ChemicalBook > CAS DataBase List > Trifluridine

Trifluridine

Product Name
Trifluridine
CAS No.
70-00-8
Chemical Name
Trifluridine
Synonyms
TFT;TRIFLUOROTHYMIDINE;viroptic;f3t;nsc75520;Triflurdine;Triflurdine (Viroptic);Thymidine, α,α,α-trifluoro-;2,4(1h,3h)-pyrimidinedione,1-(2-deoxy-beta-d-ribofuranosyl)-5-(trifluorometh;FTD
CBNumber
CB6768812
Molecular Formula
C10H11F3N2O5
Formula Weight
296.2
MOL File
70-00-8.mol
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Trifluridine Property

Melting point:
190-193 °C (lit.)
Density 
1.4365 (estimate)
refractive index 
50 ° (C=1, H2O)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 25 mg/ml) or in Water (up to 14 mg/ml)
form 
solid
pka
pKa 7.85 (Uncertain)
color 
Off-white
biological source
synthetic
Water Solubility 
water: 50mg/mL, clear, colorless
Merck 
14,9687
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month.
CAS DataBase Reference
70-00-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-40
Safety Statements 
22-36
WGK Germany 
3
RTECS 
XP2087500
Hazard Note 
Keep Cold
HS Code 
29349990
Hazardous Substances Data
70-00-8(Hazardous Substances Data)
Toxicity
LD50 intraperitoneal in mouse: 1931mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H341Suspected of causing genetic defects

H351Suspected of causing cancer

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T2255
Product name
Trifluorothymidine
Purity
≥99% (HPLC)
Packaging
1g
Price
$1880
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3150
Product name
Trifluridine
Purity
pharmaceutical secondary standard, certified reference material
Packaging
200MG
Price
$293
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1126
Product name
Trifluridine
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
1686309
Product name
Trifluridine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$563
Updated
2024/03/01
TCI Chemical
Product number
T2511
Product name
Trifluorothymidine
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$211
Updated
2024/03/01
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Trifluridine Chemical Properties,Usage,Production

Description

Trifluridine (trifluorothymidine, TFT), a fluorinated pyrimidine nucleoside, is an anti-herpesvirus agent and an antitumor antimetabolite agent. It is an analog of thymidine which inhibits thymidylate synthase possesses antiviral and anticancer activity. After phosphorylation by thymidine kinase, it is incorporated into DNA where it induces DNA-damage and interferes with repair enzymes. Enhances frame shift insertion and deletion in CRISPR genome editing in pluripotent stem cells.

Chemical Properties

White to Off-White Solid

Originator

Trifluorothymidine ,Mann,W. Germany,1975

Uses

Trifluridine is used as anti-herpesvirus antiviral agent in ophthalmie preparations.

Definition

ChEBI: Trifluridine is a pyrimidine 2'-deoxyribonucleoside compound having 5-trifluoromethyluracil as the nucleobase. An antiviral drug used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis. It has a role as an antiviral drug, an antimetabolite, an EC 2.1.1.45 (thymidylate synthase) inhibitor and an antineoplastic agent. It is a nucleoside analogue, an organofluorine compound and a pyrimidine 2'-deoxyribonucleoside.

Indications

Trifluridine (Viroptic) is a fluorinated pyrimidine nucleoside that has in vitro activity against HSV-1 and HSV- 2, vaccinia, and to a lesser extent, some adenoviruses. Activation of trifluridine requires its conversion to the 5 monophosphate form by cellular enzymes.Trifluridine monophosphate inhibits the conversion of deoxyuridine monophosphate (dUMP) to deoxythymidine monophosphate (dTMP) by thymidylate synthetase. In addition, it competes with deoxythymidine triphosphate (dTTP) for incorporation by both viral and cellular DNA polymerases. Trifluridine-resistant mutants have been found to have alterations in thymidylate synthetase specificity.

brand name

Viroptic (Monarch).

Therapeutic Function

Antiviral (ophthalmic)

General Description

Trifluridine, 5-trifluoromethyl-29-deoxyuridine (Viroptic),is a fluorinated pyrimidine nucleoside that demonstrates invitro inhibitory activity against HSV-1 and HSV-2, CMV,vaccinia, and some adenoviruses.Trifluridine possesses atrifluoromethyl group instead of an iodine atom at the 5-position of the pyrimidine ring.
synthetase, and the biologically generated triphosphatecompetitively inhibits thymidine triphosphate incorporationinto DNA by DNA polymerase. In addition, trifluridine inits triphosphate form is incorporated into viral and cellularDNA, creating fragile, poorly functioning DNA.Trifluridine is approved in the United States for the treatmentof primary keratoconjunctivitis and recurrent epithelialkeratitis caused by HSV types 1 and 2. Topical trifluridineshows some efficacy in patients with acyclovir-resistantHSV cutaneous infections.

