Identification

Name
Foscarnet
Accession Number
DB00529  (APRD00669)
Type
Small Molecule
Groups
Approved
Description

An antiviral agent used in the treatment of cytomegalovirus retinitis. Foscarnet also shows activity against human herpesviruses and HIV. [PubChem]

Structure
Thumb
Synonyms
  • Carboxyphosphonic acid
  • Foscarmet
  • Phosphonoformate
  • Phosphonoformic acid
  • Phosphonomethanoic acid
External IDs
J05AD01
Product Ingredients
IngredientUNIICASInChI Key
Foscarnet sodium8C5OQ81LWT63585-09-1DFHAXXVZCFXGOQ-UHFFFAOYSA-K
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FoscavirInjection, solution24 mg/mLIntravenousClinigen Healthcare Ltd.2012-07-09Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Foscarnet SodiumInjection, solution24 mg/mLIntravenousHospira, Inc.2010-07-072017-04-29Us
International/Other Brands
Triapten
Categories
UNII
364P9RVW4X
CAS number
4428-95-9
Weight
Average: 126.0053
Monoisotopic: 125.971809718
Chemical Formula
CH3O5P
InChI Key
ZJAOAACCNHFJAH-UHFFFAOYSA-N
InChI
InChI=1S/CH3O5P/c2-1(3)7(4,5)6/h(H,2,3)(H2,4,5,6)
IUPAC Name
phosphonoformic acid
SMILES
OC(=O)P(O)(O)=O

Pharmacology

Indication

For the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS) and for treatment of acyclovir-resistant mucocutaneous HSV infections in immunocompromised patients.

Structured Indications
Pharmacodynamics

Foscarnet is an organic analogue of inorganic pyrophosphate that inhibits replication of herpes viruses in vitro including cytomegalovirus (CMV) and herpes simplex virus types 1 and 2 (HSV-1 and HSV-2). Foscarnet does not require activation (phosphorylation) by thymidine kinase or other kinases and therefore is active in vitro against HSV TK deficient mutants and CMV UL97 mutants. Thus, HSV strains resistant to acyclovir or CMV strains resistant to ganciclovir may be sensitive to foscarnet. However, acyclovir or ganciclovir resistant mutants with alterations in the viral DNA polymerase may be resistant to foscarnet and may not respond to therapy with foscarnet. The combination of foscarnet and ganciclovir has been shown to have enhanced activity in vitro.

Mechanism of action

Foscarnet exerts its antiviral activity by a selective inhibition at the pyrophosphate binding site on virus-specific DNA polymerases at concentrations that do not affect cellular DNA polymerases.

TargetActionsOrganism
ADNA polymerase catalytic subunit
inhibitor
HHV-1
ADNA polymerase catalytic subunit
inhibitor
HHV-5
Absorption

Poorly absorbed after oral administration (bioavailability from 12 to 22%).

Volume of distribution
Not Available
Protein binding

14-17%

Metabolism

Not metabolized.

Route of elimination
Not Available
Half life

3.3-6.8 hours

Clearance
  • 2.13 +/- 0.71 mL/min/kg [patients had normal renal function (CrCl > 80 mL/min]
  • 68 +/- 8 mL/min/kg [CrCl was 50-80 mL/min]
  • 34 +/- 9 mL/min/kg [CrCl was 25-49 mL/min]
  • 20 +/- 4 mL/min/kg [CrCl was 10 - 24 mL/min]
Toxicity

Oral, rat LD50: >2,000 mg/kg. Signs of overdose include renal impairment.

Affected organisms
  • Human Herpes Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AclarubicinFoscarnet may increase the nephrotoxic activities of Aclarubicin.Investigational
AmikacinFoscarnet may increase the nephrotoxic activities of Amikacin.Approved, Vet Approved
AmiodaroneFoscarnet may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
Amphotericin BFoscarnet may increase the nephrotoxic activities of Amphotericin B.Approved, Investigational
AmrubicinFoscarnet may increase the nephrotoxic activities of Amrubicin.Approved, Investigational
AnagrelideFoscarnet may increase the QTc-prolonging activities of Anagrelide.Approved
annamycinFoscarnet may increase the nephrotoxic activities of annamycin.Investigational
ApramycinFoscarnet may increase the nephrotoxic activities of Apramycin.Experimental, Vet Approved
ArbekacinFoscarnet may increase the nephrotoxic activities of Arbekacin.Approved, Investigational
Arsenic trioxideFoscarnet may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherFoscarnet may increase the QTc-prolonging activities of Artemether.Approved
AsenapineFoscarnet may increase the QTc-prolonging activities of Asenapine.Approved
AzithromycinFoscarnet may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineFoscarnet may increase the QTc-prolonging activities of Bedaquiline.Approved
BekanamycinFoscarnet may increase the nephrotoxic activities of Bekanamycin.Experimental
BumetanideThe serum concentration of Foscarnet can be increased when it is combined with Bumetanide.Approved
CeritinibFoscarnet may increase the QTc-prolonging activities of Ceritinib.Approved
ChloroquineFoscarnet may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorpromazineFoscarnet may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
CiprofloxacinFoscarnet may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideFoscarnet may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramFoscarnet may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinFoscarnet may increase the QTc-prolonging activities of Clarithromycin.Approved
ClozapineFoscarnet may increase the QTc-prolonging activities of Clozapine.Approved
CrizotinibFoscarnet may increase the QTc-prolonging activities of Crizotinib.Approved
CyclosporineFoscarnet may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DaunorubicinFoscarnet may increase the nephrotoxic activities of Daunorubicin.Approved
DibekacinFoscarnet may increase the nephrotoxic activities of Dibekacin.Experimental
DihydrostreptomycinFoscarnet may increase the nephrotoxic activities of Dihydrostreptomycin.Investigational, Vet Approved
DisopyramideFoscarnet may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideFoscarnet may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronFoscarnet may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneFoscarnet may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxorubicinFoscarnet may increase the nephrotoxic activities of Doxorubicin.Approved, Investigational
DronedaroneFoscarnet may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolFoscarnet may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
EliglustatFoscarnet may increase the QTc-prolonging activities of Eliglustat.Approved
EpirubicinFoscarnet may increase the nephrotoxic activities of Epirubicin.Approved
ErythromycinFoscarnet may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramFoscarnet may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Etacrynic acidThe serum concentration of Foscarnet can be increased when it is combined with Etacrynic acid.Approved
FlecainideFoscarnet may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluoxetineFoscarnet may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolFoscarnet may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FramycetinFoscarnet may increase the nephrotoxic activities of Framycetin.Approved
FurosemideThe serum concentration of Foscarnet can be increased when it is combined with Furosemide.Approved, Vet Approved
Gadobenic acidFoscarnet may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemifloxacinFoscarnet may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GeneticinFoscarnet may increase the nephrotoxic activities of Geneticin.Experimental
GentamicinFoscarnet may increase the nephrotoxic activities of Gentamicin.Approved, Vet Approved
GENTAMICIN C1AFoscarnet may increase the nephrotoxic activities of GENTAMICIN C1A.Experimental
GoserelinFoscarnet may increase the QTc-prolonging activities of Goserelin.Approved
GPX-150Foscarnet may increase the nephrotoxic activities of GPX-150.Investigational
GranisetronFoscarnet may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HaloperidolFoscarnet may increase the QTc-prolonging activities of Haloperidol.Approved
Hygromycin BFoscarnet may increase the nephrotoxic activities of Hygromycin B.Vet Approved
IbutilideFoscarnet may increase the QTc-prolonging activities of Ibutilide.Approved
IdarubicinFoscarnet may increase the nephrotoxic activities of Idarubicin.Approved
IloperidoneFoscarnet may increase the QTc-prolonging activities of Iloperidone.Approved
INNO-206Foscarnet may increase the nephrotoxic activities of INNO-206.Investigational
IsepamicinFoscarnet may increase the nephrotoxic activities of Isepamicin.Experimental
KanamycinFoscarnet may increase the nephrotoxic activities of Kanamycin.Approved, Investigational, Vet Approved
