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Key Documents

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C1494

Sigma-Aldrich

Carmofur

≥98% (HPLC), powder

Sinónimos:

1-Hexylcarbamoyl-5-fluorouracil, HCFU

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About This Item

Fórmula empírica (notación de Hill):
C11H16FN3O3
Número de CAS:
61422-45-5
Peso molecular:
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

signalword

Danger

hcodes

H301,H361

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Structural basis for the inhibition of SARS-CoV-2 main protease by antineoplastic drug carmofur
Jin Z, et al.
Nature Structural and Molecular Biology, 27(6), 529-532 (2020)
Nelson S Torres et al.
Antimicrobial agents and chemotherapy, 60(10), 5663-5672 (2016-07-13)
It is now well established that bacterial infections are often associated with biofilm phenotypes that demonstrate increased resistance to common antimicrobials. Further, due to the collective attrition of new antibiotic development programs by the pharmaceutical industries, drug repurposing is an
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)
S Kuzuhara et al.
Journal of neurology, 234(6), 365-370 (1987-08-01)
Three cases of leucoencephalopathy induced by carmofur (1-hexylcarbamoyl-5-fluorouracil), an antineoplastic derivative of 5-fluorouracil are reported and the literature is reviewed. Initial symptoms were unsteady gait and dementia developing several weeks or months after carmofur had been started. Symptoms increased gradually
Lysosomal glycosphingolipid catabolism by acid ceramidase: formation of glycosphingoid bases during deficiency of glycosidases
Ferraz M J, et al.
Febs Letters, 590(6), 716-725 (2016)
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