NEOSTIGMINE BROMIDE

First marketed in 1931

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H19N2O2.Br
Molecular Weight	303.195
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LULNWZDBKTWDGK-UHFFFAOYSA-M

InChI=1S/C12H19N2O2.BrH/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;/h6-9H,1-5H3;1H/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	BrH
Molecular Weight	80.912
Charge	0
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
The prevention of muscle pains associated with the use of suxamethonium.	1967 Dec	5625011
Myasthenia gravis syndrome associated with trimethadione.	1970 Jun 29	4987393
Prolonged curarization in a patient with renal failure. Case report.	1971 May	4326672
Recurarization--fact or fiction.	1971 Sep-Oct	4255898
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.	1972 May	5021954
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.	1973 Apr 23	4739612
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	623676
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983 Jan	6130710
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine.	1984 Nov	6498577
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain.	1985 Dec	2417918
Refractory bradycardia after reversal of muscle relaxant in a diabetic with vagal neuropathy.	1986 Nov	3767025
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol.	1987 Dec	3434760
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.	1987 Mar	3559705
Portal hypertension secondary to azathioprine in myasthenia gravis.	1988 Dec	3256814
Impairment of the antagonism of vecuronium-induced paralysis and intra-operative disopyramide administration.	1989 Jan	2564745
Complete heart block following glycopyrronium/neostigmine mixture.	1989 May	2742112
Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient.	1989 Oct	2573388
Prolonged paralysis following suxamethonium and the use of neostigmine.	1990 Sep	2223373
Propofol bradycardia.	1991 Jan	1989731
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.	1991 May-Jun	1665057
Effects of adrenergic blockers on central nervous system-mediated hyperglycemia in fed rats.	1992 May	1350317
Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats.	1994 Jul	8010419
Interaction between intrathecal neostigmine and epidural clonidine in human volunteers.	1996 Aug	8712447
Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep.	1996 Nov	8895282
Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia.	1996 Nov-Dec	8956398
Effect of long-term administration of berberine on scopolamine-induced amnesia in rats.	1997 Jul	9268086
Postoperative reparalysis after rocuronium following nebulized epinephrine.	1997 Mar	9067054
Effect of glyceryl trinitrate on the sphincter of Oddi spasm evoked by prostigmine-morphine administration.	1997 Nov	9431903
A multi-center study of intrathecal neostigmine for analgesia following vaginal hysterectomy.	1998 Oct	9778009
International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria.	1999 Nov	16113981
Probiotics and functional abdominal bloating.	2004 Jul	15220670
Masseter muscle spasm following atracurium.	2004 May	15096252
[Myasthenia in elderly patients: a series of 23 cases].	2005 Dec	16229927
Congenital endplate acetylcholinesterase deficiency responsive to ephedrine.	2005 Jul 12	16009904
The contribution of Dr. Mary Walker towards myasthenia gravis and periodic paralysis whilst working in poor law hospitals in London.	2005 Jun	16019657
Myasthenia gravis accompanied with hypokalemic periodic paralysis.	2006 May	16756062
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	17888667
Sphincter of Oddi and its dysfunction.	2008 Jan	19568485
Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload.	2008 Jan	17872965
Prucalopride: the evidence for its use in the treatment of chronic constipation.	2008 Jun	20694083
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats.	2008 Oct	19568538
Neostigmine decreases bupivacaine use by patient-controlled epidural analgesia during labor: a randomized controlled study.	2009 Aug	19377050
Determining the neurotransmitter concentration profile at active synapses.	2009 Dec	19844813
A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report.	2009 Dec 16	20062591
Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis.	2009 May	19438131
Dr Lazar Remen (1907-74): a forgotten pioneer in the treatment of myasthenia gravis.	2009 May	19401508
Myasthenia gravis and autoimmune Addison disease in a patient with thymoma.	2009 Sep	19808197
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.	2010 Jun 15	20350559
A comparative study of two different doses of epidural neostigmine coadministered with lignocaine for post operative analgesia and sedation.	2010 Oct	21547170
Efficacy of bupivacaine-neostigmine and bupivacaine-tramadol in caudal block in pediatric inguinal herniorrhaphy.	2010 Sep	20716080

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 17:50:13 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:13 GMT 2025`
Record UNII	005SYP50G5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NEO PROSERINE

Preferred Name

English

NEOSTIGMINE BROMIDE

Official Name

English

NEOSTIGMINE BROMIDE [MI]

Common Name

English

NEOPROSERINE

Common Name

English

SYNTOSTIGMIN BROMIDE

Common Name

English

NEOSTIGMINE BROMIDE [USP-RS]

Common Name

English

NEOSTIGMINE BROMIDE [WHO-IP]

Common Name

English

NEOSTIGMINE BROMIDE [EP MONOGRAPH]

Common Name

English

BENZENAMINIUM, 3-(((DIMETHYLAMINO)CARBONYL)OXY)-N,N,N-TRIMETHYL-, BROMIDE

Systematic Name

English

VAGOSTIGMIN

Brand Name

English

NEO PROSERINE [JAN]

Common Name

English

(M-HYDROXYPHENYL)TRIMETHYLAMMONIUM BROMIDE DIMETHYLCARBAMATE

Systematic Name

English

NEOSTIGMINE BROMIDE [JAN]

Common Name

English

NEOSTIGMINE BROMIDE [VANDF]

Common Name

English

neostigmine bromide [INN]

Common Name

English

NEOSTIGMINI BROMIDUM [WHO-IP LATIN]

Common Name

English

NEOSTIGMINE BROMIDE [MART.]

Common Name

English

KIRKSTIGMINE BROMIDE

Common Name

English

NEOSTIGMINE BROMIDE [USP MONOGRAPH]

Common Name

English

Neostigmine bromide [WHO-DD]

Common Name

English

NSC-757233

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47792