Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H19N2O2.Br |
Molecular Weight | 303.195 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
Molecular Formula | C12H19N2O2 |
Molecular Weight | 223.2915 |
Charge | 1 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB01400Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/neostigmine-methylsulfate-injection.html
Sources: http://www.drugbank.ca/drugs/DB01400
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
Sources: http://www.drugbank.ca/drugs/DB01400
Curator's Comment: Neostigmine, unlike physostigmine, does not cross the blood-brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8978837 |
91.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Prostigmin Approved UseNeostigmine is used for:
Treating myasthenia gravis. Launch Date1938 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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) Sources: https://pubmed.ncbi.nlm.nih.gov/11913717/ |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
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 |
|
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine. | 1984 Nov |
|
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain. | 1985 Dec |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria. | 1999 Nov |
|
Probiotics and functional abdominal bloating. | 2004 Jul |
|
Masseter muscle spasm following atracurium. | 2004 May |
|
[Myasthenia in elderly patients: a series of 23 cases]. | 2005 Dec |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22178337
In vitro, neostigmine (10⁻⁵ and 10⁻⁴ M) potentiated neurogenic relaxations in the rabbit corpus cavernosum.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:50:13 GMT 2025
by
admin
on
Mon Mar 31 17:50:13 GMT 2025
|
Record UNII |
005SYP50G5
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C47792
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID9041075
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
757233
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
114-80-7
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
DBSALT001191
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
82055
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | RxNorm | ||
|
204-054-8
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
401
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
NEOSTIGMINE BROMIDE
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
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. | ||
|
1459001
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
8246
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
005SYP50G5
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
CHEMBL278020
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
m7819
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | Merck Index | ||
|
100000092016
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
C76612
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
179557
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY | |||
|
SUB09195MIG
Created by
admin on Mon Mar 31 17:50:14 GMT 2025 , Edited by admin on Mon Mar 31 17:50:14 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> SALT/SOLVATE | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
IMPURITY (UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |