79.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/382915/ |
0.07 mg/kg single, intravenous dose: 0.07 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEOSTIGMINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.5 h |
0.03 mg/kg single, intravenous dose: 0.03 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEOSTIGMINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
75% |
0.03 mg/kg single, intravenous dose: 0.03 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NEOSTIGMINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | yes (co-administration study) Comment: information obtained from abstract: AUC of coadministered drug, parathion, parathion was significantly greater than control (65.1 versus 74.3 microg min/ml) |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase. | 1972 May |
|
| Train-of-four nerve stimulation in the management of prolonged neuromuscular blockade following succinylcholine. | 1975 Jan |
|
| Myasthenia associated with D-penicillamine therapy in rheumatoid arthritis. | 1977 |
|
| On the interaction of drugs with the cholinergic nervous system--V. Characterization of some effects induced by physostigmine in mice: in vivo and in vitro studies. | 1978 Jan 15 |
|
| Neuropharmacology of the parasitic trematode, Schistosoma mansoni. | 1983 Jan |
|
| Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine. | 1984 Nov |
|
| Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat. | 1987 Mar |
|
| Portal hypertension secondary to azathioprine in myasthenia gravis. | 1988 Dec |
|
| Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient. | 1989 Oct |
|
| Propofol bradycardia. | 1991 Jan |
|
| Acetylcholinesterase fiber-optic biosensor for detection of anticholinesterases. | 1991 May |
|
| Reversal of antihypertensive agent-induced postural hypotension with physostigmine. | 1991 May-Jun |
|
| Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats. | 1992 Mar |
|
| Effects of adrenergic blockers on central nervous system-mediated hyperglycemia in fed rats. | 1992 May |
|
| Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats. | 1994 Jul |
|
| Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep. | 1996 Nov |
|
| Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia. | 1996 Nov-Dec |
|
| Postoperative reparalysis after rocuronium following nebulized epinephrine. | 1997 Mar |
|
| A multi-center study of intrathecal neostigmine for analgesia following vaginal hysterectomy. | 1998 Oct |
|
| International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria. | 1999 Nov |
|
| [Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine]. | 2000 Dec |
|
| Factors affecting gallbladder motility: drugs. | 2003 Jul |
|
| Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation. | 2003 Jun 15 |
|
| Measurement of gastric contraction activity in dogs by means of AC biosusceptometry. | 2003 May |
|
| Cardiac responses of Pacific oyster Crassostrea gigas to agents modulating cholinergic function. | 2004 Dec |
|
| Probiotics and functional abdominal bloating. | 2004 Jul |
|
| Masseter muscle spasm following atracurium. | 2004 May |
|
| Ciguatera fish poisoning in industrial ship crewmembers: a retrospective study in a seaport general practice in Trinidad and Tobago. | 2004 Sep |
|
| Phosphorus-doped and undoped glassy carbon indicator electrodes in controlled-current potentiometric titrations of bromide- or chloride-containing active ingredients in some pharmaceutical preparations. | 2005 Feb 23 |
|
| Congenital endplate acetylcholinesterase deficiency responsive to ephedrine. | 2005 Jul 12 |
|
| A conscious mouse model of gastric ileus using clinically relevant endpoints. | 2005 Jun 6 |
|
| Ocular myasthenia gravis and auto-immune thyroiditis in children. | 2005 Nov |
|
| Myasthenia gravis accompanied with hypokalemic periodic paralysis. | 2006 May |
|
| Synthesis and screening for acetylcholinesterase inhibitor activity of some novel 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-ones: derivatives of irbesartan key intermediate. | 2007 Dec 1 |
|
| Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea. | 2008 Apr |
|
| Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report. | 2008 Feb |
|
| Sphincter of Oddi and its dysfunction. | 2008 Jan |
|
| Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload. | 2008 Jan |
|
| The role of Wnt signaling in neuronal dysfunction in Alzheimer's Disease. | 2008 Jul 24 |
|
| Prucalopride: the evidence for its use in the treatment of chronic constipation. | 2008 Jun |
|
| The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats. | 2008 Oct |
|
| Interventions for heartburn in pregnancy. | 2008 Oct 8 |
|
| Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing. | 2008 Sep |
|
| Neostigmine decreases bupivacaine use by patient-controlled epidural analgesia during labor: a randomized controlled study. | 2009 Aug |
|
| Determining the neurotransmitter concentration profile at active synapses. | 2009 Dec |
|
| A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report. | 2009 Dec 16 |
|
| Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis. | 2009 May |
|
| Dr Lazar Remen (1907-74): a forgotten pioneer in the treatment of myasthenia gravis. | 2009 May |
|
| Myasthenia gravis and autoimmune Addison disease in a patient with thymoma. | 2009 Sep |
|
| The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions. | 2010 Jun 15 |
Patents
Sample Use Guides
The recommended dose range of Neostigmine Methylsulfate Injection is 0.03 mg/kg to 0.07 mg/kg administered as an intravenous bolus.
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
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on
Edited
Fri Dec 15 16:14:47 GMT 2023
by
admin
on
Fri Dec 15 16:14:47 GMT 2023
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| Record UNII |
98IMH7M386
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| Record Status |
Validated (UNII)
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CFR |
21 CFR 522.1503
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FDA ORPHAN DRUG |
359611
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NCI_THESAURUS |
C47792
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C76613
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98IMH7M386
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1460000
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51-60-5
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200-109-5
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100000086473
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SUB20700
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DBSALT000128
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m7819
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CHEMBL278020
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NEOSTIGMINE METHYLSULFATE
Created by
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PRIMARY | Description: A white, crystalline powder; odourless. Solubility: Very soluble in water; freely soluble in ethanol (~750 g/l) TS. Category: Cholinergic. Storage: Neostigmine metilsulfate should be kept in a tightly closed container, protected from light. Definition: Neostigmine metilsulfate contains not less than 98.0% and not more than 100.5% of C13H22N2O6S, calculated with reference to the dried substance. | ||
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93753
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7316
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DTXSID40199003
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5824
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7514
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PARENT -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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