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C1494

Sigma-Aldrich

Carmofur

≥98% (HPLC), powder

Synonyme(s) :

1-Hexylcarbamoyl-5-fluorouracil, HCFU

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About This Item

Formule empirique (notation de Hill) :
C11H16FN3O3
Numéro CAS:
61422-45-5
Poids moléculaire :
257.26
Numéro MDL:
MFCD00866284
Code UNSPSC :
12352200
ID de substance PubChem :
329774890
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >15 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

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 .

Actions biochimiques/physiologiques

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.
Carmofur is an antineoplastic agent and a flurorouracil analog.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H301,H361

Conseils de prudence

P201 - P301 + P310 + P330

Classification des risques

Acute Tox. 3 Oral - Repr. 2

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000235912
0000235912
0000151104
0000151104
0000148215

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Consulter la Bibliothèque de documents

Zhenming Jin et al.
Nature structural & molecular biology, 27(6), 529-532 (2020-05-10)
The antineoplastic drug carmofur is shown to inhibit the SARS-CoV-2 main protease (Mpro). Here, the X-ray crystal structure of Mpro in complex with carmofur reveals that the carbonyl reactive group of carmofur is covalently bound to catalytic Cys145, whereas its
P Osterlund et al.
British journal of cancer, 87(6), 591-599 (2002-09-19)
We studied longitudinally inflammatory reactions and serum C-reactive protein (S-CRP) levels in 52 colorectal cancer patients treated with a median of six 3-weekly cycles of raltitrexed 1.5-3.0 mg m(-2) combined with oral carmofur (1-hexylcarbomoyl-5-fluorouracil) 300-400 mg m(-2) on cycle days
Junichi Sakamoto et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 22(3), 484-492 (2004-01-31)
Adjuvant therapy of colorectal cancer with oral fluorinated pyrimidines is attractive because of its ease of administration and good tolerability. The purpose of this meta-analysis is to assess the survival and disease-free survival benefits of treating patients after surgical resection
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
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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