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
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
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 |
---|---|---|
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 |
|
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 |
|
Abnormal responses to morphine-neostigmine in patients with undefined biliary type pain. | 1985 Dec |
|
Portal hypertension secondary to azathioprine in myasthenia gravis. | 1988 Dec |
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Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats. | 1992 Mar |
|
Subarachnoid neostigmine does not affect blood pressure or heart rate during bupivacaine spinal anesthesia. | 1996 Nov-Dec |
|
Postoperative reparalysis after rocuronium following nebulized epinephrine. | 1997 Mar |
|
Neuromuscular blockade after clindamycin administration: a case report. | 1999 May |
|
International Association for the Study of Pain--Ninth World congress. 22-27 August 1999, Vienna, Austria. | 1999 Nov |
|
Sex differences in cholinergic analgesia II: differing mechanisms in two models of allodynia. | 1999 Nov |
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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 |
|
Cardiac responses of Pacific oyster Crassostrea gigas to agents modulating cholinergic function. | 2004 Dec |
|
Probiotics and functional abdominal bloating. | 2004 Jul |
|
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 |
|
Prucalopride: the evidence for its use in the treatment of chronic constipation. | 2008 Jun |
|
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 |
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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admin
on
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Fri Dec 15 14:57:45 UTC 2023
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Record UNII |
3982TWQ96G
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Record Status |
Validated (UNII)
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Record Version |
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N07AA01
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WHO-ESSENTIAL MEDICINES LIST |
20
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FDA ORPHAN DRUG |
388812
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S01EB06
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QA03AB93
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677
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N07AA51
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N0000175723
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QN07AA51
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NCI_THESAURUS |
C47792
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QN07AA01
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WHO-VATC |
QS01EB06
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D009388
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SUB03411MIG
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NEOSTIGMINE
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DB01400
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1897
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m7819
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CHEMBL278020
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C75024
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59-99-4
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Neostigmine
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100000085714
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT |
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IONIC MOIETY |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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