cidofovir ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals phosphonic acid derivatives 639 113852-37-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cidofovir
  • cidofovir monophosphate
  • cidovir
  • vistide
  • sidofovir
  • cidofovir dihydrate
  • anhydrous cidofovir
  • cidofovir hydrate
An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.
  • Molecular weight: 279.19
  • Formula: C8H14N3O6P
  • CLOGP: -1.99
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 4
  • TPSA: 145.68
  • ALOGS: -1.38
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
25 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 170 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 90 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 17.91 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 5 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.49 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 26, 1996 FDA GILEAD SCIENCES INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 143.79 63.97 40 1068 18949 50585067
Adenovirus infection 140.44 63.97 28 1080 3140 50600876
BK virus infection 67.24 63.97 15 1093 2866 50601150

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 121.23 49.59 41 1077 21499 29551910
Cystitis haemorrhagic 74.24 49.59 20 1098 4822 29568587
Adenovirus infection 71.15 49.59 19 1099 4428 29568981
Drug ineffective for unapproved indication 56.71 49.59 21 1097 14193 29559216
Off label use 53.97 49.59 61 1057 300739 29272670
Progressive multifocal leukoencephalopathy 50.49 49.59 17 1101 8702 29564707

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug resistance 255.13 51.79 79 2105 35023 64461525
Adenovirus infection 179.76 51.79 43 2141 7212 64489336
Cystitis haemorrhagic 121.38 51.79 32 2152 7924 64488624
Pathogen resistance 98.35 51.79 30 2154 12513 64484035
Nephropathy toxic 92.46 51.79 31 2153 17483 64479065
Cytomegalovirus infection 86.24 51.79 36 2148 37163 64459385
Off label use 81.70 51.79 103 2081 632703 63863845
BK virus infection 76.78 51.79 22 2162 7390 64489158
Immune reconstitution inflammatory syndrome 73.52 51.79 24 2160 12446 64484102
Renal impairment 72.25 51.79 49 2135 134968 64361580
Epstein-Barr virus infection reactivation 68.28 51.79 14 2170 1152 64495396
Cytomegalovirus infection reactivation 59.22 51.79 17 2167 5739 64490809
Drug ineffective for unapproved indication 55.34 51.79 25 2159 31108 64465440

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AB12 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleosides and nucleotides excl. reverse transcriptase inhibitors
CHEBI has role CHEBI:35610 antineoplastic agents
CHEBI has role CHEBI:36044 antiviral drugs
CHEBI has role CHEBI:47868 photosensitising agent
CHEBI has role CHEBI:64946 anti-AIDS agent
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
CMV Retinitis in AIDS Patients indication
Acyclovir-Resistant Mucocutaneous HSV in Immunocompromised Patients indication
Prevention of Cytomegalovirus Disease off-label use
Acidosis contraindication 51387008
Kidney disease contraindication 90708001 DOID:557
Severe Chronic Neutropenia contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.81 acidic
pKa2 12.99 acidic
pKa3 4.1 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase catalytic subunit Enzyme INHIBITOR WOMBAT-PK CHEMBL

External reference:

IDSource
4020976 VUID
N0000148447 NUI
D00273 KEGG_DRUG
83170 RXNORM
4020976 VANDF
C0286079 UMLSCUI
CHEBI:59495 CHEBI
L8P PDB_CHEM_ID
CHEMBL152 ChEMBL_ID
DB00369 DRUGBANK_ID
D000077404 MESH_DESCRIPTOR_UI
60613 PUBCHEM_CID
JIL713Q00N UNII
194597 MMSL
4446 MMSL
6016 MMSL
d04028 MMSL
006053 NDDF
108688007 SNOMEDCT_US
386894007 SNOMEDCT_US
149394-66-1 SECONDARY_CAS_RN

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CIDOFOVIR DIHYDRATE HUMAN PRESCRIPTION DRUG LABEL 1 23155-216 INJECTION, SOLUTION 375 mg INTRAVENOUS ANDA 21 sections
Vistide HUMAN PRESCRIPTION DRUG LABEL 1 61958-0101 INJECTION 75 mg INTRAVENOUS NDA 24 sections
CIDOFOVIR HUMAN PRESCRIPTION DRUG LABEL 1 67457-210 INJECTION, SOLUTION 75 mg INTRAVENOUS ANDA 26 sections