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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Antimetabolites
- Antimetabolites, Antineoplastic
- Antineoplastic
- Antineoplastic Agents
- Antiviral
- Antiviral (COVID-19)
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Noxae
- Reproductive Effect
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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/s1InChIKey
ODKNJVUHOIMIIZ-RRKCRQDMSA-NSmiles
OC[C@H]1O[C@H](C[C@@H]1O)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.