Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H11F3N2O5 |
Molecular Weight | 296.1999 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(C(=O)NC2=O)C(F)(F)F
InChI
InChIKey=VSQQQLOSPVPRAZ-RRKCRQDMSA-N
InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)/t5-,6+,7+/m0/s1
Molecular Formula | C10H11F3N2O5 |
Molecular Weight | 296.1999 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f3a14d86-0ff2-4535-318c-ac8bc8ede42cCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00432
http://www.drugs.com/pro/trifluridine.html
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f3a14d86-0ff2-4535-318c-ac8bc8ede42c
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00432
http://www.drugs.com/pro/trifluridine.html
Trifluridine (also called trifluorothymidine or TFT) is an anti-herpesvirus antiviral drug, used primarily on the eye. It was sold under the trade name, Viroptic, by Glaxo Wellcome, now merged into GlaxoSmithKline. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the -CF3 group added to the uracil component blocks base pairing, thus interfering with DNA replication. It is a component of the experimental anti-cancer drug TAS-102. Trifluridine is a fluorinated pyrimidine nucleoside with in vitro and in vivo activity against herpes simplex virus, types 1 and 2 and vaccinia virus. Some strains of adenovirus are also inhibited in vitro. VIROPTIC is also effective in the treatment of epithelial keratitis that has not responded clinically to the topical administration of idoxuridine or when ocular toxicity or hypersensitivity to idoxuridine has occurred. In a smaller number of patients found to be resistant to topical vidarabine, VIROPTIC was also effective. The mechanism of action of trifluridine has not been fully determined, but appears to involve the inhibition of viral replication. Trifluridine does this by incorporating into viral DNA during replication, which leads to the formation of defective proteins and an increased mutation rate.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3020165
Curator's Comment: trifluorothymidine (TFT) does not cross the blood brain barrier
Originator
Sources: http://www.medkoo.com/products/5884
Curator's Comment: trifluridine, was first synthesized in 1964 by Heidelberger et al.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2155 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28111727 |
35 mg/m² single, oral dose: 35 mg/m² route of administration: Oral experiment type: SINGLE co-administered: TIPIRACIL |
TRIFLURIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
96 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28111727 |
35 mg/m² single, oral dose: 35 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
TRIFLURIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6694 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28111727 |
35 mg/m² single, oral dose: 35 mg/m² route of administration: Oral experiment type: SINGLE co-administered: TIPIRACIL |
TRIFLURIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
248 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28111727 |
35 mg/m² single, oral dose: 35 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
TRIFLURIDINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6% |
TRIFLURIDINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
35 mg/m2 2 times / day multiple, oral MTD Dose: 35 mg/m2, 2 times / day Route: oral Route: multiple Dose: 35 mg/m2, 2 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.431, 432 |
unhealthy, 59 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 59 Sex: M+F Population Size: 3 Sources: Page: p.431, 432 |
DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Sources: Page: p.431, 432 |
80 mg/m2 3 times / day multiple, oral (total daily dose) Highest studied dose Dose: 80 mg/m2, 3 times / day Route: oral Route: multiple Dose: 80 mg/m2, 3 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.797 |
unhealthy, 60 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 60 Sex: M+F Population Size: 6 Sources: Page: p.797 |
DLT: Granulocytopenia, Fatigue... Dose limiting toxicities: Granulocytopenia (grade 4, 33.3%) Sources: Page: p.797Fatigue (grade 3, 33.3%) |
70 mg/m2 3 times / day multiple, oral (total daily dose) MTD Dose: 70 mg/m2, 3 times / day Route: oral Route: multiple Dose: 70 mg/m2, 3 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.797 |
unhealthy, 60 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 60 Sex: M+F Population Size: 6 Sources: Page: p.797 |
Other AEs: Granulocytopenia... Other AEs: Granulocytopenia (grade 4, 16.7%) Sources: Page: p.797 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Neutropenia | grade 4, 33.3% DLT |
35 mg/m2 2 times / day multiple, oral MTD Dose: 35 mg/m2, 2 times / day Route: oral Route: multiple Dose: 35 mg/m2, 2 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.431, 432 |
unhealthy, 59 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 59 Sex: M+F Population Size: 3 Sources: Page: p.431, 432 |
Fatigue | grade 3, 33.3% DLT |
80 mg/m2 3 times / day multiple, oral (total daily dose) Highest studied dose Dose: 80 mg/m2, 3 times / day Route: oral Route: multiple Dose: 80 mg/m2, 3 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.797 |
unhealthy, 60 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 60 Sex: M+F Population Size: 6 Sources: Page: p.797 |
Granulocytopenia | grade 4, 33.3% DLT |
80 mg/m2 3 times / day multiple, oral (total daily dose) Highest studied dose Dose: 80 mg/m2, 3 times / day Route: oral Route: multiple Dose: 80 mg/m2, 3 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.797 |
unhealthy, 60 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 60 Sex: M+F Population Size: 6 Sources: Page: p.797 |
Granulocytopenia | grade 4, 16.7% | 70 mg/m2 3 times / day multiple, oral (total daily dose) MTD Dose: 70 mg/m2, 3 times / day Route: oral Route: multiple Dose: 70 mg/m2, 3 times / day Co-administed with:: thymidine phosphorylase, p.o Sources: Page: p.797 |
unhealthy, 60 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 60 Sex: M+F Population Size: 6 Sources: Page: p.797 |
PubMed
Title | Date | PubMed |
---|---|---|
Improved synthesis and in vitro antiviral activities of 5-cyanouridine and 5-cyano-2'-deoxyuridine. | 1977 Jul |
|
Therapeutic response of herpes simplex virus-induced corneal edema to trifluridine in combination with immunosuppressive agents. | 1991 Aug |
|
[Trifluridine therapy in herpetic in keratitis]. | 2004 Apr-Jun |
|
Herpes simplex uveitis. | 2004 Mar-Apr |
|
Intracellular thymidylate synthase inhibition by trifluorothymidine in FM3A cells. | 2004 Oct |
|
Intracellular immunity to HIV-1: newly defined retroviral battles inside infected cells. | 2005 Apr 13 |
|
Potentiation of the antitumor activity of alpha, alpha, alpha-trifluorothymidine by the co-administration of an inhibitor of thymidine phosphorylase at a suitable molar ratio in vivo. | 2005 Aug |
|
Efficacy of topical aciclovir for the treatment of feline herpetic keratitis: results of a prospective clinical trial and data from in vitro investigations. | 2005 Aug 27 |
|
Dipeptide monoester ganciclovir prodrugs for treating HSV-1-induced corneal epithelial and stromal keratitis: in vitro and in vivo evaluations. | 2005 Dec |
|
Multinodular goiter management in Western Saudi Arabia. | 2005 Mar |
|
Determinants of trifluorothymidine sensitivity and metabolism in colon and lung cancer cells. | 2005 Mar |
|
Herpes simplex keratitis misdiagnosed as rheumatoid arthritis-related peripheral ulcerative keratitis. | 2005 Nov |
|
Viral infections affecting the skin in organ transplant recipients: epidemiology and current management strategies. | 2006 |
|
In vitro comparison of antiviral drugs against feline herpesvirus 1. | 2006 Apr 26 |
|
American Society of Clinical Oncology--42nd annual meeting. Poster presentations on leukemia and cytotoxic chemotherapy. 2-6 June 2006, Atlanta, GA, USA. | 2006 Aug |
|
Corneal ulceration associated with naturally occurring canine herpesvirus-1 infection in two adult dogs. | 2006 Aug 1 |
|
Imiquimod 5% cream for the treatment of recurrent, acyclovir-resistant genital herpes. | 2006 Feb 15 |
|
3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods. | 2006 Feb 15 |
|
Ocular vaccinia infection in laboratory worker, Philadelphia, 2004. | 2006 Jan |
|
Low folate conditions may enhance the interaction of trifluorothymidine with antifolates in colon cancer cells. | 2006 Jan |
|
Phase I study to determine the safety and pharmacokinetics of oral administration of TAS-102 in patients with solid tumors. | 2006 Sep 15 |
|
Microarray analysis distinguishes differential gene expression patterns from large and small colony Thymidine kinase mutants of L5178Y mouse lymphoma cells. | 2006 Sep 6 |
|
Collisionally-induced dissociation of substituted pyrimidine antiviral agents: mechanisms of ion formation using gas phase hydrogen/deuterium exchange and electrospray ionization tandem mass spectrometry. | 2007 Aug |
|
Ganciclovir ophthalmic gel, 0.15%: a valuable tool for treating ocular herpes. | 2007 Dec |
|
Dendritic keratitis caused by an acyclovir-resistant herpes simplex virus with frameshift mutation. | 2007 Jan |
|
Irinotecan-induced cytotoxicity to colon cancer cells in vitro is stimulated by pre-incubation with trifluorothymidine. | 2007 Jan |
|
A method to distinguish between the de novo induction of thymidine kinase mutants and the selection of pre-existing thymidine kinase mutants in the mouse lymphoma assay. | 2007 Jan 10 |
|
The Hollow Fibre Assay as a model for in vivo pharmacodynamics of fluoropyrimidines in colon cancer cells. | 2007 Jan 15 |
|
Therapeutic interventions for herpes simplex virus epithelial keratitis. | 2007 Jan 24 |
|
Mechanism of trifluorothymidine potentiation of oxaliplatin-induced cytotoxicity to colorectal cancer cells. | 2007 Jan 29 |
|
Evidence-based treatment of herpes simplex virus keratitis: a systematic review. | 2007 Jul |
|
Therapeutic potential of the dual-targeted TAS-102 formulation in the treatment of gastrointestinal malignancies. | 2007 Jun |
|
High level glucose increases mutagenesis in human lymphoblastoid cells. | 2007 Sep 4 |
|
Collision induced dissociation studies of alkali metal adducts of tetracyclines and antiviral agents by electrospray ionization, hydrogen/deuterium exchange and multiple stage mass spectrometry. | 2008 |
|
Progressive hypertrophic genital herpes in an HIV-infected woman despite immune recovery on antiretroviral therapy. | 2008 |
