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 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 |
---|---|---|
Susceptibility of human cytomegalovirus to two-drug combinations in vitro. | 1996 Dec |
|
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
|
Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells. | 2000 |
|
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections. | 2001 |
|
[Ocular complications after treatment with intravenous cidofovir for cytomegalovirus retinitis]. | 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 |
|
An efficient process for the synthesis of cyclic HPMPC. | 2001 Apr-Jul |
|
Cidofovir in AIDS-associated progressive multifocal leukoencephalopathy: a monocenter observational study with clinical and JC virus load monitoring. | 2001 Aug |
|
The good and evil of HAART in HIV-related progressive multifocal leukoencephalopathy. | 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 |
|
Antiviral prophylaxis with twice daily topical cidofovir protects against challenge in the adenovirus type 5/New Zealand rabbit ocular model. | 2001 Dec |
|
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 |
|
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 |
|
Effects of diclofenac or ketorolac on the inhibitory activity of cidofovir in the Ad5/NZW rabbit model. | 2001 Jan |
|
Failure of cidofovir therapy in progressive multifocal leukoencephalopathy unrelated to human immunodeficiency virus. | 2001 Jan |
|
Use of cidofovir in progressive multifocal leukoencephalopathy. | 2001 Jun |
|
Efficacy and tolerability of topical 1% cidofovir cream for the treatment of external anogenital warts in HIV-infected persons. | 2001 Jun |
|
Cidofovir. | 2001 Mar |
|
Early diagnosis of adenovirus infection and treatment with cidofovir after bone marrow transplantation in children. | 2001 Mar |
|
[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 |
|
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 |
|
Anti-CD20 monoclonal antibody (Rituximab) and Cidofovir as successful treatment of an EBV-associated lymphoma with CNS involvement. | 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 |
|
Infection due to acyclovir resistant herpes simplex virus in patients undergoing allogeneic hematopoietic stem cell transplantation. | 2001 Sep |
|
Quantification of cytomegalovirus (CMV) viral load by the hybrid capture assay allows for early detection of CMV disease in lung transplant recipients. | 2001 Sep |
|
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 |
|
Cidofovir for cytomegalovirus-preemptive therapy in stem cell transplant recipients. | 2001 Sep 1 |
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
Fri Dec 15 21:39:33 GMT 2023
by
admin
on
Fri Dec 15 21:39:33 GMT 2023
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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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FDA ORPHAN DRUG |
640518
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NCI_THESAURUS |
C29575
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NCI_THESAURUS |
C281
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2599518
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DB12151
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100000163520
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CHEMBL203321
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6794O900AX
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444805-28-1
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Brincidofovir
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YY-58
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483477
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SUB177826
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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