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Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N5O4
Molecular Weight 255.2306
Optical Activity NONE
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
Molecular Formula C9H13N5O4
Molecular Weight 255.2306
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.drugs.com/monograph/valganciclovir-hydrochloride.html | http://www.rxlist.com/valcyte-drug/indications-dosage.htm

Ganciclovir is a synthetic acyclic nucleoside analogue of 2'-deoxyguanosine active against cytomegalovirus. Ganciclovir has been shown to be active against cytomegalovirus (CMV) and herpes simplex virus (HSV) in humans. To achieve anti-CMV activity, ganciclovir is phosphorylated first to the monophosphate form by a CMV-encoded (UL97 gene) protein kinase homologue, then to the di- and triphosphate forms by cellular kinases. Ganciclovir triphosphate concentrations may be 100-fold greater in CMV-infected than in uninfected cells, indicating preferential phosphorylation in infected cells. Ganciclovir triphosphate, once formed, persists for days in the CMV-infected cell. Ganciclovir triphosphate is believed to inhibit viral DNA synthesis by (1) competitive inhibition of viral DNA polymerases; and (2) incorporation into viral DNA, resulting in eventual termination of viral DNA elongation. Ganciclovir is indicated for the treatment of CMV retinitis in immunocompromised patients, including patients with acquired immunodeficiency syndrome (AIDS) and for the treatment of acute herpetic keratitis.

CNS Activity

Originator

Syntex
47
Curator's Comment: The first synthesis of ganciclovir was reported by Julien Verheyden and John Martin at Syntex Research in California in 1980 and is marketed as sodium salt (Ganciclovir sodium) under the trade names Cytovene and Cymevene.

Approval Year

1989
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
DNA polymerase catalytic subunit
14
Target ID: P08546
Gene ID: NA
Gene Symbol: UL54
Target Organism: Human cytomegalovirus (strain AD169) (HHV-5) (Human herpesvirus 5)
Antagonist
2849
Inhibitor
8504
 0.08 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ZIRGAN

Approved Use

ZIRGAN is a topical ophthalmic antiviral that is indicated for the treatment of acute herpetic keratitis (dendritic ulcers).

Launch Date

1995
Primary
Approved
8583
CYTOVENE

Approved Use

CYTOVENE-IV is indicated for the treatment of CMV retinitis in immunocompromised patients, including patients with acquired immunodeficiency syndrome (AIDS). CYTOVENE-IV is also indicated for the prevention of CMV disease in transplant recipients at risk for CMV disease.

Launch Date

1994
Primary
Approved
8583
VALCYTE

Approved Use

VALCYTE is indicated for the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)

Launch Date

2001
Primary
Approved
8583
VALCYTE

Approved Use

VALCYTE is indicated for the prevention of CMV disease in kidney, heart, and kidney-pancreas transplant patients at high risk

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.8 mg/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/10747829
1 g 3 times / day multiple, oral
dose: 1 g
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GANCICLOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
13.3 μg/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16737936
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
GANCICLOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
35.4 mg × h/L
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/10747829
1 g 3 times / day multiple, oral
dose: 1 g
route of administration: Oral
experiment type: MULTIPLE
co-administered:
GANCICLOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
53.8 μg × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16737936
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
GANCICLOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.2 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16737936
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
GANCICLOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg 6 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 6 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 6 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 37.4
Health Status: unhealthy
Age Group: 37.4
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 38.6
Health Status: unhealthy
Age Group: 38.6
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Other AEs: Neutropenia, Thrombocytopenia...
Other AEs:
Neutropenia (18%)
Thrombocytopenia (4%)
Anemia (severe, 4%)
Renal impairment (4%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
50 mg/kg 3 times / day multiple, oral
Highest studied dose
Dose: 50 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11069232/
unhealthy, 7.4 years (range: 0.5-16.9 years)
Health Status: unhealthy
Age Group: 7.4 years (range: 0.5-16.9 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11069232/
Other AEs: Neutropenia...
Other AEs:
Neutropenia (22%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11069232/
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Other AEs: Fever, Infection...
Other AEs:
Fever (48%)
Infection (13%)
Chills (10%)
Sepsis (15%)
Diarrhea (44%)
Anorexia (14%)
Vomiting (13%)
Leukopenia (41%)
Anemia (25%)
Thrombocytopenia (6%)
Neuropathy (9%)
Sweating (12%)
Pruritus (5%)
Catheter infection (9%)
Catheter sepsis (8%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Neutropenia 18%
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 38.6
Health Status: unhealthy
Age Group: 38.6
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Renal impairment 4%
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 38.6
Health Status: unhealthy
Age Group: 38.6
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Thrombocytopenia 4%
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 38.6
Health Status: unhealthy
Age Group: 38.6
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Anemia severe, 4%
2000 mg 3 times / day multiple, oral
Highest studied dose
Dose: 2000 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2000 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
unhealthy, 38.6
Health Status: unhealthy
Age Group: 38.6
Sources:
https://pubmed.ncbi.nlm.nih.gov/7769276/
Neutropenia 22%
50 mg/kg 3 times / day multiple, oral
Highest studied dose
Dose: 50 mg/kg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg/kg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11069232/
unhealthy, 7.4 years (range: 0.5-16.9 years)
Health Status: unhealthy
Age Group: 7.4 years (range: 0.5-16.9 years)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11069232/
Chills 10%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Sweating 12%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Infection 13%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Vomiting 13%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Anorexia 14%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Sepsis 15%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Anemia 25%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Leukopenia 41%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Diarrhea 44%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Fever 48%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Pruritus 5%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Thrombocytopenia 6%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Catheter sepsis 8%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Catheter infection 9%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Neuropathy 9%
5 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
supressor
10

