CAS 50-91-9|Floxuridine

Introduction：Basic information about CAS 50-91-9|Floxuridine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Floxuridine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles51
8. Synonyms

Common Name	Floxuridine
CAS Number	50-91-9	Molecular Weight	246.192
Density	1.8±0.1 g/cm3	Boiling Point	483.0±55.0 °C at 760 mmHg
Molecular Formula	C₉H₁₁FN₂O₅	Melting Point	148 °C(lit.)
MSDS	ChineseUSA	Flash Point	245.9±31.5 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	5-fluoro-2'-deoxyuridine
Synonym	More Synonyms

Floxuridine BiologicalActivity

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	Signaling Pathways >>Cell Cycle/DNA Damage >>Nucleoside Antimetabolite/AnalogResearch Areas >>Cancer
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.

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

Signaling Pathways >>Cell Cycle/DNA Damage >>Nucleoside Antimetabolite/AnalogResearch Areas >>Cancer

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.

Chemical & Physical Properties

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

Toxicological Information

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)

Safety Information

Symbol	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

Customs

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles51

Synthesis and Characterization of New 1,2,4-Triazolo[1,5-a]pyridines That Extend the Life Span of Caenorhabiditis elegans via Their Anti-Inflammatory/Antioxidant Effects.

Arch. Pharm. (Weinheim) 348 , 650-65, (2015)

In the present study, we describe the synthesis of a new set of 1,2,4-triazolo[1,5-a]pyridines and their fused ring systems. The products were assayed for various types of biological activities like a...

KCNQ channels in nociceptive cold-sensing trigeminal ganglion neurons as therapeutic targets for treating orofacial cold hyperalgesia.

Mol. Pain 11 , 45, (2015)

Hyperexcitability of nociceptive afferent fibers is an underlying mechanism of neuropathic pain and ion channels involved in neuronal excitability are potentially therapeutic targets. KCNQ channels, a...

Transcriptional expression of myelin basic protein in oligodendrocytes depends on functional syntaxin 4: a potential correlation with autocrine signaling.

Mol. Cell. Biol. 35(4) , 675-87, (2015)

Myelination of axons by oligodendrocytes is essential for saltatory nerve conduction. To form myelin membranes, a coordinated synthesis and subsequent polarized transport of myelin components are nece...

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

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