CAS 70-00-8|Trifluorothymidine
| Common Name | Trifluorothymidine | ||
|---|---|---|---|
| CAS Number | 70-00-8 | Molecular Weight | 296.200 |
| Density | 1.6±0.1 g/cm3 | Boiling Point | / |
| Molecular Formula | C10H11F3N2O5 | Melting Point | 190-193 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | / |
| Symbol | GHS07, GHS08 | Signal Word | Warning |
Names
| Name | trifluridine |
|---|---|
| Synonym | More Synonyms |
Trifluorothymidine BiologicalActivity
| 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/AnalogSignaling Pathways >>Apoptosis >>Thymidylate SynthaseResearch 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. |
Chemical & Physical Properties
| 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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)
Safety Information
| 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 |
Articles8
More Articles| Mechanistic evaluation of Ginkgo biloba leaf extract-induced genotoxicity in L5178Y cells. Toxicol. Sci. 139(2) , 338-49, (2014) Ginkgo biloba has been used for many thousand years as a traditional herbal remedy and its extract has been consumed for many decades as a dietary supplement. Ginkgo biloba leaf extract is a complex m... | |
| Quantitative high-throughput identification of drugs as modulators of human constitutive androstane receptor. Sci. Rep. 5 , 10405, (2015) The constitutive androstane receptor (CAR, NR1I3) plays a key role in governing the transcription of numerous hepatic genes that involve xenobiotic metabolism/clearance, energy homeostasis, and cell p... | |
| 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... |
Synonyms
| 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 |
| 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-D-ribofuranosyl)-5-(trifluoromethyl)- |
| 2,4(1H,3H)-pyrimidinedione, 1-(2-deoxy-β-D-glycero-pentofuranosyl)-5-(trifluoromethyl)- |
| 2'-Deoxy-5-trifluoromethyluridine |
| Virophta |
| Uridine, 2'-deoxy-5-(trifluoromethyl)- |
| a,a,a-Trifluorothymidine |
| MFCD00006534 |
