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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 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

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

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

-9.7839363E11
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
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine.
1984 Nov
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
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
Interaction between intrathecal neostigmine and epidural clonidine in human volunteers.
1996 Aug
Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep.
1996 Nov
Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia.
1996 Nov-Dec
International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria.
1999 Nov
[Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine].
2000 Dec
Probiotics and functional abdominal bloating.
2004 Jul
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
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea.
2008 Apr
Determining the neurotransmitter concentration profile at active synapses.
2009 Dec
Myasthenia gravis and autoimmune Addison disease in a patient with thymoma.
2009 Sep
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.
2010 Jun 15
A comparative study of two different doses of epidural neostigmine coadministered with lignocaine for post operative analgesia and sedation.
2010 Oct
Efficacy of bupivacaine-neostigmine and bupivacaine-tramadol in caudal block in pediatric inguinal herniorrhaphy.
2010 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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:29:46 UTC 2023
Edited
by admin
on Wed Jul 05 22:29:46 UTC 2023
Record UNII
3982TWQ96G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEOSTIGMINE
HSDB   MART.   MI   VANDF  
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
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
FDA ORPHAN DRUG 388812
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-ATC S01EB06
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-VATC QA03AB93
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
LIVERTOX 677
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-ATC N07AA51
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
NDF-RT N0000175723
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-VATC QN07AA51
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
NCI_THESAURUS C47792
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-VATC QN07AA01
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
WHO-VATC QS01EB06
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
Code System Code Type Description
DAILYMED
3982TWQ96G
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
MESH
D009388
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023360
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
PUBCHEM
4456
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
RXCUI
7315
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY RxNorm
EVMPD
SUB03411MIG
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
WIKIPEDIA
NEOSTIGMINE
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
DRUG BANK
DB01400
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
DRUG CENTRAL
1897
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
MERCK INDEX
M7819
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY Merck Index
FDA UNII
3982TWQ96G
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL278020
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
NCI_THESAURUS
C75024
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
HSDB
3921
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
CAS
59-99-4
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
LACTMED
Neostigmine
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
SMS_ID
100000085714
Created by admin on Wed Jul 05 22:29:46 UTC 2023 , Edited by admin on Wed Jul 05 22:29:46 UTC 2023
PRIMARY
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