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Details

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

SHOW SMILES / InChI
Structure of NEOSTIGMINE BROMIDE

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 BrH
Molecular Weight 80.912
Charge 0
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
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

CNS Non-penetrant
1050
Curator's Comment: Neostigmine, unlike physostigmine, does not cross the blood-brain barrier.

Originator

Approval Year

1931
27
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 91.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
Prostigmin

Approved Use

Neostigmine is used for: Treating myasthenia gravis.

Launch Date

-9.7839363E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
211
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A
295
 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)
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Myasthenia gravis syndrome associated with trimethadione.
1970 Jun 29
Train-of-four nerve stimulation in the management of prolonged neuromuscular blockade following succinylcholine.
1975 Jan
Myasthenia syndrome during penicillamine treatment.
1975 Jun 28
Myasthenia associated with D-penicillamine therapy in rheumatoid arthritis.
1977
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine.
1984 Nov
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol.
1987 Dec
Complete heart block following glycopyrronium/neostigmine mixture.
1989 May
Acetylcholinesterase fiber-optic biosensor for detection of anticholinesterases.
1991 May
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
[Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine].
2000 Dec
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
[Slow channel syndrome due to an autosomal translocation at 2q31-9p27].
2002 May
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea.
2008 Apr
Interventions for heartburn in pregnancy.
2008 Oct 8
Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis.
2009 May
Patents

Patents

1905990
5
US20140335021
5

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 Wed Jul 05 22:44:02 UTC 2023
Edited
by admin
on Wed Jul 05 22:44:02 UTC 2023
Record UNII
005SYP50G5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEOSTIGMINE BROMIDE
EP   INN   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
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
NEO PROSERINE
JAN  
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
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID9041075
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
NSC
757233
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
CAS
114-80-7
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
DRUG BANK
DBSALT001191
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
RXCUI
82055
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
204-054-8
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
INN
401
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NEOSTIGMINE BROMIDE
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Very soluble in water; freely soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Cholinergic. Storage: Neostigmine bromide should be kept in a tightly closed container, protected from light. Definition: Neostigmine bromide contains not less than 98.0% and not more than 101.0% of C12H19BrN2O2, calculated withreference to the dried substance.
RS_ITEM_NUM
1459001
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
PUBCHEM
8246
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
FDA UNII
005SYP50G5
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL278020
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
MERCK INDEX
M7819
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY Merck Index
SMS_ID
100000092016
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
NCI_THESAURUS
C76612
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
CHEBI
179557
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
EVMPD
SUB09195MIG
Created by admin on Wed Jul 05 22:44:02 UTC 2023 , Edited by admin on Wed Jul 05 22:44:02 UTC 2023
PRIMARY
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Structure of NEOSTIGMINE BROMIDE
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BASIS OF STRENGTH->SUBSTANCE
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Related Record Type Details
Structure of NEOSTIGMINE
ACTIVE MOIETY
NIH
NCATS
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