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
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 | BrH |
Molecular Weight | 80.912 |
Charge | 0 |
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 |
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 Date-9.7839363E11 |
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 |
---|---|---|
Myasthenia gravis syndrome associated with trimethadione. | 1970 Jun 29 |
|
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 |
|
Effect of halogenated anaesthetics on heart rate changes during reversal of neuromuscular block with glycopyrrolate and neostigmine. | 1984 Nov |
|
Prolonged bradycardia and hypotension after neostigmine administration in a patient receiving atenolol. | 1987 Dec |
|
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 |
|
Spinal neostigmine diminishes, but does not abolish, hypotension from spinal bupivacaine in sheep. | 1996 Nov |
|
[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 |
|
Fresh frozen plasma transfusion for reversal of prolonged post-anaesthesia apnoea. | 2008 Apr |
|
Interventions for heartburn in pregnancy. | 2008 Oct 8 |
|
Relationship between anti-acetylcholine receptor antibody titres and severity of myasthenia gravis. | 2009 May |
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
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on
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Wed Jul 05 22:44:02 UTC 2023
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Record UNII |
005SYP50G5
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Validated (UNII)
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NCI_THESAURUS |
C47792
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NEOSTIGMINE BROMIDE
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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. | ||
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M7819
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SUB09195MIG
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