CIDOFOVIR ANHYDROUS

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 Search

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human herpesvirus 5 DNA polymerase 17	Inhibitor 7468	Cytomegalovirus Retinitis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cytomegalovirus Retinitis 15	Primary	Human herpesvirus 5 DNA polymerase	Approved 7883	VISTIDE

PubMed

Title	Date	PubMed
Susceptibility of human cytomegalovirus to two-drug combinations in vitro.	1996 Dec	11324826
In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas.	2000 Nov	11114415
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.	2001	11594682
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.	2001 Apr	11292644
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	11292409
Cytomegalovirus treatment options in immunocompromised patients.	2001 Aug	11584992
Potent anti-retroviral therapy with or without cidofovir for AIDS-associated progressive multifocal leukoencephalopathy: extended follow-up of an observational study.	2001 Aug	11517418
Glass vials for small volume parenterals: influence of drug and manufacturing processes on glass delamination.	2001 Aug	11485181
Antiviral drugs: current state of the art.	2001 Aug	11418355
Acute renal failure in a lung transplant patient after therapy with cidofovir.	2001 Dec	11793044
Novel non-nucleoside inhibitors of cytomegaloviruses (BAY 38-4766): in vitro and in vivo antiviral activity and mechanism of action.	2001 Dec	11733458
Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy.	2001 Dec 1	11719390
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	11248363
Genetic risks of antiviral nucleoside analogues--a survey.	2001 Feb	11248359
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor.	2001 Feb	11233794
Systemic cidofovir in papillomatosis.	2001 Feb 1	11170974
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.	2001 Jan	11437324
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient.	2001 Jan	11215088
In vitro effects of antiviral agents on human keratocytes.	2001 Jan	11189008
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.	2001 Jan	11166858
Effects of diclofenac or ketorolac on the inhibitory activity of cidofovir in the Ad5/NZW rabbit model.	2001 Jan	11133861
Failure of cidofovir therapy in progressive multifocal leukoencephalopathy unrelated to human immunodeficiency virus.	2001 Jan	11112674
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.	2001 Jan 15	11170910
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	11154213
Long-term remission of an AIDS-related primary effusion lymphoma with antiviral therapy.	2001 Jan 26	11216942
Use of cidofovir in progressive multifocal leukoencephalopathy.	2001 Jun	11408993
Successful treatment of recurrent vulvar intraepithelial neoplasia resistant to interferon and isotretinoin with cidofovir.	2001 Jun	11360253
[Oncogenic human papillomaviruses in extra-genital Bowen disease revealed by in situ hybridization].	2001 Jun-Jul	11460032
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis.	2001 Mar	11429040
Topical cidofovir for bowenoid papulosis in an HIV-infected patient.	2001 Mar	11260042
[Anterior uveitis and cidofovir].	2001 May	11397985
The effects of cidofovir on progressive multifocal leukoencephalopathy: an MRI case study.	2001 May	11396742
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.	2001 May 1	11303263
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.	2001 May-Jun	11419030
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.	2001 Nov	11781649
Successful treatment of foscarnet-resistant herpes simplex stomatitis with intravenous cidofovir in a child.	2001 Nov	11734717
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	11602788
Nucleoside phosphonate interactions with multiple organic anion transporters in renal proximal tubule.	2001 Nov	11602668
Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs.	2001 Nov 1	11691806
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance.	2001 Nov 1	11577375
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.	2001 Oct	11781635
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.	2001 Oct	11694778
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study.	2001 Oct	11594949
Effects of cidofovir on the pathogenesis of a lethal vaccinia virus respiratory infection in mice.	2001 Oct	11530188
Efficacy of cidofovir on human herpesvirus 8 viraemia and Kaposi's sarcoma progression in two patients with AIDS.	2001 Oct 19	11600842
Quantification of cytomegalovirus (CMV) viral load by the hybrid capture assay allows for early detection of CMV disease in lung transplant recipients.	2001 Sep	11557186
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	11505446
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients.	2001 Sep 1	11547768
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	11477525
Cidofovir-induced end-stage renal failure.	2002 Jan	11773481

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