General Description Medical Uses Side Effects Indications and Dosage Precautions Drug Interactions Mechanism of Action
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Trifluridine

General Description Medical Uses Side Effects Indications and Dosage Precautions Drug Interactions Mechanism of Action
Product Name
Trifluridine
CAS No.
70-00-8
Chemical Name
Trifluridine
Synonyms
f3t;FTD;TFT;tfdu;F3TDR;f3dthd;nsc75520;viroptic;NSC 529182;Triflurdine
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
pka
pKa 7.85 (Uncertain)
Merck 
14,9687
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

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

H351Suspected of causing cancer

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1686309
Product name
Trifluridine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$447
Updated
2021/12/16
Sigma-Aldrich
Product number
T2255
Product name
Trifluorothymidine
Purity
≥99% (HPLC)
Packaging
1g
Price
$1490
Updated
2021/12/16
Sigma-Aldrich
Product number
T2255
Product name
Trifluorothymidine
Purity
≥99% (HPLC)
Packaging
100mg
Price
$230
Updated
2021/03/22
TCI Chemical
Product number
T2511
Product name
Trifluorothymidine
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$173
Updated
2021/12/16
TCI Chemical
Product number
T2511
Product name
Trifluorothymidine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$515
Updated
2021/12/16
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Trifluridine Chemical Properties,Usage,Production

General Description

Trifluridine, also known as trifluorothymidine, F3TdR,F3T is a fluorinated pyrimidine nucleoside that has in vitro inhibitory activity against epithelial keratitis caused by herpes simplex (HSV) types 1 and 2, certain adenoviruses, vaccinia, and CMV. It is sold under the brand name Viroptic, and its chemical name is αα α –trifluorothymidine.

Medical Uses

Trifluridine is used in treating herpes infection of the eye. It is noteworthy that the herpes virus does not manifest itself in the body until an outbreak is triggered. Trifluridine is not a cure for HSV infection, but treatment of an outbreak can expedite the healing of sores in the eye and minimize the risk of complications such as vision loss.

Side Effects

Common side effects of trifluridine eye drops include temporary mild burning, irritation, and stinging. Chronic side effects include eye pain/redness, swelling eyelids, feeling as if there is a foreign object in the eye, and persistent blurred vision. Serious allergic reactions include itching, rash, severe dizziness, and troubled breathing.

Indications and Dosage

Trifluridine ophthalmic solution is indicated for the treatment of recurrent epithelial keratitis and primary keratoconjunctivitis.
1% of trifluridine ophthalmic solution is instilled into the cornea of the affected eye every 2 hours while awake for a maximum daily dosage of the nine drops. This should be done until the complete re-epithelialization of the corneal ulcer. After re-epithelialization, there should be a treatment for 7 days of one drop every 4 hours.
Other forms of therapy should be considered if re-epithelialization has not occurred or if there are no signs of improvement after 7 days of treatment. Due to potential ocular toxicity, trifluridine ophthalmic solution should not be administered for periods exceeding 21 days.

Precautions

It is important to inform the doctor or physician if one is allergic to trifluridine before using it. Trifluridine ophthalmic solution may contain other inactive ingredients that can lead to allergic reactions or other complications. Also, inform the doctor regarding your medical history, especially if you have previous eye problems. It is not safe to use machinery after applying the drug as it may impair one's vision. The medication should only be used when necessary in case of pregnancy.

Drug Interactions

Do not start, change, or stop trifluridine ophthalmic solution medication before checking with the doctor. It is essential to inform the doctor if you are using any other form of herbal medicine.

Mechanism of Action

Trifluridine ophthalmic solution is a nucleotide analogue, which is similar enough to be integrated into viral DNA replication. However, the –CF3 group added to the uracil component blocks base pairing, therefore interfering with viral DNA replication.

Chemical Properties

White to Off-White Solid

Originator

Trifluorothymidine ,Mann,W. Germany,1975

Uses

sunscreen

Uses

anti-herpesvirus antiviral agent

Uses

Trifluridine is used as antiviral agent in ophthalmie preparations.

