Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H20N6O4 |
Molecular Weight | 324.3362 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@@]([H])(C(=O)OCCOCn1cnc2c1[nH]c(=N)nc2O)N
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 | 324.3362 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfCurator's Comment:: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01682109 | https://www.ncbi.nlm.nih.gov/pubmed/19957998 | https://www.ncbi.nlm.nih.gov/pubmed/7625798 | https://www.ncbi.nlm.nih.gov/pubmed/11454935
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdf
Curator's Comment:: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01682109 | https://www.ncbi.nlm.nih.gov/pubmed/19957998 | https://www.ncbi.nlm.nih.gov/pubmed/7625798 | https://www.ncbi.nlm.nih.gov/pubmed/11454935
Valacyclovir is the hydrochloride salt of the L-valyl ester of the antiviral drug acyclovir. Valacyclovir is a nucleoside analog DNA polymerase inhibitor. Valacyclovir hydrochloride is rapidly converted to acyclovir which has demonstrated antiviral activity against HSV types 1 (HSV-1) and 2 (HSV-2) and VZV both in cell culture and in vivo. The inhibitory activity of acyclovir is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts acyclovir into acyclovir monophosphate, a nucleotide analog. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. In biochemical assays, acyclovir triphosphate inhibits replication of herpes viral DNA. This is accomplished in 3 ways: 1) competitive inhibition of viral DNA polymerase, 2) incorporation and termination of the growing viral DNA chain, and 3) inactivation of the viral DNA polymerase. The greater antiviral activity of acyclovir against HSV compared with VZV is due to its more efficient phosphorylation by the viral TK. The resistance of HSV and VZV to acyclovir can result from qualitative and quantitative changes in the viral TK and/or DNA polymerase. Clinical isolates of VZV with reduced susceptibility to acyclovir have been recovered from patients with AIDS. Valaciclovir is indicated for the treatment of HSV and VZV infections, including Oral and genital herpes simplex (treatment and prophylaxis), Reduction of HSV transmission from people with recurrent infection to uninfected individuals, Prevention of cytomegalovirus following organ transplantation, Prophylaxis against herpesviruses in immunocompromised patients (such as patients undergoing cancer chemotherapy). Common adverse drug reactions (≥1% of patients) associated with valaciclovir therapy are the same as for aciclovir, its active metabolite, and include nausea, vomiting, diarrhea, and headache. Infrequent adverse effects (0.1–1% of patients) include agitation, vertigo, confusion, dizziness, edema, arthralgia, sore throat, constipation, abdominal pain, rash, weakness and/or renal impairment. Rare adverse effects (<0.1% of patients) include coma, seizures, neutropenia, leukopenia, tremor, ataxia, encephalopathy, psychotic symptoms, crystalluria, anorexia, fatigue, hepatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis and/or anaphylaxis.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12878501 | https://www.ncbi.nlm.nih.gov/pubmed/20038622https://www.ncbi.nlm.nih.gov/pubmed/12878501
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 |
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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 |
---|---|---|
The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir: part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2-thioethyl)phosphotriester derivatives of acyclovir. | 1999 Jan |
|
Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'alpha-C-branched-chain sugar pyrimidine nucleosides. | 1999 Jul 29 |
|
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 |
|
Synthesis and antiviral activity of acyclovir-5'-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug. | 2000 Apr 3 |
|
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. | 2000 Feb 24 |
|
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 |
|
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
Flow cytometric evaluation of antiviral agents against human herpesvirus 6. | 2001 |
|
Cough syncope with herpetic tracheobronchitis. | 2001 Apr |
|
Treatment of EBV driven lymphoproliferation with erythrophagocytosis: 12 year follow up. | 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 |
|
Acyclovir treatment in 2 patients with benign trigeminal sensory neuropathy. | 2001 Apr |
|
Practice parameter: Steroids, acyclovir, and surgery for Bell's palsy (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology. | 2001 Apr 10 |
|
Hydrophilic interaction chromatography using amino and silica columns for the determination of polar pharmaceuticals and impurities. | 2001 Apr 13 |
|
Postherpetic neuralgia. Treatment with amitriptyline is cheaper than with aciclovir. | 2001 Apr 7 |
|
Painful skin erosions and fever in an infant. Eczema herpeticum. | 2001 Feb |
|
Genetic risks of antiviral nucleoside analogues--a survey. | 2001 Feb |
|
Viral etiologies of encephalitis in Thai children. | 2001 Feb |
|
Meta-analysis of prophylaxis of CMV disease in solid organ transplantation: is Ganciclovir a superior agent to Acyclovir? | 2001 Feb-Mar |
|
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients. | 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 |
|
Aseptic meningitis related to valacyclovir. | 2001 Jan |
|
Herpetic folliculitis and syringitis simulating acne excoriée. | 2001 Jan |
|
Successful outcome with a "quintuple approach" of posttransplant lymphoproliferative disorder. | 2001 Jan 15 |
|
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 |
|
Long-term high-dose acyclovir and AIDS-related non-Hodgkins lymphoma. | 2001 Mar 15 |
|
The management of varicella-zoster virus exposure and infection in pregnancy and the newborn period. Australasian Subgroup in Paediatric Infectious Diseases of the Australasian Society for Infectious Diseases. | 2001 Mar 19 |
|
Neurotoxicity of valacyclovir in peritoneal dialysis: a pharmacokinetic study. | 2001 Mar-Apr |
|
Coexpression of guanylate kinase with thymidine kinase enhances prodrug cell killing in vitro and suppresses vascular smooth muscle cell proliferation in vivo. | 2001 May |
|
Oral recurrent human herpes virus infection and bone marrow transplantation survival. | 2001 May |
|
Chemical stability, enzymatic hydrolysis, and nasal uptake of amino acid ester prodrugs of acyclovir. | 2001 May |
|
Enhancement of the anti-herpetic effect of trichosanthin by acyclovir and interferon. | 2001 May 11 |
|
Synthesis and biological evaluation of purine-containing butenolides. | 2001 May 24 |
Sample Use Guides
Acute Treatment of Herpes Zoster: 800 mg every 4 hours orally, 5 times daily for 7 to 10 days.
Genital Herpes: Treatment of Initial Genital Herpes: 200 mg every 4 hours, 5 times daily for
10 days.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1329640
Penciclovir (PCV) and acyclovir are acyclic guanine analogs which inhibit herpes simplex virus (HSV) DNA polymerase. Their 50% infective doses were 0.5 to 0.8 microgram/ml for clinical isolates of HSV-1 and 1.3 to 2.2 micrograms/ml for HSV-2.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 12:07:49 UTC 2021
by
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on
Sat Jun 26 12:07:49 UTC 2021
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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 |
1014
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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
Created by
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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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PRIMARY | |||
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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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PRIMARY | |||
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7106
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PRIMARY | |||
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124832-26-4
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PRIMARY | |||
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VALACICLOVIR
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PRIMARY | |||
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135398742
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PRIMARY | |||
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M11355
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PRIMARY | Merck Index | ||
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2798
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PRIMARY | |||
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DB00577
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PRIMARY | |||
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MZ1IW7Q79D
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PRIMARY | |||
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Valacyclovir
Created by
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PRIMARY | |||
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C28235
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PRIMARY | |||
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4824
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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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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