Tegafur 替加氟

CAS 17902-23-7 MFCD00012351

化学结构图

17902-23-7
SMILES: O=c1[nH]c(=O)n(C2CCCO2)cc1F

化学属性

Mol. FormulaC8
Mol. Weight200
Melting Point168-171
Density1.422
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameTegafur
CAS Number17902-23-7
Synonym 1-(2-Tetrahydroformyl)-5-fluorouracil, FT 207, NSC 148958 1-(2-Tetrahydrofuryl)-5-fluorouracil 1-(Tetrahydro-2-furanyl)-5-fluoro-2,4-pyrimidinedione 1-(Tetrahydro-2-furanyl)-5-fluorouracil 5-Fluor-1-(tetrahydro-2-furyl)-uracil 5-Fluoro-1-(2-tetrahydrofuranyl)uracil 5-Fluoro-1-(tetrahydro-2'-furyl)uracil 5-Fluoro-1-(tetrahydro-2-furanyl)-2,4-pyrimidinedione 5-Fluoro-1-(tetrahydro-2-furyl)uracil Ftora 5-Fluoro-1-(tetrahydro-3-furyl)uracil Citofur Coparogin Exonal FT 207 Fental Fluaid Fluorafur Fulaid Furflucil Furofutran Futraful N1-(2'-Tetrahydrofura N1-(2'-Tetrahydrofuryl)-5-fluorouracil Phthorafur Tegafur Uracil, 5-fluoro-1-(tetrahydro-2-furyl)- oral f
MDL NumberMFCD00012351
PubChem Substance ID87559743
EC Number241-846-2
Reaxys-RN525766
Beilstein Registry Number525766
Merck Number9112
Chemical Name Translation替加氟
Wiswesser Line NotationT6NVMVJ EF A- BT5OTJ
LabNetwork Molecule IDLN01745202
FormulaC8H9FN2O3
IUPAC Name5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChIKeyWFWLQNSHRPWKFK-UHFFFAOYSA-N
InChIInChI=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)
Canonical SMILESO=C1NC(C(F)=CN1C2OCCC2)=O
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分类

  • {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, DNA Synthesis Inhibitors, DNA metabolism, T
  • {uni_hamburg} no charge; oxygen heterocycle; nitrogen heterocycle; alicycle; 5ring; 6ring; urea; amide; lactame; racemate; 1fragment
  • Pharmaceuticals
  • {SNA} Biochemicals and Reagents, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides
  • {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, DNA Synthesis Inhibitors, DNA metabolism, T, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学
  • {SA} Biochemicals and Reagents, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides
  • Intermediates & Fine Chemicals,

产品应用

  • Tegafur (INN) is a chemotherapeutic 5-FU prodrug used in the treatment of cancers. It is a component of tegafur-uracil. When metabolized, it becomes 5-FU. T egafur-uracil is a formulated therapeutic oral agent consisting of a combination of the 5-fluorouracil (5-FU) congener prodrug tegafur (tetrahydrofuranyl-5-fluorouracil) and uracil (1:4). The high concentration of uracil reversibly inhibits the uracil-reducing enzyme dihydropyrimidine dehydrogenase (DPD), thereby inhibiting first-pass DPD-mediated hepatic metabolism of the uracil analogue 5-FU and permitting administration of 5-FU as the orally bioavailable prodrug tegafur. Tegafur is bioactivated to 5-FU by liver microsomal cytochrome P450 enzymes.

相关文献及参考

  • Au., J.L., et al.: Cancer Treat. Rep., 63, 343 (1979),
  • Short: III/20a Title: Nuclear Quadrupole Resonance Spectroscopy Data: Nuclei D ... Cl Author: Chihara, H.; Nakamura, N. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: III/20a Year: 1988 Keyword: NQR ISBN: 3-540-18161-X ISBN: 978-3-540-18161-3 Internet Resource: DOI:10.1007/b31153 RefComment: IX,677 pages. Hardcover Abstract: Nuclear Quadrupole Resonance Spectroscopy has become a standard method for structural research in molecular and solid state physics as well as for different branches of chemistry. The volumes cover data for more than 8,000 substances in the solid state. Data for free molecules have been published in volumes II/14 and II/15 of the New Series. The tables are arranged according to the atomic number of the elements.
  • Short: EINECS Title: EINECS (European Inventory of Existing Commercial Chemical Substances) Source: Official Journal of the European Communities Volume: C 146 A (15.06.1990) Page: 1 Year: 1990 Internet Resource: http://ecb.jrc.ec.europa.eu/esis/index.php?PGM=ein Publish_Date: 1990/06/15

