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Details

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

SHOW SMILES / InChI
Structure of NEOSTIGMINE

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

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

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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
91.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Prostigmin

Approved Use

Neostigmine is used for: Treating myasthenia gravis.

Launch Date

1938
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
300 ng/mL
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
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
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
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%
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

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
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)
PubMed

PubMed

TitleDatePubMed
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.
1972 May
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.
1983 Jan
Refractory bradycardia after reversal of muscle relaxant in a diabetic with vagal neuropathy.
1986 Nov
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol.
1987 Dec
Portal hypertension secondary to azathioprine in myasthenia gravis.
1988 Dec
Impairment of the antagonism of vecuronium-induced paralysis and intra-operative disopyramide administration.
1989 Jan
Complete heart block following glycopyrronium/neostigmine mixture.
1989 May
Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient.
1989 Oct
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.
1991 May-Jun
Effects of adrenergic blockers on central nervous system-mediated hyperglycemia in fed rats.
1992 May
Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia.
1996 Nov-Dec
Effect of long-term administration of berberine on scopolamine-induced amnesia in rats.
1997 Jul
Postoperative reparalysis after rocuronium following nebulized epinephrine.
1997 Mar
Effect of glyceryl trinitrate on the sphincter of Oddi spasm evoked by prostigmine-morphine administration.
1997 Nov
A multi-center study of intrathecal neostigmine for analgesia following vaginal hysterectomy.
1998 Oct
[Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine].
2000 Dec
Factors affecting gallbladder motility: drugs.
2003 Jul
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation.
2003 Jun 15
Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report.
2008 Feb
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats.
2008 Oct
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.
2008 Sep
Patents

Sample Use Guides

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, neostigmine (10⁻⁵ and 10⁻⁴ M) potentiated neurogenic relaxations in the rabbit corpus cavernosum.
Name Type Language
NEOSTIGMINE
HSDB   MART.   MI   VANDF  
Common Name English
NEOSTIGMINE (CATION)
Preferred 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 [HSDB]
Common Name English
NEOSTIGMINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N07AA01
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
FDA ORPHAN DRUG 388812
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-ATC S01EB06
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-VATC QA03AB93
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
LIVERTOX 677
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-ATC N07AA51
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
NDF-RT N0000175723
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-VATC QN07AA51
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
NCI_THESAURUS C47792
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-VATC QN07AA01
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
WHO-VATC QS01EB06
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
Code System Code Type Description
DAILYMED
3982TWQ96G
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PRIMARY
MESH
D009388
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023360
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PRIMARY
PUBCHEM
4456
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PRIMARY
RXCUI
7315
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PRIMARY RxNorm
EVMPD
SUB03411MIG
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PRIMARY
WIKIPEDIA
NEOSTIGMINE
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
PRIMARY
DRUG BANK
DB01400
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
PRIMARY
DRUG CENTRAL
1897
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PRIMARY
MERCK INDEX
m7819
Created by admin on Mon Mar 31 17:33:00 GMT 2025 , Edited by admin on Mon Mar 31 17:33:00 GMT 2025
PRIMARY Merck Index
FDA UNII
3982TWQ96G
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PRIMARY
ChEMBL
CHEMBL278020
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PRIMARY
NCI_THESAURUS
C75024
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PRIMARY
HSDB
3921
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PRIMARY
CAS
59-99-4
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PRIMARY
LACTMED
Neostigmine
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PRIMARY
SMS_ID
100000085714
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PRIMARY