tipiracil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
uracil type antineoplastics 4893 183204-74-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tipiracil
  • tipiracil hydrochloride
  • tipiracil HCl
tipiracil increases trifluridine exposure by inhibiting its metabolism by thymidine phosphorylase
  • Molecular weight: 242.66
  • Formula: C9H11ClN4O2
  • CLOGP: -0.31
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 3
  • TPSA: 85.29
  • ALOGS: -2.52
  • ROTB: 2

  • Status: ONP

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

Drug dosage:

None

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
Sept. 22, 2015 FDA TAIHO ONCOLOGY INC
March 24, 2014 PMDA Taiho Pharmaceutical Co., Ltd.

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
Disease progression 1044.31 36.89 368 4055 101552 53243091
Death 644.23 36.89 384 4039 356848 52987795
Nausea 202.63 36.89 277 4146 755814 52588829
Fatigue 175.06 36.89 254 4169 730252 52614391
Diarrhoea 139.89 36.89 211 4212 625335 52719308
Decreased appetite 129.79 36.89 121 4302 214853 53129790
Vomiting 106.86 36.89 165 4258 496974 52847669
White blood cell count decreased 100.96 36.89 83 4340 124392 53220251
Cytopenia 77.45 36.89 29 4394 9141 53335502
Abdominal pain 53.26 36.89 84 4339 255819 53088824
Neutropenia 52.14 36.89 65 4358 159120 53185523
Intestinal obstruction 43.45 36.89 28 4395 28713 53315930
Inappropriate schedule of product administration 42.74 36.89 41 4382 74837 53269806
Malignant neoplasm progression 40.51 36.89 39 4384 71502 53273141
Dysgeusia 37.59 36.89 30 4393 42901 53301742

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
Disease progression 1261.98 34.52 496 5272 86366 32421392
Death 735.95 34.52 571 5197 381946 32125812
Fatigue 327.73 34.52 352 5416 350349 32157409
Nausea 195.53 34.52 260 5508 320589 32187169
Diarrhoea 182.66 34.52 269 5499 364533 32143225
Decreased appetite 145.93 34.52 160 5608 160653 32347105
White blood cell count decreased 95.29 34.52 98 5670 91100 32416658
Blood alkaline phosphatase abnormal 62.93 34.52 15 5753 457 32507301
Neutropenia 56.63 34.52 95 5673 142080 32365678
Colorectal cancer metastatic 54.48 34.52 16 5752 1101 32506657
Vomiting 51.06 34.52 122 5646 235435 32272323
Abdominal pain 50.58 34.52 93 5675 149436 32358322
Intestinal obstruction 47.52 34.52 35 5733 20763 32486995
Dysgeusia 47.45 34.52 38 5730 25493 32482265
Malignant neoplasm progression 46.23 34.52 63 5705 78433 32429325
Cytopenia 42.81 34.52 25 5743 10039 32497719
Carcinoembryonic antigen increased 42.33 34.52 12 5756 728 32507030
Therapy cessation 38.96 34.52 28 5740 15985 32491773
Alopecia 38.83 34.52 31 5737 20699 32487059
Stoma site haemorrhage 38.32 34.52 12 5756 1026 32506732
Blood count abnormal 37.06 34.52 25 5743 12901 32494857
Anaemia 36.27 34.52 104 5664 223520 32284238

Pharmacologic Action:

SourceCodeDescription
FDA MoA N0000191869 Thymidine Phosphorylase Inhibitors
FDA EPC N0000191870 Thymidine Phosphorylase Inhibitor
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:90878 EC 2.4.2.4 inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Malignant tumor of stomach indication 363349007 DOID:10534
Malignant tumor of colon indication 363406005 DOID:219

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.78 acidic
pKa2 9.98 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL RE46284 Sept. 22, 2029 TREATMENT OF ADULTS WITH METASTATIC GASTRIC OR GJA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, EITHER A TAXANE OR IRINOTECAN, AND IF APPROPIATE, HER2/NEU-TARGETED THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL RE46284 Sept. 22, 2029 TREATMENT OF PATIENTS WITH METASTATIC COLORECTAL CANCER WHO HAVE BEEN PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN-BASED CHEMOTHERAPY, AN ANTI-VEGF BIOLOGICAL THERAPY, AND IF RAS WILD-TYPE, AN ANTI-EGFR THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL RE46284 Sept. 22, 2029 TREATMENT OF ADULTS WITH METASTATIC GASTRIC OR GJA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, EITHER A TAXANE OR IRINOTECAN, AND IF APPROPIATE, HER2/NEU-TARGETED THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL RE46284 Sept. 22, 2029 TREATMENT OF PATIENTS WITH METASTATIC COLORECTAL CANCER WHO HAVE BEEN PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN-BASED CHEMOTHERAPY, AN ANTI-VEGF BIOLOGICAL THERAPY, AND IF RAS WILD-TYPE, AN ANTI-EGFR THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10456399 Feb. 3, 2037 METHOD OF TREATING CANCER BY DETECTING A CREATININE CLEARANCE OF A PATIENT AND ADMINISTERING LONSURF
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 METHOD OF TREATING CANCER BY DETECTING A CREATININE CLEARANCE OF A PATIENT AND ADMINISTERING LONSURF
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10456399 Feb. 3, 2037 METHOD OF TREATING CANCER BY DETECTING A CREATININE CLEARANCE OF A PATIENT AND ADMINISTERING LONSURF
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 METHOD OF TREATING CANCER BY DETECTING A CREATININE CLEARANCE OF A PATIENT AND ADMINISTERING LONSURF

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL Feb. 22, 2022 TREATMENT OF ADULT PATIENTS WITH METASTATIC GASTRIC OR GASTROESOPHAGEAL JUNCTION ADENOCARCINOMA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL Feb. 22, 2022 TREATMENT OF ADULT PATIENTS WITH METASTATIC GASTRIC OR GASTROESOPHAGEAL JUNCTION ADENOCARCINOMA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL Feb. 22, 2026 TREATMENT OF ADULT PATIENTS WITH METASTATIC GASTRIC OR GASTROESOPHAGEAL JUNCTION ADENOCARCINOMA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL Feb. 22, 2026 TREATMENT OF ADULT PATIENTS WITH METASTATIC GASTRIC OR GASTROESOPHAGEAL JUNCTION ADENOCARCINOMA PREVIOUSLY TREATED WITH AT LEAST TWO PRIOR LINES OF CHEMOTHERAPY, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidine phosphorylase Enzyme INHIBITOR IC50 7.70 SCIENTIFIC LITERATURE DRUG LABEL
Thymidine phosphorylase Enzyme IC50 7.70 CHEMBL

External reference:

IDSource
NGO10K751P UNII
D10467 KEGG_DRUG
183204-72-0 SECONDARY_CAS_RN
4034880 VANDF
C4056441 UMLSCUI
CHEBI:90879 CHEBI
CMU PDB_CHEM_ID
CHEMBL235668 ChEMBL_ID
6323266 PUBCHEM_CID
DB09343 DRUGBANK_ID
CHEMBL65375 ChEMBL_ID
C000613754 MESH_SUPPLEMENTAL_RECORD_UI
8696 IUPHAR_LIGAND_ID
9500 INN_ID
1670303 RXNORM
31200 MMSL
d08381 MMSL
016454 NDDF
016455 NDDF
724029008 SNOMEDCT_US
724030003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
LONSURF HUMAN PRESCRIPTION DRUG LABEL 2 64842-1020 TABLET, FILM COATED 8.19 mg ORAL NDA 27 sections
LONSURF HUMAN PRESCRIPTION DRUG LABEL 2 64842-1025 TABLET, FILM COATED 6.14 mg ORAL NDA 27 sections