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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

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
Susceptibility of human cytomegalovirus to two-drug combinations in vitro.
1996 Dec
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
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.
2001
[Ocular complications after treatment with intravenous cidofovir for cytomegalovirus retinitis].
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
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
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
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
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
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
Use of cidofovir in progressive multifocal leukoencephalopathy.
2001 Jun
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons.
2001 Jun
Cidofovir.
2001 Mar
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children.
2001 Mar
[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
Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs.
2001 Nov 1
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.
2001 Nov-Dec
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.
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
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
Strategies for management of cytomegalovirus (CMV) infection after allogeneic bone marrow transplantation: the "doubling of baseline CMV pp65 antigenemia" and the "cidofovir as rescue treatment approaches.
2001 Sep 1
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 21:39:33 GMT 2023
Edited
by admin
on Fri Dec 15 21:39:33 GMT 2023
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
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 Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
FDA ORPHAN DRUG 640518
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
Code System Code Type Description
RXCUI
2599518
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
DRUG BANK
DB12151
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
DAILYMED
6794O900AX
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
SMS_ID
100000163520
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL203321
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
FDA UNII
6794O900AX
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
NCI_THESAURUS
C90587
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
CAS
444805-28-1
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
WIKIPEDIA
Brincidofovir
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
USAN
YY-58
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID60196190
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
INN
9853
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
PUBCHEM
483477
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
EVMPD
SUB177826
Created by admin on Fri Dec 15 21:39:33 GMT 2023 , Edited by admin on Fri Dec 15 21:39:33 GMT 2023
PRIMARY
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