BRINCIDOFOVIR

First approved in 1996

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 Search

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
Sources: http://www.gilead.com/~/media/files/pdfs/medicines/other/vistide/vistide.pdf |https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/020638s003lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human herpesvirus 1 DNA polymerase 24 Target ID: CHEMBL1872 Sources: https://pubmed.ncbi.nlm.nih.gov/17913252	Inhibitor 8504		0.9 null [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cytomegalovirus retinitis 16 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/020638s003lbl.pdf	Primary		Approved 8583	VISTIDE Approved Use Cidofovir injection is indicated for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome (AIDS). Launch Date 1996

C_max

Value	Dose	Analyte	Population
23.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7574510	10 mg/kg 1 times / week other, intravenous dose: 10 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
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

AUC

Value	Dose	Analyte	Population
68.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7574510	10 mg/kg 1 times / week other, intravenous dose: 10 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
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

T_1/2

Value	Dose	Analyte	Population
3.14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7574510	10 mg/kg 1 times / week other, intravenous dose: 10 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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% EXPERIMENT https://journals.asm.org/doi/full/10.1128/cmr.16.4.569-596.2003	1 times / day other, intravenous		CIDOFOVIR serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 % single, topical Highest studied dose Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/9797239	unhealthy, 21–66 Health Status: unhealthy Age Group: 21–66 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9797239	Disc. AE: Ulceration... AEs leading to discontinuation/dose reduction: Ulceration (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/9797239
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	unhealthy Health Status: unhealthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8739595	Sources: https://pubmed.ncbi.nlm.nih.gov/8739595
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	unhealthy Health Status: unhealthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8739595	Sources: https://pubmed.ncbi.nlm.nih.gov/8739595
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	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display	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

AEs

AE	Significance	Dose	Population
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	unhealthy, 21–66 Health Status: unhealthy Age Group: 21–66 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9797239
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	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display
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	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=90639fc6-0295-4115-98f0-054b783850ce&type=display

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 246 MRP4 290 BSEP 550 OAT1 725 MRP2 499	OCT2 434 BCRP 697 MRP2 252 MRP4 91 OAT3 391 OAT1 395

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://transportal.compbio.ucsf.edu/compounds/cidofovir/ \| https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://transportal.compbio.ucsf.edu/compounds/cidofovir/ \| https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://transportal.compbio.ucsf.edu/compounds/cidofovir/ \| https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://transportal.compbio.ucsf.edu/compounds/cidofovir/ \| https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10929807/ \| https://transportal.compbio.ucsf.edu/compounds/cidofovir/	yes [IC50 60 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17110501/	no
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17110501/	no
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17110501/	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: -	no
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ \| https://pubmed.ncbi.nlm.nih.gov/7574510/ Page: -	yes	no (co-administration study) Comment: Oral probenecid to hydrated patients had no significant effect on the pharmacokinetics of cidofovir at a 3.0-mg/kg dose. Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ \| https://pubmed.ncbi.nlm.nih.gov/7574510/ Page: -
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: -	yes	no (co-administration study) Comment: Oral probenecid to hydrated patients had no significant effect on the pharmacokinetics of cidofovir at a 3.0-mg/kg dose. Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
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
eMolecules	2729368	https://www.emolecules.com/cgi-bin/more?vid=2729368
Selleck Chemicals	Cidofovir	http://www.selleckchem.com/products/Cidofovir.html
ZINC	ZINC000001530600	http://zinc15.docking.org/substances/ZINC000001530600

PubMed

Title	Date	PubMed
Combined surgical-medical treatment of genital warts in HIV positive patients.	2002-01-05	11765191
Cidofovir-induced end-stage renal failure.	2002-01	11773481
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.	2001-12-18	11747000
Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy.	2001-12-01	11719390
Acute renal failure in a lung transplant patient after therapy with cidofovir.	2001-12	11793044
Novel non-nucleoside inhibitors of cytomegaloviruses (BAY 38-4766): in vitro and in vivo antiviral activity and mechanism of action.	2001-12	11733458
Antiviral activity of NMSO3 against adenovirus in vitro.	2001-12	11675145
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model.	2001-12	11675144
Prevention and inhibition of nasopharyngeal carcinoma growth by antiviral phosphonated nucleoside analogs.	2001-11-01	11691806
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance.	2001-11-01	11577375
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections.	2001-11	11781649
Successful treatment of foscarnet-resistant herpes simplex stomatitis with intravenous cidofovir in a child.	2001-11	11734717
Cidofovir treatment of progressive multifocal leukoencephalopathy in a patient receiving highly active antiretroviral therapy.	2001-11	11702907
Selection of the same mutation in the U69 protein kinase gene of human herpesvirus-6 after prolonged exposure to ganciclovir in vitro and in vivo.	2001-11	11602788
Nucleoside phosphonate interactions with multiple organic anion transporters in renal proximal tubule.	2001-11	11602668
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome.	2001-10-22	11606156
Bioterrorism. Blocking smallpox: a second defense.	2001-10-19	11641477
Efficacy of cidofovir on human herpesvirus 8 viraemia and Kaposi's sarcoma progression in two patients with AIDS.	2001-10-19	11600842
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient.	2001-10	11781635
Cidofovir for KS lesions.	2001-10	11768871
Progressive multifocal leukoencephalopathy in a child with hyperimmunoglobulin E recurrent infection syndrome and review of the literature.	2001-10	11748496
Cytomegalovirus infection: the point in 2001.	2001-10	11737406
[Prospects for therapy and prevention of adenovirus keratoconjunctivitis].	2001-10	11699326
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement.	2001-10	11694778
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study.	2001-10	11594949
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products.	2001-10	11533171
Effects of cidofovir on the pathogenesis of a lethal vaccinia virus respiratory infection in mice.	2001-10	11530188
Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs.	2001-09-21	11563082
Pharmacokinetics of salicylate ester prodrugs of cyclic HPMPC in dogs.	2001-09-21	11563033
An efficient process for the synthesis of cyclic HPMPC.	2001-09-21	11562964
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.	2001-09-01	11547769
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients.	2001-09-01	11547768
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.	2001-09-01	11477525
Infection due to acyclovir resistant herpes simplex virus in patients undergoing allogeneic hematopoietic stem cell transplantation.	2001-09	11642018
Quantification of cytomegalovirus (CMV) viral load by the hybrid capture assay allows for early detection of CMV disease in lung transplant recipients.	2001-09	11557186
Aciclovir selects for ganciclovir-cross-resistance of human cytomegalovirus in vitro that is only in part explained by known mutations in the UL97 protein.	2001-09	11505446
Cytomegalovirus treatment options in immunocompromised patients.	2001-08	11584992
Infections after stem cell transplantation in children: state of the art and recommendations.	2001-08	11571529
Cidofovir in AIDS-associated progressive multifocal leukoencephalopathy: a monocenter observational study with clinical and JC virus load monitoring.	2001-08	11517420
Potent anti-retroviral therapy with or without cidofovir for AIDS-associated progressive multifocal leukoencephalopathy: extended follow-up of an observational study.	2001-08	11517418
The good and evil of HAART in HIV-related progressive multifocal leukoencephalopathy.	2001-08	11517417
Glass vials for small volume parenterals: influence of drug and manufacturing processes on glass delamination.	2001-08	11485181
A case of human orf in an immunocompromised patient treated successfully with cidofovir cream.	2001-08	11468742
[Efficacy of cidofovir in an HIV infected patient with an acyclovir and foscarnet resistant herpes simplex virus infection].	2001-07-19	11460038
Cidofovir.	2001-03	11682777
Reversal of CSF positivity for JC virus genome by cidofovir in a patient with systemic lupus erythematosus and progressive multifocal leukoencephalopathy.	2001-02	11487186
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections.	2001	11594682
Adenoviral infections and a prospective trial of cidofovir in pediatric hematopoietic stem cell transplantation.	2001	11529489
Economic evaluation of systemic treatments for cytomegalovirus retinitis in patients with AIDS.	2001	11465299
Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells.	2000	11697818

Patents

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 `Mon Mar 31 20:21:15 GMT 2025` Edited by `admin` on `Mon Mar 31 20:21:15 GMT 2025`
Record UNII	6794O900AX
Record Status	`Validated (UNII)`
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Name

Type

Language

BRINCIDOFOVIR

Official Name

English

brincidofovir [INN]

Preferred 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

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