CAS 2968-28-7 5-Fluoro-2'-deoxyuridine (HCID 3363)

Overview

5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)-2-oxolanyl]pyrimidine-2,4-dione is a pyrimidine 2'-deoxyribonucleoside.

Names & identifiers

Preferred name: 5-Fluoro-2'-deoxyuridine
IUPAC: 5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
English name: Floxuridine
Molecular formula: C9H11FN2O5
Molecular weight: 246.19

Names & synonyms

5-Fluoro-2'-deoxyuridineDTXSID70274397RefChem:913372DTXCID402258765-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione2968-28-71397179-21-35-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dioneRo 5-0360(+)-5-fluoro-2'-deoxyuridineUridine, 2'-deoxy-5'-fluoro-

Show more names

FUDRFDUR5-FLUORODEOXYURIDINE5-FUDR5-Fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione5-FLUORO-2-DEOXYURIDINE2'-Deoxy-5-fluorouridineFUDFloxuridinfluorodeoxyuridine

floxuridine (fudr)2'-Deoxy-5-fluoro-uridinNeuro_000015CHEMBL6628NCIOpen2_002917SCHEMBL2050487SCHEMBL27146731CHEBI:94445

Database identifiers

CAS: 2968-28-7、50-91-9、955-24-8
PubChem CID: 3363
DTXSID: DTXSID70274397
ChEMBL: CHEMBL6628
ChEBI: CHEBI:94445

Properties

Computed structural properties

XLogP: -1.2
Topological polar surface area: 99.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 6
Rotatable bonds: 2
Heavy atoms: 17
Formal charge: 0
Complexity: 386

Physicochemical properties

Melting point: 148 °C · 148 °C(lit.)
Boiling point: 150 °C · 150 °C
alpha: 35.9 · 35.9 º (c=1, water)
Density: 1.3751 · 1.3751 (estimate)
storage temp.: room temp
solubility: 100 mM · Soluble to 100 mM in water and to 100 mM in DMSO
pka: 7.44 · pKa 7.44 (Uncertain)
form: Powder
color: White to almost white
biological source: synthetic (organic)
Water Solubility: soluble
Merck: 14 · 14,4112
BRN: 2645818 · 2645818
Stability: Stable. Incompatible with strong oxidizing agents.
Major Application: pharmaceutical small molecule
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-GFCOJPQKSA-N
SMILES: OC[C@H]1O[C@H](C[C@@H]1O)N2C=C(F)C(=O)NC2=O
CAS DataBase Reference: 50 · 50-91-9(CAS DataBase Reference)
NCI Dictionary of Cancer Terms: floxuridine
FDA UNII: 39 LU44I5M · 039LU44I5M
NCI Drug Dictionary: floxuridine
ATC code: 1 BC09 · L01BC09
NIST Chemistry Reference: 2 · Uridine, 2'-deoxy-5-fluoro-(50-91-9)
EPA Substance Registry System: Floxuridine (50-91-9)
UNSPSC Code: 41116107 · 41116107
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301
Precautionary statements: 264 · P264-P270-P301+P310-P405-P501
Hazard Codes: Xn,T,Xi
Risk Statements: 22 · 22-68-36/37/38-40-20/21/22
Safety Statements: 22 · 22-36-36/37/39-26
RIDADR: 2811 · UN 2811 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 7525000 · YU7525000
F: 10 · 10-23
Hazard Note: Toxic
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29349990 · 29349990
Storage Class: 6.1 D · 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications: 3 Oral · Acute Tox. 3 Oral
Hazardous Substances Data: 50 · 50-91-9(Hazardous Substances Data)
Toxicity: 50 oral · LD50 oral in rat: 215mg/kg

Safety & regulation

Safety data

F: 10-23
wgk: 3
rtecs: YU7525000
ridadr: UN 2811 6.1/PG 3
hs_code: 29349990
Toxicity: LD50 oral in rat: 215mg/kg
risk_code: 22-68-36/37/38-40-20/21/22
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: Xn,T,Xi
hazard_note: Toxic
safety_code: 22-36-36/37/39-26
hazard_class: 6.1
Storage Class: 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
packing_group: III
Hazard statements: H301
Hazard Classifications: Acute Tox. 3 Oral
Precautionary statements: P264-P270-P301+P310-P405-P501
Hazardous Substances Data: 50-91-9(Hazardous Substances Data)

Chemistry & industry

Applications · 6 items

DescriptionFloxuridine is a nucleoside analog that inhibits the enzyme ribonucleotide reductase, which is involved in the synthesis of DNA. Floxuridine has been shown to inhibit the growth of cancer cells and induce apoptosis in vivo. Floxuridine has also been shown to inhibit tumor growth in animal models by inhibiting the production of reactive oxygen species and upregulating tumor suppressor genes, such as p53. This drug also has inhibitory effects on enzymes that are involved in cell proliferation, such as protein kinase C and tyrosine kinases.

UsesFloxuridine USP is used in Palliative treatment of gastrointestinal adenocarcinoma with liver metastases.

UsesAntiviral; antineoplastic.

Usesrenal function diagnosis

General DescriptionThe drug is available as a 500-mg vial of lyophilized powder.The drug is used to treat metastatic GI adenocarcinoma.The mechanism of action of this fluoropyrimidine deoxynucleosideanalog involves metabolic conversion to 5-fluorouracil(5-FU) metabolites resulting in inhibition of TSthus disrupting DNA synthesis, function, and repair.Resistance can occur because of increased expression of TS,decreased levels of reduced folate 5,10-methylenetetrahydrofolate,increased activity of DNA repair enzymes, and increasedexpression of dihydropyrimidine dehydrogenase(the major catabolic enzyme). The drug is poorly absorbedfrom the GI tract and is extensive metabolized to 5-FU and5-FU metabolites. Dihydropyrimidine dehydrogenase is themain enzyme responsible for 5-FU catabolism, and it ispresent in liver, GI mucosa, white blood cells, and kidney.The drug interaction and toxicity profiles are equivalent tothose of 5-FU.

General DescriptionInhibits DNA synthesis.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

LGM Pharma1-(800)-881-8210 · [email protected]

Additional notes · 1 item

DefinitionChEBI: A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.