LenvatinibFoscarnet may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideFoscarnet may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinFoscarnet may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LopinavirFoscarnet may increase the QTc-prolonging activities of Lopinavir.Approved
LumefantrineFoscarnet may increase the QTc-prolonging activities of Lumefantrine.Approved
MethadoneFoscarnet may increase the QTc-prolonging activities of Methadone.Approved
MethotrexateFoscarnet may increase the nephrotoxic activities of Methotrexate.Approved
MetrizamideFoscarnet may increase the nephrotoxic activities of Metrizamide.Approved
MicronomicinFoscarnet may increase the nephrotoxic activities of Micronomicin.Experimental
MifepristoneMifepristone may increase the QTc-prolonging activities of Foscarnet.Approved, Investigational
MoxifloxacinFoscarnet may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
NeamineFoscarnet may increase the nephrotoxic activities of Neamine.Experimental
NeomycinFoscarnet may increase the nephrotoxic activities of Neomycin.Approved, Vet Approved
NetilmicinFoscarnet may increase the nephrotoxic activities of Netilmicin.Approved, Investigational
NilotinibFoscarnet may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
OfloxacinFoscarnet may increase the QTc-prolonging activities of Ofloxacin.Approved
OndansetronFoscarnet may increase the QTc-prolonging activities of Ondansetron.Approved
PaliperidoneFoscarnet may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatFoscarnet may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
ParomomycinFoscarnet may increase the nephrotoxic activities of Paromomycin.Approved, Investigational
PazopanibFoscarnet may increase the QTc-prolonging activities of Pazopanib.Approved
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Foscarnet.Approved
PerflutrenFoscarnet may increase the QTc-prolonging activities of Perflutren.Approved
PimozideFoscarnet may increase the QTc-prolonging activities of Pimozide.Approved
PirarubicinFoscarnet may increase the nephrotoxic activities of Pirarubicin.Investigational
PiretanideThe serum concentration of Foscarnet can be increased when it is combined with Piretanide.Experimental
PlazomicinFoscarnet may increase the nephrotoxic activities of Plazomicin.Investigational
PlicamycinFoscarnet may increase the nephrotoxic activities of Plicamycin.Approved, Investigational, Withdrawn
PrimaquineFoscarnet may increase the QTc-prolonging activities of Primaquine.Approved
ProcainamideFoscarnet may increase the QTc-prolonging activities of Procainamide.Approved
PromazineFoscarnet may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PropafenoneFoscarnet may increase the QTc-prolonging activities of Propafenone.Approved
PuromycinFoscarnet may increase the nephrotoxic activities of Puromycin.Experimental
QuetiapineFoscarnet may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineFoscarnet may increase the QTc-prolonging activities of Quinidine.Approved
QuinineFoscarnet may increase the QTc-prolonging activities of Quinine.Approved
RibostamycinFoscarnet may increase the nephrotoxic activities of Ribostamycin.Approved, Investigational
SabarubicinFoscarnet may increase the nephrotoxic activities of Sabarubicin.Investigational
SaquinavirFoscarnet may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SisomicinFoscarnet may increase the nephrotoxic activities of Sisomicin.Investigational
SotalolFoscarnet may increase the QTc-prolonging activities of Sotalol.Approved
SP1049CFoscarnet may increase the nephrotoxic activities of SP1049C.Investigational
SpectinomycinFoscarnet may increase the nephrotoxic activities of Spectinomycin.Approved, Investigational, Vet Approved
StreptomycinFoscarnet may increase the nephrotoxic activities of Streptomycin.Approved, Vet Approved
StreptozocinFoscarnet may increase the nephrotoxic activities of Streptozocin.Approved
SulfisoxazoleFoscarnet may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
TacrolimusFoscarnet may increase the nephrotoxic activities of Tacrolimus.Approved, Investigational
TelavancinFoscarnet may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinFoscarnet may increase the QTc-prolonging activities of Telithromycin.Approved
TetrabenazineFoscarnet may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThioridazineFoscarnet may increase the QTc-prolonging activities of Thioridazine.Approved, Withdrawn
TobramycinFoscarnet may increase the nephrotoxic activities of Tobramycin.Approved, Investigational
TorasemideThe serum concentration of Foscarnet can be increased when it is combined with Torasemide.Approved
ToremifeneFoscarnet may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
ValaciclovirFoscarnet may increase the nephrotoxic activities of Valaciclovir.Approved, Investigational
ValrubicinFoscarnet may increase the nephrotoxic activities of Valrubicin.Approved
VandetanibFoscarnet may increase the QTc-prolonging activities of Vandetanib.Approved
VemurafenibFoscarnet may increase the QTc-prolonging activities of Vemurafenib.Approved
ZiprasidoneFoscarnet may increase the QTc-prolonging activities of Ziprasidone.Approved
Zoptarelin doxorubicinFoscarnet may increase the nephrotoxic activities of Zoptarelin doxorubicin.Investigational
ZorubicinFoscarnet may increase the nephrotoxic activities of Zorubicin.Experimental
ZuclopenthixolFoscarnet may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Charles E. McKenna, "Preparation and use of thiophosphonates and thio-analogues of phosphonoformic acid." U.S. Patent US5072032, issued February, 1953.

