Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H12N3O6P.2Na |
| Molecular Weight | 323.1507 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].NC1=NC(=O)N(C[C@@H](CO)OCP([O-])([O-])=O)C=C1
InChI
InChIKey=HKIAHFPOQYDOHP-ILKKLZGPSA-L
InChI=1S/C8H14N3O6P.2Na/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16;;/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16);;/q;2*+1/p-2/t6-;;/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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3414 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Susceptibility of human cytomegalovirus to two-drug combinations in vitro. | 1996 Dec |
|
| Design and SAR study of a novel class of nucleotide analogues as potent anti-HCMV agents. | 1999 Apr-May |
|
| Remission of AIDS-associated progressive multifocal leukoencephalopathy after cidofovir therapy. | 1999 Aug |
|
| Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
|
| 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 |
|
| Human cytomegalovirus: challenges, opportunities and new drug development. | 1999 Sep |
|
| Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells. | 2000 |
|
| The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. | 2000 Feb 24 |
|
| A novel peptide aldehyde with activity against human cytomegalovirus in two different in vivo models. | 2000 Jan |
|
| In vivo anti-papillomavirus activity of nucleoside analogues including cidofovir on CRPV-induced rabbit papillomas. | 2000 Nov |
|
| Adenoviral infections and a prospective trial of cidofovir in pediatric hematopoietic stem cell transplantation. | 2001 |
|
| [Ocular complications after treatment with intravenous cidofovir for cytomegalovirus retinitis]. | 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 |
|
| Cytomegalovirus treatment options in immunocompromised patients. | 2001 Aug |
|
| Cidofovir in AIDS-associated progressive multifocal leukoencephalopathy: a monocenter observational study with clinical and JC virus load monitoring. | 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 |
|
| Long-term remission of Kaposi sarcoma-associated herpesvirus-related multicentric Castleman disease with anti-CD20 monoclonal antibody therapy. | 2001 Dec 1 |
|
| 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 |
|
| Failure of cidofovir therapy in progressive multifocal leukoencephalopathy unrelated to human immunodeficiency virus. | 2001 Jan |
|
| Progress in understanding cytomegalovirus drug resistance. | 2001 Jun |
|
| Successful treatment of recurrent vulvar intraepithelial neoplasia resistant to interferon and isotretinoin with cidofovir. | 2001 Jun |
|
| [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 |
|
| 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 |
|
| 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 Nov |
|
| 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 |
|
| Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient. | 2001 Oct |
|
| Cidofovir for KS lesions. | 2001 Oct |
|
| Progressive multifocal leukoencephalopathy in a child with hyperimmunoglobulin E recurrent infection syndrome and review of the literature. | 2001 Oct |
|
| Cytomegalovirus infection: the point in 2001. | 2001 Oct |
|
| [Prospects for therapy and prevention of adenovirus keratoconjunctivitis]. | 2001 Oct |
|
| Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement. | 2001 Oct |
|
| 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 |
|
| Combined surgical-medical treatment of genital warts in HIV positive patients. | 2001 Sep-Oct |
|
| Cidofovir-induced end-stage renal failure. | 2002 Jan |
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 |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID30923359
Created by
admin on Fri Dec 15 18:11:54 GMT 2023 , Edited by admin on Fri Dec 15 18:11:54 GMT 2023
|
PRIMARY | |||
|
135406
Created by
admin on Fri Dec 15 18:11:54 GMT 2023 , Edited by admin on Fri Dec 15 18:11:54 GMT 2023
|
PRIMARY | |||
|
120362-37-0
Created by
admin on Fri Dec 15 18:11:54 GMT 2023 , Edited by admin on Fri Dec 15 18:11:54 GMT 2023
|
NON-SPECIFIC STOICHIOMETRY | |||
|
127749-27-3
Created by
admin on Fri Dec 15 18:11:54 GMT 2023 , Edited by admin on Fri Dec 15 18:11:54 GMT 2023
|
PRIMARY | |||
|
M83JB37U61
Created by
admin on Fri Dec 15 18:11:54 GMT 2023 , Edited by admin on Fri Dec 15 18:11:54 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
