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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H12N3O6P.2Na
Molecular Weight 323.1507
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIDOFOVIR SODIUM

SMILES

[Na+].[Na+].NC1=NC(=O)N(C[C@@H](CO)OCP([O-])([O-])=O)C=C1

InChI

InChIKey=HKIAHFPOQYDOHP-ILKKLZGPSA-L
InChI=1S/C8H14N3O6P.2Na/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);;/q;2*+1/p-2/t6-;;/m0../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H12N3O6P
Molecular Weight 277.1711
Charge -2
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
Remission of AIDS-associated progressive multifocal leukoencephalopathy after cidofovir therapy.
1999 Aug
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Comparative study of the anti-human cytomegalovirus activities and toxicities of a tetrahydrofuran phosphonate analogue of guanosine and cidofovir.
1999 Mar
Cidofovir-induced end-stage renal failure.
1999 Oct
Human cytomegalovirus: challenges, opportunities and new drug development.
1999 Sep
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
Adenoviral infections and a prospective trial of cidofovir in pediatric hematopoietic stem cell transplantation.
2001
Cytomegalovirus treatment options in immunocompromised patients.
2001 Aug
Infections after stem cell transplantation in children: state of the art and recommendations.
2001 Aug
Acute renal failure in a lung transplant patient after therapy with cidofovir.
2001 Dec
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor.
2001 Feb
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
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
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis.
2001 Mar
[Anterior uveitis and cidofovir].
2001 May
Successful treatment of aids related PML with HAART and cidofovir.
2001 May 29
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.
2001 Nov
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.
2001 Oct
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome.
2001 Oct 22
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients.
2001 Sep 1
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 Dec 15 18:11:54 UTC 2023
Edited
by admin
on Fri Dec 15 18:11:54 UTC 2023
Record UNII
M83JB37U61
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIDOFOVIR SODIUM
Common Name English
PHOSPHONIC ACID, ((2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, DISODIUM SALT, (S)-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30923359
Created by admin on Fri Dec 15 18:11:54 UTC 2023 , Edited by admin on Fri Dec 15 18:11:54 UTC 2023
PRIMARY
PUBCHEM
135406
Created by admin on Fri Dec 15 18:11:54 UTC 2023 , Edited by admin on Fri Dec 15 18:11:54 UTC 2023
PRIMARY
CAS
120362-37-0
Created by admin on Fri Dec 15 18:11:54 UTC 2023 , Edited by admin on Fri Dec 15 18:11:54 UTC 2023
NON-SPECIFIC STOICHIOMETRY
CAS
127749-27-3
Created by admin on Fri Dec 15 18:11:54 UTC 2023 , Edited by admin on Fri Dec 15 18:11:54 UTC 2023
PRIMARY
FDA UNII
M83JB37U61
Created by admin on Fri Dec 15 18:11:54 UTC 2023 , Edited by admin on Fri Dec 15 18:11:54 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY