Identification

Name
Valganciclovir
Accession Number
DB01610
Type
Small Molecule
Groups
Approved, Investigational
Description

Valganciclovir hydrochloride (Valcyte, manufactured by Roche) is an antiviral medication used to treat cytomegalovirus infections. As the L-valyl ester of ganciclovir, it is actually a prodrug for ganciclovir. After oral administration, it is rapidly converted to ganciclovir by intestinal and hepatic esterases.

Structure
Thumb
Synonyms
  • Cymeval
  • L-valine, ester with ganciclovir
  • Valganciclovir
Product Ingredients
IngredientUNIICASInChI Key
Valganciclovir hydrochloride4P3T9QF9NZ175865-59-5Not applicable
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-valganciclovirTablet450 mgOralAuro Pharma Inc2015-04-10Not applicableCanada
Mylan-valganciclovirTablet450 mgOralMylan PharmaceuticalsNot applicableNot applicableCanada
Nat-valganciclovirTablet450 mgOralNatco Pharma LimitedNot applicableNot applicableCanada
Teva-valganciclovirTablet450 mgOralTeva2014-11-27Not applicableCanada
ValcyteTablet450 mgOralHoffmann La Roche2002-07-16Not applicableCanada
ValcyteTablet, film coated450 mg/1OralGenentech, Inc.2001-03-29Not applicableUs
ValcytePowder, for solution50 mgOralHoffmann La Roche2008-08-13Not applicableCanada
ValcytePowder, for solution50 mg/mLOralGenentech, Inc.2009-08-28Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-valganciclovirTablet450 mgOralApotex Corporation2013-07-09Not applicableCanada
ValganciclovirTablet, film coated450 mg/1OralQualitest2014-11-04Not applicableUs00603 6330 20 nlmimage10 d14368cb
ValganciclovirTablet, film coated450 mg/1OralDr Reddy's Laboratories2014-12-15Not applicableUs
ValganciclovirTablet, film coated450 mg/1OralCamber Pharmaceuticals2016-03-18Not applicableUs
ValganciclovirTablet, film coated450 mg/1OralAv Kare, Inc.2016-06-21Not applicableUs
ValganciclovirTablet, film coated450 mg/1OralAmerincan Health Packaging2015-01-01Not applicableUs
ValganciclovirTablet, film coated450 mg/1OralAv Pak2016-07-27Not applicableUs
Valganciclovir HydrochlorideTablet450 mg/1OralMc Kesson2016-03-31Not applicableUs
Valganciclovir HydrochlorideTablet450 mg/1OralAurobindo Pharma2016-03-31Not applicableUs
Valganciclovir hydrochloride for OralPowder, for solution50 mg/mLOralActavis Pharma Company2016-08-26Not applicableUs
International/Other Brands
Cymeval / Valcyt / Valcyte
Categories
UNII
GCU97FKN3R
CAS number
175865-60-8
Weight
Average: 354.3617
Monoisotopic: 354.165167844
Chemical Formula
C14H22N6O5
InChI Key
WPVFJKSGQUFQAP-GKAPJAKFSA-N
InChI
InChI=1S/C14H22N6O5/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22)/t8?,9-/m0/s1
IUPAC Name
2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate
SMILES
CC(C)[[email protected]](N)C(=O)OCC(CO)OCN1C=NC2=C1NC(N)=NC2=O

Pharmacology

Indication

Valganciclovir is an antiviral medication used for the treatment of cytomegalovirus infections.

Structured Indications
Pharmacodynamics

Valganciclovir is an antiviral medication used to treat cytomegalovirus infections. As the L-valyl ester of ganciclovir, it is actually a prodrug for ganciclovir. After oral administration, it is rapidly converted to ganciclovir by intestinal and hepatic esterases. After this, it (being an analogue of guanosine) gets incorporated into DNA and thus cannot be properly read by DNA polymerase. This results in the termination of the elongation of viral DNA.

