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Substance Name: Trifluridine [USAN:USP:INN]
RN: 70-00-8
UNII: RMW9V5RW38
InChIKey: VSQQQLOSPVPRAZ-RRKCRQDMSA-N

Note

  • An antiviral derivative of THYMIDINE used mainly in the treatment of primary keratoconjunctivitis and recurrent epithelial keratitis due to HERPES SIMPLEX virus. (From Martindale, The Extra Pharmacopoeia, 30th ed, p557).

Molecular Formula

  • C10-H11-F3-N2-O5

Molecular Weight

  • 296.1999
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antiviral (COVID-19)
  • Antiviral (Ophthalmic)
  • Antiviral Agents
  • Mutation Data
  • Noxae
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Names and Synonyms

Name of Substance

  • Trifluridine
  • Trifluridine [USAN:USP:INN]

MeSH Heading

  • Trifluridine

Synonyms

  • 2'-Deoxy-5-(trifluoromethyl)uridine
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-5-(trifluoromethyl)-
  • 5-(Trifluoromethyl)deoxyuridine
  • 5-Trifluoro-2'-deoxythymidine
  • 5-Trifluoromethyl-2-deoxyuridine
  • BRN 0568095
  • CCRIS 2348
  • EINECS 200-722-8
  • F3DThd
  • F3T
  • F3TDR
  • HSDB 8126
  • NSC 529182
  • NSC 75520
  • TFDU
  • Trifluoromethyldeoxyuridine
  • Trifluorothymidine
  • Trifluridina
  • Trifluridina [INN-Spanish]
  • Trifluridine
  • Trifluridinum
  • Trifluridinum [INN-Latin]
  • UNII-RMW9V5RW38
  • Uridine, 2'-deoxy-5-(trifluoromethyl)-
  • Viroptic

Systematic Names

  • 5-Trifluorothymidine
  • Thymidine, alpha,alpha,alpha-trifluoro-
  • Trifluridine

Registry Numbers

CAS Registry Number

  • 70-00-8

FDA UNII

  • RMW9V5RW38

System Generated Number

  • 0000070008

Structure Descriptors

InChI

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

InChIKey

VSQQQLOSPVPRAZ-RRKCRQDMSA-N

Smiles

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(C(=O)NC2=O)C(F)(F)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LDLo intravenous 400mg/kg (400mg/kg)   Government Reports Announcements. Vol. 74(9), Pg. 60, 1974.
mouse LD50 intraperitoneal 1931mg/kg (1931mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 3381mg/kg (3381mg/kg)   Progress Report Submitted to the National Cancer Institute by Arthur D. Little, Inc. Vol. -, Pg. 260, 1967.
rat LD50 intravenous 2946mg/kg (2946mg/kg) LIVER: OTHER CHANGES Progress Report Submitted to the National Cancer Institute by Arthur D. Little, Inc. Vol. -, Pg. 260, 1967.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 186-189 deg C   EXP
pKa Dissociation Constant 7.95 (none)   EXP
log P (octanol-water) -0.46 (none)   EXP
Water Solubility 1560 mg/L 25 EST
Vapor Pressure 9.27E-14 mm Hg 25 EST
Henry's Law Constant 9.53E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.53E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.