Biochem/physiol Actions

Trifluorothymidine is a thymidine analog and is light sensitive. TFT serves as a thymidine kinase substrate to study enzyme specificity and kinetics. Incorporation of phosphorylated TFT into DNA induces damage, making it useful for DNA repair studies. TFT may also be used in the inhibition of thymidylate synthase and in screening mutant thymidine kinase gene.. It elicits antitumor activity in gastrointestinal (GI) cancers and has therapeutic potential to treat herpetic keratitis.

Mechanism of action

Trifluorothymidine is a fluorinated pyridine nucleoside structurally related to idoxuridine. It has been approved by the U.S. FDA and is a potent, specific inhibitor of replication of HSV-1 in vitro. Its mechanism of action is similar to that of idoxuridine. Like other antiherpes drugs, it is first phos-phorylated by thymidine kinase to mono-, di-, and triphosphate forms, which are then incorporated into viral DNA in place of thymidine to stop the formation of late virus mRNA and subsequent synthesis of the virion proteins.

Pharmacokinetics

Trifluorothymidine is a synthetic halogenated pyrimidine nucleoside, first synthesized as an antitumor agent. It inhibits enzymes of the DNA pathway and is incorporated into both cellular and progeny viral DNA, causing faulty transcription of late messenger RNA and the production of incompetent virion protein. It does not require a viral thymidine kinase for monophosphorylation and is far less selective and more toxic than other analogs. It is active against HSV-1 and HSV-2, vaccinia virus, CMV and possibly adenovirus. Trifluorothymidine, when given IV, shows a plasma half-life of 18 minutes and is excreted in the urine either unchanged or as the inactive metabolite 5-carboxyuracil. When applied as a 1% ophthalmic solution, it rapidly enters the aqueous humor of HSV-infected rabbits’ eyes but is cleared within 60–90 min.

Side effects

The most frequent adverse reactions to trifluridine administration are transient burning or stinging and palpebral edema. Other adverse reactions include superficial punctate keratopathy, epithelial keratopathy, hypersensitivity, stromal edema, irritation, keratitis sicca, hyperemia, and increased intraocular pressure.
Trifluridine is mutagenic in vitro and carcinogenic and teratogenic when administered subcutaneously to animals. Topical trifluridine was not teratogenic in animal studies. Because it is applied topically in humans, the likelihood of systemic effects is low.

Synthesis

Trifluridine, 5-trifluoromethyl-1-(2-deoxyribofuranosyl)pyrimidin-2, 4-(1H.3H)-dione (36.1.22), is synthesized from 5-trifluoromethyluracil. This is synthesized by the following scheme. It begins with trifluoroacetone, from which the oxynitrile (36.1.16) is synthesized. Acetylation of this product gives the corresponding trifluoroacetate (36.1.16). Pyrrolysis of this compound gives trifluoromethylacrylonitrile (36.1.17). Adding to this dry hydrogen bromide in methanol solution in a process of which methanolysis of the nitrile group takes place the bromide 36.1.19 is obtained, which upon acidic hydrolysis undergoes heterocyclization to the dihydropyrimidine 36.1.20. Brominating of the obtained dihydropyrimidine with molecular bromine and subsequent dehydrobromination of the resulting product 36.1.21 on heating in dimethylformamide gives 5-trifluoromethyluracil (36.1.22). This is reacted with 2-deoxy-D-ribos-1-phosphate using the nucleoside phosphorylase enzyme, or by treating it with hyxamethyldisylazane and then with trichloromethylsilane to make 2,4- trimethylsilyloxy-5-trifluoromethyl pyrimidine (36.1.23).
Hexamethyldisilazane, which itself does not form trimethylsilyl ethers, is used because using a combination of two reagents leads to optimal yield of trimethylsilyl ethers. Reacting the resulting pyrimidine derivative with 3,5-bis-(4-nitrobenzoate)-2-deoxyribofuranosyl chloride in the presence of mercury (II) acetate makes the corresponding ditrimethylsilyloxy nucleoside, which when treated with an aqueous solution of potassium iodide to remove the protecting groups. The resulting product undergoes preliminary purification by chromatography, and then is treated with a methanol solution of diisopropylamine to remove the 4-nitrobenzoyl protection from the furanosyl part, giving the desired trifluridine.

Veterinary Drugs and Treatments

Trifluridine (trifluorothymidine; Viroptic?) is a pyrimidine nucleoside analog. It is structurally related to 2-deoxythymidine, the natural precursor of DNA synthesis. Trifluridine is poorly absorbed by the cornea and is virostatic. Viroptic? interrupts viral replication by substituting “nonsense” pyrimidine analogues. For this reason, a competent surface immunity is necessary to resolve ocular disease, with or without antiviral therapy. A recent in vitro study in which several strains of feline herpes virus were collected from the United States and were used to infect kidney epithelial cells showed that trifluridine was more effective at lower concentrations compared with several other agents. For this reason, trifluridine was the first choice drug employed in the treatment of feline herpes virus ocular disease for many years. Because of the topical toxicity associated with use of trifluridine in cats, its popularity has diminished greatly. In many milder cases, the irritation associated with topical trifluridine is more intense then the inflammation induced by viral infection. Antiviral agents have also been used in the treatment of superficial punctate keratitis in the horse, thought to be associated with equine herpes virus-2 (EHV-2) infection of the cornea.