Mechanism of action

Valganciclovir is a prodrug of ganciclovir that exists as a mixture of two diastereomers. After administration, these diastereomers are rapidly converted to ganciclovir by hepatic and intestinal esterases. In cytomegalovirus (CMV)-infected cells, ganciclovir is initially phosphorylated to the monophosphate form by viral protein kinase, then it is further phosphorylated via cellular kinases to produce the triphosphate form. This triphosphate form is slowly metabolized intracellularly. The phosphorylation is dependent upon the viral kinase and occurs preferentially in virus-infected cells. The virustatic activity of ganciclovir is due to the inhibition of viral DNA synthesis by ganciclovir triphosphate. Ganciclovir triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand. Ganciclovir inhibits viral DNA polymerases more effectively than it does cellular polymerase, and chain elongation resumes when ganciclovir is removed.

TargetActionsOrganism
ADNA
adduct
Human
Absorption

Valganciclovir is well absorbed from the gastrointestinal tract and the absolute bioavailability from valganciclovir tablets (following administration with food) is approximately 60%.

Volume of distribution
  • 0.703 ± 0.134 L/kg
Protein binding

Plasma protein binding of ganciclovir is 1% to 2% over concentrations of 0.5 and 51 mg/mL.

Metabolism

Rapidly hydrolyzed in the intestinal wall and liver to ganciclovir. No other metabolites have been detected.

Route of elimination

The major route of elimination of valganciclovir is by renal excretion as ganciclovir through glomerular filtration and active tubular secretion.

Half life

Approximately 4.08 hours. Increased in patients with renal function impairment.

Clearance
  • 3.07+/- 0.64 mL/min/kg [IV administration]
  • 5.3 L/hr [Patient with creatinine clearance of 70.4 mL/min]
Toxicity

It is expected that an overdose of valganciclovir could also possibly result in increased renal toxicity.

Affected organisms
  • Human Herpes Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbacavirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Abacavir.Approved, Investigational
DidanosineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Didanosine.Approved
EmtricitabineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Emtricitabine.Approved, Investigational
EntecavirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Entecavir.Approved, Investigational
ImipenemThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Imipenem.Approved
LamivudineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Lamivudine.Approved, Investigational
Mycophenolic acidThe serum concentration of Valganciclovir can be increased when it is combined with Mycophenolic acid.Approved
ProbenecidThe serum concentration of Valganciclovir can be increased when it is combined with Probenecid.Approved
StavudineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Stavudine.Approved, Investigational
Tenofovir disoproxilThe serum concentration of Tenofovir disoproxil can be increased when it is combined with Valganciclovir.Approved, Investigational
ZalcitabineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Zalcitabine.Approved, Investigational
ZidovudineThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Zidovudine.Approved
Food Interactions
Not Available

References

Synthesis Reference

Romi Singh, Vishnubhotla Nagaprasad, Nidhi Singh, "Processes for the Preparation of Solid Dosage Forms of Amorphous Valganciclovir Hydrochloride." U.S. Patent US20070292499, issued December 20, 2007.

US20070292499
General References
  1. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873]
External Links
Human Metabolome Database
HMDB15548
PubChem Compound
64147
PubChem Substance
46505524
ChemSpider
57721
ChEBI
63635
ChEMBL
CHEMBL1201314
Therapeutic Targets Database
DAP000646
PharmGKB
PA10227
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Valganciclovir
ATC Codes
J05AB14 — Valganciclovir
AHFS Codes
  • 08:18.32 — Nucleosides and Nucleotides

