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17902-23-7

17902-23-7 structure
17902-23-7 structure
  • Name: Tegafur
  • Chemical Name: Tegafur
  • CAS Number: 17902-23-7
  • Molecular Formula: C8H9FN2O3
  • Molecular Weight: 200.167
  • Catalog: API Antineoplastic agents Antimetabolite antineoplastic
  • Create Date: 2018-03-08 08:00:00
  • Modify Date: 2024-01-01 17:09:13
  • Tegafur (also known as Ftorafur) is a chemotherapeutic 5-FU prodrug used in the treatment of cancers; is a component of tegafur-uracil. IC50 value: Target: Nucleoside antimetabolite/analogTegafur is bioactivated to 5-FU by liver microsomal cytochrome P450 enzymes. 5-FU is subsequently converted into its active metabolites 5-fluoro-deoxyuridine-monophosphate (FdUMP) and 5-fluorouridine-triphosphate (FUTP) intracellularly; these metabolites inhibit the enzyme thymidylate synthase and intercalate into RNA, resulting in decreased thymidine synthesis, reduced DNA synthesis, disrupted RNA function, and tumor cell cytotoxicity.
Name Tegafur
Synonyms riol
neberk
Tegafur
EXONAL
5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
tetrahydrofuryl-5-fluorouracil
MFCD00012351
5-Fluoro-1-(tetrahydro-2-furanyl)-2,4(1H,3H)-pyrimidinedione
Carzonal
fulaid
lifril
EINECS 241-846-2
5-fluoro-1-tetrahydrofuran-2-ylpyrimidine-2,4(1H,3H)-dione
FT-207
5-Fluoro-1-(tetrahydro-2-furyl)uracil
5-Fluoro-1-(tetrahydro-2-furfuryl)uracil
FENTAL
Fluaid
lamar
2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-(tetrahydro-2-furanyl)-
N1-(2'-Furanidyl)-5-fluorouracil
Description Tegafur (also known as Ftorafur) is a chemotherapeutic 5-FU prodrug used in the treatment of cancers; is a component of tegafur-uracil. IC50 value: Target: Nucleoside antimetabolite/analogTegafur is bioactivated to 5-FU by liver microsomal cytochrome P450 enzymes. 5-FU is subsequently converted into its active metabolites 5-fluoro-deoxyuridine-monophosphate (FdUMP) and 5-fluorouridine-triphosphate (FUTP) intracellularly; these metabolites inhibit the enzyme thymidylate synthase and intercalate into RNA, resulting in decreased thymidine synthesis, reduced DNA synthesis, disrupted RNA function, and tumor cell cytotoxicity.
Related Catalog
References

[1]. Sotaro Sadahiro, Toshiyuki Suzuki, Akira Tanaka, et al. Association of right-sided tumors with high thymidine phosphorylase gene expression levels and the response to oral uracil and tegafur/leucovorin chemotherapy among patients with colorectal cancer. Cancer Chemotherapy and Pharmacology. 2012, 70 (2): 285-291.

[2]. José L. Ariasa, et al. Engineering of an antitumor (core/shell) magnetic nanoformulation based on the chemotherapy agent ftorafur. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2011,384(1-3): 157-163.

[3]. Gabriel N. Hortobagyi, William Heim, Laura Hutchins, et al. A phase 2 study of a fixed combination of uracil and ftorafur (UFT) and leucovorin given orally in a 3-times-daily regimen to treat patients with recurrent metastatic breast cancer. Cancer. 2010, 116(6): 1440-1445.

[4]. K. Fujita, H. Nakayama, W. Ichikawa, et al. Pharmacokinetics of 5-Fluorouracil in Elderly Japanese Patients with Cancer Treated with S-1 (a Combination of Tegafur and Dihydropyrimidine Dehydrogenase Inhibitor 5-Chloro-2,4-dihydroxypyridine). Drug Metab Dispos. 2009 Jul;37(7):1375-7. doi: 10.1124/dmd.109.027052. Epub 2009 Apr 23.

[5]. Tegafur-uracil
Density 1.5±0.1 g/cm3
Melting Point 171-173 °C(lit.)
Molecular Formula C8H9FN2O3
Molecular Weight 200.167
Exact Mass 200.059723
PSA 64.09000
LogP -0.77
Index of Refraction 1.557
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YR0450000
CHEMICAL NAME :
Uracil, 5-fluoro-1-(tetrahydro-2-furyl)-
CAS REGISTRY NUMBER :
17902-23-7
BEILSTEIN REFERENCE NO. :
0525766
LAST UPDATED :
199706
DATA ITEMS CITED :
43
MOLECULAR FORMULA :
C8-H9-F-N2-O3
MOLECULAR WEIGHT :
200.19
WISWESSER LINE NOTATION :
T6NVMVJ EF A- BT5OTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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
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
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
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
930 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - ulceration or bleeding from stomach Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
685 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
775 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
493 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
760 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
36 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
44 mg/kg
TOXIC EFFECTS :
Vascular - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17640 mg/kg/12W-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14040 mg/kg/13W-I
TOXIC EFFECTS :
Endocrine - changes in thymus weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
700 mg/kg/40W-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7 gm/kg/5W-I
TOXIC EFFECTS :
Blood - normocytic anemia Blood - changes in bone marrow (not otherwise specified) Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20160 mg/kg/24W-I
TOXIC EFFECTS :
Blood - changes in bone marrow (not otherwise specified) Blood - changes in leukocyte (WBC) count Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
880 mg/kg/80D-I
TOXIC EFFECTS :
Endocrine - changes in adrenal weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1170 mg/kg/9D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1365 mg/kg/13W-I
TOXIC EFFECTS :
Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1820 mg/kg/26W-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
350 mg/kg/5W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - chronic pulmonary edema Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
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)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
420 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
630 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
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
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
630 mg/kg
SEX/DURATION :
female 6-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Fibroblast
DOSE/DURATION :
100 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 88,241,1981
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H311-H331
Precautionary Statements P261-P280-P301 + P310-P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R23/24/25
Safety Phrases S22-S36/37/39-S45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS YR0450000
HS Code 2942000000
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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