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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N2O2
Molecular Weight 147.1957
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of CARBAMOYLCHOLINE

SMILES

C[N+](C)(C)CCOC(=N)O

InChI

InChIKey=VPJXQGSRWJZDOB-UHFFFAOYSA-O
InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1

HIDE SMILES / InChI

Molecular Formula C6H15N2O2
Molecular Weight 147.1957
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Carbachol is a potent cholinergic (parasympathomimetic) agent which produces constriction of the iris and ciliary body resulting in reduction in intraocular pressure.

CNS Activity

Curator's Comment:: Carbachol does not pass the blood-brain-barrier (BBB) however it produces cholinergic effects on brain blood vessels from the luminal side, whereas the effects on dural and extracranial vessels are from both the luminal and abluminal side since they are devoid of BBB

Originator

Curator's Comment:: reference retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1550933/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MIOSTAT

Approved Use

Intraocular use for obtaining miosis during surgery. In addition, MIOSTAT (carbachol intraocular solution, USP) reduces the intensity of intraocular pressure elevation in the first 24 hours after cataract surgery.

Launch Date

8.6486401E10
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.
1975 Feb
Midbrain interaction with the hypothalamus in expression of aggressive behavior in cats.
1977
Muscarine- and carbachol-induced aggressions: fear and irritable kinds of aggressions.
1977 Dec 28
Evidence that a nigral gabaergic--cholinergic balance controls posture.
1979 Jan 1
[Effects of atropine and scopolamine on the aggressive behavior and convulsions induced by carbachol and eserine injected into the cerebral ventricles of the cat].
1980
Seizures induced by carbachol, morphine, and leucine-enkephalin: a comparison.
1983 Apr
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.
1983 Jan
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.
1984 Oct
Cardiovascular characterization of UL-FS 49, 1,3,4,5-tetrahydro-7,8-dimethoxy-3-[3-][2-(3,4-dimethoxyphenyl)ethyl] methylimino]propyl]-2H-3-benzazepin-2-on hydrochloride, a new "specific bradycardic agent".
1984 Sep 3
Cardiovascular effects of cholinergic agents in the ventral-lateral midbrain periaqueductal gray of the rat.
1987 Dec
Novel 'soft' anticholinergic agents.
1988 Feb
The effect of cholinergic stimulation in the nucleus accumbens on locomotor behavior.
1988 Feb 16
Anatomical analysis of frontal cortex sites at which carbachol induces motor seizures in the rat.
1988 May
Renal function during onset of carbachol-induced hypertension in conscious rats.
1990
Studies on the development of tolerance and potential spinal neurotoxicity after chronic intrathecal carbachol-antinociception in the rat.
1991 Feb
Susceptibility to seizures produced by chemical convulsants and maximal electric shock in rats after electrolytic lesions into the red nucleus.
1992 Jan
Sites at which neuropeptide Y modulates parasympathetic control of heart rate in guinea pigs and rats.
1992 May 1
Myoclonic and tonic seizures elicited by microinjection of cholinergic drugs into the inferior colliculus.
1999 Sep-Oct
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat.
2000 Dec
Cardiovascular studies on different classes of soft drugs.
2000 Mar
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.
2002 Apr 19
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
Impaired parasympathetic heart rate control in mice with a reduction of functional G protein betagamma-subunits.
2002 Feb
Physiological antagonism between ventricular beta 1-adrenoceptors and alpha 1-adrenoceptors but no evidence for beta 2- and beta 3-adrenoceptor function in murine heart.
2002 May
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.
2003 Dec
Critical role for NHE1 in intracellular pH regulation in pancreatic acinar cells.
2003 Nov
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.
2003 Oct
Crucial role of histamine for regulation of gastric acid secretion ascertained by histidine decarboxylase-knockout mice.
2003 Oct
Role of phospholipase D signaling in ethanol-induced inhibition of carbachol-stimulated DNA synthesis of 1321N1 astrocytoma cells.
2004 Aug
Cyclic AMP/protein kinase a signal attenuates Ca(2+)-induced fibroblast growth factor-1 synthesis in rat cortical neurons.
2004 Aug 15
Regulation of antiprotease and antimicrobial protein secretion by airway submucosal gland serous cells.
2004 Sep 10
[Effects of carbachol on apoptosis of peripheral white blood cells and expression of cytokines in rats suffering from gut ischemia/reperfusion injury].
2005 Feb
Case report: acute unintentional carbachol intoxication.
2006
Roles of protein kinase C, Ca2+, Pyk2, and c-Src in agonist activation of rat lacrimal gland p42/p44 MAPK.
2006 Aug
Muscarinic cholinoceptor activation modulates DNA synthesis and CD40 expression in fibroblast cells.
2006 Jul
[Effects of carbachol on apoptosis of intestinal epithelial cells after gut ischemia/reperfusion in rat].
2007 Aug
Enhanced proliferation of SNU-407 human colon cancer cells by muscarinic acetylcholine receptors.
2008 Nov 30
Muscarinic receptors prevent oxidative stress-mediated apoptosis induced by domoic acid in mouse cerebellar granule cells.
2009 Apr
Carbachol induces headache, but not migraine-like attacks, in patients with migraine without aura.
2010 Mar
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.
2010 Oct
Molecular basis of inhibition of substrate hydrolysis by a ligand bound to the peripheral site of acetylcholinesterase.
2010 Sep 6
Characterisation of acetylcholinesterase release from neuronal cells.
2013 Mar 25
Patents

Patents

Sample Use Guides

MIOSTAT (CARBACHOL INTRAOCULAR SOLUTION, USP) 0.01% Aseptically remove the sterile vial from the blister package by peeling the backing paper and dropping the vial onto a sterile tray. Withdraw the contents into a dry sterile syringe, and replace the needle with an atraumatic cannula prior to intraocular instillation. No more than one-half milliliter should be gently instilled into the anterior chamber for the production of satisfactory miosis. It may be instilled before or after securing sutures. Miosis is usually maximal within two to five minutes after application.
Route of Administration: Other
In the dose-course studies, carbachol showed significant increase in phosphorylation of MYPT1 at Thr696 (p-MYPT1) from concentrations of 15-100 μM based on Western blot results (p < 0.05, ANOVA test). In the time-course studies, treatment of cells with 15 μM of carbachol significantly enhanced the expression of p-MYPT1 from 3 to 15 h (p < 0.05, ANOVA test) and induced the expression of Rho A from 10 to 120 min (p < 0.05, ANOVA test).
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:27:56 UTC 2021
Edited
by admin
on Sat Jun 26 01:27:56 UTC 2021
Record UNII
54Z8M50D6Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBAMOYLCHOLINE
Systematic Name English
ETHANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-
Systematic Name English
CARBAMYLCHOLINE
Systematic Name English
CHOLINE CARBAMATE
Systematic Name English
CARBACHOLINE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175884
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
NDF-RT N0000175369
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
Code System Code Type Description
EPA CompTox
462-58-8
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY
DRUG BANK
DB00411
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY
PUBCHEM
2551
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY
RXCUI
1546387
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY RxNorm
CAS
462-58-8
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY
FDA UNII
54Z8M50D6Q
Created by admin on Sat Jun 26 01:27:56 UTC 2021 , Edited by admin on Sat Jun 26 01:27:56 UTC 2021
PRIMARY
Related Record Type Details
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