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 |
---|---|---|
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 |
|
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat. | 1987 Mar |
|
Impairment of the antagonism of vecuronium-induced paralysis and intra-operative disopyramide administration. | 1989 Jan |
|
Propofol bradycardia. | 1991 Jan |
|
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 |
|
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 |
|
[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 |
|
Measurement of gastric contraction activity in dogs by means of AC biosusceptometry. | 2003 May |
|
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 |
|
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 |
|
Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report. | 2008 Feb |
|
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing. | 2008 Sep |
|
Determining the neurotransmitter concentration profile at active synapses. | 2009 Dec |
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
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Wed Jul 05 22:29:46 UTC 2023
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Wed Jul 05 22:29:46 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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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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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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