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P310
  • P301+P310+P330
  • P305+P351+P338
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医，如果你觉得不舒服
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H331 Toxic if inhaled 吸入中毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H301 Toxic if swallowed 吞食有毒
  • H300 Fatal if swallowed 吞食致命
RTECSYR0450000
Signal word Danger
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes 6.1 T
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
Risk Statements
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
UN Number 2811
Packing GroupII
Hazard Class6.1 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 11046 mg/kg/4.7Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Gastrointestinal - tumors
REFERENCE :
   ARSUAX Archives of Surgery (Chicago).  (AMA, 535 N. Dearborn St., Chicago,
   IL 60610)  V.1-61, 1920-50; V.81-    1960-  Volume(issue)/page/year:
   118,1454,1983

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 197 mg/kg/23D-I
TOXIC EFFECTS :
   Brain and Coverings - encephalitis
   Behavioral - muscle contraction or spasticity
   Behavioral - antipsychotic
REFERENCE :
   IEDIEP Internal Medicine.  (The Japanese Society of Internal Medicine, 34-3,
   3-chome, Hongo, Bunkyo-ku, Tokyo 113, Japan)  V.31-    1992-
   Volume(issue)/page/year: 31,828,1992

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human
DOSE/DURATION           : 640 mg/kg/8D
TOXIC EFFECTS :
   Behavioral - hallucinations, distorted perceptions
   Vascular - BP lowering not characterized in autonomic section
   Gastrointestinal - nausea or vomiting
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/page/year: 36,103,1975

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human
DOSE/DURATION           : 23 mg/kg
TOXIC EFFECTS :
   Behavioral - hallucinations, distorted perceptions
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Li

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 34 mg/kg
TOXIC EFFECTS :
   Behavioral - tremor
   Vascular - other changes
   Gastrointestinal - nausea or vomiting
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 20,1009,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED

{ha

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human HeLa cell
DOSE/DURATION           : 200 mg/L
REFERENCE :
   JMCMAR Journal of Medicinal Chemistry.  (American Chemical Soc.,
   Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC
   20037)  V.6-    1963-  Volume(issue)/page/year: 22,1096,1979

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Intravenous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 60 mg/kg
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,

TYPE OF TEST            : Micronucleus test
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 320 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 291,29,1993

TYPE OF TEST            : Specific locus test
ROUTE OF EXPOSURE       : Multiple routes
TEST SYSTEM             : Insect - Drosophila melanogaster

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 40 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 88,301,1981

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Intravenous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 60 mg/kg
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,33,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 810 mg/kg
SEX/DURATION            : female 17-22 day(s) after conception
                          lactating female 21 day(s) post-birth
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - urogenital system
   Reproductive - Effects on Newborn - behavioral
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 22,109,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 210 mg/kg
SEX/DURATION            : female 6-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Effects on Embryo or Fetus - fetal death
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 5,555,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 550 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - extra-embryonic structures
   (e.g., placenta, umbilical cord)
REFERENCE :
   KSRNAM Kiso to Rinsho.  Clinical Report.  (Yubunsha Co., Ltd., 1-5, Kanda
   Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan)  V.1-    1960-
   Volume(issue)/page/year: 14,1373,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleoside Analogs - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleosides - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleotide Analogs - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleotides - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. T - Bioactive Small Molecules
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Nucleosides, Nucleotides, Oligonucleotides
  4. NAD and Analogs
  1. Medical Research Areas
  2. Metabolism
  3. Dehydrogenase

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