Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H19N2O2 |
Molecular Weight | 223.2915 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 1 |
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
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 |
---|---|---|
Antagonism of succinylcholine paralysis in a patient with atypical pseudocholinesterase. | 1972 May |
|
Neuropharmacology of the parasitic trematode, Schistosoma mansoni. | 1983 Jan |
|
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 |
|
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 |
|
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 |
|
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 |
|
[Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine]. | 2000 Dec |
|
Factors affecting gallbladder motility: drugs. | 2003 Jul |
|
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation. | 2003 Jun 15 |
|
Heart block and prolonged Q-Tc interval following muscle relaxant reversal: a case report. | 2008 Feb |
|
The effect of piroxicam on the formation of postoperative, intraabdominal adhesion in rats. | 2008 Oct |
|
Neostigmine but not sugammadex impairs upper airway dilator muscle activity and breathing. | 2008 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.
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N07AA01
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FDA ORPHAN DRUG |
388812
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S01EB06
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N07AA51
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QN07AA51
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C47792
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QN07AA01
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QS01EB06
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NEOSTIGMINE
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DB01400
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Neostigmine
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ACTIVE MOIETY
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