NEOSTIGMINE

First marketed in 1931

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H19N2O2
Molecular Weight	223.2915
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ALWKGYPQUAPLQC-UHFFFAOYSA-N

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

HIDE SMILES / InChI

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

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 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8978837	Inhibitor 8297		91.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myasthenia gravis 21 Sources: https://www.drugs.com/cdi/prostigmin.html	Primary		Approved 8429	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 214

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 298	inhibitor 3277 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
ZINC	ZINC000000001792	http://zinc15.docking.org/substances/ZINC000000001792
eMolecules	31796384	https://www.emolecules.com/cgi-bin/more?vid=31796384

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
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.	1972 May	5021954
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.	1973 Apr 23	4739612
Train-of-four nerve stimulation in the management of prolonged neuromuscular blockade following succinylcholine.	1975 Jan	122883
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
Propofol bradycardia.	1991 Jan	1989731
Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats.	1992 Mar	1630594
Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep.	1996 Nov	8895282
[Slow channel syndrome due to an autosomal translocation at 2q31-9p27].	2002 May	12072832
Measurement of gastric contraction activity in dogs by means of AC biosusceptometry.	2003 May	12812419
Probiotics and functional abdominal bloating.	2004 Jul	15220670
Ciguatera fish poisoning in industrial ship crewmembers: a retrospective study in a seaport general practice in Trinidad and Tobago.	2004 Sep	15622674
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
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea.	2008 Apr	18399847
Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload.	2008 Jan	17872965
Dr Lazar Remen (1907-74): a forgotten pioneer in the treatment of myasthenia gravis.	2009 May	19401508
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 `Fri Dec 15 14:57:45 GMT 2023` Edited by `admin` on `Fri Dec 15 14:57:45 GMT 2023`
Record UNII	3982TWQ96G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEOSTIGMINE

Common Name

English

NEOSTIGMINE [VANDF]

Common Name

English

NEOSTIGMINE ION

Common Name

English

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

Systematic Name

English

NEOSTIGMINE [MI]

Common Name

English

NEOSTIGMINE CATION

Common Name

English

NEOSTIGMINE (CATION)

Common Name

English

NEOSTIGMINE [HSDB]

Common Name

English

NEOSTIGMINE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N07AA01