US5072032
General References
Not Available
External Links
Human Metabolome Database
HMDB14670
KEGG Drug
D00579
KEGG Compound
C06456
PubChem Compound
3415
PubChem Substance
46507873
ChemSpider
3297
BindingDB
50011181
ChEBI
127780
ChEMBL
CHEMBL666
Therapeutic Targets Database
DAP001383
PharmGKB
PA449706
HET
PPF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Foscarnet
ATC Codes
J05AD01 — Foscarnet
PDB Entries
1ei6 / 1nki / 2it4 / 2rk8 / 3kd5 / 3t01 / 4mv7 / 5hp1
FDA label
Download (101 KB)
MSDS
Download (50.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections2
1CompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1WithdrawnTreatmentEncephalopathies / Human Immunodeficiency Virus (HIV) Infections / Radiculitis1
2CompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections3
2RecruitingTreatmentHerpes Simplex Infection1
2Unknown StatusSupportive CareGraft Versus Host Disease (GVHD) / Nonneoplastic Condition1
2WithdrawnTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Cytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentGastrointestinal Diseases / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Hypocalcemia / Infections, Cytomegalovirus1
4CompletedTreatmentViral sepsis1
4RecruitingTreatmentHematological Diseases / Infections, Cytomegalovirus1
4Unknown StatusTreatmentHerpes Zoster1
Not AvailableCompletedSupportive CareAccelerated Phase Chronic Myelogenous Leukemia / Acute Undifferentiated Leukemia (AUL) / Adult Acute Lymphoblastic Leukemia in Remission / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Grade III Lymphomatoid Granulomatosis / Adult Nasal Type Extranodal NK/T-Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Aplastic Anaemia (AA) / Atypical Chronic Myeloid Leukemia, BCR-ABL Negative / Blastic Phase Chronic Myelogenous Leukemia / Chronic Eosinophilic Leukemia (CEL) / Chronic Myelomonocytic Leukemia / Chronic Neutrophilic Leukemia / Chronic Phase Chronic Myelogenous Leukemia / Contiguous Stage II Adult Burkitt Lymphoma / Contiguous Stage II Adult Diffuse Large Cell Lymphoma / Contiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Contiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Contiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Contiguous Stage II Adult Lymphoblastic Lymphoma / Contiguous Stage II Grade 1 Follicular Lymphoma / Contiguous Stage II Grade 2 Follicular Lymphoma / Contiguous Stage II Grade 3 Follicular Lymphoma / Contiguous Stage II Mantle Cell Lymphoma / Contiguous Stage II Marginal Zone Lymphoma / Contiguous Stage II Small Lymphocytic Lymphoma / Cutaneous B-Cell Non-Hodgkin Lymphoma / De Novo Myelodysplastic Syndromes / Essential Thrombocythemia (ET) / Extramedullary Plasmacytoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Hematopoietic/Lymphoid Cancer / Infections, Cytomegalovirus / Intraocular Lymphoma / Isolated Plasmacytoma of Bone / Leukemia, Prolymphocytic / Malignant mast cell neoplasm / Meningeal Chronic Myelogenous Leukemia / Myelodysplastic/Myeloproliferative Neoplasm, Unclassifiable / Nodal marginal zone B-cell lymphomas / Noncontiguous Stage II Adult Burkitt Lymphoma / Noncontiguous Stage II Adult Diffuse Large Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Mixed Cell Lymphoma / Noncontiguous Stage II Adult Diffuse Small Cleaved Cell Lymphoma / Noncontiguous Stage II Adult Immunoblastic Large Cell Lymphoma / Noncontiguous Stage II Adult Lymphoblastic Lymphoma / Noncontiguous Stage II Grade 1 Follicular Lymphoma / Noncontiguous Stage II Grade 2 Follicular Lymphoma / Noncontiguous Stage II Grade 3 Follicular Lymphoma / Noncontiguous Stage II Mantle Cell Lymphoma / Noncontiguous Stage II Marginal Zone Lymphoma / Noncontiguous Stage II Small Lymphocytic Lymphoma / Polycythemia Vera (PV) / Post-Transplant Lymphoproliferative Disorder / Previously Treated Myelodysplastic Syndromes / Primary Myelofibrosis / Primary Systemic Amyloidosis / Progressive Hairy Cell Leukemia, Initial