Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H20N6O4 |
Molecular Weight | 324.3357 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N=C(N)NC2=O
InChI
InChIKey=HDOVUKNUBWVHOX-QMMMGPOBSA-N
InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
Molecular Formula | C13H20N6O4 |
Molecular Weight | 324.3357 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/3680558 | https://www.ncbi.nlm.nih.gov/pubmed/3790156 | https://www.ncbi.nlm.nih.gov/pubmed/2159990 | Leoung, G.S. (1989) Opportunistic Infections in Patients with the Acquired Immunodeficiency Syndrome, page 207, retrieved from: https://books.google.ru/books?id=As56gGv7E_YChttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdfCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6313598 | https://www.ncbi.nlm.nih.gov/pubmed/2828440 | https://www.ncbi.nlm.nih.gov/pubmed/202961
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3680558 | https://www.ncbi.nlm.nih.gov/pubmed/3790156 | https://www.ncbi.nlm.nih.gov/pubmed/2159990 | Leoung, G.S. (1989) Opportunistic Infections in Patients with the Acquired Immunodeficiency Syndrome, page 207, retrieved from: https://books.google.ru/books?id=As56gGv7E_YChttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6313598 | https://www.ncbi.nlm.nih.gov/pubmed/2828440 | https://www.ncbi.nlm.nih.gov/pubmed/202961
Acyclovir is a synthetic antiviral nucleoside analogue. A screening program for antiviral drugs begun at Burroughs Wellcome in the 1960s resulted in the discovery of acyclovir in 1974. Preclinical investigation brought the drug to clinical trials in 1977 and the first form of the drug (topical) was available to physicians in 1982. Activity of acyclovir is greatest against herpes 1 and herpes 2, less against varicella zoster, still less against Epstein-Barr, and very little against cytomegalovirus. Acyclovir is an antiviral agent only after it is phosphorylated in infected cells by a viral-induced thymidine kinase. Acyclovir monophosphate is phosphorylated to diphosphate and triphosphate forms by cellular enzymes in the infected host cell where the drug is concentrated. Acyclovir triphosphate inactivates viral deoxyribonucleic acid polymerase.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12878501https://www.ncbi.nlm.nih.gov/pubmed/12878501 | https://www.ncbi.nlm.nih.gov/pubmed/20038622
Curator's Comment: Valacyclovir hydrochloride is rapidly converted to acyclovir which was detected in CSF after oral administration of valacyclovir.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1820 |
|||
Target ID: CHEMBL1872 |
0.08 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZOVIRAX Approved UseOral ZOVIRAX® (acyclovir) is indicated for the treatment:
Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles).
Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes.
Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella).
Injectable ZOVIRAX® (acyclovir) is indicated for the treatment:
Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is
indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients.
Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients.
Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis.
Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections.
Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is
indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients. Launch Date3.86208006E11 |
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Primary | ZOVIRAX Approved UseOral ZOVIRAX® (acyclovir) is indicated for the treatment:
Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles).
Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes.
Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella).
Injectable ZOVIRAX® (acyclovir) is indicated for the treatment:
Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is
indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients.
Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients.
Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis.
Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections.
Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is
indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients. Launch Date3.86208006E11 |
|||
Primary | VALTREX Approved UseINDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date1.07896321E12 |
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Primary | VALTREX Approved UseINDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date1.07887683E12 |
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Primary | VALTRE Approved UseINDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date1.07887683E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
599.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACYCLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3015.7 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACYCLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACYCLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
79% |
ACYCLOVIR plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Selective activity of various antiviral compounds against HHV-7 infection. | 1999 Aug |
|
Evaluation of anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]- guanine (A-5021) in mice. | 1999 Jun |
|
[Cerebral and renal toxicity of acyclovir in a patient treated for meningoencephalitis]. | 1999 Nov |
|
Hepatic and renal effects of azidothymidine and acyclovir on pregnant rats. | 2000 |
|
A rapid phenotypic assay for detection of acyclovir-resistant varicella-zoster virus with mutations in the thymidine kinase open reading frame. | 2000 Apr |
|
Synthesis and antiviral activity of acyclovir-5'-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug. | 2000 Apr 3 |
|
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. | 2000 Dec 28 |
|
Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants. | 2000 Jan |
|
Antiviral effect of brassinosteroids against herpes virus and arenaviruses. | 2000 Jan |
|
Acyclovir induced coma in the intensive care unit. | 2000 Jun |
|
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
Metabolism and mode of inhibition of varicella-zoster virus by L-beta-5-bromovinyl-(2-hydroxymethyl)-(1,3-dioxolanyl)uracil is dependent on viral thymidine kinase. | 2000 Nov |
|
Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes. | 2000 Oct 15 |
|
Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
Interventions for herpes simplex virus epithelial keratitis. | 2001 |
|
Management of neonatal herpes simplex virus infection. | 2001 |
