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 |
---|---|---|
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine. | 2000 Feb 24 |
|
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 2001 Apr |
|
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 |
|
Acute renal failure in a lung transplant patient after therapy with cidofovir. | 2001 Dec |
|
Treatment of lethal vaccinia virus respiratory infections in mice with cidofovir. | 2001 Jan |
|
Diagnostic and therapeutic dilemmas of a large scrotal lesion in an AIDS patient. | 2001 Jan |
|
The antiviral resistance and replication of cidofovir-resistant adenovirus variants in the New Zealand White rabbit ocular model. | 2001 Jul |
|
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 |
|
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis. | 2001 Mar |
|
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation. | 2001 May 1 |
|
Cidofovir as primary pre-emptive therapy for post-transplant cytomegalovirus infections. | 2001 Nov |
|
Cytomegalovirus ventriculoencephalitis in a bone marrow transplant recipient receiving antiviral maintenance: clinical and molecular evidence of drug resistance. | 2001 Nov 1 |
|
Cidofovir for KS lesions. | 2001 Oct |
|
Topical treatment of acute adenoviral keratoconjunctivitis with 0.2% cidofovir and 1% cyclosporine: a controlled clinical pilot study. | 2001 Oct |
|
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 Sep 1 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 04:28:05 UTC 2023
by
admin
on
Thu Jul 06 04:28:05 UTC 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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444805-28-1
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Brincidofovir
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483477
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SUB177826
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TARGET ORGANISM->INHIBITOR |
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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