Definition

ChEBI: 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.

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.

Manufacturing Process

A suspension of 4.00g (6.75 mmol) of 3',5'-bis-O-(p-nitrobenzoyl)-2'-deoxy-5- (trifluoromethyl)uridine in 250 ml of methanol was treated with 10 ml of diisopropylamine and refluxed until it had dissolved (about 18 minutes), and the solution was concentrated. The dry residue was partitioned between 50 ml of chloroform and 50 ml of water. The chloroform layer was washed with 20 ml of water, and the combined aqueous layers were concentrated. A low ultraviolet extinction (ε 7200 and 262 μm; pH 1) and the presence of isopropyl signals in the NMR spectrum (two singlets at γ8.73 and 8.85) indicated the dry residue contained diisopropylamine, probably as a salt with the relatively acidic heterocyclic N-H in 14.
A solution in 75 ml of water was treated with 8 ml (volume of resin) of Dowex 50 (H), prewashed with water and methanol. The resin was removed on a filter and washed with 25 ml of methanol and 50 ml of water, The combined filtrate was evaporated in vacuo to form 1.99 g of 2'-deoxy-4- (trifluoromethyl)uridine (100%), melting point 171°C to 175°C.

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.

Pharmaceutical Applications

Trifluorothymidine. 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. 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.
It causes sister chromatid exchange – an indicator of mutagenicity – at 0.5 mg/L in human lymphocytes and fibroblasts. It is teratogenic to chick embryos when injected directly into the yolk sac. Its principal adverse effects in humans following systemic administration include leukopenia, anemia, fever and hypocalcemia. Accordingly, it is restricted to topical ophthalmic use in HSV ocular infections. The ophthalmic 1% aqueous solution produces occasional punctate lesions; other side effects are similar to those of idoxuridine but arise less frequently.

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, 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.

Clinical Use

Trifluridine is administered as a topical ophthalmic solution for the treatment of primary keratoconjunctivitis and recurrent keratitis due to HSV-1 or HSV-2. It is not effective in the prophylaxis of these infections; however, it is effective in treating patients who were unresponsive or intolerant to topical idoxuridine or vidarabine.

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.

Chemical 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.

Trifluridine Preparation Products And Raw materials

Raw materials

Preparation Products

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Trifluridine Suppliers

Shanghai YuLue Chemical Co., Ltd.
Tel
021-60345187
Fax
021-34702061
Email
lzz841106@aliyun.com
Country
China
ProdList
10081
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55
Lihan (Shanghai) Biotechnology Co., Ltd.
Tel
Fax
QQ1984683225
Email
sales@lihan-bio.com
Country
China
ProdList
610
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58
Shanghaizehan biopharma technology co., Ltd.
Tel
021-61350663
Fax
021-61350662
Email
sales@zehanbiopharma.com;
Country
China
ProdList
1000
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55
Shanghai Boyle Chemical Co., Ltd.
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2926
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
+86-021-61259100
Fax
86-21-61259102
Email
int02@meryer.com
Country
China
ProdList
40264
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Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5947
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61
TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2346
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56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24555
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BeiJing Hwrk Chemicals Limted
Tel
0757-86329057- ;021-51691807
Fax
0757-86311057
Email
sales.gd@hwrkchemical.com;peter.shi@hwrkchemical.com
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China
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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
Dideu Industries Group Limited
Product
Trifluridine USP/EP/BP 70-00-8
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-15
Zhuozhou Wenxi import and Export Co., Ltd
Product
Trifluorothymidine 70-00-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

70-00-8, TrifluridineRelated Search:


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  • ALPHA,ALPHA,ALPHA-TRIFLUOROTHYMIDINE
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  • 70-00-8
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  • C10H11F3N2O5
  • Biochemicals and Reagents
  • BioChemical
  • Nucleoside Analogs
  • Nucleosides, Nucleotides, Oligonucleotides