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
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
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 |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P20309 Gene ID: 1131.0 Gene Symbol: CHRM3 Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | SALAGEN Approved UseSALAGEN Tablets are indicated for 1) the treatment of symptoms of dry mouth from salivary gland hypofunction caused by radiotherapy for cancer of the head and neck; and 2) the treatment of symptoms of dry mouth in patients with Sjogren's syndrome. Launch Date1994 |
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Palliative | SALAGEN Approved UseSALAGEN Tablets are indicated for 1) the treatment of symptoms of dry mouth from salivary gland hypofunction caused by radiotherapy for cancer of the head and neck; and 2) the treatment of symptoms of dry mouth in patients with Sjogren's syndrome. Launch Date1994 |
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Primary | ISOPTO CARPINE Approved UseIsopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular
hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis. Launch Date2010 |
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Primary | ISOPTO CARPINE Approved UseIsopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular
hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis. Launch Date2010 |
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Primary | ISOPTO CARPINE Approved UseIsopto Carpine is a muscarinic cholinergic agonist indicated for (1) the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular
hypertension; (2) the management of acute angle-closure glaucoma; (3) the prevention of postoperative elevated IOP associated with laser surgery; (4) the induction of miosis. Launch Date2010 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15 ng/mL |
5 mg 3 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PILOCARPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33 ng × h/mL |
5 mg 3 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PILOCARPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.76 h |
5 mg 3 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PILOCARPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
5 mg 3 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PILOCARPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 % 4 times / day multiple, ophthalmic Recommended Dose: 2 %, 4 times / day Route: ophthalmic Route: multiple Dose: 2 %, 4 times / day Sources: |
unhealthy, 44-75 years Health Status: unhealthy Age Group: 44-75 years Sex: M Sources: |
Disc. AE: Vision blurred... AEs leading to discontinuation/dose reduction: Vision blurred (moderate, 2 patients) Sources: |
20 mg single, oral Overdose |
unhealthy, 46 years |
Other AEs: Increased salivation, Lacrimation... Other AEs: Increased salivation (1 patient) Sources: Lacrimation (1 patient) Vomiting (1 patient) Anxiety (1 patient) Tremor (1 patient) |
100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
1.54 % 3 times / day multiple, topical Recommended Dose: 1.54 %, 3 times / day Route: topical Route: multiple Dose: 1.54 %, 3 times / day Sources: |
unhealthy |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Vision blurred | moderate, 2 patients Disc. AE |
2 % 4 times / day multiple, ophthalmic Recommended Dose: 2 %, 4 times / day Route: ophthalmic Route: multiple Dose: 2 %, 4 times / day Sources: |
unhealthy, 44-75 years Health Status: unhealthy Age Group: 44-75 years Sex: M Sources: |
Anxiety | 1 patient | 20 mg single, oral Overdose |
unhealthy, 46 years |
Increased salivation | 1 patient | 20 mg single, oral Overdose |
unhealthy, 46 years |
Lacrimation | 1 patient | 20 mg single, oral Overdose |
unhealthy, 46 years |
Tremor | 1 patient | 20 mg single, oral Overdose |
unhealthy, 46 years |
Vomiting | 1 patient | 20 mg single, oral Overdose |
unhealthy, 46 years |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 3.0 |
moderate | |||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
yes [Ki 1 uM] | |||
yes [Ki 360 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
weak | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=20 Page: 20.0 |
||
yes | ||||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
yes | |||
Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
yes | unlikely (co-administration study) Comment: Given the low systemic exposure following topical ocular administration of ISOPTO® Carpine, clinically relevant drug-drug interactions based on CYP450 interactions is not expected for ISOPTO Carpine Sources: https://www.fda.gov/media/79033/download#page=3 Page: 3.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Altered residual ATP content in rat brain cortex subcellular fractions following status epilepticus induced by lithium and pilocarpine. | 1998 Dec |
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Effects of pilocarpine- and kainate-induced seizures on thyrotropin-releasing hormone biosynthesis and receptors in the rat brain. | 1999 |
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N-methyl-D-aspartate receptor activation regulates refractoriness of status epilepticus to diazepam. | 1999 |
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Loss of NADPH diaphorase-positive neurons in the hippocampal formation of chronic pilocarpine-epileptic rats. | 1999 |
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Growth-associated phosphoprotein expression is increased in the supragranular regions of the dentate gyrus following pilocarpine-induced seizures in rats. | 1999 |
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p75 neurotrophin receptor expression is induced in apoptotic neurons after seizure. | 1999 Aug 15 |
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Inhibition of dentate granule cell neurogenesis with brain irradiation does not prevent seizure-induced mossy fiber synaptic reorganization in the rat. | 1999 Jun 1 |
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Effects of diazepam on extracellular brain neurotransmitters in pilocarpine-induced seizures in rats. | 1999 Jun 4 |
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Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. | 1999 Nov |
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Selective alterations of glycosaminoglycans synthesis and proteoglycan expression in rat cortex and hippocampus in pilocarpine-induced epilepsy. | 1999 Nov 1 |
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Differential regulation of cytokine expression following pilocarpine-induced seizure. | 1999 Oct |
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Zinc inhibition of gamma-aminobutyric acid(A) receptor function is decreased in the cerebral cortex during pilocarpine-induced status epilepticus. | 1999 Oct |