Treatment / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Refractory Chronic Lymphocytic Leukemia / Refractory Hairy Cell Leukemia / Refractory Multiple Myeloma / Relapsing Chronic Myelogenous Leukemia / Secondary Acute Myeloid Leukemia / Secondary Myelodysplastic Syndromes / Secondary Myelofibrosis / Splenic Marginal Zone Lymphoma / Stage 0 Chronic Lymphocytic Leukemia / Stage I Adult Burkitt Lymphoma / Stage I Adult Diffuse Large Cell Lymphoma / Stage I Adult Diffuse Mixed Cell Lymphoma / Stage I Adult Diffuse Small Cleaved Cell Lymphoma / Stage I Adult Hodgkin Lymphoma / Stage I Adult Immunoblastic Large Cell Lymphoma / Stage I Adult Lymphoblastic Lymphoma / Stage I Adult T-Cell Leukemia/Lymphoma / Stage I Chronic Lymphocytic Leukemia / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage I Grade 1 Follicular Lymphoma / Stage I Grade 2 Follicular Lymphoma / Stage I Grade 3 Follicular Lymphoma / Stage I Mantle Cell Lymphoma / Stage I Marginal Zone Lymphoma / Stage I Multiple Myeloma / Stage I Mycosis Fungoides/Sezary Syndrome / Stage I Small Lymphocytic Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage II Adult T-Cell Leukemia/Lymphoma / Stage II Chronic Lymphocytic Leukemia / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Multiple Myeloma / Stage II Mycosis Fungoides/Sezary Syndrome / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Adult T-Cell Leukemia/Lymphoma / Stage III Chronic Lymphocytic Leukemia / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Multiple Myeloma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Adult T-Cell Leukemia/Lymphoma / Stage IV Chronic Lymphocytic Leukemia / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma / T-Cell Large Granular Lymphocyte Leukemia / Waldenstrom's Macroglobulinemia (WM)1
Not AvailableCompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableUnknown StatusTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • Clinigen healthcare ltd
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous24 mg/mL
Prices
Unit descriptionCostUnit
Sodium phosphonoformate powder286.3USD g
Foscavir 24 mg/ml infus bottle0.43USD ml
Foscarnet 24 mg/ml infus bttl0.37USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)88.06 °CNot Available
water solubilityCompleteNot Available
logP-2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP-1.6ALOGPS
logP-0.83ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)-0.096ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.07 m3·mol-1ChemAxon
Polarizability7.89 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9396
Blood Brain Barrier+0.9382
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.8162
P-glycoprotein inhibitor INon-inhibitor0.9783
P-glycoprotein inhibitor IINon-inhibitor0.9962
Renal organic cation transporterNon-inhibitor0.9731
CYP450 2C9 substrateNon-substrate0.8114
CYP450 2D6 substrateNon-substrate0.861
CYP450 3A4 substrateNon-substrate0.7282
CYP450 1A2 substrateNon-inhibitor0.8825
CYP450 2C9 inhibitorNon-inhibitor0.9124
CYP450 2D6 inhibitorNon-inhibitor0.9086
CYP450 2C19 inhibitorNon-inhibitor0.9202
CYP450 3A4 inhibitorNon-inhibitor0.9608
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.996
Ames testNon AMES toxic0.9139
CarcinogenicityNon-carcinogens0.5461
BiodegradationNot ready biodegradable0.5449
Rat acute toxicity1.7117 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9831
hERG inhibition (predictor II)Non-inhibitor0.96
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Organic phosphonic acids
Direct Parent
Organic phosphonic acids
Alternative Parents
Organic carbonic acids and derivatives / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Organophosphonic acid / Carbonic acid derivative / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organophosphorus compound / Organooxygen compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
one-carbon compound, phosphonic acids, carboxylic acid (CHEBI:127780)

Targets

Kind
Protein
Organism
HHV-1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
Gene Name
Not Available
Uniprot ID
P04293
Uniprot Name
DNA polymerase catalytic subunit
Molecular Weight
136419.66 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Ducancelle A, Alain S, Petit F, Sanson Le Pors MJ, Mazeron MC: Development and validation of a non-radioactive DNA polymerase assay for studying cytomegalovirus resistance to foscarnet. J Virol Methods. 2007 May;141(2):212-5. Epub 2007 Jan 2. [PubMed:17197042]
  4. Bonnafous P, Naesens L, Petrella S, Gautheret-Dejean A, Boutolleau D, Sougakoff W, Agut H: Different mutations in the HHV-6 DNA polymerase gene accounting for resistance to foscarnet. Antivir Ther. 2007;12(6):877-88. [PubMed:17926642]
  5. Tchesnokov EP, Gilbert C, Boivin G, Gotte M: Role of helix P of the human cytomegalovirus DNA polymerase in resistance and hypersusceptibility to the antiviral drug foscarnet. J Virol. 2006 Feb;80(3):1440-50. [PubMed:16415021]
Kind
Protein
Organism
HHV-5
Pharmacological action
Yes
Actions
Inhibitor
General Function
Nucleotide binding
Specific Function
Replicates viral genomic DNA in the late phase of lytic infection, producing long concatemeric DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity facto...
Gene Name
UL54
Uniprot ID
P08546
Uniprot Name
DNA polymerase catalytic subunit
Molecular Weight
137100.705 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Ducancelle A, Alain S, Petit F, Sanson Le Pors MJ, Mazeron MC: Development and validation of a non-radioactive DNA polymerase assay for studying cytomegalovirus resistance to foscarnet. J Virol Methods. 2007 May;141(2):212-5. Epub 2007 Jan 2. [PubMed:17197042]
  4. Bonnafous P, Naesens L, Petrella S, Gautheret-Dejean A, Boutolleau D, Sougakoff W, Agut H: Different mutations in the HHV-6 DNA polymerase gene accounting for resistance to foscarnet. Antivir Ther. 2007;12(6):877-88. [PubMed:17926642]
  5. Tchesnokov EP, Gilbert C, Boivin G, Gotte M: Role of helix P of the human cytomegalovirus DNA polymerase in resistance and hypersusceptibility to the antiviral drug foscarnet. J Virol. 2006 Feb;80(3):1440-50. [PubMed:16415021]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
Molecular Weight
53943.685 Da
References
  1. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [PubMed:10579682]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:39