Drug Information

General Information
Drug ID
DR00153
Drug Name
Fluorouracil
Synonyms
1-fluoro-1h-pyrimidine-2,4-dione; 2,4-Dihydroxy-5-fluoropyrimidine; 2,4-Dioxo-5-fluoropryimidine; 2,4-Dioxo-5-fluoropyrimidine; 5 FU Lederle; 5 FU medac; 5 Fluorouracil; 5 Fluorouracil biosyn; 5 HU Hexal; 5-FU; 5-FU (TN); 5-FU Lederle; 5-FU medac; 5-Faracil; 5-Fluor-2,4(1H,3H)-pyrimidindion; 5-Fluor-2,4(1H,3H)-pyrimidindion [Czech]; 5-Fluor-2,4-dihydroxypyrimidin; 5-Fluor-2,4-dihydroxypyrimidin [Czech]; 5-Fluor-2,4-pyrimidindiol; 5-Fluor-2,4-pyrimidindiol [Czech]; 5-Fluoracil; 5-Fluoracil [German]; 5-Fluoracyl; 5-Fluoro-2,4(1H,3H)-pyrimidinedione; 5-Fluoro-2,4-pyrimidinedione; 5-Fluoropyrimidin-2,4-diol; 5-Fluoropyrimidine-2,4-dione; 5-Fluorouracil; 5-Fluorouracil-biosyn; 5-Fluoruracil; 5-Fluoruracil [German]; 5-Ftouracyl; 5-HU Hexal; 5-fluoro uracil; 5-fluoro-1H-pyrimidine-2,4-dione; 5-fluoropyrimidine-2,4(1H,3H)-dione; 5FU; Adrucil; Adrucil (TN); Allergan Brand of Fluorouracil; Arumel; Biosyn Brand of Fluorouracil; CSP Brand of Fluorouracil; Carac; Carac (TN); Carzonal; Cinco FU; Dakota Brand of Fluorouracil; Dakota, Fluorouracile; Dermatech Brand of Fluorouracil; Dermik Brandof Fluorouracil; Effluderm; Effluderm (free base); Efudex; Efudex (TN); Efudix; Efurix; F 6627; F0151; Ferrer Brand of Fluorouracil; Fluoro Uracile ICN; Fluoro-Uracile ICN; Fluoro-uracile; Fluoro-uracilo; Fluoroblastin; Fluoroplex; Fluoroplex (TN); Fluorouracil (JP15/USP/INN); Fluorouracil GRY; Fluorouracil Mononitrate; Fluorouracil Monopotassium Salt; Fluorouracil Monosodium Salt; Fluorouracil Potassium Salt; Fluorouracil Teva Brand; Fluorouracil [USAN:INN:BAN:JAN]; Fluorouracil-GRY; Fluorouracile; Fluorouracile Dakota; Fluorouracile [DCIT]; Fluorouracilo; Fluorouracilo Ferrer Far; Fluorouracilo [INN-Spanish]; Fluorouracilum; Fluorouracilum [INN-Latin]; Fluoruracil; Fluracedyl; Fluracil; Fluracilum; Fluri; Fluril; Fluro Uracil; Fluroblastin; Flurodex; Ftoruracil; Gry Brand of Fluorouracil; Haemato Brand of Fluorouracil; Haemato fu; Haemato-fu; Hexal Brand of Fluorouracil; ICN Brand of Fluorouracil; IN1335; Inhibits thymilidate synthetase; Kecimeton; Medac Brand of Fluorouracil; Neocorp Brand of Fluorouracil; Neofluor; Onkofluor; Onkoworks Brand of Fluorouracil; Phthoruracil; Phtoruracil; Queroplex; Ribofluor; Ribosepharm Brand of Fluorouracil; Riemser Brand of Fluorouracil; Ro 2-9757; Ro-2-9757; Roche Brand of Fluorouracil; Tetratogen; Teva Brand of Fluorouracil; Timazin; U 8953; U-8953; URF; Ulup
Drug Type
Small molecular drug
Indication Colon cancer [ICD11:2B90.Z] Approved [1]
Esophageal cancer [ICD11:2B70] Approved [1]
Stomach cancer [ICD11:2B72] Approved [1]
Pancreatic cancer [ICD11:2C10] Approved [1]
Therapeutic Class
Immunosuppressive Agents
Structure
3D MOL 2D MOL
Formula
C4H3FN2O2
Canonical SMILES
C1=C(C(=O)NC(=O)N1)F
InChI
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey
GHASVSINZRGABV-UHFFFAOYSA-N
CAS Number
CAS 51-21-8
Pharmaceutical Properties Molecular Weight 130.08 Topological Polar Surface Area 58.2
Heavy Atom Count 9 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
XLogP
-0.9
PubChem CID
3385
PubChem SID
10524722 ,11111190 ,11335229 ,11360468 ,11363735 ,11366297 ,11368859 ,11371368 ,11374392 ,11377021 ,11406045 ,11461440 ,11484027 ,11487892 ,11490250 ,11492372 ,11494655 ,11538022 ,15218968 ,17389875 ,17405099 ,22391543 ,24276773 ,24278439 ,24871165 ,24894963 ,25346604 ,25621761 ,26611750 ,26679238 ,26697058 ,26747342 ,26747343 ,26747344 ,26752979 ,26758708 ,3139714 ,5132902 ,5367838 ,595836 ,603131 ,7847650 ,7891022 ,7978600 ,8139872 ,8149350 ,8152156 ,82653 ,841046 ,9851
ChEBI ID
ChEBI:46345
TTD Drug ID
D05LEO
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
ENT1 Transporter Info Equilibrative nucleoside transporter 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [5]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [5]
MRP5 Transporter Info Multidrug resistance-associated protein 5 Substrate [5]
OAT2 Transporter Info Organic anion transporter 2 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OAT2 Transporter Info Km =0.0538 microM Oocytes-OAT2 [6]
References
1 Fluorouracil was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10.
3 Human equilibrative nucleoside transporter 1, as a predictor of 5-fluorouracil resistance in human pancreatic cancer. Anticancer Res. 2007 Jul-Aug;27(4B):2241-9.
4 Enhancing chemosensitivity in oral squamous cell carcinoma by lentivirus vector-mediated RNA interference targeting EGFR and MRP2. Oncol Lett. 2016 Sep;12(3):2107-2114.
5 ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44.
6 Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8.
7 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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