etoposide phosphate Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
3944 117091-64-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • etoposide phosphate
  • etopofos
  • etopophos
Etoposide phosphate is a prodrug that is converted to its active moiety, etoposide, by dephosphorylation. Etoposide causes the induction of DNA strand breaks by an interaction with DNA-topoisomerase II or the formation of free radicals, leading to cell cycle arrest, primarily at the G2 stage of the cell cycle, and cell death.
  • Molecular weight: 668.54
  • Formula: C29H33O16P
  • CLOGP: -1.57
  • LIPINSKI: 2
  • HAC: 16
  • HDO: 4
  • TPSA: 207.36
  • ALOGS: -2.97
  • ROTB: 7

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
May 17, 1996 FDA BRISTOL MYERS SQUIBB

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
Dilatation intrahepatic duct acquired 95.56 44.66 15 576 741 46684730
Venoocclusive liver disease 75.39 44.66 16 575 4235 46681236

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
Venoocclusive liver disease 67.16 45.63 18 716 6595 29945149

Pharmacologic Action:

SourceCodeDescription
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:59517 dna synthesis inhibitors
MeSH PA D000970 Antineoplastic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Small cell carcinoma of lung indication 254632001 DOID:5409
Malignant tumor of testis indication 363449006 DOID:2998
Allogeneic bone marrow transplantation off-label use 58390007
Ewing's sarcoma off-label use 76909002 DOID:3369
Acute myeloid leukemia, disease off-label use 91861009
Kaposi's sarcoma off-label use 109385007
Diffuse non-Hodgkin's lymphoma, large cell off-label use 109969005
Multiple myeloma off-label use 109989006 DOID:9538
Hodgkin's disease off-label use 118599009
Burkitt's lymphoma off-label use 118617000
Non-small cell lung cancer off-label use 254637007 DOID:3908
Osteosarcoma of bone off-label use 307576001 DOID:3376
Neuroblastoma off-label use 432328008 DOID:769
Testicular Germ Cell Tumor off-label use
Ovarian Germ Cell Tumor Carcinoma off-label use
Neuroendocrine Prostate Carcinoma off-label use
Progressive Diffuse Large B-Cell Lymphoma off-label use
Acute hemorrhage contraindication 8573003
Fibrosis of lung contraindication 51615001 DOID:3770
Metabolic acidosis contraindication 59455009
Acute infectious disease contraindication 63171007
Interstitial pneumonia contraindication 64667001
Leukopenia contraindication 84828003 DOID:615
Hypoalbuminemia contraindication 119247004
Impaired renal function disorder contraindication 197663003
Drug-induced hepatitis contraindication 235876009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.64 acidic
pKa2 6.69 acidic
pKa3 13.08 acidic
pKa4 13.86 acidic

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 topoisomerase 2-alpha Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
4020979 VUID
N0000179127 NUI
D04107 KEGG_DRUG
4020979 VANDF
C0904036 UMLSCUI
CHEBI:135867 CHEBI
CHEMBL1200645 ChEMBL_ID
C061400 MESH_SUPPLEMENTAL_RECORD_UI
6918092 PUBCHEM_CID
528XYJ8L1N UNII
DB00773 DRUGBANK_ID
24614 RXNORM
160598 MMSL
4710 MMSL
d07388 MMSL
006055 NDDF
426891005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ETOPOPHOS HUMAN PRESCRIPTION DRUG LABEL 1 61269-410 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 18 sections