Trifluorothymidine

Modify Date: 2025-08-21 10:28:33

Trifluorothymidine structure	Common Name	Trifluorothymidine
	CAS Number	70-00-8	Molecular Weight	296.200
	Density	1.6±0.1 g/cm3	Boiling Point	N/A
	Molecular Formula	C₁₀H₁₁F₃N₂O₅	Melting Point	190-193 °C(lit.)
	MSDS	Chinese USA	Flash Point	N/A
	Symbol	GHS07, GHS08	Signal Word	Warning

Use of Trifluorothymidine

Trifluridine is an irreversible thymidylate synthase inhibitor, and thereby suppresses DNA synthesis. Trifluridine is an antiviral drug for herpes simplex virus (HSV) infection.

Name	trifluridine
Synonym	More Synonyms

Description	Trifluridine is an irreversible thymidylate synthase inhibitor, and thereby suppresses DNA synthesis. Trifluridine is an antiviral drug for herpes simplex virus (HSV) infection.
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Signaling Pathways >> Apoptosis >> Thymidylate Synthase Research Areas >> Cancer
References	[1]. Suzuki N, et al. Mode of action of trifluorothymidine (TFT) against DNA replication and repair enzymes. Int J Oncol. 2011 Jul;39(1):263-70. [2]. Suzuki N, et al. Trifluorothymidine exhibits potent antitumor activity via the induction of DNA double-strand breaks. Exp Ther Med. 2011 May;2(3):393-397. [3]. Temmink OH, et al. Irinotecan-induced cytotoxicity to colon cancer cells in vitro is stimulated by pre-incubation withtrifluorothymidine. Eur J Cancer. 2007 Jan;43(1):175-83. [4]. Okayama T, et al. Involvement of concentrative nucleoside transporter 1 in intestinal absorption of trifluorothymidine, a novel antitumor nucleoside, in rats. J Pharmacol Exp Ther. 2012 Feb;340(2):457-62.

Description

Trifluridine is an irreversible thymidylate synthase inhibitor, and thereby suppresses DNA synthesis. Trifluridine is an antiviral drug for herpes simplex virus (HSV) infection.

Related Catalog

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Signaling Pathways >> Apoptosis >> Thymidylate Synthase

Research Areas >> Cancer

References

[1]. Suzuki N, et al. Mode of action of trifluorothymidine (TFT) against DNA replication and repair enzymes. Int J Oncol. 2011 Jul;39(1):263-70.

[2]. Suzuki N, et al. Trifluorothymidine exhibits potent antitumor activity via the induction of DNA double-strand breaks. Exp Ther Med. 2011 May;2(3):393-397.

[3]. Temmink OH, et al. Irinotecan-induced cytotoxicity to colon cancer cells in vitro is stimulated by pre-incubation withtrifluorothymidine. Eur J Cancer. 2007 Jan;43(1):175-83.

[4]. Okayama T, et al. Involvement of concentrative nucleoside transporter 1 in intestinal absorption of trifluorothymidine, a novel antitumor nucleoside, in rats. J Pharmacol Exp Ther. 2012 Feb;340(2):457-62.

Density	1.6±0.1 g/cm3
Melting Point	190-193 °C(lit.)
Molecular Formula	C₁₀H₁₁F₃N₂O₅
Molecular Weight	296.200
Exact Mass	296.062012
PSA	104.55000
LogP	0.07
Index of Refraction	1.534
InChIKey	VSQQQLOSPVPRAZ-RRKCRQDMSA-N
SMILES	O=c1[nH]c(=O)n(C2CC(O)C(CO)O2)cc1C(F)(F)F
Storage condition	−20°C

Trifluorothymidine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XP2087500

CHEMICAL NAME :: Thymidine, alpha,alpha,alpha-trifluoro-

CAS REGISTRY NUMBER :: 70-00-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C10-H11-F3-N2-O5

MOLECULAR WEIGHT :: 296.23

WISWESSER LINE NOTATION :: T6NVMVJ EXFFF A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2946 mg/kg

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1931 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3381 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 187 mg/kg/15D-I

TOXIC EFFECTS :: Gastrointestinal - changes in structure or function of salivary glands Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - leukopenia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 2600 mg/kg/90D-I

TOXIC EFFECTS :: Liver - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 2100 mg/kg/14D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Gastrointestinal - hypermotility, diarrhea Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 4 mg/L

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 86,180,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3218 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 82 (estimated) No. of Female Employees: 14 (estimated)

Symbol	GHS07, GHS08
Signal Word	Warning
Hazard Statements	H302 + H312 + H332-H351
Precautionary Statements	P261-P280-P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi:Irritant
Risk Phrases	R20/21/22;R40
Safety Phrases	S22-S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	XP2087500

Precursor 8
CAS#:2314-97-8 Iodotrifluoromethane CAS#:951-78-0 2'-deoxyuridine CAS#:65499-42-5 Thymidine, 2.al... CAS#:887144-94-7 1-Trifluorometh...
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DownStream 2
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Differential activation of cell death and autophagy results in an increased cytotoxic potential for trifluorothymidine compared to 5-fluorouracil in colon cancer cells.

Int. J. Cancer 126 , 2457-2468, (2010)

Trifluorothymidine (TFT) is part of the oral drug formulation TAS-102. Both 5-fluorouracil (5-FU) and TFT can inhibit thymidylate synthase and be incorporated into DNA. TFT shows only moderate cross-r...

Name: Primary qHTS assay for inhibitors of alpha-synuclein gene (SNCA) expression
Source: NCGC
External Id: SNCA-p-activity-luciferase

Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN

Name: Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: lu...
Source: 824
External Id: CYP273

Name: Evaluation of antiviral activity against Vaccinia virus
Source: ChEMBL
Target: Vaccinia virus
External Id: CHEMBL816930

Name: Fluorescence-based cell-based primary high throughput screening assay to identify pos...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_PAM_FLUO8_1536_1X%ACT PRUN

Name: Antiviral activity against HSV1 CL-101 infected in African green monkey Vero cells as...
Source: ChEMBL
Target: NON-PROTEIN TARGET
External Id: CHEMBL3282724

Name: Cytotoxicity against African green monkey Vero cells at 1 uM after 3 days by haemocyt...
Source: ChEMBL
Target: Vero
External Id: CHEMBL3282727

Name: Cytotoxicity against mouse Sarcoma 180 cells after 1 to 3 days by coulter counter ana...
Source: ChEMBL
Target: Sarcoma-180
External Id: CHEMBL3282729

Name: qHTS Assay for Small Molecule Inhibitors of the Human hERG Channel Activity
Source: NCGC
External Id: HERG01

Name: qHTS for Inhibitors of TGF-b: Cytotox Counterscreen
Source: NCGC
Target: N/A
External Id: SMAD3201

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1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-5-(trifluorométhyl)pyrimidine-2,4(1H,3H)-dione

Viroptic

α,α,α-Trifluorothymidine

2'-Deoxy-5-(trifluoromethyl)uridine

UNII-RMW9V5RW38

Trifluorothymidine

1-(2-Deoxy-β-D-glycero-pentofuranosyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

Trifluridine

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

EINECS 200-722-8

1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion

2'-Deoxy-5-trifluoromethyluridine

Virophta

a,a,a-Trifluorothymidine

MFCD00006534

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Trifluorothymidine

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