ISOPILOCARPINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N2O2
Molecular Weight	208.2569
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=QCHFTSOMWOSFHM-WCBMZHEXSA-N

InChI=1S/C11H16N2O2/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/t8-,10+/m0/s1

HIDE SMILES / InChI

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 159 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 2578

PubMed

Title	Date	PubMed
Norepinephrine in treatment of ocular hypertension and glaucoma.	1975 Mar	1138682
[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
A new medication for treatment of dry mouth in Sjögren's syndrome.	2001 Apr	11404944
Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study.	2001 Apr	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 Apr	11311893
Alkaline phosphatase activity in whitefly salivary glands and saliva.	2001 Apr	11304750
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.	2001 Apr	11274068
Stress response to surgical procedures in the submandibular region and its influence on salivary secretion in mice.	2001 Apr	11269873
Initiation of network bursts by Ca2+-dependent intrinsic bursting in the rat pilocarpine model of temporal lobe epilepsy.	2001 Apr 1	11283235
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.	2001 Apr 17	11303773
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.	2001 Apr 27	11392629
Alteration of cardiovascular and neuronal function in M1 knockout mice.	2001 Apr 27	11392617
The effect of pilocarpine on salivary constituents in patients with chronic graft-versus-host disease.	2001 Aug	11389860
Beta-adrenergic blocker therapy and the trabecular meshwork.	2001 Feb	11372544
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.	2001 Feb	11336078
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.	2001 Feb	11322611
The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension.	2001 Feb	11318298
Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma.	2001 Feb	11318297
Normalization of spatial learning despite brain damage in rats receiving ketamine after seizure-induction: evidence for the neuromatrix.	2001 Feb	11293016
G(q/11) and G(i/o) activation profiles in CHO cells expressing human muscarinic acetylcholine receptors: dependence on agonist as well as receptor-subtype.	2001 Feb	11181437
Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide.	2001 Feb 28	11248357
Protection by selenium of lead-acetate-induced alterations on rat submandibular gland function.	2001 Jan	11339622
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat.	2001 Jan 1	11149716
[Dry mouth].	2001 Jan 31	11252939
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system.	2001 Jul	11431452
Prophylactic effects of pilocarpine hydrochloride on xerostomia models induced by X-ray irradiation in rats.	2001 Jul	11422222
Poly(2-hydroxyethyl methacrylate) film as a drug delivery system for pilocarpine.	2001 Jul	11396879
Defective fluid secretion and NaCl absorption in the parotid glands of Na+/H+ exchanger-deficient mice.	2001 Jul 20	11358967
Activity-induced expression of common reference genes in individual cns neurons.	2001 Jun	11406652
Potential mechanism for the additivity of pilocarpine and latanoprost.	2001 Jun	11384567
Behavioral and electroencephalographic analysis of seizures induced by intrahippocampal injection of granulitoxin, a neurotoxic peptide from the sea anemone Bunodosoma granulifera.	2001 Jun	11378671
Acupuncture for pilocarpine-resistant xerostomia following radiotherapy for head and neck malignancies.	2001 Jun 1	11380221
Modulators with convergent cellular actions elicit distinct circuit outputs.	2001 Jun 1	11356892
Agonistic behavior in groups of limbic epileptic male rats: pattern of brain damage and moderating effects from normal rats.	2001 Jun 29	11423076
Salivary acinar cells from aquaporin 5-deficient mice have decreased membrane water permeability and altered cell volume regulation.	2001 Jun 29	11290736
Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy.	2001 Jun 8	11382382
Normal spatial memory following postseizure treatment with ketamine: selective damage attenuates memory deficits in brain-damaged rodents.	2001 Mar	11328682
Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil.	2001 Mar	11262695
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.	2001 Mar	11259499
Reduced excitatory drive onto interneurons in the dentate gyrus after status epilepticus.	2001 Mar 15	11245688
Lithium does not synergize the peripheral action of cholinomimetics as seen in the central nervous system.	2001 Mar 23	11324716
In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug.	2001 Mar-Apr	11253934
Amino acid derivatives with anticonvulsant activity.	2001 May	11383620
Function of pulmonary neuronal M(2) muscarinic receptors in stable chronic obstructive pulmonary disease.	2001 May	11371395
Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy.	2001 May	11353010
Diurnal variation in pilocarpine-induced generalized tonic-clonic seizure activity.	2001 May	11325576
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.	2001 May 1	11316558
Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats.	2001 May 15	11331388
Loss of vesicular zinc and appearance of perikaryal zinc after seizures induced by pilocarpine.	2001 May 25	11388441

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ISOPILOCARPINE

Common Name

English

3-ISOPILOCARPINE

Common Name

English

PILOCARPINE IMPURITY, ISOPILOCARPINE- [USP IMPURITY]

Common Name

English

PILOCARPINE HYDROCHLORIDE IMPURITY ISOPILOCARPINE [USP IMPURITY]

Common Name

English

PILOCARPINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]

Common Name

English

(3R,4R)-3-ETHYL-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)DIHYDROFURAN-2(3H)-ONE

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

208-506-5