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionCytomegalovirus Infections, Heart Transplantation1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentInfections, Cytomegalovirus1
1Not Yet RecruitingTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
1RecruitingTreatmentNasopharyngeal Carcinoma1
1RecruitingTreatmentTransplantation, Liver1
1, 2CompletedTreatmentInfections, Cytomegalovirus1
1, 2CompletedTreatmentKidney Diseases / Transplant, Kidney / Transplantation, Kidney / Transplantation, Renal1
1, 2Unknown StatusTreatmentMyalgic Encephalomyelitis (ME)1
2CompletedPreventionCritical Illness1
2CompletedPreventionCytomegalovirus Viraemia / EBV Viremia1
2CompletedPreventionHuman Herpesvirus 81
2CompletedTreatmentChronic Lymphocytic Leukaemia (CLL) / Leukemias1
2CompletedTreatmentInfections, Cytomegalovirus1
2CompletedTreatmentMalignant Lymphomas1
2Not Yet RecruitingTreatmentCytomegalovirus Congenital Infection1
2RecruitingPreventionEpstein-Barr Virus Infections / Infections, Cytomegalovirus / Transplantation Infection1
2RecruitingTreatmentCastleman's Disease / Giant Lymph Node Hyperplasia1
2RecruitingTreatmentCongenital Cytomegalovirus / Hard of Hearing1
2RecruitingTreatmentHHV-8 / Human Immunodeficiency Virus (HIV) / Lymphoproliferative Disorders / Malignancies1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Immune Reconstitution Syndrome / Kaposi s Sarcoma (KS)1
2TerminatedTreatmentEBV Lymphomas / Lympho-proliferative Diseases1
2TerminatedTreatmentLymphoid Malignancies / Lymphoproliferative Disorders1
2Unknown StatusTreatmentCytomegalovirus Disease1
2Unknown StatusTreatmentHead and Neck Carcinoma / Lymphoproliferative Disorders / Malignant Lymphomas / Malignant Neoplasm of Stomach1
2, 3CompletedTreatmentInfections, Cytomegalovirus1
2, 3Not Yet RecruitingTreatmentCongenital Cytomegalovirus (CMV)1
3CompletedPreventionBone Marrow Stem Cell Transplant1
3CompletedPreventionCytomegalovirus / Transplantation, Bone Marrow1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
3CompletedPreventionInfections, Cytomegalovirus2
3CompletedSupportive CareInfection NOS1
3CompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentInfections, Cytomegalovirus2
3Not Yet RecruitingTreatmentCMV / Cmv Congenital / Congenital Cmv / Sensorineural Hearing Loss / SNHL1
3RecruitingNot AvailableRenal Transplanted Recipients1
3RecruitingTreatmentCytomegalovirus (CMV)1
3RecruitingTreatmentCytomegalovirus Congenital Infection / Sensorineural Hearing Loss1
3TerminatedPreventionAllogeneic Stem Cell Transplantation1
3TerminatedPreventionCompare Efficacy of BCV to vGCV for Prevention of CMV Disease in Kidney Transplant Recipients Who Are CMV Seropositive Pretransplant1
3TerminatedPreventionCytomegalovirus Disease1
3TerminatedTreatmentCytomegalovirus Congenital Infection / Sensorineural Hearing Loss1
3TerminatedTreatmentInfections, Cytomegalovirus1
3TerminatedTreatmentInfections, Cytomegalovirus / Inflammatory Bowel Diseases (IBD)1
3TerminatedTreatmentTransplant, Kidney1
3Unknown StatusTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionCytomegalovirus Disease1
4CompletedPreventionInfection in Solid Organ Transplant Recipients1
4CompletedPreventionKidney Transplantation, Cytomegalovirus Infections1
4CompletedTreatmentChronic Lymphocytic Leukaemia (CLL)1
4CompletedTreatmentHeart Transplant Recipients / Kidney Transplant Recipients1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
4CompletedTreatmentInfections, Cytomegalovirus2
4CompletedTreatmentKidney Trasplant1
4CompletedTreatmentViral sepsis1
4WithdrawnTreatmentGiant Lymph Node Hyperplasia1
Not AvailableCompletedPreventionInfections, Cytomegalovirus1
Not AvailableCompletedSupportive CareAccelerated Phase Chronic Myelogenous Leukemia / Acute Undifferentiated Leukemia (AUL) / Adult Acute Lymphoblastic Leukemia in Remission / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Grade III Lymphomatoid Granulomatosis / Adult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Aplastic Anaemia (AA) / Atypical Chronic Myeloid Leukemia, BCR-ABL Negative / Blastic Phase Chronic Myelogenous Leukemia / Chronic Eosinophilic Leukemia (CEL) / Chronic Myelomonocytic Leukemia / Chronic Neutrophilic Leukemia / Chronic Phase Chronic Myelogenous Leukemia / Contiguous Stage II Adult Burkitt Lymphoma / Contiguous Stage II Adult Diffuse Large Cell Lymphoma / Contiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Contiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Contiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Contiguous Stage II Adult Lymphoblastic Lymphoma / Contiguous Stage II Grade 1 Follicular Lymphoma / Contiguous Stage II Grade 2 Follicular Lymphoma / Contiguous Stage II Grade 3 Follicular Lymphoma / Contiguous Stage II Mantle Cell Lymphoma / Contiguous Stage II Marginal Zone Lymphoma / Contiguous Stage II Small Lymphocytic Lymphoma / Cutaneous B-Cell Non-Hodgkin Lymphoma / De Novo Myelodysplastic Syndromes / Essential Thrombocythemia (ET) / Extramedullary Plasmacytoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Hematopoietic/Lymphoid Cancer / Infections, Cytomegalovirus / Intraocular Lymphoma / Isolated