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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H51N3O7P.Na
Molecular Weight 583.6733
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRINCIDOFOVIR SODIUM

SMILES

[Na+].CCCCCCCCCCCCCCCCOCCCOP([O-])(=O)CO[C@H](CO)CN1C=CC(N)=NC1=O

InChI

InChIKey=CRDDLOITBKEPRN-UQIIZPHYSA-M
InChI=1S/C27H52N3O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32;/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32);/q;+1/p-1/t25-;/m0./s1

HIDE SMILES / InChI

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

1996
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
Design and SAR study of a novel class of nucleotide analogues as potent anti-HCMV agents.
1999 Apr-May
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Cidofovir in the treatment of HPV-associated lesions.
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
Cidofovir added to highly active antiretroviral therapy in AIDS-associated progressive multifocal leukoencephalopathy.
2001 Apr 13
Successful preemptive cidofovir treatment for CMV antigenemia after dose-reduced conditioning and allogeneic blood stem cell transplantation.
2001 Apr 15
Potent inhibition of hemangiosarcoma development in mice by cidofovir.
2001 Apr 15
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
An efficient process for the synthesis of cyclic HPMPC.
2001 Apr-Jul
Infections after stem cell transplantation in children: state of the art and recommendations.
2001 Aug
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
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.
2001 Jan
In vitro effects of antiviral agents on human keratocytes.
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
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons.
2001 Jun
[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
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children.
2001 Mar
[Anterior uveitis and cidofovir].
2001 May
The effects of cidofovir on progressive multifocal leukoencephalopathy: an MRI case study.
2001 May
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology.
2001 May-Jun
Cytomegalovirus infection: the point in 2001.
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
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)
Name Type Language
BRINCIDOFOVIR SODIUM
Common Name English
PHOSPHONIC ACID, (((1S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, MONO(3-(HEXADECYLOXY)PROPYL) ESTER, MONOSODIUM SALT
Common Name English
PHOSPHONIC ACID, P-(((1S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, MONO(3-(HEXADECYLOXY)PROPYL)ESTER, SODIUM SALT (1:1)
Common Name English
HEXADECYLOXYPROPYL-CIDOFOVIR SODIUM
Common Name English
SODIUM 3-(HEXADECYLOXY)PROPYL (((1S)-2-(4-AMINO-2-OXOPYRIMIDIN-1(2H)-YL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)PHOSPHONATE
Systematic Name English
Code System Code Type Description
PUBCHEM
24848765
Created by admin on Fri Dec 15 15:49:41 GMT 2023 , Edited by admin on Fri Dec 15 15:49:41 GMT 2023
PRIMARY
FDA UNII
8UN8SA9Z5C
Created by admin on Fri Dec 15 15:49:41 GMT 2023 , Edited by admin on Fri Dec 15 15:49:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT002145
Created by admin on Fri Dec 15 15:49:41 GMT 2023 , Edited by admin on Fri Dec 15 15:49:41 GMT 2023
PRIMARY
CAS
496765-79-8
Created by admin on Fri Dec 15 15:49:41 GMT 2023 , Edited by admin on Fri Dec 15 15:49:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID60197965
Created by admin on Fri Dec 15 15:49:41 GMT 2023 , Edited by admin on Fri Dec 15 15:49:41 GMT 2023
PRIMARY