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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N5O4
Molecular Weight 255.2306
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GANCICLOVIR

SMILES

NC1=NC2=C(N=CN2COC(CO)CO)C(=O)N1

InChI

InChIKey=IRSCQMHQWWYFCW-UHFFFAOYSA-N
InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)

HIDE SMILES / InChI

Description

There is no information in the literature about pharmacological and biological application of definite isomer: R of valganciclovir. However, is known, that valganciclovir, existing, as a mixture of R and S diasteriomers, is the active ingredient in Valcyte, which is used as an antiviral medication given to patients who have a high chance of developing cytomegalovirus (CMV) disease after receiving a heart, kidney, or kidney-pancreas transplant. It was proposed, that stable aqueous solutions of valganciclovir can be prepared in aqueous solutions at acidic pHs but these solutions will exist as a mixture of isomers: R and S

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Prophylaxis against herpesvirus infections in transplant recipients.
2001
Recent advances in imaging endogenous or transferred gene expression utilizing radionuclide technologies in living subjects: applications to breast cancer.
2001
Pharmacokinetics of the ganciclovir implant in the silicone-filled eye.
2001
Suicide gene therapy for human oral squamous cell carcinoma cell lines with adeno-associated virus vector.
2001 Apr
Intravitreal pharmacokinetics and retinal concentrations of ganciclovir and foscarnet after intravitreal administration in rabbits.
2001 Apr
Cytological monitoring of peripheral blood, bronchoalveolar lavage fluid, and transbronchial biopsy specimens during acute rejection and cytomegalovirus infection in lung and heart--lung allograft recipients.
2001 Apr
Suspension of anticytomegalovirus maintenance therapy following immune recovery due to highly active antiretroviral therapy.
2001 Apr
Risk for cytomegalovirus disease in patients receiving polymerase chain reaction-based preemptive antiviral therapy after allogeneic stem cell transplantation depends on transplantation modality.
2001 Apr 1
Protection from lethal murine graft-versus-host disease without compromise of alloengraftment using transgenic donor T cells expressing a thymidine kinase suicide gene.
2001 Apr 15
A time to live, a time to die.
2001 Apr 15
Adenoviral-mediated gene therapy for thyroid carcinoma using thymidine kinase controlled by thyroglobulin promoter demonstrates high specificity and low toxicity.
2001 Feb
[Cytomegalovirus rhombencephalomyelitis in an immunocompetent subject].
2001 Feb
Gamma-rays enhance rAAV-mediated transgene expression and cytocidal effect of AAV-HSVtk/ganciclovir on cancer cells.
2001 Feb
Human prostate carcinoma cells as targets for herpes simplex virus thymidine kinase-mediated suicide gene therapy.
2001 Feb
Immune-dependent distant bystander effect after adenovirus-mediated suicide gene transfer in a rat model of liver colorectal metastasis.
2001 Feb
Effect of the complexation with cyclodextrins on the in vitro antiviral activity of ganciclovir against human cytomegalovirus.
2001 Feb
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Conditional abatement of tissue fibrosis using nucleoside analogs to selectively corrupt DNA replication in transgenic fibroblasts.
2001 Feb
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor.
2001 Feb
Stimulation of intercellular communication of poor-communicating cells by gap-junction-competent cells enhances the HSV-TK/GCV bystander effect in vitro.
2001 Feb 15
Ovarian epithelial cell lineage-specific gene expression using the promoter of a retrovirus-like element.
2001 Feb 15
Coexpression of the partial androgen receptor enhances the efficacy of prostate-specific antigen promoter-driven suicide gene therapy for prostate cancer cells at low testosterone concentrations.
2001 Feb 15
A tightly regulated immortalized human fetal hepatocyte cell line to develop a bioartificial liver.
2001 Feb-Mar
Meta-analysis of prophylaxis of CMV disease in solid organ transplantation: is Ganciclovir a superior agent to Acyclovir?
2001 Feb-Mar
Preemptive ganciclovir for CMV viremia in liver transplantation.
2001 Feb-Mar
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients.
2001 Feb-Mar
Is preemptive therapy for CMV infection following liver transplantation superior to symptom-triggered treatment?
2001 Feb-Mar
Cytomegalovirus infection-enhanced chronic rejection in the rat is prevented by antiviral prophylaxis.
2001 Feb-Mar
Ganciclovir prophylaxis for cytomegalovirus infection in simultaneous kidney-pancreas transplant recipients receiving tacrolimus, mycophenolate mofetil, and prednisone.
2001 Feb-Mar
CMV in kidney transplants in the tacrolimus-mycophenolate era.
2001 Feb-Mar
Rat glioma cell death induced by cationic liposome-mediated transfer of the herpes simplex virus thymidine kinase gene followed by ganciclovir treatment.
2001 Jan
Targeting the replication of adenovirus to p53-defective thyroid carcinoma with a p53-regulated Cre/loxP system.
2001 Jan
Epstein-Barr virus encephalitis in a renal allograft recipient diagnosed by polymerase chain reaction on cerebrospinal fluid and successfully treated with ganciclovir.
2001 Jan
Antiviral drugs in chronic hepatitis B: review and meta-analysis.
2001 Jan
Recurrent disseminated herpes zoster and cytomegalic perianal ulcer: a case report and review of the literature.
2001 Jan
Fatal primary infection due to human herpesvirus 6 variant A in a renal transplant recipient.
2001 Jan 27
Toxic megacolon: remember cytomegalovirus.
2001 Mar
Cytomegalovirus colitis complicating ulcerative colitis in the steroid-naive patient.
2001 Mar
Prevalence of cytomegalovirus infection in severe refractory ulcerative and Crohn's colitis.
2001 Mar
Characterization of the cyclooxygenase-2 promoter in an adenoviral vector and its application for the mitigation of toxicity in suicide gene therapy of gastrointestinal cancers.
2001 Mar
The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host.
2001 Mar
High-dose intravitreal ganciclovir and foscarnet for cytomegalovirus retinitis.
2001 Mar
Frosted branch angiitis in a child with HIV infection.
2001 Mar
New developments in the management of cytomegalovirus infection and disease after renal transplantation.
2001 Mar
Protease pretreatment increases the efficacy of adenovirus-mediated gene therapy for the treatment of an experimental glioblastoma model.
2001 Mar 1
Expression of herpes simplex virus-thymidine kinase gene controlled by a promoter region of the midkine gene confers selective cytotoxicity to ganciclovir in human carcinoma cells.
2001 Mar 1
Preevaluation of clinical trial data: the case of preemptive cytomegalovirus therapy in patients with human immunodeficiency virus.
2001 Mar 1
Preemptive therapy versus universal prophylaxis with ganciclovir for cytomegalovirus in solid organ transplant recipients.
2001 Mar 1
Adenovirus-mediated gene therapy specific for small cell lung cancer cells using a Myc-Max binding motif.
2001 Mar 15
Prophylaxis for CMV should not now replace pre-emptive therapy in solid organ transplantation.
2001 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
5 mg/kg every 12 hours (given intravenously at a constant rate over 1 hour) (induction treatment) and 5 mg/kg given as a constant-rate intravenous infusion over 1 hour once daily, 7 days per week, or 6 mg/kg once daily, 5 days per week (maintenance treatment).
Route of Administration: Intravenous
In Vitro Use Guide
IC50 is from 0.02 to 3.48 ug/mL
Name Type Language
GANCICLOVIR
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
BW 759U
Code English
GANCICLOVIR [HSDB]
Common Name English
VITRASERT IMPLANT
Brand Name English
GANCICLOVIR [EP]
Common Name English
GANCICLOVIR [WHO-DD]
Common Name English
GANCICLOVIR [EMA EPAR]
Common Name English
9-((2-HYDROXY-1-(HYDROXYMETHYL)ETHOXY)METHYL)GUANINE
Systematic Name English
GANCICLOVIR [USP]
Common Name English
GANCICLOVIR [USAN]
Common Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((2-HYDROXY-1-(HYDROXYMETHYL)ETHOXY)METHYL)-
Systematic Name English
GANCICLOVIR [MART.]
Common Name English
VITRASERT
Brand Name English
ZIRGAN
Brand Name English
GANCICLOVIR [ORANGE BOOK]
Common Name English
RS-21592
Code English
BW-759U
Code English
GANCICLOVIR [INN]
Common Name English
GANCICLOVIR [VANDF]
Common Name English
GANCICLOVIR [MI]
Common Name English
GANCICLOVIR [USP-RS]
Common Name English
GANCICLOVIR [JAN]
Common Name English
GANCYCLOVIR
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS VITRASERT IMPLANT (WITHDRAWN: HIV INFECTIONS)
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000020060
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
LIVERTOX 449
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000175461
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
EMA ASSESSMENT REPORTS VITRASERT IMPLANT (WITHDRAWN: CYTOMEGALOVIRUS RETINITIS)
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000175466
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
WHO-VATC QS01AD09
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
WHO-ATC J05AB06
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
WHO-VATC QJ05AB06
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
WHO-ATC S01AD09
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
NDF-RT N0000175459
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
Code System Code Type Description
EVMPD
SUB07881MIG
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
EPA CompTox
82410-32-0
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
DRUG BANK
DB01004
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
NCI_THESAURUS
C517
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
PUBCHEM
3454
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY SWITZERF
ChEMBL
CHEMBL182
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
RXCUI
4678
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY RxNorm
INN
6023
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
MERCK INDEX
M5663
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY Merck Index
HSDB
82410-32-0
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
CAS
82410-32-0
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
MESH
D015774
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY
WIKIPEDIA
GANCICLOVIR
Created by admin on Tue Mar 06 12:08:08 UTC 2018 , Edited by admin on Tue Mar 06 12:08:08 UTC 2018
PRIMARY