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Details

Stereochemistry ACHIRAL
Molecular Formula C12H19N2O2.CH3O3S
Molecular Weight 318.389
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEOSTIGMINE MESYLATE

SMILES

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

InChI

InChIKey=UQDIHHVDTJLVSO-UHFFFAOYSA-M
InChI=1S/C12H19N2O2.CH4O3S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula CH3O3S
Molecular Weight 95.098
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
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
The prevention of muscle pains associated with the use of suxamethonium.
1967 Dec
Myasthenia gravis syndrome associated with trimethadione.
1970 Jun 29
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
On the interaction of drugs with the cholinergic nervous system--V. Characterization of some effects induced by physostigmine in mice: in vivo and in vitro studies.
1978 Jan 15
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.
1983 Jan
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain.
1985 Dec
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
Sensitivity to both vecuronium and neostigmine in a sero-negative myasthenic patient.
1989 Oct
Prolonged paralysis following suxamethonium and the use of neostigmine.
1990 Sep
Propofol bradycardia.
1991 Jan
Acetylcholinesterase fiber-optic biosensor for detection of anticholinesterases.
1991 May
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.
1991 May-Jun
Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats.
1992 Mar
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
Postoperative reparalysis after rocuronium following nebulized epinephrine.
1997 Mar
A multi-center study of intrathecal neostigmine for analgesia following vaginal hysterectomy.
1998 Oct
International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria.
1999 Nov
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
Congenital endplate acetylcholinesterase deficiency responsive to ephedrine.
2005 Jul 12
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
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
Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report.
2008 Feb
Sphincter of Oddi and its dysfunction.
2008 Jan
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
Neostigmine decreases bupivacaine use by patient-controlled epidural analgesia during labor: a randomized controlled study.
2009 Aug
Determining the neurotransmitter concentration profile at active synapses.
2009 Dec
A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report.
2009 Dec 16
Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis.
2009 May
Dr Lazar Remen (1907-74): a forgotten pioneer in the treatment of myasthenia gravis.
2009 May
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 Sat Dec 16 11:01:05 UTC 2023
Edited
by admin
on Sat Dec 16 11:01:05 UTC 2023
Record UNII
6F5UW4E5CF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEOSTIGMINE MESYLATE
Common Name English
Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methanesulfonate
Systematic Name English
Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-, methanesulfonate (1:1)
Systematic Name English
3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium methanesulfonate
Systematic Name English
Code System Code Type Description
PUBCHEM
11659722
Created by admin on Sat Dec 16 11:01:05 UTC 2023 , Edited by admin on Sat Dec 16 11:01:05 UTC 2023
PRIMARY
CAS
873090-02-9
Created by admin on Sat Dec 16 11:01:05 UTC 2023 , Edited by admin on Sat Dec 16 11:01:05 UTC 2023
PRIMARY
FDA UNII
6F5UW4E5CF
Created by admin on Sat Dec 16 11:01:05 UTC 2023 , Edited by admin on Sat Dec 16 11:01:05 UTC 2023
PRIMARY
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