U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H19N5O4
Molecular Weight 321.3318
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAMCICLOVIR

SMILES

CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O

InChI

InChIKey=GGXKWVWZWMLJEH-UHFFFAOYSA-N
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

HIDE SMILES / InChI

Molecular Formula C14H19N5O4
Molecular Weight 321.3318
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3040998 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020363s037lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2754699

Penciclovir (DENAVIR®) is a synthetic acyclic guanine derivative with antiviral activity, mainly used to treat infections from herpes simplex virus (HSV) types 1 and 2. In cells infected with HSV-1 or HSV-2, the viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted by cellular kinases to the active form penciclovir triphosphate. Biochemical studies demonstrate that penciclovir triphosphate inhibits HSV polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited. Famciclovir (FAMVIR®) is a prodrug form of penciclovir with improved oral bioavailability.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.0 µM [Ki]
Target ID: P89453
Gene ID: 1487316.0
Gene Symbol: NA
Target Organism: Human herpesvirus 2 (strain HG52) (HHV-2) (Human herpes simplex virus|||2)
9.5 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DENAVIR

Approved Use

DENAVIR® is a nucleoside analog HSV DNA polymerase inhibitor indicated for the treatment of recurrent herpes labialis (cold sores) in adults and children 12 years of age and older.

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0 ng/mL
1.8 mg single, topical
dose: 1.8 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
PENCICLOVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0 ng/mL
1.8 mg 1 times / day steady-state, topical
dose: 1.8 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
PENCICLOVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6.6 μg/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.6 μg/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.3 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.9 μg/mL
125 mg single, oral
dose: 125 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
17.9 μg × h/mL
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.48 μg × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.95 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
12.1 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.24 μg × h/mL
125 mg single, oral
dose: 125 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PENCICLOVIR unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 12 times / day multiple, topical
Recommended
Dose: 1 %, 12 times / day
Route: topical
Route: multiple
Dose: 1 %, 12 times / day
Sources: Page: Study 024
unhealthy, 39
n = 782
Health Status: unhealthy
Condition: Recurrent Herpes Simplex Labialis
Age Group: 39
Sex: M+F
Population Size: 782
Sources: Page: Study 024
Disc. AE: Dissociative disorder...
AEs leading to
discontinuation/dose reduction:
Dissociative disorder
Sources: Page: Study 024
750 mg 3 times / day multiple, oral
MTD
unhealthy
1500 mg single, oral
Recommended
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Herpes labialis
Sources: Page: p.1
Other AEs: Acute renal failure...
AEs