|
Heart transplantation and the Batista operation for children with refractory heart failure. | 2001 Apr |
|
Famciclovir vs. aciclovir in immunocompetent patients with recurrent genital herpes infections: a parallel-groups, randomized, double-blind clinical trial. | 2001 Apr |
|
[Peptide transporter family]. | 2001 Apr |
|
Prophylaxis of intravenous immunoglobulin and acyclovir in perinatal varicella. | 2001 Feb |
|
Pretransplant varicella vaccination is cost-effective in pediatric renal transplantation. | 2001 Feb |
|
Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo. | 2001 Feb |
|
Genetic risks of antiviral nucleoside analogues--a survey. | 2001 Feb |
|
Viral etiologies of encephalitis in Thai children. | 2001 Feb |
|
Eczema herpeticum in parthenium dermatitis. | 2001 Feb |
|
Recurrent eczema herpeticum: an underrecognised condition. | 2001 Feb |
|
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients. | 2001 Feb-Mar |
|
Antiviral drugs can inhibit lymphocyte apoptosis induced by cytomegalovirus antigens. | 2001 Feb-Mar |
|
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir). | 2001 Jan |
|
Topical treatment of recurrent herpes labialis. | 2001 Jan |
|
Aerobic bacterial and fungal infections in peripheral blood stem cell transplants. | 2001 Jan |
|
Recurrent lumbosacral herpes simplex in the bedridden hospitalized patient. | 2001 Jan |
|
8-[18F]Fluoropenciclovir: an improved reporter probe for imaging HSV1-tk reporter gene expression in vivo using PET. | 2001 Jan |
|
Reporter genes and imagene. | 2001 Jan |
|
Aseptic meningitis related to valacyclovir. | 2001 Jan |
|
Management of the neonate whose mother received suppressive acyclovir therapy during late pregnancy. | 2001 Jan |
|
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant. | 2001 Jan |
|
Longitudinal analysis of varicella-zoster virus DNA on the ocular surface associated with herpes zoster ophthalmicus. | 2001 Jan |
|
Varicella myocarditis in an adult. | 2001 Jan |
|
Successful outcome with a "quintuple approach" of posttransplant lymphoproliferative disorder. | 2001 Jan 15 |
|
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol. | 2001 Jan-Feb |
|
Progressive outer retinal necrosis in a patient with nephrotic syndrome. | 2001 Jan-Feb |
|
Selection and characterization of varicella-zoster virus variants resistant to (R)-9-[4-hydroxy-2-(hydroxymethy)butyl]guanine. | 2001 Jun |
|
Mild herpes simplex encephalitis worsening despite acyclovir treatment. | 2001 Mar |
|
A pilot study of treatment of herpes labialis with 1072 nm narrow waveband light. | 2001 Mar |
|
A 35-year-old man with recurrent aseptic meningitis. | 2001 Mar |
|
Predictive modeling and heterogeneity of baseline risk in meta-analysis of individual patient data. | 2001 Mar |
|
Oral recurrent human herpes virus infection and bone marrow transplantation survival. | 2001 May |
|
Contact dermatitis from topical antiviral drugs. | 2001 May |
|
Diagnosis and Treatment of Acute Retinal Necrosis: A Report by the American Academy of Ophthalmology. | 2017 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2159990
250 mg three times a day for 14 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454935
In uptake studies using valacyclovir, the extraction solution (water/methanol, 50:50) was added to the Caco-2 cells after the uptake period. After standing for 1 h at room temperature, the solutions were centrifuged and the supernatants were filtered. The filtrate was analyzed by highperformance liquid chromatography (HPLC). Valacyclovir showed a marked inhibitory effect (K=440 +/- 29mkM) on [14C]glycylsarcosine uptake via the apical PEPT1.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:44:02 UTC 2023
by
admin
on
Sat Dec 16 16:44:02 UTC 2023
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Record UNII |
MZ1IW7Q79D
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175459
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NDF-RT |
N0000180187
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WHO-ATC |
J05AB11
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NCI_THESAURUS |
C29575
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NCI_THESAURUS |
C1556
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NDF-RT |
N0000175459
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LIVERTOX |
NBK548655
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WHO-VATC |
QJ05AB11
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NDF-RT |
N0000020060
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NDF-RT |
N0000175459
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NDF-RT |
N0000175468
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NDF-RT |
N0000180188
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Code System | Code | Type | Description | ||
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SUB00003MIG
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73645
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PRIMARY | RxNorm | ||
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CHEMBL1349
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C084555
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PRIMARY | |||
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124832-26-4
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PRIMARY | |||
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8084
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7106
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DTXSID1023732
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35854
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VALACICLOVIR
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135398742
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m11355
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PRIMARY | Merck Index | ||
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2798
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MZ1IW7Q79D
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100000092738
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DB00577
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MZ1IW7Q79D
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Valacyclovir
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C28235
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4824
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Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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