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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H14N3O6P
Molecular Weight 279.187
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIDOFOVIR ANHYDROUS

SMILES

NC1=NC(=O)N(C[C@@H](CO)OCP(O)(O)=O)C=C1

InChI

InChIKey=VWFCHDSQECPREK-LURJTMIESA-N
InChI=1S/C8H14N3O6P/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)/t6-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H14N3O6P
Molecular Weight 279.187
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VISTIDE
PubMed

PubMed

TitleDatePubMed
Susceptibility of human cytomegalovirus to two-drug combinations in vitro.
1996 Dec
In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas.
2000 Nov
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.
2001
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
The ganciclovir implant plus oral ganciclovir versus parenteral cidofovir for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome: The Ganciclovir Cidofovir Cytomegalovirus Retinitis Trial.
2001 Apr
Cytomegalovirus treatment options in immunocompromised patients.
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
Glass vials for small volume parenterals: influence of drug and manufacturing processes on glass delamination.
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
Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy.
2001 Dec 1
Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo.
2001 Feb
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor.
2001 Feb
Systemic cidofovir in papillomatosis.
2001 Feb 1
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.
2001 Jan
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient.
2001 Jan
In vitro effects of antiviral agents on human keratocytes.
2001 Jan
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.
2001 Jan
Effects of diclofenac or ketorolac on the inhibitory activity of cidofovir in the Ad5/NZW rabbit model.
2001 Jan
Failure of cidofovir therapy in progressive multifocal leukoencephalopathy unrelated to human immunodeficiency virus.
2001 Jan
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
Long-term remission of an AIDS-related primary effusion lymphoma with antiviral therapy.
2001 Jan 26
Use of cidofovir in progressive multifocal leukoencephalopathy.
2001 Jun
Successful treatment of recurrent vulvar intraepithelial neoplasia resistant to interferon and isotretinoin with cidofovir.
2001 Jun
[Oncogenic human papillomaviruses in extra-genital Bowen disease revealed by in situ hybridization].
2001 Jun-Jul
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis.
2001 Mar
Topical cidofovir for bowenoid papulosis in an HIV-infected patient.
2001 Mar
[Anterior uveitis and cidofovir].
2001 May
The effects of cidofovir on progressive multifocal leukoencephalopathy: an MRI case study.
2001 May
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 May 1
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
Successful treatment of foscarnet-resistant herpes simplex stomatitis with intravenous cidofovir in a child.
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
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance.
2001 Nov 1
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.
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
Effects of cidofovir on the pathogenesis of a lethal vaccinia virus respiratory infection in mice.
2001 Oct
Efficacy of cidofovir on human herpesvirus 8 viraemia and Kaposi's sarcoma progression in two patients with AIDS.
2001 Oct 19
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
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
Cidofovir-induced end-stage renal failure.
2002 Jan
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Mon Oct 21 22:33:10 UTC 2019
Edited
by admin
on Mon Oct 21 22:33:10 UTC 2019
Record UNII
768M1V522C
Record Status Validated (UNII)
Record Version
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Name Type Language
CIDOFOVIR ANHYDROUS
Common Name English
CIDOFOVIR [INN]
Common Name English
ANHYDROUS CIDOFOVIR
Common Name English
PHOSPHONIC ACID, ((2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, (S)-
Common Name English
1-((S)-3-HYDROXY-2-(PHOSPHONOMETHOXY)PROPYL)CYTOSINE
Systematic Name English
HPMPC
Common Name English
CIDOFOVIR [HSDB]
Common Name English
(((S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)PHOSPHONIC ACID
Systematic Name English
CIDOFOVIR [MI]
Common Name English
CIDOFOVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB12
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NCI_THESAURUS C29575
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NDF-RT N0000020060
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
EMA ASSESSMENT REPORTS VISTIDE (WITHDRAWN: CYTOMEGALOVIRUS RETINITIS)
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
NDF-RT N0000175461
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
Code System Code Type Description
EVMPD
SUB25415
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
EVMPD
SUB06257MIG
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
EPA CompTox
113852-37-2
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
DRUG BANK
DB00369
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
MERCK INDEX
M3541
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY Merck Index
CAS
113852-37-2
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
PUBCHEM
60613
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
RXCUI
1546007
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C77925
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
INN
7314
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
HSDB
113852-37-2
Created by admin on Mon Oct 21 22:33:10 UTC 2019 , Edited by admin on Mon Oct 21 22:33:10 UTC 2019
PRIMARY
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ACTIVE MOIETY