AEs

AESignificanceDosePopulation
Dissociative disorder Disc. AE
1 % 12 times / day multiple, topical
Recommended
Dose: 1 %, 12 times / day
Route: topical
Route: multiple
Dose: 1 %, 12 times / day
Sources: Page: Study 024
unhealthy, 39
n = 782
Health Status: unhealthy
Condition: Recurrent Herpes Simplex Labialis
Age Group: 39
Sex: M+F
Population Size: 782
Sources: Page: Study 024
Acute renal failure
1500 mg single, oral
Recommended
Dose: 1500 mg
Route: oral
Route: single
Dose: 1500 mg
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Herpes labialis
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
In vitro activities of penciclovir and acyclovir against herpes simplex virus types 1 and 2.
1992 Sep
Absence of rapid selection for acyclovir or penciclovir resistance following suboptimal oral prodrug therapy of HSV-infected mice.
2001
Current and potential therapies for the treatment of herpesvirus infections.
2001
Current and potential therapies for the treatment of herpesvirus infections.
2001
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.
2001 Apr-Jul
Antiviral drugs: current state of the art.
2001 Aug
In vitro and in vivo activity of 1-O-hexadecylpropanediol-3-phospho-ganciclovir and 1-O-hexadecylpropanediol-3-phospho-penciclovir in cytomegalovirus and herpes simplex virus infections.
2001 Jan
Pharmacokinetic studies of 2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyl-oxybut-1-yl)purine, an oral prodrug for the antiviral agent penciclovir.
2001 Jul
Recent developments in herpesvirus therapy.
2001 Mar
Ganciclovir and penciclovir, but not acyclovir, induce apoptosis in herpes simplex virus thymidine kinase-transformed baby hamster kidney cells.
2001 May
Herpes simplex virus: clinical presentation and treatment.
2001 May
Penciclovir for the treatment of herpes simplex labialis: a review.
2001 May-Jun
Preclinical evaluation of the penciclovir analog 9-(4-[(18)F]fluoro-3-hydroxymethylbutyl)guanine for in vivo measurement of suicide gene expression with PET.
2001 Nov
Novel 5-vinyl pyrimidine nucleosides with potent anti-hepatitis B virus activity.
2001 Nov 19
Separation methods for acyclovir and related antiviral compounds.
2001 Nov 25
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.
2001 Nov-Dec
A simplified one-pot synthesis of 9-[(3-[18F]fluoro-1-hydroxy-2-propoxy)methyl]guanine([18F]FHPG) and 9-(4-[18F]fluoro-3-hydroxymethylbutyl)guanine ([18F]FHBG) for gene therapy.
2001 Oct
Lack of effect of treatment with penciclovir or acyclovir on the establishment of latent HSV-1 in primary sensory neurons in culture.
2001 Oct
A review of antiviral therapy for herpes labialis.
2001 Sep
Comparison of new topical treatments for herpes labialis: efficacy of penciclovir cream, acyclovir cream, and n-docosanol cream against experimental cutaneous herpes simplex virus type 1 infection.
2001 Sep
Comparison of methods for identifying resistant herpes simplex virus and measuring antiviral susceptibility.
2002 Jan
The A167Y mutation converts the herpes simplex virus type 1 thymidine kinase into a guanosine analogue kinase.
2002 May 21
Antiviral agents: Non-antiretroviral [correction of Nonantiviral] drugs.
2002 Oct
CL1-SR39: A noninvasive molecular imaging model of prostate cancer suicide gene therapy using positron emission tomography.
2002 Sep
[4'-Thio-5-ethyl-2'-deoxyuridine 5'-phosphonates: synthesis and antiviral activity].
2002 Sep-Oct
Current and potential therapies for the treatment of herpes-virus infections.
2003
Molecular imaging of protein-protein interactions: controlled expression of p53 and large T-antigen fusion proteins in vivo.
2003 Apr 15
Susceptibility of herpes simplex virus isolates to nucleoside analogues and the proportion of nucleoside-resistant variants after repeated topical application of penciclovir to recurrent herpes labialis.
2003 Apr 15
Review of antiviral therapy for herpes labialis, genital herpes and herpes zoster.
2003 Aug
Novel agents and strategies to treat herpes simplex virus infections.
2003 Feb
Profiling penciclovir susceptibility and prevalence of resistance of herpes simplex virus isolates across eleven clinical trials.
2003 Sep
Changing paradigms in dermatology: antivirals in dermatology.
2003 Sep-Oct
Efficacy of antiviral agents in feline herpetic keratitis: results of an in vitro study.
2004 Aug-Sep
Can clinical trials requiring frequent participant contact be conducted over the Internet? Results from an online randomized controlled trial evaluating a topical ointment for herpes labialis.
2004 Feb 17
Therapeutic options for herpes labialis, II: Topical agents.
2004 Jul
Topical treatment of herpes labialis.
2004 Nov
Recent clinical experience with famciclovir--a "third generation" nucleoside prodrug.
2004 Sep
Penciclovir cream--improved topical treatment for herpes simplex infections.
2004 Sep-Oct
Drugs for non-HIV viral infections.
2005 Apr
Altered deoxyribonucleotide pools in T-lymphoblastoid cells expressing the multisubstrate nucleoside kinase of Drosophila melanogaster.
2005 Aug
Murine cytomegalovirus resistant to antivirals has genetic correlates with human cytomegalovirus.
2005 Aug
Agents and strategies in development for improved management of herpes simplex virus infection and disease.
2005 Feb
Recurrent antiviral-resistant genital herpes in an immunocompetent patient.
2005 Jul 1
Comparison of [14C]FMAU, [3H]FEAU, [14C]FIAU, and [3H]PCV for monitoring reporter gene expression of wild type and mutant herpes simplex virus type 1 thymidine kinase in cell culture.
2005 Jul-Aug
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.
2005 Mar
Antiadenovirus activities of several classes of nucleoside and nucleotide analogues.
2005 Mar
Platinum(II) complexes with antitumoral/antiviral aromatic heterocycles: effect of glutathione upon in vitro cell growth inhibition.
2005 May 5
Development and validation of a new reversed-phase ion pairing liquid chromatographic method with fluorescence detection for penciclovir analysis in plasma and aqueous humor.
2005 Nov 5
Clinic-initiated, twice-daily oral famciclovir for treatment of recurrent genital herpes: a randomized, double-blind, controlled trial.
2005 Oct 15
In vitro activity of cycloSal-nucleoside monophosphates and polyhydroxycarboxylates against orthopoxviruses.
2005 Sep
Patents

