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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

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
1014
Curator's Comment: Neostigmine, unlike physostigmine, does not cross the blood-brain barrier.

Originator

Approval Year

1931
27
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 91.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
214
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A
298
 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
Recurarization--fact or fiction.
1971 Sep-Oct
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.
1972 May
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.
1973 Apr 23
Myasthenia syndrome during penicillamine treatment.
1975 Jun 28
Myasthenia associated with D-penicillamine therapy in rheumatoid arthritis.
1977
Refractory bradycardia after reversal of muscle relaxant in a diabetic with vagal neuropathy.
1986 Nov
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.
1987 Mar
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
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.
1991 May-Jun
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
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
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
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation.
2003 Jun 15
Cardiac responses of Pacific oyster Crassostrea gigas to agents modulating cholinergic function.
2004 Dec
Probiotics and functional abdominal bloating.
2004 Jul
Ciguatera fish poisoning in industrial ship crewmembers: a retrospective study in a seaport general practice in Trinidad and Tobago.
2004 Sep
[Myasthenia in elderly patients: a series of 23 cases].
2005 Dec
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
The contribution of Dr. Mary Walker towards myasthenia gravis and periodic paralysis whilst working in poor law hospitals in London.
2005 Jun
A conscious mouse model of gastric ileus using clinically relevant endpoints.
2005 Jun 6
Ocular myasthenia gravis and auto-immune thyroiditis in children.
2005 Nov
Myasthenia gravis accompanied with hypokalemic periodic paralysis.
2006 May
Neostigmine and pilocarpine attenuated tumour necrosis factor alpha expression and cardiac hypertrophy in the heart with pressure overload.
2008 Jan
The role of Wnt signaling in neuronal dysfunction in Alzheimer's Disease.
2008 Jul 24
Prucalopride: the evidence for its use in the treatment of chronic constipation.
2008 Jun
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats.
2008 Oct
Interventions for heartburn in pregnancy.
2008 Oct 8
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.
2008 Sep
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
Efficacy of bupivacaine-neostigmine and bupivacaine-tramadol in caudal block in pediatric inguinal herniorrhaphy.
2010 Sep
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.
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 Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
FDA ORPHAN DRUG 388812
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-ATC S01EB06
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-VATC QA03AB93
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
LIVERTOX 677
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-ATC N07AA51
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
NDF-RT N0000175723
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-VATC QN07AA51
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
NCI_THESAURUS C47792
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-VATC QN07AA01
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
WHO-VATC QS01EB06
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
Code System Code Type Description
DAILYMED
3982TWQ96G
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
MESH
D009388
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023360
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
PUBCHEM
4456
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
RXCUI
7315
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY RxNorm
EVMPD
SUB03411MIG
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
WIKIPEDIA
NEOSTIGMINE
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
DRUG BANK
DB01400
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
DRUG CENTRAL
1897
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
MERCK INDEX
m7819
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY Merck Index
FDA UNII
3982TWQ96G
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL278020
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
NCI_THESAURUS
C75024
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
HSDB
3921
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
CAS
59-99-4
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
LACTMED
Neostigmine
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
SMS_ID
100000085714
Created by admin on Fri Dec 15 14:57:45 UTC 2023 , Edited by admin on Fri Dec 15 14:57:45 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of NEOSTIGMINE
SALT/SOLVATE (PARENT)
Structure of NEOSTIGMINE BROMIDE
SALT/SOLVATE (PARENT)
Structure of NEOSTIGMINE METHYLSULFATE
SALT/SOLVATE (PARENT)
Structure of NEOSTIGMINE MESYLATE
NIH
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