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Tegafur
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Name

Tegafur

 EINECS 241-846-2
CAS No. 17902-23-7 Density 1.45 g/cm3
PSA 64.09000 LogP -0.01530
Solubility N/A Melting Point 171-173 °C(lit.)
Formula C8H9FN2O3 Boiling Point N/A
Molecular Weight 200.169 Flash Point N/A
Transport Information UN 2811 6.1/PG 2 Appearance white crystalline powder
Safety 22-36/37/39-45 Risk Codes 23/24/25
Molecular Structure Molecular Structure of 17902-23-7 (Tegafur) Hazard Symbols ToxicT
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;

Article Data 63

Tegafur Synthetic route

tert-butyl 5-fluoro-2,6-dioxo-3-(tetrahydrofuran-2-yl)-3,6-dihydropyrimidine-1(2H)-carboxylate

17902-23-7

tegafur

Conditions
ConditionsYield
With isopropyl alcohol at 75℃; for 4h; Inert atmosphere;100%
51-21-8

5-fluorouracil

692-29-5

Succinic semialdehyde

17902-23-7

tegafur

Conditions
ConditionsYield
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In tetrahydrofuran at 15 - 20℃; for 12h; Solvent; Reagent/catalyst; Temperature;99.8%
1191-99-7

2,3-dihydro-2H-furan

51-21-8

5-fluorouracil

17902-23-7

tegafur

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); tris(2,2′-bipyridine)ruthenium(II) bis(tetrafluoroborate) In tetrahydrofuran at 25 - 30℃; Temperature; Solvent; Wavelength; Reagent/catalyst; Irradiation;98.7%
With calcium chloride; trifluoroacetic acid In chloroform; N,N-dimethyl-formamide; toluene85.2%
With dimethylmonochlorosilane; triethylamine In acetonitrile at 16℃; Temperature;85%
51-21-8

5-fluorouracil

3333-44-6

tetrahydrofuran-2-yl benzoate

17902-23-7

tegafur

Conditions
ConditionsYield
With sodium acetate; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 35℃; for 2h; Solvent; Temperature; Reagent/catalyst;95.2%
90162-98-4

5-Fluoro-2,6-dioxo-3-(tetrahydro-furan-2-yl)-3,6-dihydro-2H-pyrimidine-1-carbothioic acid S-octyl ester

17902-23-7

tegafur

Conditions
ConditionsYield
With isopropylamine In diethyl ether Ambient temperature;95%
109-99-9

tetrahydrofuran

51-21-8

5-fluorouracil

17902-23-7

tegafur

Conditions
ConditionsYield
With dihydrogen peroxide; copper diacetate In N,N-dimethyl-formamide at 40℃; for 5h; Reagent/catalyst; Time; Solvent; Temperature;92.35%
With carbon tetrabromide; potassium carbonate In ethanol; water at 50 - 60℃; for 9.5h; Temperature; Reagent/catalyst; Inert atmosphere;82%
With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; caesium carbonate at 90℃; for 12h; Inert atmosphere; Sealed tube;39%
1191-99-7

2,3-dihydro-2H-furan

51-21-8

5-fluorouracil

75-78-5

dimethylsilicon dichloride

17902-23-7

tegafur

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In chloroform; acetonitrile85.5%
With pyridine In acetonitrile75.4%
65906-08-3

5-fluoro-1-(2-tetrahydrofuryl)-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil

17902-23-7

tegafur

Conditions
ConditionsYield
With trifluoroacetic acid In water at 0℃; for 1104h;84%
70325-85-8

(4,4-Dimethoxy-butoxy)-trimethyl-silane

17242-85-2

5-fluoro-2,4-bis(trimethylsilyloxy)pyrimidine

17902-23-7

tegafur

Conditions
ConditionsYield
With tin(IV) chloride In 1,2-dichloro-ethane; acetonitrile addition at 0 deg C, stirring at 23-25 deg C, 1h;84%
13369-70-5

2-chlorotetrahydrofuran

51-21-8

5-fluorouracil

A

17902-23-7

tegafur

B

62987-05-7

1,3-bis(tetrahydro-2-furyl)-5-fluorouracil

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 30℃; for 5h;A 75%
B 80%

Tegafur Chemical Properties

IUPAC Name: 5-Fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
Synonyms of  5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7): 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 ; FT-207 ; Furafluor ; Furflucil ; 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 ; NSC-148958 ; Neberk ; Nitobanil ; Phthorafur ; Phthorafur [Czech] ; Racemic Ftorafur ; Riol ; Sinoflurol ; Sunfral ; Tefsiel C ; Tegafur ; Tegafurum ; Tegafurum [INN-Latin] ; UNII-1548R74NSZ ; Uracil, 1-(tetrahydrofuran-2-yl)-5-fluoro-  ; Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-
CAS NO: 17902-23-7
Classification Code: Antimetabolites ; Antimetabolites, antineoplastic ; Antineoplastic ; Antineoplastic Agents ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Noxae ; Reproductive Effect ; Tumor data
Molecular Formula: C8H9FN2O3
Molecular Weight: 200.1671
Molecular Structure:

Melting Point: 171-173 °C 
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 49.85 Å2
Index of Refraction: 1.557
Molar Refractivity: 44.28 cm3
Molar Volume: 137.4 cm3
Surface Tension: 51.1 dyne/cm
Density of  5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7): 1.45 g/cm3

Tegafur Uses

 5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7) can be used as an antineoplastic

Tegafur Production

  5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7) can be derived from condensation 5 - fluorouracil and 2 - acetoxy-tetrahydrofuran with the yield of the Act only about 15%.
Another production method is based on  the synthesis of fluoride withthe starting material of 5 - fluorouracil, 6 methyl-2, and 3-methyl silicone alkyl ammonium chloride.

Tegafur Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 36mg/kg (36mg/kg) BEHAVIORAL: TREMOR

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

VASCULAR: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980.
human LDLo intravenous 640mg/kg/8D (640mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: NAUSEA OR VOMITING		 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) BRAIN AND COVERINGS: ENCEPHALITIS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ANTIPSYCHOTIC		 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: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 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) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH 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.

Tegafur Consensus Reports

Reported in EPA TSCA Inventory.

Tegafur Safety Profile

Poison by ingestion. Moderately toxic to humans by intravenous route. Moderately toxic experimentally by intraperitoneal, intravenous, and subcutaneous routes. Experimental teratogenic data. Human systemic effects: nausea and vomiting. Experimental reproductive effects. Questionable human carcinogen producing gastrointestinal tumors. Human mutation data reported. Used as an anti-cancer agent. When heated to decomposition it emits very toxic fumes of F− and NOx.
Safety Information of  5-Fluoro-1-(tetrahydro-2-furyl)uracil (CAS NO.17902-23-7).
Hazard Codes: ToxicT
Risk Statements: 23/24/25 
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-45 
S22: Do not breathe dust. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: YR0450000

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