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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H14N3O6P.2H2O
Molecular Weight 315.2179
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIDOFOVIR

SMILES

c1cn(C[C@@]([H])(CO)OCP(=O)(O)O)c(nc1=N)O.O.O

InChI

InChIKey=FPKARFMSZDBYQF-ILKKLZGPSA-N
InChI=1S/C8H14N3O6P.2H2O/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16;;/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16);2*1H2/t6-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H14N3O6P
Molecular Weight 279.1874
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10473024 | https://www.ncbi.nlm.nih.gov/pubmed/8630098

Cidofovir is an antiviral nucleotide analogue with significant activity against cytomegalovirus (CMV) and other herpesviruses. Cidofovir suppresses cytomegalovirus (CMV) replication by selective inhibition of viral DNA synthesis. Biochemical data support selective inhibition of CMV DNA polymerase by cidofovir diphosphate, the active intracellular metabolite of cidofovir. Incorporation of cidofovir into the growing viral DNA chain results in reductions in the rate of viral DNA synthesis. Cidofovir is indicated for the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome.

CNS Activity

Curator's Comment:: In rabbits, radiolabelled cidofovir crossed the blood brain barrier but were found at much lower levels than were observed in the kidney tissue. In rats i.v. administered cidofovir does not seem to cross the blood-brain barrier efficiently. No human data available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VISTIDE

Approved Use

Cidofovir injection is indicated for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome (AIDS).

Launch Date

8.3574718E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.34 μg/mL
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11.5 μg/mL
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.12 μg/mL
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19.96 μg × h/mL
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
28.34 μg × h/mL
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.35 μg × h/mL
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.72 h
3 mg/kg 1 times / week other, intravenous
dose: 3 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.42 h
5 mg/kg 1 times / week other, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.44 h
1 mg/kg 1 times / week other, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: OTHER
co-administered:
CIDOFOVIR serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 % single, topical
Highest studied dose
Dose: 5 %
Route: topical
Route: single
Dose: 5 %
Sources: Page: p.2998
unhealthy, 21–66
n = 96
Health Status: unhealthy
Condition: Recurrent genital herpes
Age Group: 21–66
Sex: M+F
Population Size: 96
Sources: Page: p.2998
Disc. AE: Ulceration...
AEs leading to
discontinuation/dose reduction:
Ulceration (2%)
Sources: Page: p.2998
10 mg/kg single, intravenous
Highest studied dose
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources: Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources: Page: p.154
10 mg/kg single, oral
Highest studied dose
Dose: 10 mg/kg
Route: oral
Route: single
Dose: 10 mg/kg
Sources: Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources: Page: p.154
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Disc. AE: Acute renal failure...
Other AEs: Renal impairment, Neutropenia...
AEs leading to
discontinuation/dose reduction:
Acute renal failure
Other AEs:
Renal impairment
Neutropenia
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Ulceration 2%
Disc. AE
5 % single, topical
Highest studied dose
Dose: 5 %
Route: topical
Route: single
Dose: 5 %
Sources: Page: p.2998
unhealthy, 21–66
n = 96
Health Status: unhealthy
Condition: Recurrent genital herpes
Age Group: 21–66
Sex: M+F
Population Size: 96
Sources: Page: p.2998
Neutropenia
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Renal impairment
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Acute renal failure Disc. AE
5 mg/kg 1 times / week multiple, intravenous
Recommended
Dose: 5 mg/kg, 1 times / week
Route: intravenous
Route: multiple
Dose: 5 mg/kg, 1 times / week
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources: Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes
PubMed