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MATE1
182

MATE2
98

OCT1
393

OAT1
395

OAT2
125

OAT3
391

OCT2
434

P-gp
2052

MRP4
91
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OAT3
391
 no
OCT2
434
 no
MATE1
182
 yes
MATE2
98
 yes
MRP4
91
 yes
OAT1
395
 yes
OAT2
125
 yes
OCT1
393
 yes
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:465284
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:465284
ChemicalBook
CB6203364
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6203364
eMolecules
31410312
https://www.emolecules.com/cgi-bin/more?vid=31410312
eMolecules
538661
https://www.emolecules.com/cgi-bin/more?vid=538661
MolPort
MolPort-000-758-398
https://www.molport.com/shop/molecule-link/MolPort-000-758-398
MolPort
MolPort-002-507-301
https://www.molport.com/shop/molecule-link/MolPort-002-507-301
MolPort
MolPort-006-167-681
https://www.molport.com/shop/molecule-link/MolPort-006-167-681
Selleck Chemicals
ganciclovir
http://www.selleckchem.com/products/ganciclovir.html
ZINC
ZINC000000001505
http://zinc15.docking.org/substances/ZINC000000001505
PubMed

PubMed

TitleDatePubMed
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.
1999 Jun 17
Comparative study of the anti-human cytomegalovirus activities and toxicities of a tetrahydrofuran phosphonate analogue of guanosine and cidofovir.
1999 Mar
Phenotypic and genetic characterization of thymidine kinase from clinical strains of varicella-zoster virus resistant to acyclovir.
1999 Oct
Human cytomegalovirus: challenges, opportunities and new drug development.
1999 Sep
Psychotic symptoms and confusion associated with intravenous ganciclovir in a heart transplant recipient.
2000 Apr
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
A novel peptide aldehyde with activity against human cytomegalovirus in two different in vivo models.
2000 Jan
Synthesis of 4-substituted imidazo[4,5-d][1,2,3]triazine (2-azapurine)nucleosides.
2000 Jan-Feb
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Indolocarbazoles exhibit strong antiviral activity against human cytomegalovirus and are potent inhibitors of the pUL97 protein kinase.
2000 Oct
Prophylaxis against herpesvirus infections in transplant recipients.
2001
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
Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells.
2001 Feb
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
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
Rat glioma cell death induced by cationic liposome-mediated transfer of the herpes simplex virus thymidine kinase gene followed by ganciclovir treatment.
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
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.
2001 Jan
Retinal detachment risk in cytomegalovirus retinitis related to the acquired immunodeficiency syndrome.
2001 Jan
Molecular mechanism for ganciclovir resistance in human T lymphocytes transduced with retroviral vectors carrying the herpes simplex virus thymidine kinase gene.
2001 Jan 1
Administration of herpes simplex-thymidine kinase-expressing donor T cells with a T-cell-depleted allogeneic marrow graft.
2001 Jan 1
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.
2001 Jan 15
Cidofovir for cytomegalovirus infection and disease in allogeneic stem cell transplant recipients. The Infectious Diseases Working Party of the European Group for Blood and Marrow Transplantation.
2001 Jan 15
Mutations conferring ganciclovir resistance in a cohort of patients with acquired immunodeficiency syndrome and cytomegalovirus retinitis.
2001 Jan 15
Human beta-herpesvirus interactions in solid organ transplant recipients.
2001 Jan 15
Fatal primary infection due to human herpesvirus 6 variant A in a renal transplant recipient.
2001 Jan 27
The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host.
2001 Mar
Preevaluation of clinical trial data: the case of preemptive cytomegalovirus therapy in patients with human immunodeficiency virus.
2001 Mar 1
Prophylaxis for CMV should not now replace pre-emptive therapy in solid organ transplantation.
2001 Mar-Apr
Patents

