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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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
SALAGEN

Approved Use

SALAGEN 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 Date

1994
Palliative
SALAGEN

Approved Use

SALAGEN 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 Date

1994
Primary
ISOPTO CARPINE

Approved Use

Isopto 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 Date

2010
Primary
ISOPTO CARPINE

Approved Use

Isopto 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 Date

2010
Primary
ISOPTO CARPINE

Approved Use

Isopto 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 Date

2010
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Other AEs: Increased salivation, Lacrimation...
Other AEs:
Increased salivation (1 patient)
Lacrimation (1 patient)
Vomiting (1 patient)
Anxiety (1 patient)
Tremor (1 patient)
Sources:
100 mg single, oral
Overdose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
unhealthy
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
Health Status: unhealthy
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Increased salivation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Lacrimation 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Tremor 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Vomiting 1 patient
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, 46 years
Health Status: unhealthy
Age Group: 46 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
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
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
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
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
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
Page: 20.0
yes
yes
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
Page: 3.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Altered residual ATP content in rat brain cortex subcellular fractions following status epilepticus induced by lithium and pilocarpine.
1998 Dec
Effects of pilocarpine- and kainate-induced seizures on thyrotropin-releasing hormone biosynthesis and receptors in the rat brain.
1999
N-methyl-D-aspartate receptor activation regulates refractoriness of status epilepticus to diazepam.
1999
Loss of NADPH diaphorase-positive neurons in the hippocampal formation of chronic pilocarpine-epileptic rats.
1999
Growth-associated phosphoprotein expression is increased in the supragranular regions of the dentate gyrus following pilocarpine-induced seizures in rats.
1999
p75 neurotrophin receptor expression is induced in apoptotic neurons after seizure.
1999 Aug 15
Inhibition of dentate granule cell neurogenesis with brain irradiation does not prevent seizure-induced mossy fiber synaptic reorganization in the rat.
1999 Jun 1
Effects of diazepam on extracellular brain neurotransmitters in pilocarpine-induced seizures in rats.
1999 Jun 4
Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate.
1999 Nov
Selective alterations of glycosaminoglycans synthesis and proteoglycan expression in rat cortex and hippocampus in pilocarpine-induced epilepsy.
1999 Nov 1
Differential regulation of cytokine expression following pilocarpine-induced seizure.
1999 Oct
Zinc inhibition of gamma-aminobutyric acid(A) receptor function is decreased in the cerebral cortex during pilocarpine-induced status epilepticus.
1999 Oct
Cognitive functions after pilocarpine-induced status epilepticus: changes during silent period precede appearance of spontaneous recurrent seizures.
1999 Sep
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
Patterns of status epilepticus-induced substance P expression during development.
2000
Similar increases in extracellular lactic acid in the limbic system during epileptic and/or olfactory stimulation.
2000
Differential progression of Dark Neuron and Fluoro-Jade labelling in the rat hippocampus following pilocarpine-induced status epilepticus.
2000
Nonconvulsive status epilepticus in rats: impaired responsiveness to exteroceptive stimuli.
2000 Dec 20
Motor and electrographic response of refractory experimental status epilepticus in rats and effect of calcium channel blockers.
2000 Feb
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.
2000 Nov
Rapid alterations in diffusion-weighted images with anatomic correlates in a rodent model of status epilepticus.
2000 Nov-Dec
Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy.
2001
Immediate diode laser peripheral iridoplasty as treatment of acute attack of primary angle closure glaucoma: a preliminary study.
2001 Apr
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
Alkaline phosphatase activity in whitefly salivary glands and saliva.
2001 Apr
Adenosine A2A receptor knockout mice are partially protected against drug-induced catalepsy.
2001 Apr 17
Randomized double blind, placebo-controlled study of pilocarpine administered during head and neck irradiation to reduce xerostomia.
2001 Feb
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.
2001 Feb
The acute effect of pilocarpine on pulsatile ocular blood flow in ocular hypertension.
2001 Feb
Twenty-four hour intraocular pressure reduction with latanoprost compared with pilocarpine as third-line therapy in exfoliation glaucoma.
2001 Feb
An animal model of nonconvulsive status epilepticus: a contribution to clinical controversies.
2001 Feb
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
Regional and subunit-specific downregulation of acid-sensing ion channels in the pilocarpine model of epilepsy.
2001 Feb
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
The role of sensory signals from the insect coxa-trochanteral joint in controlling motor activity of the femur-tibia joint.
2001 Feb
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
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
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
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
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
Patents

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
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
by admin
on Mon Mar 31 17:55:15 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:15 GMT 2025
Record UNII
01MI4Q9DI3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pilocarpine
HSDB   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
OCUSERT PILO
Preferred Name English
PILOCARPINUM [HPUS]
Common Name English
PILOCARPOL
Common Name English
2(3H)-FURANONE, 3-ETHYLDIHYDRO-4-((1-METHYL-1H-IMIDAZOL-5-YL)METHYL)-, (3S-CIS)-
Systematic Name English
PILOCARPINE [USP MONOGRAPH]
Common Name English
PILOCARPINE [MI]
Common Name English
Pilocarpine [WHO-DD]
Common Name English
PILOCARPINE [MART.]
Common Name English
SPERSACARPINE
Common Name English
OCUCARPINE
Common Name English
PILOCARPINE [VANDF]
Common Name English
PILOCARPINE [HSDB]
Common Name English
PILOCARPINE [USP-RS]
Common Name English
PILOCARPINE [ORANGE BOOK]
Common Name English
PILOCARPINE [JAN]
Common Name English
SYNCARPINE
Common Name English
PILOKARPIN
Common Name English
Classification Tree Code System Code
WHO-VATC QN07AX01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC N07AX01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-VATC QS01EB01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
FDA ORPHAN DRUG 45990
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 21.4
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NCI_THESAURUS C47796
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000175884
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC S01EB01
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-VATC QS01EB51
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
WHO-ATC S01EB51
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000175369
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
NDF-RT N0000000104
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
Code System Code Type Description
DRUG BANK
DB01085
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
RXCUI
8328
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID1021162
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
HSDB
3163
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-128-4
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
LACTMED
Pilocarpine
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
FDA UNII
01MI4Q9DI3
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL550
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
DAILYMED
01MI4Q9DI3
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
WIKIPEDIA
PILOCARPINE
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
IUPHAR
305
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
CAS
92-13-7
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
MESH
D010862
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
PUBCHEM
5910
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
EVMPD
SUB03818MIG
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
MERCK INDEX
m8806
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY Merck Index
CHEBI
8207
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
SMS_ID
100000085284
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
DRUG CENTRAL
2166
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
NCI_THESAURUS
C62068
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1538505
Created by admin on Mon Mar 31 17:55:15 GMT 2025 , Edited by admin on Mon Mar 31 17:55:15 GMT 2025
PRIMARY
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