NEOSTIGMINE MESYLATE

First marketed in 1931

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H19N2O2.CH3O3S
Molecular Weight	318.389
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS([O-])(=O)=O.CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

InChI

InChIKey=UQDIHHVDTJLVSO-UHFFFAOYSA-M

InChI=1S/C12H19N2O2.CH4O3S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C12H19N2O2
Molecular Weight	223.2915
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	CH3O3S
Molecular Weight	95.098
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8978837	Inhibitor 8504		91.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myasthenia gravis 21 Sources: https://www.drugs.com/cdi/prostigmin.html	Primary		Approved 8583	Prostigmin Approved Use Neostigmine is used for: Treating myasthenia gravis. Launch Date 1938

C_max

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

T_1/2

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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204078s007lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
75% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/204078s007lbl.pdf	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
CYP3A 227

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11913717/	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) Sources: https://pubmed.ncbi.nlm.nih.gov/11913717/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7514	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7514
eMolecules	31796384	https://www.emolecules.com/cgi-bin/more?vid=31796384
ZINC	ZINC000000001792	http://zinc15.docking.org/substances/ZINC000000001792

PubMed

Title	Date	PubMed
A comparative study of two different doses of epidural neostigmine coadministered with lignocaine for post operative analgesia and sedation.	2010-10	21547170
Efficacy of bupivacaine-neostigmine and bupivacaine-tramadol in caudal block in pediatric inguinal herniorrhaphy.	2010-09	20716080
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.	2010-06-15	20350559
A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report.	2009-12-16	20062591
Determining the neurotransmitter concentration profile at active synapses.	2009-12	19844813
Myasthenia gravis and autoimmune Addison disease in a patient with thymoma.	2009-09	19808197
Neostigmine decreases bupivacaine use by patient-controlled epidural analgesia during labor: a randomized controlled study.	2009-08	19377050
Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis.	2009-05	19438131
Dr Lazar Remen (1907-74): a forgotten pioneer in the treatment of myasthenia gravis.	2009-05	19401508
Interventions for heartburn in pregnancy.	2008-10-08	18843742
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats.	2008-10	19568538
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.	2008-09	18559352
The role of Wnt signaling in neuronal dysfunction in Alzheimer's Disease.	2008-07-24	18652670
Prucalopride: the evidence for its use in the treatment of chronic constipation.	2008-06	20694083
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea.	2008-04	18399847
Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report.	2008-02	18323319
Sphincter of Oddi and its dysfunction.	2008-01	19568485
Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload.	2008-01	17872965
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.	2007-12-01	17888667
Myasthenia gravis accompanied with hypokalemic periodic paralysis.	2006-05	16756062
Ocular myasthenia gravis and auto-immune thyroiditis in children.	2005-11	16681065
A multi-center study of intrathecal neostigmine for analgesia following vaginal hysterectomy.	1998-10	9778009
Effect of glyceryl trinitrate on the sphincter of Oddi spasm evoked by prostigmine-morphine administration.	1997-11	9431903
Effect of long-term administration of berberine on scopolamine-induced amnesia in rats.	1997-07	9268086
Postoperative reparalysis after rocuronium following nebulized epinephrine.	1997-03	9067054
Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia.	1996-11-01	8956398
Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep.	1996-11	8895282
Interaction between intrathecal neostigmine and epidural clonidine in human volunteers.	1996-08	8712447
Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats.	1994-07	8010419
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.	1991-05-01	1665057
Acetylcholinesterase fiber-optic biosensor for detection of anticholinesterases.	1991-05	1909249
Propofol bradycardia.	1991-01	1989731
Prolonged paralysis following suxamethonium and the use of neostigmine.	1990-09	2223373
Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient.	1989-10	2573388
Complete heart block following glycopyrronium/neostigmine mixture.	1989-05	2742112
Impairment of the antagonism of vecuronium-induced paralysis and intra-operative disopyramide administration.	1989-01	2564745
Portal hypertension secondary to azathioprine in myasthenia gravis.	1988-12	3256814
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol.	1987-12	3434760
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.	1987-03	3559705
Refractory bradycardia after reversal of muscle relaxant in a diabetic with vagal neuropathy.	1986-11	3767025
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain.	1985-12	2417918
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine.	1984-11	6498577
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983-01	6130710
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.	1978-01-15	623676
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.	1973-04-23	4739612
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.	1972-05	5021954
Recurarization--fact or fiction.	1971-09-01	4255898
Prolonged curarization in a patient with renal failure. Case report.	1971-05	4326672
Myasthenia gravis syndrome associated with trimethadione.	1970-06-29	4987393
The prevention of muscle pains associated with the use of suxamethonium.	1967-12	5625011

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

In vitro, neostigmine (10⁻⁵ and 10⁻⁴ M) potentiated neurogenic relaxations in the rabbit corpus cavernosum.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:34:36 GMT 2025` Edited by `admin` on `Mon Mar 31 23:34:36 GMT 2025`
Record UNII	6F5UW4E5CF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEOSTIGMINE MESYLATE

Common Name

English

3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium methanesulfonate

Preferred Name

English

Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methanesulfonate

Systematic Name

English

Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methanesulfonate (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

11659722

Created by admin on Mon Mar 31 23:34:36 GMT 2025 , Edited by admin on Mon Mar 31 23:34:36 GMT 2025

PRIMARY

CAS

873090-02-9

Created by admin on Mon Mar 31 23:34:36 GMT 2025 , Edited by admin on Mon Mar 31 23:34:36 GMT 2025

PRIMARY

FDA UNII

6F5UW4E5CF

Created by admin on Mon Mar 31 23:34:36 GMT 2025 , Edited by admin on Mon Mar 31 23:34:36 GMT 2025

PRIMARY

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NEOSTIGMINE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Description
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

C_max

T_1/2

F_unbound

Drug as perpetrator