References

1) Bijnsdorp et al. (2010), 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
2) Temmink et al. (2010), Trifluorothymidine resistance is associated with decreased thymidine kinase and equilibrative nucleoside transporter expression or increased secretory phospholipase A2; Mol. Cancer Ther., 9 1047
3) Suzuki et al. (2011), Mode of action of trifluorothymidine (TFT) against DNA replication and repair enzymes; Int. J. Oncol., 39 263 4) Yu et al. (2015), Small molecules enhance CRISPR genome editing in pluripotent stem cells; Cell Stem Cell, 16 142

Trifluridine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Trifluridine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Trifluridine 70-00-8
Price
US $0.00/g
Min. Order
1g
Purity
98%min
Supply Ability
1000g
Release date
2021-10-25
Cangzhou Kangrui Pharma Tech Co. Ltd.,
Product
Trifluridine 70-00-8
Price
US $0.00-0.00/g
Min. Order
10g
Purity
99%
Supply Ability
200
Release date
2024-10-16
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Trifluridine 70-00-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 TONS
Release date
2022-11-07

70-00-8, TrifluridineRelated Search:

Floxuridine Trifluorothymine Doxifluridine Thymine Cytidine Thymidine Fluorocytosine (Trifluoromethyl)trimethylsilane Uracil Starch soluble 1-beta-D-Arabinofuranosyluracil Zidovudine 3-(Trifluoromethyl)benzaldehyde Gemcitabine 1,2,3-Triacetyl-5-deoxy-D-ribose Gemcitabine hydrochloride 5-Carboxy-2'-deoxyuridine Uridine

  • 2,4(1h,3h)-pyrimidinedione,1-(2-deoxy-beta-d-ribofuranosyl)-5-(trifluorometh
  • Trifluridine (Viroptic)
  • VIROPTIC; TRIFLUOROTHYMIDINE
  • Triflurdine (Viroptic)
  • 2’-deoxy-5-(trifluoromethyl)-uridin
  • 5-(trifluoromethyl)deoxyuridine
  • 5-trifluoro-2’-deoxythymidine
  • alpha,alpha,alpha-trifluoro-thymidin
  • f3dthd
  • f3t
  • nsc75520
  • 5-TRIFLUOROTHYMIDINE extrapure (Trifluridine)
  • α,α,α-Trifluorothymidine, 2μ-Deoxy-5-trifluoromethyluridine, Trifluorothymine deoxyriboside, Trifluridine
  • 2'-Deoxy-5-trifluoromethyluridine, Trifluridine
  • Trifluridine (100 mg)
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)oxolan-2-yl]-5-(trifluoroMethyl)-1,2,3,4-tetrahydropyriMidine-2,4-dione
  • Trifluridine API
  • alpha,alpha,alpha-Trifluorothymidine Trifluridine 2'-Deoxy-5-trifluoromethyluridine
  • FTD
  • NSC 529182
  • Trifluridine, Trifluorothymidine, 1-(2-Deoxy-beta-D-ribofuranosyl)-5-(trifluoromethyl)uracil
  • 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-(trifluoroMethyl)pyriMidine-2,4(1H,3H)-dione
  • Trifluorothymidine (TFT)
  • Trifluridine(FTD)
  • TFT
  • TRIFLUORO-D-THYMIDINE
  • TRIFLURIDINE
  • TRIFLUOROTHYMIDINE
  • TRIFLUOROTHYMINE DEOXYRIBOSIDE
  • tfdu
  • trifluoromethyldeoxyuridine
  • viroptic
  • 2'-DEOXY-5-TRIFLUOROMETHYLURIDINE
  • ALPHA,ALPHA,ALPHA-TRIFLUOROTHYMIDINE
  • Trifluridine, Trifluorothymine Deoxyriboside, a,a,a-Trifluorothymidine
  • 2'-DEOXY-5-(TRIFLUOROMETHYL)URIOINE
  • 2''-DEOXY-5-(TRILIUOROMETHYL)URIDINE
  • 5-TRIFLUOROMETHYL-2'-DEOXYURIDINE
  • F3TDR
  • 5-TRIFLUORO THYMIDINE
  • 2''-DEOXY-5-(TRIFLUOROMETHYL)URIDINE (TRIFLUOROTHYMIDINE)
  • Triflurdine
  • Trafluuridine
  • MA-1 hydrochloride
  • Trifluridina
  • Fluorine urea glycosides
  • Thymidine, α,α,α-trifluoro-
  • Trifluorothymidine, 5-Trifluoromethyl-2’-deoxyuridine
  • Trifluridine USP/EP/BP
  • Trifluridine (trifluorothymidine)
  • TIANFU-CHEM Trifluridine
  • 5-Trifluorothymidine extrapure, 99%
  • Trifluridine (1686309)
  • Viroptic, Trifluorothymidine, F3Thd
  • 3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine 153719-38-1
  • 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)-2-tetrahydrofuryl]-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
  • 2'-5-CF3-dU
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione