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
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
DescriptionCurator'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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3414 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8630098 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VISTIDE Approved UseCidofovir injection is indicated for the treatment of cytomegalovirus retinitis in patients with acquired immunodeficiency syndrome (AIDS). Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 Sources: Page: p.1Neutropenia |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17372702/ Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Design and SAR study of a novel class of nucleotide analogues as potent anti-HCMV agents. | 1999 Apr-May |
|
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
|
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. | 2000 Feb 24 |
|
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
Cidofovir in the treatment of HPV-associated lesions. | 2001 |
|
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 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 |
|
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 |
|
Infections after stem cell transplantation in children: state of the art and recommendations. | 2001 Aug |
|
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 |
|
Genetic risks of antiviral nucleoside analogues--a survey. | 2001 Feb |
|
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir. | 2001 Jan |
|
In vitro effects of antiviral agents on human keratocytes. | 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 |
|
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons. | 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 |
|
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children. | 2001 Mar |
|
[Anterior uveitis and cidofovir]. | 2001 May |
|
The effects of cidofovir on progressive multifocal leukoencephalopathy: an MRI case study. | 2001 May |
|
Clinical applications of a novel sustained-release injectable drug delivery system: DepoFoam technology. | 2001 May-Jun |
|
Cytomegalovirus infection: the point in 2001. | 2001 Oct |
|
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products. | 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 |
|
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome. | 2001 Oct 22 |
|
Infection due to acyclovir resistant herpes simplex virus in patients undergoing allogeneic hematopoietic stem cell transplantation. | 2001 Sep |
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
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD