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
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
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 |
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 Date8.3574718E11 |
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 |
---|---|---|
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 |
|
Economic evaluation of systemic treatments for cytomegalovirus retinitis in patients with AIDS. | 2001 |
|
Cidofovir in the treatment of HPV-associated lesions. | 2001 |
|
Prophylaxis against herpesvirus infections in transplant recipients. | 2001 |
|
Successful treatment of severe respiratory papillomatosis with intravenous cidofovir and interferon alpha-2b. | 2001 Apr |
|
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 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 |
|
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 |
|
Cytomegalovirus treatment options in immunocompromised patients. | 2001 Aug |
|
Infections after stem cell transplantation in children: state of the art and recommendations. | 2001 Aug |
|
Potent anti-retroviral therapy with or without cidofovir for AIDS-associated progressive multifocal leukoencephalopathy: extended follow-up of an observational study. | 2001 Aug |
|
Antiviral activity of NMSO3 against adenovirus in vitro. | 2001 Dec |
|
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model. | 2001 Dec |
|
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 |
|
Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor. | 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 |
|
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 |
|
The antiviral resistance and replication of cidofovir-resistant adenovirus variants in the New Zealand White rabbit ocular model. | 2001 Jul |
|
Inhibition of fibroblast growth factor-2-induced vascular tumor formation by the acyclic nucleoside phosphonate cidofovir. | 2001 Jul 1 |
|
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons. | 2001 Jun |
|
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 |
|
[Oncogenic human papillomaviruses in extra-genital Bowen disease revealed by in situ hybridization]. | 2001 Jun-Jul |
|
[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 |
|
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 |
|
Multiple herpes simplex virus infections with various resistance patterns in a matched unrelated donor transplant recipient. | 2001 Oct |
|
Cytomegalovirus infection: the point in 2001. | 2001 Oct |
|
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement. | 2001 Oct |
|
Treatment of a bowenoid papulosis of the penis with local applications of cidofovir in a patient with acquired immunodeficiency syndrome. | 2001 Oct 22 |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 06:57:21 UTC 2022
by
admin
on
Sat Dec 17 06:57:21 UTC 2022
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Record UNII |
6794O900AX
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Record Status |
Validated (UNII)
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Record Version |
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EU-Orphan Drug |
EU/3/16/1644
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NCI_THESAURUS |
C29575
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FDA ORPHAN DRUG |
640518
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NCI_THESAURUS |
C281
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DB12151
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6794O900AX
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CHEMBL203321
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6794O900AX
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C90587
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444805-28-1
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Brincidofovir
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YY-58
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DTXSID60196190
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9853
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483477
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SUB177826
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INHIBITOR->TARGET ORGANISM |
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |