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C1494

Sigma-Aldrich

Carmofur

≥98% (HPLC), powder

Synonym(s):

1-Hexylcarbamoyl-5-fluorouracil, HCFU

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About This Item

Empirical Formula (Hill Notation):
C11H16FN3O3
CAS Number:
61422-45-5
Molecular Weight:
257.26
MDL number:
MFCD00866284
UNSPSC Code:
12352200
PubChem Substance ID:
329774890
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >15 mg/mL

storage temp.

2-8°C

SMILES string

CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O

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)

InChI key

AOCCBINRVIKJHY-UHFFFAOYSA-N

Application

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 .

Biochem/physiol Actions

Carmofur acts as an inhibitor of fatty acid amide hydrolase (FAAH), N-acylethanolamine acid amidase (NAAA) and acid ceramidase (ASAH1). Carmofur has a therapeutic activity against colorectal and cervical cancer. It can inhibit the severe acute respiratory syndrome (SARS)-CoV-2 main protease (Mpro) in vitro.
Carmofur is a derivative of fluorouracil, an antimetabolite used as an antineoplastic agent.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H361

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Kenjiro Kotake et al.
Oncology reports, 14(1), 129-134 (2005-06-10)
To verify the effectiveness of oral 1-hexylcarbamoyl-5-fluorouracil (HCFU) in improving the surgical cure rate in advanced colorectal cancer, a multicenter randomized comparative study was conducted. A total of 429 patients who had had curative resection for stage II and III
Natalia Realini et al.
Scientific reports, 3, 1035-1035 (2013-01-10)
The expression of acid ceramidase (AC) - a cysteine amidase that hydrolyses the proapoptotic lipid ceramide - is abnormally high in several human tumors, which is suggestive of a role in chemoresistance. Available AC inhibitors lack, however, the potency and
Sheetal Soni et al.
Journal of drug targeting, 14(2), 87-95 (2006-04-13)
Random copolymeric micelles composed of N-isopropylacrylamide (NIPAAM) and N-vinylpyrrolidone (VP) cross-linked with N,N'-methylenebisacrylamide (MBA) have been used as nanogel carriers to encapsulate N-hexylcarbamoyl-5-fluorouracil (HCFU), a prodrug of 5-FU, and have been targeted to brain tissue across blood-brain barrier (BBB) after
Jaeyong Lee et al.
Nature communications, 11(1), 5877-5877 (2020-11-20)
Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2), the pathogen that causes the disease COVID-19, produces replicase polyproteins 1a and 1ab that contain, respectively, 11 or 16 nonstructural proteins (nsp). Nsp5 is the main protease (Mpro) responsible for cleavage at eleven
A new use for an old drug: carmofur attenuates lipopolysaccharides (LPS) induced acute lung injury via inhibition of FAAH and NAAA activities
Li Y, et al.
Frontiers in Pharmacology, 10(6), 818-818 (2019)
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