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 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
Altered residual ATP content in rat brain cortex subcellular fractions following status epilepticus induced by lithium and pilocarpine.	1998 Dec	10344793
p75 neurotrophin receptor expression is induced in apoptotic neurons after seizure.	1999 Aug 15	10436046
Prevalence of epileptic seizures along the wakefulness-sleep cycle in adult rats submitted to status epilepticus in early life.	1999 Nov	10575257
Selective alterations of glycosaminoglycans synthesis and proteoglycan expression in rat cortex and hippocampus in pilocarpine-induced epilepsy.	1999 Nov 1	10582521
Infiltration of lymphocytes in the limbic brain following stimulation of subclinical cellular immunity and low dosages of lithium and a cholinergic agent.	1999 Sep 20	10514033
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.	2000 Nov	11205735
Electroshocks delay seizures and subsequent epileptogenesis but do not prevent neuronal damage in the lithium-pilocarpine model of epilepsy.	2000 Nov	10996502
Pilocarpine-induced status epilepticus causes N-methyl-D-aspartate receptor-dependent inhibition of microsomal Mg(2+)/Ca(2+) ATPase-mediated Ca(2+) uptake.	2000 Sep	10936204
[The effect of physiological and extreme irritants on zinc metabolism in pancreatic islets and hippocampus cells].	2001	11392117
A new medication for treatment of dry mouth in Sjögren's syndrome.	2001 Apr	11404944
Exploring the potential for subtype-selective muscarinic agonists in glaucoma.	2001 Apr 27	11392632
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
An animal model of nonconvulsive status epilepticus: a contribution to clinical controversies.	2001 Feb	11240586
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
[Dry mouth].	2001 Jan 31	11252939
Visual discrimination learning impairments produced by combined transections of the anterior temporal stem, amygdala and fornix in marmoset monkeys.	2001 Jan 5	11146050
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
Evaluation of spontaneous contamination of ocular medications.	2001 Jul-Aug	11399868
Activity-induced expression of common reference genes in individual cns neurons.	2001 Jun	11406652
Salivary scintigraphy for assessing the protective effect of pilocarpine in head and neck irradiated tumours.	2001 Jun	11403176
Potential mechanism for the additivity of pilocarpine and latanoprost.	2001 Jun	11384567
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
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
Lack of effect of mossy fiber-released zinc on granule cell GABA(A) receptors in the pilocarpine model of epilepsy.	2001 May	11353010
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland.	2001 May 1	11316558
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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:36:53 GMT 2023` Edited by `admin` on `Sat Dec 16 08:36:53 GMT 2023`
Record UNII	5NX545O53Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOPILOCARPINE HYDROCHLORIDE

Common Name

English

NSC-117178

Code

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