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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

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
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.
2001 Apr
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
Acute renal failure in a lung transplant patient after therapy with cidofovir.
2001 Dec
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir.
2001 Jan
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient.
2001 Jan
The antiviral resistance and replication of cidofovir-resistant adenovirus variants in the New Zealand White rabbit ocular model.
2001 Jul
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
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis.
2001 Mar
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 May 1
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.
2001 Nov
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance.
2001 Nov 1
Cidofovir for KS lesions.
2001 Oct
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study.
2001 Oct
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
Cidofovir-induced end-stage renal failure.
2002 Jan
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 Thu Jul 06 04:28:05 UTC 2023
Edited
by admin
on Thu Jul 06 04:28:05 UTC 2023
Record UNII
6794O900AX
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
FDA ORPHAN DRUG 640518
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
NCI_THESAURUS C29575
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
NCI_THESAURUS C281
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
Code System Code Type Description
RXCUI
2599518
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
DRUG BANK
DB12151
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
DAILYMED
6794O900AX
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
SMS_ID
100000163520
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
ChEMBL
CHEMBL203321
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
FDA UNII
6794O900AX
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
NCI_THESAURUS
C90587
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
CAS
444805-28-1
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
WIKIPEDIA
Brincidofovir
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
USAN
YY-58
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
EPA CompTox
DTXSID60196190
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
INN
9853
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
PUBCHEM
483477
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
EVMPD
SUB177826
Created by admin on Thu Jul 06 04:28:05 UTC 2023 , Edited by admin on Thu Jul 06 04:28:05 UTC 2023
PRIMARY
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TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY