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50-91-9

50-91-9 structure
50-91-9 structure
  • Name: Floxuridine
  • Chemical Name: 5-fluoro-2'-deoxyuridine
  • CAS Number: 50-91-9
  • Molecular Formula: C9H11FN2O5
  • Molecular Weight: 246.192
  • Catalog: API Antineoplastic agents Antimetabolite antineoplastic
  • Create Date: 2018-04-24 08:00:00
  • Modify Date: 2024-01-02 10:05:54
  • Floxuridine (5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites with an GI50 of 5.1 μM for the inhibition of PEPT1. IC50 value: Target: Nucleoside antimetabolite/analogFloxuridine (Fludara) is a prodrug of floxuridine and an oncology agent with an GI50 of 5.1 μM for the inhibition of MDCK/PEPT1. Floxuridine (Fludara) belongs to the class known as antimetabolites. Floxuridine (Fludara) is most often used in the treatment of colorectal cancer. Floxuridine, an analog of 5-fluorouracil, is a fluorinated pyrimidine. Floxuridine (Fludara) works because it is broken down by the body into its active form, which is the same as a metabolite of 5-Fluorouracil [1]. FdUrd induced an immediate increase in tumor uptake of 5-[(125)I]iodo-2'-deoxyuridine, that vanished after 6 h, as also confirmed by flow cytometry. Biodistribution measurements showed that FdUrd pretreatment increased [(18)F]FLT uptake in all tumors by factors of 3.2 to 7.8 compared with controls, while [(18)F]FDG tumor uptake was about fourfold and sixfold lower in breast cancers and lymphoma. Dynamic PET in FdUrd pretreated mice showed that [(18)F]FLT uptake in all tumors increased steadily up to 1.5 h. MRI showed a well-vascularized homogenous lymphoma with high [(18)F]FLT uptake, while in breast cancer, a central necrosis shown by MRI was inactive in PET, consistent with the histomorphological analysis [2].Clinical indications: Colorectal tumor; Liver tumorFDA Approved Date: December 1970
Name 5-fluoro-2'-deoxyuridine
Synonyms 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-fluorpyrimidin-2,4(1H,3H)-dion
5-Fluoro-2'-deoxyuridine
1-(2-Deoxy-β-D-ribofuranosyl)-5-fluorouracil
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
(+)-5-Fluoro-2-deoxyuridine
Floxuridin
(+)-5-Fluoro-2‘-deoxyuridine
2(1H)-Pyrimidinone, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-4-hydroxy-
Floxuridinum
Floxuridine
5-Fluoro-2'-deoxy-b-uridine
5-Fluoro-2'-deoxy-β-uridine
(+)-5-fluoro-2′-deoxyuridine
Fluorodeoxyuridine
Deoxyfluorouridine
2'-Deoxy-5-fluorouridine
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Fluoruridine deoxyribose
5-Fluorodeoxyuridine
5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
EINECS 200-072-5
Uridine, 2'-deoxy-5-fluoro-
5-Fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
(+)-5-Fluoro-2'-deoxyuridine
MFCD00006530
1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-4-hydroxy-2(1H)-pyrimidinone
5-Fluor-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2,4(1H,3H)-dion
1-(2-Deoxy-b-D-ribofuranosyl)-5-fluorouracil
5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione
2′-Deoxy-5-fluorouridine
FUDR
Description Floxuridine (5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites with an GI50 of 5.1 μM for the inhibition of PEPT1. IC50 value: Target: Nucleoside antimetabolite/analogFloxuridine (Fludara) is a prodrug of floxuridine and an oncology agent with an GI50 of 5.1 μM for the inhibition of MDCK/PEPT1. Floxuridine (Fludara) belongs to the class known as antimetabolites. Floxuridine (Fludara) is most often used in the treatment of colorectal cancer. Floxuridine, an analog of 5-fluorouracil, is a fluorinated pyrimidine. Floxuridine (Fludara) works because it is broken down by the body into its active form, which is the same as a metabolite of 5-Fluorouracil [1]. FdUrd induced an immediate increase in tumor uptake of 5-[(125)I]iodo-2'-deoxyuridine, that vanished after 6 h, as also confirmed by flow cytometry. Biodistribution measurements showed that FdUrd pretreatment increased [(18)F]FLT uptake in all tumors by factors of 3.2 to 7.8 compared with controls, while [(18)F]FDG tumor uptake was about fourfold and sixfold lower in breast cancers and lymphoma. Dynamic PET in FdUrd pretreated mice showed that [(18)F]FLT uptake in all tumors increased steadily up to 1.5 h. MRI showed a well-vascularized homogenous lymphoma with high [(18)F]FLT uptake, while in breast cancer, a central necrosis shown by MRI was inactive in PET, consistent with the histomorphological analysis [2].Clinical indications: Colorectal tumor; Liver tumorFDA Approved Date: December 1970
Related Catalog
References

[1]. Landowski CP, et al. Targeted delivery to PEPT1-overexpressing cells: acidic, basic, and secondary floxuridine amino acid ester prodrugs. Mol Cancer Ther. 2005 Apr;4(4):659-67.

[2]. Viertl D, et al. Increase of [(18)F]FLT tumor uptake in vivo mediated by FdUrd: toward improving cell proliferation positron emission tomography. Mol Imaging Biol. 2011 Apr;13(2):321-31.
Density 1.8±0.1 g/cm3
Boiling Point 483.0±55.0 °C at 760 mmHg
Melting Point 148 °C(lit.)
Molecular Formula C9H11FN2O5
Molecular Weight 246.192
Flash Point 245.9±31.5 °C
Exact Mass 246.065201
PSA 104.55000
LogP -1.22
Vapour Pressure 0.0±2.8 mmHg at 25°C
Index of Refraction 1.676
Storage condition 2~8°C
Water Solubility soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YU7525000
CHEMICAL NAME :
Uridine, 2'-deoxy-5-fluoro-
CAS REGISTRY NUMBER :
50-91-9
BEILSTEIN REFERENCE NO. :
0090221
LAST UPDATED :
199710
DATA ITEMS CITED :
77
MOLECULAR FORMULA :
C9-H11-F-N2-O5
MOLECULAR WEIGHT :
246.22
WISWESSER LINE NOTATION :
T6NVMVJ EF A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
5 mg/kg/14D-C
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
173 mg/kg/82W-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, allergic (after systemic exposure)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
215 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 - rat
DOSE/DURATION :
1600 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 :
147 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 :
650 mg/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
550 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 :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
100 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
50 mg/kg
SEX/DURATION :
female 11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
10 mg/kg
SEX/DURATION :
female 16 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
60 mg/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
10 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
5 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
25 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
45 mg/kg
SEX/DURATION :
female 12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material) Reproductive - Specific Developmental Abnormalities - Central Nervous System
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
150 nmol/L
REFERENCE :
PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 24,285,1983 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5648 No. of Facilities: 120 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 10039 (estimated) No. of Female Employees: 8310 (estimated)
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements Missing Phrase - N15.00950417
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/37/38;R68
Safety Phrases 22-36-36/37/39-26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS YU7525000
Packaging Group III
Hazard Class 6.1
HS Code 2934999090
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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