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
Adenovirus infection 263.55 62.66 48 1181 3360 56287478
Drug resistance 149.82 62.66 42 1187 20500 56270338
BK virus infection 82.91 62.66 18 1211 3046 56287792
Cytomegalovirus infection reactivation 82.27 62.66 18 1211 3158 56287680
Cystitis haemorrhagic 78.42 62.66 18 1211 3919 56286919
Cytomegalovirus infection 77.75 62.66 25 1204 19271 56271567

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
Adenovirus infection 143.49 49.30 34 1215 4720 31691375
Drug resistance 116.07 49.30 41 1208 23412 31672683
Cystitis haemorrhagic 80.90 49.30 22 1227 5267 31690828
Progressive multifocal leukoencephalopathy 72.99 49.30 23 1226 9190 31686905
Cytomegalovirus infection 57.35 49.30 25 1224 24682 31671413
Off label use 52.65 49.30 66 1183 347208 31348887
Drug ineffective for unapproved indication 51.26 49.30 21 1228 17769 31678326

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
Adenovirus infection 349.49 50.46 75 2356 7693 70918320
Drug resistance 255.78 50.46 81 2350 38109 70887904
Cystitis haemorrhagic 142.41 50.46 37 2394 8556 70917457
Cytomegalovirus infection 124.78 50.46 48 2383 39710 70886303
BK virus infection 106.66 50.46 29 2402 7960 70918053
Cytomegalovirus infection reactivation 106.55 50.46 28 2403 6753 70919260
Pathogen resistance 96.29 50.46 30 2401 13249 70912764
Nephropathy toxic 94.30 50.46 32 2399 18482 70907531
Epstein-Barr virus infection reactivation 93.26 50.46 19 2412 1497 70924516
Off label use 82.45 50.46 113 2318 742947 70183066
Progressive multifocal leukoencephalopathy 81.59 50.46 29 2402 19185 70906828
Renal impairment 75.87 50.46 52 2379 143885 70782128
Cytomegalovirus viraemia 74.75 50.46 24 2407 11661 70914352
Immune reconstitution inflammatory syndrome 72.25 50.46 24 2407 12966 70913047
Polyomavirus-associated nephropathy 70.03 50.46 19 2412 5164 70920849
Aplastic anaemia 55.29 50.46 21 2410 16695 70909318

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
149394-66-1 SECONDARY_CAS_RN
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

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