Plasmacytoma of Bone / Leukemia, Prolymphocytic / Malignant mast cell neoplasm / Meningeal Chronic Myelogenous Leukemia / Myelodysplastic/Myeloproliferative Neoplasm, Unclassifiable / Nodal marginal zone B-cell lymphomas / Noncontiguous Stage II Adult Burkitt Lymphoma / Noncontiguous Stage II Adult Diffuse Large Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Noncontiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Noncontiguous Stage II Adult Lymphoblastic Lymphoma / Noncontiguous Stage II Grade 1 Follicular Lymphoma / Noncontiguous Stage II Grade 2 Follicular Lymphoma / Noncontiguous Stage II Grade 3 Follicular Lymphoma / Noncontiguous Stage II Mantle Cell Lymphoma / Noncontiguous Stage II Marginal Zone Lymphoma / Noncontiguous Stage II Small Lymphocytic Lymphoma / Polycythemia Vera (PV) / Post-Transplant Lymphoproliferative Disorder / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Primary Systemic Amyloidosis / Progressive Hairy Cell Leukemia, Initial Treatment / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Refractory Chronic Lymphocytic Leukemia / Refractory Hairy Cell Leukemia / Refractory Multiple Myeloma / Relapsing Chronic Myelogenous Leukemia / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Secondary Myelofibrosis / Splenic Marginal Zone Lymphoma / Stage 0 Chronic Lymphocytic Leukemia / Stage I Adult Burkitt Lymphoma / Stage I Adult Diffuse Large Cell Lymphoma / Stage I Adult Diffuse Mixed Cell Lymphoma / Stage I Adult Diffuse Small Cleaved Cell Lymphoma / Stage I Adult Hodgkin Lymphoma / Stage I Adult Immunoblastic Large Cell Lymphoma / Stage I Adult Lymphoblastic Lymphoma / Stage I Adult T-Cell Leukemia/Lymphoma / Stage I Chronic Lymphocytic Leukemia / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage I Grade 1 Follicular Lymphoma / Stage I Grade 2 Follicular Lymphoma / Stage I Grade 3 Follicular Lymphoma / Stage I Mantle Cell Lymphoma / Stage I Marginal Zone Lymphoma / Stage I Multiple Myeloma / Stage I Mycosis Fungoides/Sezary Syndrome / Stage I Small Lymphocytic Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage II Adult T-Cell Leukemia/Lymphoma / Stage II Chronic Lymphocytic Leukemia / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Multiple Myeloma / Stage II Mycosis Fungoides/Sezary Syndrome / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Adult T-Cell Leukemia/Lymphoma / Stage III Chronic Lymphocytic Leukemia / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Multiple Myeloma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Adult T-Cell Leukemia/Lymphoma / Stage IV Chronic Lymphocytic Leukemia / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma / T-Cell Large Granular Lymphocyte Leukemia / Waldenstrom's Macroglobulinemia (WM)1
Not AvailableCompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentSarcomas1
Not AvailableNo Longer AvailableNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableUnknown StatusTreatmentGlioblastoma Multiforme / Infections, Cytomegalovirus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionOral50 mg
Powder, for solutionOral50 mg/mL
TabletOral450 mg
Tablet, film coatedOral450 mg/1
TabletOral450 mg/1
Prices
Unit descriptionCostUnit
Valcyte48.87USD tablet
Valcyte 450 mg tablet46.99USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2154721No2001-01-022015-07-26Canada
US6083953Yes1995-09-292015-09-29Us
US9642911No2007-12-112027-12-11Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.79 mg/mLALOGPS
logP-0.81ALOGPS
logP-1.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)7.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area167.08 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity86.6 m3·mol-1ChemAxon
Polarizability34.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9104
Blood Brain Barrier+0.9383
Caco-2 permeable-0.8874
P-glycoprotein substrateSubstrate0.6534
P-glycoprotein inhibitor INon-inhibitor0.9314
P-glycoprotein inhibitor IINon-inhibitor0.9395
Renal organic cation transporterNon-inhibitor0.9026
CYP450 2C9 substrateNon-substrate0.8915
CYP450 2D6 substrateNon-substrate0.8351
CYP450 3A4 substrateNon-substrate0.5362
CYP450 1A2 substrateNon-inhibitor0.8981
CYP450 2C9 inhibitorNon-inhibitor0.8585
CYP450 2D6 inhibitorNon-inhibitor0.889
CYP450 2C19 inhibitorNon-inhibitor0.8334
CYP450 3A4 inhibitorNon-inhibitor0.9232
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.918
Ames testNon AMES toxic0.6023
CarcinogenicityNon-carcinogens0.8588
BiodegradationNot ready biodegradable0.9356
Rat acute toxicity2.1981 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9804
hERG inhibition (predictor II)Non-inhibitor0.8918
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0239000000-850143c9c0e2faa19d0f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0gbi-0930000000-c4c88d5b9acc354dad95
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0gb9-0900000000-6c74a9e70b949b0b1a00
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0159-0900000000-a71a2b4b1f37329ca7f0
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0159-1900000000-58d3e9baef3c5fcd5255
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0159-4900000000-dc9a9c630ba915c7aec2

