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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 C12H19N2O2
Molecular Weight 223.2915
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
The prevention of muscle pains associated with the use of suxamethonium.
1967 Dec
Myasthenia gravis syndrome associated with trimethadione.
1970 Jun 29
Prolonged curarization in a patient with renal failure. Case report.
1971 May
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase.
1972 May
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy.
1973 Apr 23
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
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain.
1985 Dec
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol.
1987 Dec
Complete heart block following glycopyrronium/neostigmine mixture.
1989 May
Prolonged paralysis following suxamethonium and the use of neostigmine.
1990 Sep
Propofol bradycardia.
1991 Jan
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
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
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
Low-dose clonidine and neostigmine prolong the duration of intrathecal bupivacaine-fentanyl for labor analgesia.
2000 Feb
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
Factors affecting gallbladder motility: drugs.
2003 Jul
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation.
2003 Jun 15
Measurement of gastric contraction activity in dogs by means of AC biosusceptometry.
2003 May
A conscious mouse model of gastric ileus using clinically relevant endpoints.
2005 Jun 6
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea.
2008 Apr
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
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing.
2008 Sep
A two cases clinical report of mandragora poisoning in primary care in Crete, Greece: two case report.
2009 Dec 16
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 Fri Dec 15 15:12:33 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:33 GMT 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 Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9041075
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
NSC
757233
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
CAS
114-80-7
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
DRUG BANK
DBSALT001191
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
RXCUI
82055
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
204-054-8
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
INN
401
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NEOSTIGMINE BROMIDE
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 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 Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
PUBCHEM
8246
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
FDA UNII
005SYP50G5
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL278020
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
MERCK INDEX
m7819
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY Merck Index
SMS_ID
100000092016
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
NCI_THESAURUS
C76612
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
CHEBI
179557
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
EVMPD
SUB09195MIG
Created by admin on Fri Dec 15 15:12:33 GMT 2023 , Edited by admin on Fri Dec 15 15:12:33 GMT 2023
PRIMARY
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