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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H52N3O7P
Molecular Weight 561.6914
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRINCIDOFOVIR

SMILES

CCCCCCCCCCCCCCCCOCCCOP(O)(=O)CO[C@H](CO)CN1C=CC(N)=NC1=O

InChI

InChIKey=WXJFKKQWPMNTIM-VWLOTQADSA-N
InChI=1S/C27H52N3O7P/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)/t25-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H52N3O7P
Molecular Weight 561.6914
Charge 0
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
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
Economic evaluation of systemic treatments for cytomegalovirus retinitis in patients with AIDS.
2001
Cidofovir in the treatment of HPV-associated lesions.
2001
Prophylaxis against herpesvirus infections in transplant recipients.
2001
Successful treatment of severe respiratory papillomatosis with intravenous cidofovir and interferon alpha-2b.
2001 Apr
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
Successful preemptive cidofovir treatment for CMV antigenemia after dose-reduced conditioning and allogeneic blood stem cell transplantation.
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
Cytomegalovirus treatment options in immunocompromised patients.
2001 Aug
Infections after stem cell transplantation in children: state of the art and recommendations.
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
Antiviral activity of NMSO3 against adenovirus in vitro.
2001 Dec
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model.
2001 Dec
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
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor.
2001 Feb
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.
2001 Jan
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.
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
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
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons.
2001 Jun
Progress in understanding cytomegalovirus drug resistance.
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
[Anterior uveitis and cidofovir].
2001 May
Successful treatment of aids related PML with HAART and cidofovir.
2001 May 29
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
Cidofovir treatment of progressive multifocal leukoencephalopathy in a patient receiving highly active antiretroviral therapy.
2001 Nov
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.
2001 Oct
Cytomegalovirus infection: the point in 2001.
2001 Oct
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.
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
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 Sat Dec 17 06:57:21 UTC 2022
Edited
by admin
on Sat Dec 17 06:57:21 UTC 2022
Record UNII
6794O900AX
Record Status Validated (UNII)
Record Version
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Name Type Language
BRINCIDOFOVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
BRINCIDOFOVIR [USAN]
Common Name English
TEMBEXA
Brand Name English
HDP-CIDOFOVIR
Common Name English
Brincidofovir [WHO-DD]
Common Name English
BRINCIDOFOVIR [ORANGE BOOK]
Common Name English
CMX 001
Code English
HEXADECYLOXYPROPYL CIDOFOVIR
Common Name English
HEXADECYLOXYPROPYL-CIDOFOVIR
Common Name English
brincidofovir [INN]
Common Name English
CMX001
Code English
PHOSPHONIC ACID, P-(((1S)-2-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1-(HYDROXYMETHYL)ETHOXY)METHYL)-, MONO(3-(HEXADECYLOXY)PROPYL) ESTER
Common Name English
CMX-001
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/16/1644
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
NCI_THESAURUS C29575
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
FDA ORPHAN DRUG 640518
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
NCI_THESAURUS C281
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
Code System Code Type Description
DRUG BANK
DB12151
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
DAILYMED
6794O900AX
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
ChEMBL
CHEMBL203321
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
FDA UNII
6794O900AX
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
NCI_THESAURUS
C90587
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
CAS
444805-28-1
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
WIKIPEDIA
Brincidofovir
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
USAN
YY-58
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
EPA CompTox
DTXSID60196190
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
INN
9853
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
PUBCHEM
483477
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
EVMPD
SUB177826
Created by admin on Sat Dec 17 06:57:22 UTC 2022 , Edited by admin on Sat Dec 17 06:57:22 UTC 2022
PRIMARY
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SALT/SOLVATE -> PARENT
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