trifluridine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
uridine derivatives used as antiviral agents and as antineoplastics 2743 70-00-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • trifluridine
  • trifluorothymidine
  • 5-Trifluorothymidine
An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557)
  • Molecular weight: 296.20
  • Formula: C10H11F3N2O5
  • CLOGP: -0.41
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 99.10
  • ALOGS: -1.65
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2B,BRAF,CAMK2D,CDK5,CDK9,EIF2AK3,ERBB2,GRK2,ITK,MAP3K21,NTRK2,PDK1,PDK2,PRKDC 14
kinase-selectivity-class AXL,GRK2,PDK1 3
pfas-class PFAS structural alert (1 = True, 0 = False) 1
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 0 Moderate 0.70

Approvals:

DateAgencyCompanyOrphan
April 10, 1980 FDA MONARCH PHARMS
March 24, 2014 PMDA Taiho Pharmaceutical Co., Ltd.

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

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
Therapy partial responder 60.51 51.40 17 528 37044 110551710

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L01BC59 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
ATC S01AD02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antivirals
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EXT N0000175459 Nucleoside Analog
FDA EPC N0000175466 Nucleoside Analog Antiviral
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000998 Antiviral Agents
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:36044 antiviral drug
CHEBI has role CHEBI:63720 EC 2.1.1.45 (thymidylate synthase) inhibitor
CHEBI has role CHEBI:66981 ophthalmology drug

Related Drugs by ATC class:

L01BC Pyrimidine analogues 9 drugs
azacitidinecapecitabinecarmofurcytarabinedecitabinefloxuridinefluorouracilgemcitabinetegafur
S01AD Antivirals 6 drugs
acyclovirfamciclovirfomivirsengancicloviridoxuridinevidarabine

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

DiseaseRelationSNOMED_IDDOID
Herpes simplex keratitis indication 9389005
Herpes simplex keratoconjunctivitis indication 72321008
Malignant tumor of stomach indication 363349007 DOID:10534
Malignant tumor of colon indication 363406005 DOID:219




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.95 acidic
pKa2 13.02 acidic
pKa3 13.7 acidic

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 APPROPRIATE, 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 METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN PATIENTS 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 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 APPROPRIATE, 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 METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN PATIENTS 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 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 9943537 Sept. 5, 2034 TREATMENT OF METASTATIC COLORECTAL CANCER WITH BEVACIZUMAB IN PATIENTS 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 9943537 Sept. 5, 2034 TREATMENT OF METASTATIC COLORECTAL CANCER WITH BEVACIZUMAB IN PATIENTS 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 TREATMENT OF METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN SEVERELY RENALLY IMPAIRED PATIENTS PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN THERAPY, AN ANTI-VEGF BIOLOGIC, AND IF RAS WILD-TYPE, ANTI-EGFR THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10456399 Feb. 3, 2037 TREATMENT OF METASTATIC GASTRIC OR GJA IN SEVERELY RENALLY IMPAIRED PATIENTS TREATED WITH AT LEAST TWO LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, A TAXANE OR IRINOTECAN, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 TREATMENT OF METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN SEVERELY RENALLY IMPAIRED PATIENTS PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN THERAPY, AN ANTI-VEGF BIOLOGIC, AND IF RAS WILD-TYPE, ANTI-EGFR THERAPY
EQ 6.14MG BASE;15MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 TREATMENT OF METASTATIC GASTRIC OR GJA IN SEVERELY RENALLY IMPAIRED PATIENTS TREATED WITH AT LEAST TWO LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, A TAXANE OR IRINOTECAN, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10456399 Feb. 3, 2037 TREATMENT OF METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN SEVERELY RENALLY IMPAIRED PATIENTS PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN THERAPY, AN ANTI-VEGF BIOLOGIC, AND IF RAS WILD-TYPE, ANTI-EGFR THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10456399 Feb. 3, 2037 TREATMENT OF METASTATIC GASTRIC OR GJA IN SEVERELY RENALLY IMPAIRED PATIENTS TREATED WITH AT LEAST TWO LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, A TAXANE OR IRINOTECAN, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 TREATMENT OF METASTATIC COLORECTAL CANCER ALONE OR WITH BEVACIZUMAB IN SEVERELY RENALLY IMPAIRED PATIENTS PREVIOUSLY TREATED WITH FLUOROPYRIMIDINE-, OXALIPLATIN- AND IRINOTECAN THERAPY, AN ANTI-VEGF BIOLOGIC, AND IF RAS WILD-TYPE, ANTI-EGFR THERAPY
EQ 8.19MG BASE;20MG LONSURF TAIHO ONCOLOGY N207981 Sept. 22, 2015 RX TABLET ORAL 10960004 Feb. 3, 2037 TREATMENT OF METASTATIC GASTRIC OR GJA IN SEVERELY RENALLY IMPAIRED PATIENTS TREATED WITH AT LEAST TWO LINES OF CHEMOTHERAPY THAT INCLUDED A FLUOROPYRIMIDINE, A PLATINUM, A TAXANE OR IRINOTECAN, AND IF APPROPRIATE, HER2/NEU-TARGETED THERAPY

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, 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 kinase Kinase IC50 5.70 CHEMBL
Thymidylate kinase Kinase Ki 4.01 CHEMBL

External reference:

IDSource
4018780 VUID
N0000147083 NUI
D00391 KEGG_DRUG
4018780 VANDF
C0040987 UMLSCUI
CHEBI:75179 CHEBI
CHEMBL1129 ChEMBL_ID
DB00432 DRUGBANK_ID
D014271 MESH_DESCRIPTOR_UI
6256 PUBCHEM_CID
8697 IUPHAR_LIGAND_ID
4146 INN_ID
RMW9V5RW38 UNII
10803 RXNORM
5627 MMSL
6442 MMSL
d08380 MMSL
003015 NDDF
373512003 SNOMEDCT_US
58892008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Trifluridine HUMAN PRESCRIPTION DRUG LABEL 1 61314-044 SOLUTION 10 mg OPHTHALMIC ANDA 18 sections
LONSURF HUMAN PRESCRIPTION DRUG LABEL 2 64842-1020 TABLET, FILM COATED 20 mg ORAL NDA 27 sections
LONSURF HUMAN PRESCRIPTION DRUG LABEL 2 64842-1025 TABLET, FILM COATED 15 mg ORAL NDA 27 sections