Patents

04355032
8
04609661
8
04803271
8
20100226943
186
JP2000514093A
8
JP2002541233A
406
JP2004016051A
8
JP2007508039A
116
JP2011525180A
180
JP4733833B2
8
JP4758474B2
87
JPH0841061A
8
JPH0853452A
8
JPS57203086A
8
US20120121700 A1
8
US8586738 B2
8
US8889109 B2
8

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ganciclovir can be used as ophthalmic gel 1 drop in the affected eye 5 times per day in patients with acute herpetic keratitis.
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: The median concentration of ganciclovir that inhibits CMV replication (IC50) in vitro (laboratory strains or clinical isolates) has ranged from 0.02 to 3.48 ug/mL.
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:20 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:20 GMT 2025
Record UNII
P9G3CKZ4P5
Record Status Validated (UNII)
Record Version
  • Download
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
VITRASERT
Preferred Name English
BW 759U
Code English
GANCICLOVIR [HSDB]
Common Name English
GANCICLOVIR [EP IMPURITY]
Common Name English
GANCICLOVIR [EMA EPAR]
Common Name English
9-[[2-Hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine
Systematic Name English
Ganciclovir [WHO-DD]
Common Name English
VALGANCICLOVIR HYDROCHLORIDE IMPURITY A [USP IMPURITY]
Common Name English
GANCICLOVIR [USAN]
Common Name English
GANCICLOVIR [USP MONOGRAPH]
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
ZIRGAN
Brand Name English
GANCICLOVIR [ORANGE BOOK]
Common Name English
RS-21592
Code English
BW-759U
Code English
ganciclovir [INN]
Common Name English
GANCICLOVIR [EP MONOGRAPH]
Common Name English
GANCICLOVIR [VANDF]
Common Name English
NSC-759656
Code 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
FDA ORPHAN DRUG 237607
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NCI_THESAURUS C29575
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
EMA ASSESSMENT REPORTS VITRASERT IMPLANT (WITHDRAWN: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000020060
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
LIVERTOX NBK548760
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000175461
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
EMA ASSESSMENT REPORTS VITRASERT IMPLANT (WITHDRAWN: CYTOMEGALOVIRUS RETINITIS)
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000175466
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
WHO-VATC QS01AD09
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
FDA ORPHAN DRUG 5885
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NCI_THESAURUS C281
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
WHO-ATC J05AB06
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
WHO-VATC QJ05AB06
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
WHO-ATC S01AD09
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
FDA ORPHAN DRUG 86494
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
Code System Code Type Description
CHEBI
465284
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
SMS_ID
100000085455
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
EVMPD
SUB07881MIG
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
PUBCHEM
135398740
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
DRUG CENTRAL
1277
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
USAN
W-148
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID8041032
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
DRUG BANK
DB01004
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
RS_ITEM_NUM
1288306
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
NCI_THESAURUS
C517
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
DAILYMED
P9G3CKZ4P5
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL182
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
NSC
759656
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
RXCUI
4678
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY RxNorm
LACTMED
Ganciclovir
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
INN
6023
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
MERCK INDEX
m5663
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY Merck Index
FDA UNII
P9G3CKZ4P5
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
HSDB
6512
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
CAS
82410-32-0
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
MESH
D015774
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
WIKIPEDIA
GANCICLOVIR
Created by admin on Mon Mar 31 17:45:20 GMT 2025 , Edited by admin on Mon Mar 31 17:45:20 GMT 2025
PRIMARY
Related Record Type Details
MATE-2
TRANSPORTER -> SUBSTRATE
Vmax
OCT-1
TRANSPORTER -> SUBSTRATE
HUMAN HERPESVIRUS 1
TARGET ORGANISM->INHIBITOR
OAT-2
TRANSPORTER -> SUBSTRATE
Structure of Ganciclovir
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> SUBSTRATE
Km
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> SUBSTRATE
Vmax
Structure of Ganciclovir
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
HUMAN HERPESVIRUS 5
TARGET ORGANISM->INHIBITOR
MATE-2
TRANSPORTER -> SUBSTRATE
Km
Structure of GANCICLOVIR SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of GANCICLOVIR TRIPHOSPHATE
METABOLITE ACTIVE -> PARENT
Structure of ROCICLOVIR
PRODRUG -> METABOLITE ACTIVE
Structure of VALGANCICLOVIR
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of 2-AMINO-9-(((2-HYDROXY-1-(HYDROXYMETHYL)ETHOXY)METHOXY)METHYL)-1,9-DIHYDRO-6H-PURIN-6-ONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Guanine
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ISOGANCICLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Valganciclovir Hydrochloride
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-Amino-9-(((2-chloroprop-2-en-1-yl)oxy)methyl)-1,9-dihydro-6H-purin-6-one
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-((2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)-3-hydroxypropyl propionate, (±)-
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-Amino-9-[[(1RS)-2-chloro-1-(hydroxymethyl)ethoxy]methyl]-1,9-dihydro-6H-purin-6-one
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ISOGANCICLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of Ganciclovir
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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