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Substance Name: Floxuridine [USAN:USP:INN]
RN: 50-91-9
UNII: 039LU44I5M
InChIKey: ODKNJVUHOIMIIZ-RRKCRQDMSA-N

Note

  • An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.

Molecular Formula

  • C9-H11-F-N2-O5

Molecular Weight

  • 246.1929
 

Classification Codes

  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Antiviral
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Floxuridine
  • Floxuridine [USAN:USP:INN]

MeSH Heading

  • Floxuridine

Synonyms

  • 1-(2-Deoxy-beta-D-ribofuranosyl)-5-fluorouracil
  • 1-beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 1beta-D-2'-Deoxyribofuranosyl-5-flurouracil
  • 2'-Deoxy-5-fluorouridine
  • 5-24-06-00291 (Beilstein Handbook Reference)
  • 5-FdUrd
  • 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion
  • 5-Fluor-1-(beta-2'-deoxyribofuranosyl)pyrimidin-2,4(1H,3H)-dion [Czech]
  • 5-Fluoro-2-desoxyuridine
  • 5-Fluorodeoxyuridine
  • 5-Fluorouracil 2'-deoxyriboside
  • 5-Fluorouracil deoxyriboside
  • 5-FUDR
  • AI3-50691
  • beta-5-Fluoro-2'-deoxyuridine
  • BRN 0090221
  • Deoxyfluorouridine
  • EINECS 200-072-5
  • Fdur
  • FdUrd
  • Floxiridina
  • Floxiridina [INN-Spanish]
  • Floxuridin
  • Floxuridine
  • Floxuridinum
  • Floxuridinum [INN-Latin]
  • Fluorodeoxyuridine
  • Fluoruridine deoxyribose
  • FUDR
  • HSDB 3227
  • NSC 27640
  • NSC-27640
  • Ro 5-0360
  • UNII-039LU44I5M
  • Uridine, 2'-deoxy-5'-fluoro-

Systematic Names

  • Floxuridine
  • Uridine, 2'-deoxy-5-fluoro
  • Uridine, 2'-deoxy-5-fluoro-

Registry Numbers

CAS Registry Number

  • 50-91-9

FDA UNII

  • 039LU44I5M

System Generated Number

  • 0000050919

Structure Descriptors

InChI

InChI=1S/C9H11FN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChIKey

ODKNJVUHOIMIIZ-RRKCRQDMSA-N

Smiles

OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 5mg/kg/14D-C (5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES		 Cancer Vol. 34, Pg. 972, 1974.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Proceedings of the Society for Experimental Biology and Medicine. Vol. 97, Pg. 470, 1958.
mouse LD50 oral 147mg/kg (147mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
mouse LD50 unreported 550mg/kg (550mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
rat LD50 intraperitoneal 1600mg/kg (1600mg/kg)   Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.
rat LD50 oral 215mg/kg (215mg/kg)   Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,
women TDLo parenteral 173mg/kg/82W- (173mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Journal of the National Medical Association. Vol. 79, Pg. 669, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150.5 deg C   EXP
pKa Dissociation Constant 7.44 (none)   EXP
log P (octanol-water) -1.16E+00 (none)   EXP
Water Solubility 1.19E+04 mg/L 25 EST
Vapor Pressure 1.13E-13 mm Hg 25 EST
Henry's Law Constant 1.48E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.73E-11 cm3/molecule-sec 25 EST

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