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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N2O2.Cl
Molecular Weight 182.6487
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBACHOL

SMILES

C[N+](C)(C)CCOC(=N)[O-].Cl

InChI

InChIKey=AIXAANGOTKPUOY-UHFFFAOYSA-N
InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H

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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
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
Sustained atrial fibrillation induced by carbachol, methacholine and bethanechol.
1971 Apr
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.
1976 Nov
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
Subclassification of muscarinic receptors in the heart, urinary bladder and sympathetic ganglia in the pithed rat. Selectivity of some classical agonists.
1985 Dec
A crucial epileptogenic site in the deep prepiriform cortex.
1985 Oct 17-23
Cholinergic induction of seizures in the rat prefrontal cortex.
1986 Jun 23
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.
1987
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
Catalepsy induced by carbachol microinjected into the pontine reticular formation of rats.
1990 Jul 31
Excitatory modulation by a spinal cholinergic system of a descending sympathoexcitatory pathway in rats.
1992 Mar
Sites at which neuropeptide Y modulates parasympathetic control of heart rate in guinea pigs and rats.
1992 May 1
Regeneration of cardiomyocytes from bone marrow: Use of mesenchymal stem cell for cardiovascular tissue engineering.
2003 Mar
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.
2005 Dec
Actin and non-muscle myosin II facilitate apical exocytosis of tear proteins in rabbit lacrimal acinar epithelial cells.
2005 Oct 15
Theoretical and experimental investigation of calcium-contraction coupling in airway smooth muscle.
2006
Case report: acute unintentional carbachol intoxication.
2006
Muscarinic acetylcholine receptors mediate oligodendrocyte progenitor survival through Src-like tyrosine kinases and PI3K/Akt pathways.
2006 Apr
Roles of protein kinase C, Ca2+, Pyk2, and c-Src in agonist activation of rat lacrimal gland p42/p44 MAPK.
2006 Aug
Novelty exploration elicits a reversal of acute stress-induced modulation of hippocampal synaptic plasticity in the rat.
2006 Dec 1
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
Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.
2007 Feb
Testosterone and progesterone rapidly attenuate plasma membrane Gbetagamma-mediated signaling in Xenopus laevis oocytes by signaling through classical steroid receptors.
2007 Jan
Endogenous RGS proteins modulate SA and AV nodal functions in isolated heart: implications for sick sinus syndrome and AV block.
2007 May
Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells.
2007 Sep
A novel assay of Gi/o-linked G protein-coupled receptor coupling to potassium channels provides new insights into the pharmacology of the group III metabotropic glutamate receptors.
2008 Apr
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.
2008 Jul
Monitoring the reaction of carbachol with acetylcholinesterase by thioflavin T fluorescence and acetylthiocholine hydrolysis.
2008 Sep 25
Histamine H1 receptor induces cytosolic calcium increase and aquaporin translocation in human salivary gland cells.
2009 Aug
Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae.
2010 Aug
Aggravation of seizure-associated microvascular injuries by ibuprofen may involve multiple pathways.
2010 Dec
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.
2010 Jun
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.
2010 Jun 15
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
Antispasmodic effects of eugenol on rat airway smooth muscle.
2011 Dec
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.
2011 Feb 18
Interaction of bispyridinium compounds with the orthosteric binding site of human α7 and Torpedo californica nicotinic acetylcholine receptors (nAChRs).
2011 Sep 25
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 Fri Jun 25 20:52:11 UTC 2021
Edited
by admin
on Fri Jun 25 20:52:11 UTC 2021
Record UNII
8Y164V895Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBACHOL
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
CARBACHOL [USP-RS]
Common Name English
CARBACHOL [EP MONOGRAPH]
Common Name English
CARBACHOLINE CHLORIDE
Systematic Name English
MIOSTAT
Brand Name English
CARBACHOL [MART.]
Common Name English
NSC-32865
Code English
CARBACHOL [EP]
Common Name English
ETHANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-, CHLORIDE
Systematic Name English
CARBACHOL [VANDF]
Common Name English
CARBACHOL [HSDB]
Common Name English
CHOLINE CHLORIDE, CARBAMATE
Systematic Name English
CARBACHOL CHLORIDE
Common Name English
CARBASTAT
Brand Name English
CARBACHOL [JAN]
Common Name English
CARBACHOL [INN]
Common Name English
CARBACHOL [MI]
Common Name English
CARBACHOL [USP MONOGRAPH]
Common Name English
CARBACHOL [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29705
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-ATC S01EB02
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-ATC N07AB01
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
NDF-RT N0000175884
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-VATC QS01EB02
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
WHO-VATC QA03AB92
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
Code System Code Type Description
PUBCHEM
5831
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
NCI_THESAURUS
C47430
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
DRUG BANK
DB00411
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
DRUG CENTRAL
488
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
EVMPD
SUB06087MIG
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
IUPHAR
298
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
USP_CATALOG
1092009
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M3051
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY Merck Index
MESH
D002217
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL965
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
EPA CompTox
51-83-2
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
CAS
51-83-2
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
HSDB
6373
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
RXCUI
1999
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY RxNorm
INN
383
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
FDA UNII
8Y164V895Y
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
LACTMED
Carbachol
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-127-3
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
WIKIPEDIA
Carbachol
Created by admin on Fri Jun 25 20:52:11 UTC 2021 , Edited by admin on Fri Jun 25 20:52:11 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Duration of Action PHARMACOKINETIC INTRAOCULAR ADMINISTRATION
PHARMACOKINETIC