PubMed

TitleDatePubMed
Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells.
2000
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.
2001
Adenoviral infections and a prospective trial of cidofovir in pediatric hematopoietic stem cell transplantation.
2001
Economic evaluation of systemic treatments for cytomegalovirus retinitis in patients with AIDS.
2001
Cidofovir in the treatment of HPV-associated lesions.
2001
Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs.
2001 Apr-Jul
Pharmacokinetics of salicylate ester prodrugs of cyclic HPMPC in dogs.
2001 Apr-Jul
Cytomegalovirus treatment options in immunocompromised patients.
2001 Aug
Cidofovir in AIDS-associated progressive multifocal leukoencephalopathy: a monocenter observational study with clinical and JC virus load monitoring.
2001 Aug
Potent anti-retroviral therapy with or without cidofovir for AIDS-associated progressive multifocal leukoencephalopathy: extended follow-up of an observational study.
2001 Aug
The good and evil of HAART in HIV-related progressive multifocal leukoencephalopathy.
2001 Aug
Glass vials for small volume parenterals: influence of drug and manufacturing processes on glass delamination.
2001 Aug
A case of human orf in an immunocompromised patient treated successfully with cidofovir cream.
2001 Aug
Antiviral drugs: current state of the art.
2001 Aug
Acute renal failure in a lung transplant patient after therapy with cidofovir.
2001 Dec
Novel non-nucleoside inhibitors of cytomegaloviruses (BAY 38-4766): in vitro and in vivo antiviral activity and mechanism of action.
2001 Dec
Antiviral activity of NMSO3 against adenovirus in vitro.
2001 Dec
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model.
2001 Dec
Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy.
2001 Dec 1
Reversal of CSF positivity for JC virus genome by cidofovir in a patient with systemic lupus erythematosus and progressive multifocal leukoencephalopathy.
2001 Feb
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.
2001 Jan
The antiviral resistance and replication of cidofovir-resistant adenovirus variants in the New Zealand White rabbit ocular model.
2001 Jul
Inhibition of fibroblast growth factor-2-induced vascular tumor formation by the acyclic nucleoside phosphonate cidofovir.
2001 Jul 1
[Efficacy of cidofovir in an HIV infected patient with an acyclovir and foscarnet resistant herpes simplex virus infection].
2001 Jun-Jul
[Oncogenic human papillomaviruses in extra-genital Bowen disease revealed by in situ hybridization].
2001 Jun-Jul
Cidofovir.
2001 Mar
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis.
2001 Mar
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001 May-Jun
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.
2001 Nov
Cidofovir treatment of progressive multifocal leukoencephalopathy in a patient receiving highly active antiretroviral therapy.
2001 Nov
Selection of the same mutation in the U69 protein kinase gene of human herpesvirus-6 after prolonged exposure to ganciclovir in vitro and in vivo.
2001 Nov
Nucleoside phosphonate interactions with multiple organic anion transporters in renal proximal tubule.
2001 Nov
Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs.
2001 Nov 1
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.
2001 Oct
Cidofovir for KS lesions.
2001 Oct
[Prospects for therapy and prevention of adenovirus keratoconjunctivitis].
2001 Oct
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.
2001 Oct
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study.
2001 Oct
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products.
2001 Oct
Effects of cidofovir on the pathogenesis of a lethal vaccinia virus respiratory infection in mice.
2001 Oct
Bioterrorism. Blocking smallpox: a second defense.
2001 Oct 19
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome.
2001 Oct 22
Infection due to acyclovir resistant herpes simplex virus in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 Sep
Quantification of cytomegalovirus (CMV) viral load by the hybrid capture assay allows for early detection of CMV disease in lung transplant recipients.
2001 Sep
Aciclovir selects for ganciclovir-cross-resistance of human cytomegalovirus in vitro that is only in part explained by known mutations in the UL97 protein.
2001 Sep
Strategies for management of cytomegalovirus (CMV) infection after allogeneic bone marrow transplantation: the "doubling of baseline CMV pp65 antigenemia" and the "cidofovir as rescue treatment approaches.
2001 Sep 1
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients.
2001 Sep 1
Phase II double-blind, placebo-controlled study of the safety and efficacy of cidofovir topical gel for the treatment of patients with human papillomavirus infection.
2001 Sep 1
Combined surgical-medical treatment of genital warts in HIV positive patients.
2001 Sep-Oct
Cidofovir-induced end-stage renal failure.
2002 Jan
Patents

Sample Use Guides

Induction Treatment The recommended induction dose of VISTIDE (cidofovir injection) for patients with a serum creatinine of ≤1.5 mg/dL, a calculated creatinine clearance >55 mL/min, and a urine protein <100 mg/dL (equivalent to <2+ proteinuria) is 5 mg/kg body weight (given as an intravenous infusion at a constant rate over 1 hr) administered once weekly for two consecutive weeks. Maintenance Treatment The recommended maintenance dose of VISTIDE is 5 mg/kg body weight (given as an intravenous infusion at a constant rate over 1 hr), administered once every 2 weeks.
Route of Administration: Intravenous
Cidofovir is active in vitro against a variety of laboratory and clinical isolates of cytomegalovirus with IC50 values of 0.5-2.8 uM (WT isolates)
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:06:01 UTC 2021
Edited
by admin
on Fri Jun 25 22:06:01 UTC 2021
Record UNII
JIL713Q00N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIDOFOVIR
EMA EPAR   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
CIDOFOVIR [USAN]
Common Name English
CIDOFOVIR [ORANGE BOOK]
Common Name English
PHOSPHONIC ACID, ((2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, DIHYDRATE, (S)-
Common Name English
CIDOFOVIR [VANDF]
Common Name English
VISTIDE
Brand Name English
CIDOFOVIR DIHYDRATE
Common Name English
NSC-742135
Code English
CIDOFOVIR [USP MONOGRAPH]
Common Name English
(((S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)PHOSPHONIC ACID, DIHYDRATE
Common Name English
HPMPC DIHYDRATE
Common Name English
1-((S)-3-HYDROXY-2-(PHOSPHONOMETHOXY)PROPYL)CYTOSINE DIHYDRATE
Systematic Name English
CIDOFOVIR [EMA EPAR]
Common Name English
CIDOFOVIR [USP-RS]
Common Name English
GS-0504
Code English
Classification Tree Code System Code
NCI_THESAURUS C29575
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
NDF-RT N0000175461
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
LIVERTOX 206
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
WHO-VATC QJ05AB12
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
EMA ASSESSMENT REPORTS VISTIDE (WITHDRAWN: CYTOMEGALOVIRUS RETINITIS)
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
WHO-ATC J05AB12
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
NCI_THESAURUS C281
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
Code System Code Type Description
PUBCHEM
60933
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
NCI_THESAURUS
C1600
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
CAS
149394-66-1
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
WIKIPEDIA
CIDOFOVIR
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
DRUG CENTRAL
639
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
DRUG BANK
DB00369
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
MESH
C059262
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
FDA UNII
JIL713Q00N
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
USP_CATALOG
1133853
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY USP-RS
EVMPD
SUB26395
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
EPA CompTox
149394-66-1
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
ChEMBL
CHEMBL152
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY
RXCUI
83171
Created by admin on Fri Jun 25 22:06:02 UTC 2021 , Edited by admin on Fri Jun 25 22:06:02 UTC 2021
PRIMARY RxNorm
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ACTIVE MOIETY