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Cognitive functions after pilocarpine-induced status epilepticus: changes during silent period precede appearance of spontaneous recurrent seizures. | 1999 Sep |
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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 |
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Patterns of status epilepticus-induced substance P expression during development. | 2000 |
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Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation. | 2000 |
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Differential progression of Dark Neuron and Fluoro-Jade labelling in the rat hippocampus following pilocarpine-induced status epilepticus. | 2000 |
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Nonconvulsive status epilepticus in rats: impaired responsiveness to exteroceptive stimuli. | 2000 Dec 20 |
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Motor and electrographic response of refractory experimental status epilepticus in rats and effect of calcium channel blockers. | 2000 Feb |
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In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy. | 2000 Nov |
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Rapid alterations in diffusion-weighted images with anatomic correlates in a rodent model of status epilepticus. | 2000 Nov-Dec |
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Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy. | 2001 |
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Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study. | 2001 Apr |
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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 |
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Alkaline phosphatase activity in whitefly salivary glands and saliva. | 2001 Apr |
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Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy. | 2001 Apr 17 |
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Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia. | 2001 Feb |
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Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats. | 2001 Feb |
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The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension. | 2001 Feb |
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Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma. | 2001 Feb |
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An animal model of nonconvulsive status epilepticus: a contribution to clinical controversies. | 2001 Feb |
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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 |
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Regional and subunit-specific downregulation of acid-sensing ion channels in the pilocarpine model of epilepsy. | 2001 Feb |
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Relationship between neuronal loss and interictal glucose metabolism during the chronic phase of the lithium-pilocarpine model of epilepsy in the immature and adult rat. | 2001 Feb |
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The role of sensory signals from the insect coxa-trochanteral joint in controlling motor activity of the femur-tibia joint. | 2001 Feb |
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Do recurrent febrile convulsions decrease the threshold for pilocarpine-induced seizures? Effects of nitric oxide. | 2001 Feb 28 |
|
Uveal effusion after cataract surgery: an echographic study. | 2001 Jan |
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Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat. | 2001 Jan 1 |
|
Innervation of sweat glands in the forehead. A study in patients with Horner's syndrome. | 2001 Jan 15 |
|
[Dry mouth]. | 2001 Jan 31 |
|
Visual discrimination learning impairments produced by combined transections of the anterior temporal stem, amygdala and fornix in marmoset monkeys. | 2001 Jan 5 |
|
Reliable measurement of mouse intraocular pressure by a servo-null micropipette system. | 2001 Jul |
|
Long-term alteration of calcium homeostatic mechanisms in the pilocarpine model of temporal lobe epilepsy. | 2001 Jun 8 |
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Cocaine abuse, generalized myasthenia, complete external ophthalmoplegia, and pseudotonic pupil. | 2001 Mar |
|
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model. | 2001 Mar |
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Reconstruction of an in vitro cornea and its use for drug permeation studies from different formulations containing pilocarpine hydrochloride. | 2001 Mar |
|
Reduced excitatory drive onto interneurons in the dentate gyrus after status epilepticus. | 2001 Mar 15 |
|
Metabotropic glutamate receptor 8 in the rat hippocampus after pilocarpine induced status epilepticus. | 2001 Mar 16 |
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In vivo evaluation of submicron emulsions with pilocarpine: the effect of pH and chemical form of the drug. | 2001 Mar-Apr |
|
Calculation of the uncertainty in complication probability for various dose-response models, applied to the parotid gland. | 2001 May 1 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25886199
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
Created
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Record UNII |
01MI4Q9DI3
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WHO-VATC |
QN07AX01
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WHO-ATC |
N07AX01
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QS01EB01
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FDA ORPHAN DRUG |
45990
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WHO-ESSENTIAL MEDICINES LIST |
21.4
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NDF-RT |
N0000000104
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NCI_THESAURUS |
C47796
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N0000175884
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WHO-ATC |
S01EB01
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QS01EB51
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S01EB51
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N0000175369
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N0000000104
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N0000000104
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
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TARGET -> AGONIST | |||
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TARGET -> AGONIST | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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