5-フルオロデオキシウリジン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/13 11:10:16」(JST)
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Floxuridine
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Systematic (IUPAC) name |
5-Fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
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Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a682006 |
Pregnancy
category |
|
Routes of
administration |
Intra-arterial |
Identifiers |
CAS Registry Number |
50-91-9 Y |
ATC code |
None |
PubChem |
CID: 5790 |
IUPHAR/BPS |
4801 |
DrugBank |
DB00322 Y |
ChemSpider |
5586 Y |
UNII |
039LU44I5M Y |
KEGG |
D04197 Y |
ChEBI |
CHEBI:60761 Y |
ChEMBL |
CHEMBL917 Y |
Chemical data |
Formula |
C9H11FN2O5 |
Molecular mass |
246.192 g/mol |
SMILES
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FC=1C(=O)NC(=O)N(C=1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
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InChI
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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 Y
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Key:ODKNJVUHOIMIIZ-RRKCRQDMSA-N Y
|
Y (what is this?) (verify) |
Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. The drug is most often used in the treatment of colorectal cancer.
Contents
- 1 Pharmacology
- 2 Mechanism of action
- 3 History
- 4 Suppliers
Pharmacology
Floxuridine, an analog of 5-fluorouracil, is a fluorinated pyrimidine.
Mechanism of action
Floxuridine works because it is broken down by the body into its active form, which is the same as a metabolite of 5-Fluorouracil.
History
Floxuridine first gained FDA approval in December 1970 under the brand name FUDR. The drug was initially marketed by Roche, which also did a lot of the initial work on 5-fluorouracil. The National Cancer Institute was an early developer of the drug. Roche sold its FUDR product line in 2001 to F H Faulding, which became Mayne Pharma.
Suppliers
In the US the drug is supplied by APP Pharmaceuticals, LLC; Hospira, Inc.; and Bedford Laboratories.
UpToDate Contents
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English Journal
- Hepatic Arterial Infusion in Combination with Modern Systemic Chemotherapy is Associated with Improved Survival Compared with Modern Systemic Chemotherapy Alone in Patients with Isolated Unresectable Colorectal Liver Metastases: A Case-Control Study.
- Dhir M1, Jones HL1, Shuai Y2, Clifford AK1, Perkins S1, Steve J1, Hogg ME1, Choudry MH1, Pingpank JF1, Holtzman MP1, Zeh HJ 3rd1, Bahary N3, Bartlett DL1, Zureikat AH4.
- Annals of surgical oncology.Ann Surg Oncol.2017 Jan;24(1):150-158. doi: 10.1245/s10434-016-5418-6. Epub 2016 Jul 18.
- BACKGROUND: In the era of effective modern systemic chemotherapy (CT), the role of hepatic arterial infusion of fluoxuridine (HAI-FUDR) in the treatment of isolated unresectable colorectal liver metastasis (IU-CRCLM) remains controversial. This study aimed to compare the overall survival (OS) of HAI
- PMID 27431415
- Glycogen Synthase Kinase 3 (GSK-3)-mediated Phosphorylation of Uracil N-Glycosylase 2 (UNG2) Facilitates the Repair of Floxuridine-induced DNA Lesions and Promotes Cell Survival.
- Baehr CA1, Huntoon CJ1,2, Hoang SM1, Jerde CR1, Karnitz LM3,2,4.
- The Journal of biological chemistry.J Biol Chem.2016 Dec 23;291(52):26875-26885. doi: 10.1074/jbc.M116.746081. Epub 2016 Nov 14.
- Uracil N-glycosylase 2 (UNG2), the nuclear isoform of UNG, catalyzes the removal of uracil or 5-fluorouracil lesions that accumulate in DNA following treatment with the anticancer agents 5-fluorouracil and 5-fluorodeoxyuridine (floxuridine), a 5-fluorouracil metabolite. By repairing these DNA lesion
- PMID 27875297
- Intra-arterial therapies for colorectal cancer liver metastases (radioembolization excluded).
- de Baere T1, Tselikas L2, Boige V2, Ducreux M2, Malka D2, Goéré D2, Benahim E2, Deschamps F2.
- Bulletin du cancer.Bull Cancer.2016 Dec 16. pii: S0007-4551(16)30350-2. doi: 10.1016/j.bulcan.2016.10.025. [Epub ahead of print]
- During the past 20 years, advances in systemic therapies have improved overall survival of patients with Colorectal cancer Liver metastases (CRLM) from 6 to 24 months. By reaching CRLM via their preferential arterial vascularization, hepatic arterial infusion of chemotherapy (HAIC) has demonstrate
- PMID 27993355
Japanese Journal
- 大腸癌肝転移に対する動注化学療法 (特集 大腸癌肝転移up to date) -- (非手術療法)
- Interaction of Intestinal Nucleoside Transporter hCNT2 with Amino Acid Ester Prodrugs of Floxuridine and 2-Bromo-5,6-dichloro-1-β-D-ribofuranosylbenzimidazole(Pharmacology)
- Shin Ho-Chul,Kim Jin-Suk,Vig Balvinder Singh [他],SONG Xueqin,DRACH John Charles,AMIDON Gordon Lewis
- Biological & pharmaceutical bulletin 29(2), 247-252, 2006-02-01
- … We studied the interaction of human concentrative nucleoside transporter (hCNT2) cloned from intestine with various amino acid ester prodrugs of floxuridine (FUdR) and 5,6-dichloro-2-bromo-1-β-D-ribofuranosylbenzimidazole (BDCRB). … FUdR significantly inhibited the uptake of both [^3H]-inosine and [^3H]-adenosine (60-70% of control), while its amino acid ester prodrugs including Val, Phe, Pro, Asp, and Lys esters exhibited markedly decreased inhibition potency (10-30% of control). …
- NAID 110005663953
- PS-190-3 FUDR(2'-deoxy-5-fluorouridine)腹腔内化学療法における急速投与と持続投与の比較
- 井上 健太郎,中根 恭司,佐藤 睦哉,中井 宏治,道浦 拓,田中 義人,神原 達也,山道 啓吾,上山 泰男
- 日本外科学会雑誌 105(臨時増刊), 632, 2004-03-15
- NAID 110003962709
Related Links
- Learn about FUDR Accomplishments Learn more >> LATEST NEWS/OUR BLOG Partners Partners of FUDR ...
- 国内未承認抗がん剤「フロクスウリジン(FUDR)」の 効果と副作用 海外承認時期 1970年 作用(効果)と特徴 フルオロウラシルのプロドラッグで、 体内にはいるとフルオロウラシルに変化して 抗腫瘍効果を発揮します。 アメリカでは ...
Related Pictures
★リンクテーブル★
[★]
- 英
- 5-fluorodeoxyuridine, FUdR
- 同
- フロクスウリジン floxuridine, 5-フルオロデオキシウリジン 5-fluoro-2′-deoxyuridine 5-FUdR
[★]
5-フルオロデオキシウリジン
[★]
- 関
- fluorouracil