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid esters
Alternative Parents
Valine and derivatives / Purines and purine derivatives / Fatty acid esters / Glycerolipids / Hydroxypyrimidines / N-substituted imidazoles / Heteroaromatic compounds / Carboxylic acid esters / Azacyclic compounds / Monocarboxylic acids and derivatives
show 6 more
Substituents
Alpha-amino acid ester / Valine or derivatives / Imidazopyrimidine / Purine / Fatty acid ester / Hydroxypyrimidine / Glycerolipid / Fatty acyl / N-substituted imidazole / Pyrimidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purines, L-valinyl ester (CHEBI:63635)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Adduct
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Martin M, Azzi A, Lin SX, Boivin G: Opposite effect of two cytomegalovirus DNA polymerase mutations on replicative capacity and polymerase activity. Antivir Ther. 2010;15(4):579-86. doi: 10.3851/IMP1565. [PubMed:20587851]
  2. Boivin G, Goyette N, Gilbert C, Covington E: Analysis of cytomegalovirus DNA polymerase (UL54) mutations in solid organ transplant patients receiving valganciclovir or ganciclovir prophylaxis. J Med Virol. 2005 Nov;77(3):425-9. [PubMed:16173018]
  3. Marfori JE, Exner MM, Marousek GI, Chou S, Drew WL: Development of new cytomegalovirus UL97 and DNA polymerase mutations conferring drug resistance after valganciclovir therapy in allogeneic stem cell recipients. J Clin Virol. 2007 Feb;38(2):120-5. Epub 2006 Dec 8. [PubMed:17157554]
  4. Potena L, Holweg CT, Chin C, Luikart H, Weisshaar D, Narasimhan B, Fearon WF, Lewis DB, Cooke JP, Mocarski ES, Valantine HA: Acute rejection and cardiac allograft vascular disease is reduced by suppression of subclinical cytomegalovirus infection. Transplantation. 2006 Aug 15;82(3):398-405. [PubMed:16906040]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Sugawara M, Huang W, Fei YJ, Leibach FH, Ganapathy V, Ganapathy ME: Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2. J Pharm Sci. 2000 Jun;89(6):781-9. [PubMed:10824137]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Sugawara M, Huang W, Fei YJ, Leibach FH, Ganapathy V, Ganapathy ME: Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2. J Pharm Sci. 2000 Jun;89(6):781-9. [PubMed:10824137]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Mediates the uptake of a broad range of neutral and cationic amino acids (with the exception of proline) in a Na(+)/Cl(-)-dependent manner.
Gene Name
SLC6A14
Uniprot ID
Q9UN76
Uniprot Name
Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+)
Molecular Weight
72152.145 Da
References
  1. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873]

Drug created on August 29, 2007 13:52 / Updated on November 19, 2017 20:33