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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 of Pilocarpine

SMILES

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

InChI

InChIKey=QCHFTSOMWOSFHM-WPRPVWTQSA-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

Molecular Formula C11H16N2O2
Molecular Weight 208.2569
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Pilocarpine is an alkaloid extracted from plants of the genus Pilocarpus. The drug stimulates the muscarinic receptors (especially M3, which is expressed in smooth muscles and glands) and thus induces salivation, hypertension and water intake. Pilocarpine was appoved by FDA for the alleviation of symptoms of xerostomia in patients who have undergone radiation therapy to their head and neck cancer and in patients with Sjogren's Syndrome. Ophthalmic solution of the drug is prescribed for the treatment of glaucoma, ocular hypertension, postoperative elevated intraocular pressure, etc.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
SALAGEN
Palliative
SALAGEN
Primary
ISOPTO CARPINE
Primary
ISOPTO CARPINE
Primary
ISOPTO CARPINE

Cmax

ValueDoseCo-administeredAnalytePopulation
15 ng/mL
5 mg 3 times / day multiple, oral
PILOCARPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
33 ng × h/mL
5 mg 3 times / day multiple, oral
PILOCARPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.76 h
5 mg 3 times / day multiple, oral
PILOCARPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
5 mg 3 times / day multiple, oral
PILOCARPINE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Ophthalmic solution: Instill one drop in the eye(s) up to four times daily. Oral formulation: the recommended dose is 5 mg taken three times a day (Head and Neck Cancer Patients) or 5 mg taken four times a day (Sjogren's Syndrome Patients).
Route of Administration: Other
In Vitro Use Guide
Rat submandibular gland cells were treated wth 100 uM pilocarpine. The drug elicited a small and sustained increase in [Ca2+]i, indicating that pilocarpine acts as a partial agonist for mAChR-mediated Ca2+ responses.
Substance Class Chemical
Record UNII
01MI4Q9DI3
Record Status Validated (UNII)
Record Version