Carmofur Chemical Properties

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

CAS DataBase Reference

61422-45-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

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

MSDS

• Language:English Provider:Carmofur

Carmofur Usage And Synthesis

Description

Carmofur is an inhibitor of acid ceramidase (IC₅₀ = 79 nM for the rat enzyme) and a derivative of 5-flurouracil . It reduces acid ceramidase activity in a dose- and time-dependent manner and induces intracellular accumulation of various ceramide species, including C18 ceramide , C16 ceramide , and C14 ceramide 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

Uses

Carmofur has been used as an inhibitor of acid ceramidase to study its effects on glucosylsphingosine (GlcSph) production in human embryonic kidney 293T (HEK293T) cells. It has also been used as an inhibitor of acid ceramidase to study its effects on acid‐mediated hydrolysis of ceramide which kicks-in consumption and the generation of sphingosine .

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.

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