Sample Use Guides

Penciclovir (DENAVIR®) should be applied every 2 hours during waking hours for a period of 4 days. Treatment should be started as early as possible (i.e., during the prodrome or when lesions appear).
Route of Administration: Topical
In cell culture studies, penciclovir has antiviral activity against the following herpes viruses: HSV-1 and HSV-2. The antiviral activity of penciclovir against wild type strains grown on human foreskin fibroblasts was assessed with a plaque reduction assay and staining with crystal violet 3 days postinfection for HSV. The median EC50 values of penciclovir against laboratory and clinical isolates of HSV-1 and HSV-2 were 2 uM (range 1.2 to 2.4 uM, n=7) and 2.6 uM (range 1.6 to 11 uM, n=6), respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:09:16 GMT 2023
Edited
by admin
on Sat Dec 16 05:09:16 GMT 2023
Record UNII
QIC03ANI02
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FAMCICLOVIR
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FAMCICLOVIR [JAN]
Common Name English
2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate (ester)
Common Name English
FAMCICLOVIR [MART.]
Common Name English
Famciclovir [WHO-DD]
Common Name English
1,3-PROPANEDIOL, 2-(2-(2-AMINO-9H-PURIN-9-YL)ETHYL)-, DIACETATE (ESTER)
Common Name English
BRL-42810
Code English
NSC-758921
Code English
FAMCICLOVIR [USP MONOGRAPH]
Common Name English
famciclovir [INN]
Common Name English
FAMCICLOVIR [USP-RS]
Common Name English
FAMCICLOVIR [MI]
Common Name English
FAMCICLOVIR [ORANGE BOOK]
Common Name English
FAMCICLOVIR [USAN]
Common Name English
FAMCICLOVIR [VANDF]
Common Name English
FAMVIR
Brand Name English
Classification Tree Code System Code
WHO-ATC J05AB09
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
WHO-ATC S01AD07
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NDF-RT N0000020060
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NDF-RT N0000180187
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
LIVERTOX NBK547978
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
WHO-VATC QS01AD07
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
WHO-VATC QJ05AB09
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NCI_THESAURUS C29575
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
Code System Code Type Description
MESH
C060590
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
MERCK INDEX
m5240
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C29044
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PRIMARY
EVMPD
SUB07501MIG
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
USAN
EE-84
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
HSDB
8121
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
CHEBI
4974
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
DAILYMED
QIC03ANI02
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
INN
6438
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PRIMARY
DRUG CENTRAL
1128
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PRIMARY
CAS
104227-87-4
Created by admin on Sat Dec 16 05:09:16 GMT 2023 , Edited by admin on Sat Dec 16 05:09:16 GMT 2023
PRIMARY
NSC
758921
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
SMS_ID
100000092280
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PRIMARY
RXCUI
68099
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
FAMCICLOVIR
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
LACTMED
Famciclovir
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
DRUG BANK
DB00426
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
FDA UNII
QIC03ANI02
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL880
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID0023038
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
RS_ITEM_NUM
1269152
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
PUBCHEM
3324
Created by admin on Sat Dec 16 05:09:17 GMT 2023 , Edited by admin on Sat Dec 16 05:09:17 GMT 2023
PRIMARY
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