ISOPILOCARPINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N2O2.ClH
Molecular Weight	244.718
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ISOPILOCARPINE HYDROCHLORIDE

Structure Search

SMILES

Cl.CC[C@@H]1[C@@H](CC2=CN=CN2C)COC1=O

InChI

InChIKey=RNAICSBVACLLGM-KXNXZCPBSA-N

InChI=1S/C11H16N2O2.ClH/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2;/h5,7-8,10H,3-4,6H2,1-2H3;1H/t8-,10+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C11H16N2O2
Molecular Weight	208.2569
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9653952 | https://www.ncbi.nlm.nih.gov/pubmed/3701611 | https://link.springer.com/chapter/10.1007/978-3-642-45410-3_21 | https://www.ncbi.nlm.nih.gov/pubmed/1255459

Isopilocarpine is a diastereomer of pilocarpine. Isopilocarpine coexists with pilocarpine in nature and is also a degradation product of pilocarpine after oral administration to humans. It can be found in the leaves of some Pilocarpus species. Pilocarpine targets the muscarinic receptors and is approved for treatment of xerostomia. Isopilocarpine is often present in formulations of pilocarpine but has no appreciable effect on muscarinic receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M3 160 Target ID: P41984 Gene ID: 281685.0 Gene Symbol: CHRM3 Target Organism: Bos taurus (Bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3701611	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The effect of pilocarpine on salivary constituents in patients with chronic graft-versus-host disease.	2001-08	11389860
Defective fluid secretion and NaCl absorption in the parotid glands of Na+/H+ exchanger-deficient mice.	2001-07-20	11358967
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.	2001-07	11431452
Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats.	2001-07	11422222
Poly(2-hydroxyethyl methacrylate) film as a drug delivery system for pilocarpine.	2001-07	11396879
Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats.	2001-06-29	11423076
Salivary acinar cells from aquaporin 5-deficient mice have decreased membrane water permeability and altered cell volume regulation.	2001-06-29	11290736
Evaluation of spontaneous contamination of ocular medications.	2001-06-16	11399868
Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy.	2001-06-08	11382382
Acupuncture for pilocarpine-resistant xerostomia following radiotherapy for head and neck malignancies.	2001-06-01	11380221
Modulators with convergent cellular actions elicit distinct circuit outputs.	2001-06-01	11356892
Activity-induced expression of common reference genes in individual cns neurons.	2001-06	11406652
Salivary scintigraphy for assessing the protective effect of pilocarpine in head and neck irradiated tumours.	2001-06	11403176
Potential mechanism for the additivity of pilocarpine and latanoprost.	2001-06	11384567
Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera.	2001-06	11378671
Loss of vesicular zinc and appearance of perikaryal zinc after seizures induced by pilocarpine.	2001-05-25	11388441
Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats.	2001-05-15	11331388
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.	2001-05-01	11316558
Amino acid derivatives with anticonvulsant activity.	2001-05	11383620
Function of pulmonary neuronal M(2) muscarinic receptors in stable chronic obstructive pulmonary disease.	2001-05	11371395
Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy.	2001-05	11353010
Diurnal variation in pilocarpine-induced generalized tonic-clonic seizure activity.	2001-05	11325576
Exploring the potential for subtype-selective muscarinic agonists in glaucoma.	2001-04-27	11392632
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.	2001-04-27	11392629
Alteration of cardiovascular and neuronal function in M1 knockout mice.	2001-04-27	11392617
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.	2001-04-17	11303773
Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy.	2001-04-01	11283235
A new medication for treatment of dry mouth in Sjögren's syndrome.	2001-04	11404944
Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study.	2001-04	11316102
2-chloro-N(6)-cyclopentyladenosine-elicited attenuation of evoked glutamate release is not sufficient to give complete protection against pilocarpine-induced seizures in rats.	2001-04	11311893
Alkaline phosphatase activity in whitefly salivary glands and saliva.	2001-04	11304750
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.	2001-04	11274068
Stress response to surgical procedures in the submandibular region and its influence on salivary secretion in mice.	2001-04	11269873
Lithium does not synergize the peripheral action of cholinomimetics as seen in the central nervous system.	2001-03-23	11324716
In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug.	2001-03-20	11253934
Normal spatial memory following postseizure treatment with ketamine: selective damage attenuates memory deficits in brain-damaged rodents.	2001-03	11328682
Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil.	2001-03	11262695
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.	2001-03	11259499
Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide.	2001-02-28	11248357
Beta-adrenergic blocker therapy and the trabecular meshwork.	2001-02	11372544
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.	2001-02	11336078
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.	2001-02	11322611
The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension.	2001-02	11318298
Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma.	2001-02	11318297
Normalization of spatial learning despite brain damage in rats receiving ketamine after seizure-induction: evidence for the neuromatrix.	2001-02	11293016
[Dry mouth].	2001-01-31	11252939
Protection by selenium of lead-acetate-induced alterations on rat submandibular gland function.	2001-01	11339622
[The effect of physiological and extreme irritants on zinc metabolism in pancreatic islets and hippocampus cells].	2001	11392117
Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy.	2001	11264918
Norepinephrine in treatment of ocular hypertension and glaucoma.	1975-03	1138682

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:12:25 GMT 2025` Edited by `admin` on `Mon Mar 31 22:12:25 GMT 2025`
Record UNII	5NX545O53Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPILOCARPINE HYDROCHLORIDE

Common Name

English

NSC-117178

Preferred Name

English

2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, MONOHYDROCHLORIDE, (3R,4R)-

Systematic Name

English

3-ISOPILOCARPINE, MONOHYDROCHLORIDE

Common Name

English

.BETA.-PILOCARPINE HYDROCHLORIDE

Common Name

English

Code System Code Type Description

FDA UNII

5NX545O53Z