U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11FN2O5
Molecular Weight 246.1924
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXIFLURIDINE

SMILES

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

InChI

InChIKey=ZWAOHEXOSAUJHY-ZIYNGMLESA-N
InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1

HIDE SMILES / InChI

Molecular Formula C9H11FN2O5
Molecular Weight 246.1924
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Doxifluridine is a 5-fluorouracil prodrug that is being tested for the treatment of cancer. The cleavage into 5-fluorouracil occurs enzymatically via a nucleoside phosphorylase. Thus, doxifluridine is not active by itself and its antitumor activity is related to its metabolic conversion into 5-fluorouracil. Doxifluridine has neurotoxic adverse effects.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Neurological manifestations in a phase 2 study of 13 patients treated with doxyfluridine.
1985 Aug
[Enhancement effect of interferon gamma on the sensitivity of RT4 bladder cancer cells to 5'-deoxy-5-fluorouridine,and 5-fluorouracil through up-regulation of PD-ECGF/TP].
2004 Aug
Doxifluridine-induced neurotoxicity with normal dihydropyrimidine dehydrogenase activity.
2004 Jun 8
Modulation of uridine phosphorylase gene expression by tumor necrosis factor-alpha enhances the antiproliferative activity of the capecitabine intermediate 5'-deoxy-5-fluorouridine in breast cancer cells.
2006 Apr
[Interferon alpha enhances the sensitivity of SMMC-7721 hepatocellular carcinoma cells to 5'-deoxy-5-fluorouridine related to up-regulation of thymidine phosphorylase].
2007 Aug 14
Patents

Sample Use Guides

460-600mg/m2/day per oral (Gastric cancer)
Route of Administration: Oral
In Vitro Use Guide
The cytotoxicity of Doxifluridine was determined in several cultured human tumor lines including tumors of the breast (47-DN, MCF-7), the colon (HCT-8), and the pancreas (Coto-357), as well as an osteosarcoma (MG-63) and a leukemia (HL-60). In vitro clonogenic assays were used to measure cytotoxicity following a 3hr drug exposure. Doxifluridine was less potent than was 5-fluorouracil or 5-fluoro-2'-deoxyuridine in all cells examined, exhibiting its best activity against the 47-DN [concentration that prevented 50% clonal growth compared to untreated control (LD50) = 32 uM] and MCF-7 (LD50= 35 uM) breast carcinomas and MG63 osteosarcoma (LD50 = 41 uM). Intermediate activity was observed against HCT-8 (LD50 = 200 uM)and Colo-357 (LD50 = 150 uM) gastrointestinal tumors. Doxifluridine had very poor activity against the HL-60 leukemia (LD50 = 470 uM).
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:21:33 UTC 2023
Edited
by admin
on Wed Jul 05 23:21:33 UTC 2023
Record UNII
V1JK16Y2JP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXIFLURIDINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
5'-DEOXY-5-FLUOROURIDINE
Systematic Name English
URIDINE, 5'-DEOXY-5-FLUORO-
Systematic Name English
NSC-758890
Code English
5-FLUORO-5'-DEOXYURIDINE
Systematic Name English
DOXIFLURIDINE [MART.]
Common Name English
RO 219738
Code English
Doxifluridine [WHO-DD]
Common Name English
CAPECITABINE RELATED COMPOUND B [USP-RS]
Common Name English
1-(.BETA.-D-5-DESOXYRIBOFURANOXYL)-5-FLUORURACIL
Common Name English
FURTULON
Brand Name English
FULTURON
Common Name English
doxifluridine [INN]
Common Name English
CAPECITABINE RELATED COMPOUND B [USP IMPURITY]
Common Name English
DOXIFLURIDINE [JAN]
Common Name English
DOXIFLURIDINE [MI]
Common Name English
FLUTRON
Common Name English
RO-219738
Code English
CAPECITABINE RELATED COMPOUND B
USP   USP-RS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
Code System Code Type Description
DRUG BANK
DB12947
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
WIKIPEDIA
Doxifluridine
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
NSC
758890
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID2022967
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
EVMPD
SUB06389MIG
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
INN
4913
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
MESH
C025034
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
NCI_THESAURUS
C978
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
RS_ITEM_NUM
1090728
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
MERCK INDEX
M4755
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY Merck Index
CAS
3094-09-5
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
PUBCHEM
18343
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
221-440-1
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
FDA UNII
V1JK16Y2JP
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1130
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
CHEBI
31521
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
DRUG CENTRAL
958
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
SMS_ID
100000080814
Created by admin on Wed Jul 05 23:21:33 UTC 2023 , Edited by admin on Wed Jul 05 23:21:33 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY