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Substance Name: Tegafur [USAN:INN:BAN:JAN]
RN: 17902-23-7
UNII: 1548R74NSZ
InChIKey: WFWLQNSHRPWKFK-UHFFFAOYSA-N

Note

  • Congener of FLUOROURACIL with comparable antineoplastic action. It has been suggested especially for the treatment of breast neoplasms.

Molecular Formula

  • C8-H9-F-N2-O3

Molecular Weight

  • 200.1681
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Tegafur
  • Tegafur [USAN:INN:BAN:JAN]

MeSH Heading

  • Tegafur

Synonyms

  • 1-(2-Tetrahydrofuryl)-5-fluorouracil
  • 1-(Tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione
  • 1-(Tetrahydrofuran-2-yl)-5-fluorouracil
  • 2,4(1H,3H)Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
  • 5-24-06-00285 (Beilstein Handbook Reference)
  • 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione
  • 5-Fluoro-1-(tetrahydro-2-furyl)uracil
  • 5-Fluoro-1-(tetrahydro-3-furyl)uracil
  • 5-Fluoro-1-(tetrahydrofuran-2-yl)uracil
  • BRN 0525766
  • CCRIS 2762
  • Citofur
  • Coparogin
  • EINECS 241-846-2
  • Exonal
  • Fental
  • Fluorofur
  • Franroze
  • FT-207
  • Ftorafur
  • Fulfeel
  • Furafluor
  • Furflucil
  • Furofutran
  • Futraful
  • Lamar
  • Lifril
  • MJF-12264
  • N(sub 1)-(2'-Furanidyl)-5-fluouracil
  • N(sub 1)-(2'-Furanidyl)-5-fluouracil [Czech]
  • N(sub 1)-(2-Tetrahydrofuryl)-5-fluorouracil
  • N1-(2-tetrahydrofuryl)-5-fluorouracil
  • Neberk
  • Nitobanil
  • NSC-148958
  • Phthorafur
  • Phthorafur [Czech]
  • Racemic Ftorafur
  • Riol
  • Sinoflurol
  • Sunfral
  • Tefsiel C
  • Tegafur
  • Tegafurum
  • Tegafurum [INN-Latin]
  • UNII-1548R74NSZ
  • Uracil, 1-(tetrahydrofuran-2-yl)-5-fluoro-

Systematic Names

  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
  • 5-Fluoro-1-(tetrahydro-2-furyl)uracil
  • Tegafur
  • Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-

Mixture Name

  • TS-1

Registry Numbers

CAS Registry Number

  • 17902-23-7

FDA UNII

  • 1548R74NSZ

Other Registry Numbers

  • 35959-67-2
  • 37308-51-3
  • 56767-38-5
  • 65732-47-0
  • 73120-84-0
  • 79107-97-4

System Generated Number

  • 0017902237

Structure Descriptors

InChI

InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)

InChIKey

WFWLQNSHRPWKFK-UHFFFAOYSA-N

Smiles

FC1=CN(C2CCCO2)C(=O)NC1=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 36mg/kg (36mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: TREMOR
Journal of Pharmaceutical Sciences. Vol. 73, Pg. 212, 1984.
dog LD50 oral 34mg/kg (34mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: TREMOR

VASCULAR: OTHER CHANGES
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980.
human LDLo intravenous 640mg/kg/8D (640mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Cancer Vol. 36, Pg. 103, 1975.
human TDLo intravenous 23mg/kg (23mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Cancer Vol. 36, Pg. 103, 1975.
man TDLo oral 197mg/kg/23D- (197mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

BRAIN AND COVERINGS: ENCEPHALITIS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Internal Medicine. Vol. 31, Pg. 828, 1992.
mouse LD50 intraperitoneal 493mg/kg (493mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 750mg/kg (750mg/kg)   United States Patent Document. Vol. #4130648,
mouse LD50 oral 775mg/kg (775mg/kg)   Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 22, Pg. 27, 1987.
mouse LD50 subcutaneous 760mg/kg (760mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 569, 1971.
rabbit LD50 oral 44mg/kg (44mg/kg) VASCULAR: OTHER CHANGES Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980.
rabbit LD50 unreported 40mg/kg (40mg/kg)   Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 7, Pg. 100, 1977.
rat LD50 intraperitoneal 700mg/kg (700mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978.
rat LD50 intravenous 685mg/kg (685mg/kg)   Gan to Kagaku Ryoho. Cancer and Chemotherapy. Vol. 10, Pg. 1987, 1983.
rat LD50 oral 930mg/kg (930mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978.
rat LD50 oral 930mg/kg (930mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978.
rat LD50 subcutaneous 600mg/kg (600mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978.
rat LD50 subcutaneous 600mg/kg (600mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 6, Pg. 2911, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 171-173 deg C   EXP
log P (octanol-water) -0.27 (none)   EXP
Water Solubility 3640 mg/L 25 EST
Vapor Pressure 3.38E-08 mm Hg 25 EST
Henry's Law Constant 8.32E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.20E-11 cm3/molecule-sec 25 EST

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