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Novel cell death mechanisms of trifluorothymidine. | 2008 |
|
Efficacy of a helicase-primase inhibitor in animal models of ocular herpes simplex virus type 1 infection. | 2008 Feb |
|
Is herpes simplex virus keratitis a different disease in children? | 2008 Jan |
|
Therapeutic interventions for herpes simplex virus epithelial keratitis. | 2008 Jan 23 |
|
Ocular pharmacokinetics of acyclovir amino acid ester prodrugs in the anterior chamber: evaluation of their utility in treating ocular HSV infections. | 2008 Jul 9 |
|
Trifluorothymidine induces cell death independently of p53. | 2008 Jun |
|
Synergistic interaction between trifluorothymidine and docetaxel is sequence dependent. | 2008 Nov |
|
Phase I clinical study of three times a day oral administration of TAS-102 in patients with solid tumors. | 2008 Oct |
|
Phase 1 study of TAS-102 administered once daily on a 5-day-per-week schedule in patients with solid tumors. | 2008 Oct |
|
A human apolipoprotein E mimetic peptide effectively inhibits HSV-1 TK-positive and TK-negative acute epithelial keratitis in rabbits. | 2009 Feb |
|
Slitlamp biomicroscopy and photographic image analysis of herpes simplex virus stromal keratitis. | 2009 Feb |
|
Molecular mechanism underlying the synergistic interaction between trifluorothymidine and the epidermal growth factor receptor inhibitor erlotinib in human colorectal cancer cell lines. | 2010 Feb |
|
Immunohistochemical characterization of pyrimidine synthetic enzymes, thymidine kinase-1 and thymidylate synthase, in various types of cancer. | 2010 May |
|
Differential activation of cell death and autophagy results in an increased cytotoxic potential for trifluorothymidine compared to 5-fluorouracil in colon cancer cells. | 2010 May 15 |
|
Prodrug activation by Cryptosporidium thymidine kinase. | 2010 May 21 |
Patents
Sample Use Guides
Instill one drop of VIROPTIC Ophthalmic Solution, 1% onto the cornea of the affected eye every 2 hours while awake for a maximum daily dosage of nine drops until the corneal ulcer has completely re-epithelialized
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21491084
HeLa cells were treated with Trifluridine (TFT) at a concentration of 1 µM (IC50 value), the concentration of TFT in the DNA was calculated as 62.2±0.9 pmol/1x106 cells for 4 h. Greater degree of incorporation of TFT into the DNA than that of 5FU or FdUrd, and that such a high degree of incorporation of TFT residues into the DNA might be related to exhibit potent cytotoxic activity to be refractory to cleavage by these DNA glycosylases; thus, the DNA-directed cytotoxic effect of the compound is quite different from that of 5FU
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 21:57:14 UTC 2023
by
admin
on
Thu Jul 06 21:57:14 UTC 2023
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Record UNII |
RMW9V5RW38
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175595
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NDF-RT |
N0000175459
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NDF-RT |
N0000175459
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WHO-VATC |
QS01AD02
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WHO-ATC |
L01BC59
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FDA ORPHAN DRUG |
564116
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NDF-RT |
N0000175466
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NDF-RT |
N0000175459
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WHO-ATC |
S01AD02
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NCI_THESAURUS |
C1557
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200-722-8
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RMW9V5RW38
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D014271
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10803
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C448389
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1686309
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75179
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DB00432
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TRIFLURIDINE
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75520
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DTXSID4046602
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8697
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C905
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8126
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70-00-8
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M11125
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100000076935
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SUB11291MIG
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CHEMBL1129
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EXCRETED UNCHANGED |
URINE
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BINDER->LIGAND |
The in vitro protein binding in human plasma is greater than 96 % for trifluridine.
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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SINGLE DOSE ADMINISTRATION |
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