| Identification | More | [Name]
Carmofur | [CAS]
61422-45-5 | [Synonyms]
1-(N-HEXYLCARBAMOYL)-5-FLUOROURACIL
5-FLUORO-1-HEXYLCARBAMOYLURACIL
CARMOFUR
HCFUTM
1,2,3,4-tetrahydro-2,4-dioxo-5-fluoro-n-hexyl-1-pyrimidinecarboxamid
1-hexylcarbamoyl-5-fluorouracil
2,4-dioxo-5-fluoro-n-hexyl-1,2,3,4-tetrahydro-1-pyrimidinecarboxamide
2,4-dioxo-5-fluoro-n-hexyl-3,4-dihydro-1(2h)-pyrimidinecarboxamidme
3,4-dihydro-2,4-dioxo-5-fluoro-n-hexyl-1(2h)-pyrimidinecarboxamid
hcfu
1(2H)-Pyrimidinecarboxamide, 3,4-dihydro-2,4-dioxo-5-fluoro-N-hexyl
1-(Hexylcarbamyl)-5-fluorouracil
5-Fluoro-N-hexyl-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinecarboxamide
Mifurol | [EINECS(EC#)]
689-431-9 | [Molecular Formula]
C11H16FN3O3 | [MDL Number]
MFCD00866284 | [Molecular Weight]
257.26 | [MOL File]
61422-45-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
110-111 | [density ]
1.2287 (estimate) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >15mg/mL | [form ]
powder | [pka]
6.94±0.10(Predicted) | [color ]
white to off-white | [Merck ]
14,1844 | [InChI]
1S/C11H16FN3O3/c1-2-3-4-5-6-13-10(17)15-7-8(12)9(16)14-11(15)18/h7H,2-6H2,1H3,(H,13,17)(H,14,16,18) | [InChIKey]
AOCCBINRVIKJHY-UHFFFAOYSA-N | [SMILES]
CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O | [CAS DataBase Reference]
61422-45-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
60-61-25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGII | [WGK Germany ]
3 | [RTECS ]
UV7714000 | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29335990 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 3 Oral
Repr. 2 |
| Hazard Information | Back Directory | [Description]
Carmofur is an inhibitor of acid ceramidase (IC50 = 79 nM for the rat enzyme) and a derivative of 5-flurouracil (Item No. 14416).1 It reduces acid ceramidase activity in a dose- and time-dependent manner and induces intracellular accumulation of various ceramide species, including C18 ceramide (Item No. 19556), C16 ceramide (Item No. 24426), and C14 ceramide (Item No. 22531) in SW403 colon and LNCaP prostate cancer cells. Carmofur induces apoptosis in SW403 cells without inhibiting DNA synthesis (IC50 = 1,212 mM for human thymidylate synthetase). It also reduces acid ceramidase activity and increases ceramide accumulation in mouse lung and brain when administered at doses of 10 and 30 mg/kg. | [Originator]
Mifurol,Mitsui,Japan,1981 | [Uses]
antineoplastic | [Definition]
ChEBI: Carmofur is an organohalogen compound and a member of pyrimidines. | [Manufacturing Process]
13.0 g (0.10 mol) of 5-fluorouracil was suspended in 60 ml of dimethyl
acetamide, then 14.0 g (0.11 mol) of n-hexyl isocyanate was added thereto at
room temperature and stirred at 50°C for 8 hours. After the reaction mixture
was concentrated under reduced pressure, the residue was poured into 400 ml
of water and resultant precipitate was filtered off. The precipitate was washed
and dried and 19.3 g (75.0% yield) of 5-fluoro-1-(n-hexylcarbamoyl)uracil
was obtained.
The product was recrystallized from ether and there were obtained white
crystals melting at 283°C (decomposition). | [Therapeutic Function]
Antineoplastic | [Biochem/physiol Actions]
Carmofur is a derivative of fluorouracil, an antimetabolite used as an antineoplastic agent. | [References]
[1] NATALIA REALINI. Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity.[J]. Scientific Reports, 2013: 1035. DOI: 10.1038/srep01035 |
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