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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
Molecular Formula C27H51N3O7P
Molecular Weight 560.6835
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
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

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

CNS Penetrant
2554
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.

Originator

Approval Year

1996
225
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7574510
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:
https://pubmed.ncbi.nlm.nih.gov/9797239
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:
https://pubmed.ncbi.nlm.nih.gov/9797239
Page: p.2998
Disc. AE: Ulceration...
AEs leading to
discontinuation/dose reduction:
Ulceration (2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9797239
Page: p.2998
10 mg/kg single, intravenous
Highest studied dose
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
Page: p.154
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
Page: p.154
10 mg/kg single, oral
Highest studied dose
Dose: 10 mg/kg
Route: oral
Route: single
Dose: 10 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
Page: p.154
unhealthy
n = 5
Health Status: unhealthy
Condition: Acquired immunodeficiency syndrome (AIDS)
Sex: M+F
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
Page: p.154
Sources:
https://pubmed.ncbi.nlm.nih.gov/8739595
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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:
https://pubmed.ncbi.nlm.nih.gov/9797239
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:
https://pubmed.ncbi.nlm.nih.gov/9797239
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
Page: p.1
unhealthy
Health Status: unhealthy
Condition: CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS)
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT1
326

OAT3
339

OCT2
355
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OCT2
355
 no
OAT1
326
 yes
OAT3
339
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:3696
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3696
ChemicalBook
CB01178278
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB01178278
ChemicalBook
CB5492709
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5492709
Selleck Chemicals
Cidofovir
http://www.selleckchem.com/products/Cidofovir.html
ZINC
ZINC000001530600
http://zinc15.docking.org/substances/ZINC000001530600
eMolecules
2729368
https://www.emolecules.com/cgi-bin/more?vid=2729368
PubMed

PubMed

TitleDatePubMed
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells.
2000
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas.
2000 Nov
Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes.
2000 Oct 15
Economic evaluation of systemic treatments for cytomegalovirus retinitis in patients with AIDS.
2001
Prophylaxis against herpesvirus infections in transplant recipients.
2001
Successful treatment of severe respiratory papillomatosis with intravenous cidofovir and interferon alpha-2b.
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
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
Cidofovir in AIDS-associated progressive multifocal leukoencephalopathy: a monocenter observational study with clinical and JC virus load monitoring.
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 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
Systemic cidofovir in papillomatosis.
2001 Feb 1
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
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
Progress in understanding cytomegalovirus drug resistance.
2001 Jun
Successful treatment of recurrent vulvar intraepithelial neoplasia resistant to interferon and isotretinoin with cidofovir.
2001 Jun
[Efficacy of cidofovir in an HIV infected patient with an acyclovir and foscarnet resistant herpes simplex virus infection].
2001 Jun-Jul
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
Contact dermatitis from topical antiviral drugs.
2001 May
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
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
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
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

Patents

JP2003502309A
18
JP2003515526A
462
JP2005537267A
15
JP2013231058A
5

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 Fri Dec 15 15:49:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:41 GMT 2023
Record UNII
8UN8SA9Z5C
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
Structure of BRINCIDOFOVIR
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CIDOFOVIR ANHYDROUS
ACTIVE MOIETY
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