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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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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
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
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