NEOSTIGMINE HYDROXIDE

First marketed in 1931

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H19N2O2.HO
Molecular Weight	240.2988
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=GTPJMRHVDZUPND-UHFFFAOYSA-M

InChI=1S/C12H19N2O2.H2O/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;/h6-9H,1-5H3;1H2/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	HO
Molecular Weight	17.0073
Charge	-1
Count

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

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
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.	1973 Apr 23	4739612
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983 Jan	6130710
Complete heart block following glycopyrronium/neostigmine mixture.	1989 May	2742112
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
Low-dose clonidine and neostigmine prolong the duration of intrathecal bupivacaine-fentanyl for labor analgesia.	2000 Feb	10691221
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.	2002 Aug	12198388
Factors affecting gallbladder motility: drugs.	2003 Jul	12974504
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation.	2003 Jun 15	12845923
Ciguatera fish poisoning in industrial ship crewmembers: a retrospective study in a seaport general practice in Trinidad and Tobago.	2004 Sep	15622674
[Myasthenia in elderly patients: a series of 23 cases].	2005 Dec	16229927
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	15708666
Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload.	2008 Jan	17872965
The role of Wnt signaling in neuronal dysfunction in Alzheimer's Disease.	2008 Jul 24	18652670
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats.	2008 Oct	19568538
Interventions for heartburn in pregnancy.	2008 Oct 8	18843742
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.	2008 Sep	18559352
A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report.	2009 Dec 16	20062591
A comparative study of two different doses of epidural neostigmine coadministered with lignocaine for post operative analgesia and sedation.	2010 Oct	21547170

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 `Sat Dec 16 01:38:43 GMT 2023` Edited by `admin` on `Sat Dec 16 01:38:43 GMT 2023`
Record UNII	5PJE4BX5PX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEOSTIGMINE HYDROXIDE

Common Name

English

MIOSTIN

Common Name

English

BENZENAMINIUM, 3-(((DIMETHYLAMINO)CARBONYL)OXY)-N,N,N-TRIMETHYL-, HYDROXIDE (1:1)

Systematic Name

English

Neostigmine [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

5PJE4BX5PX

Created by admin on Sat Dec 16 01:38:43 GMT 2023 , Edited by admin on Sat Dec 16 01:38:43 GMT 2023

PRIMARY

PUBCHEM

12313247

Created by admin on Sat Dec 16 01:38:43 GMT 2023 , Edited by admin on Sat Dec 16 01:38:43 GMT 2023

PRIMARY

CAS

588-17-0

Created by admin on Sat Dec 16 01:38:43 GMT 2023 , Edited by admin on Sat Dec 16 01:38:43 GMT 2023

PRIMARY

Related Record Type Details


					3982TWQ96G

NEOSTIGMINE

ACTIVE MOIETY

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