Carmofur

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Chemical compound

title: "Carmofur" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["pyrimidinediones", "organofluorides", "pyrimidine-antagonists", "fluoropyrimidines", "sars-cov-2-main-protease-inhibitors"] description: "Chemical compound" topic_path: "general/pyrimidinediones" source: "https://en.wikipedia.org/wiki/Carmofur" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::data[format=table title="Infobox drug"]

Field	Value
Verifiedfields	changed
verifiedrevid	388677486
IUPAC_name	5-fluoro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
image	Carmofur.svg
image_class	skin-invert-image
Drugs.com
routes_of_administration	Oral
CAS_number_Ref
CAS_number	61422-45-5
ATC_prefix	L01
ATC_suffix	BC04
PubChem	2577
ChEMBL_Ref
ChEMBL	460499
DrugBank_Ref
DrugBank	DB09010
UNII_Ref
UNII	HA82M3RAB2
ChemSpiderID_Ref
ChemSpiderID	2479
StdInChI_Ref
StdInChI	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)
StdInChIKey_Ref
StdInChIKey	AOCCBINRVIKJHY-UHFFFAOYSA-N
C	11
smiles	CCCCCCNC(=O)N1C=C(C(=O)NC1=O)F
synonyms	1-hexylcarbamoyl-5-fluorouracil, HCFU, N-hexylcarbamoyl-5-fluorouracil, Yamaful, NCGC00095165-01, Hexylcarbamoyl fluorouracil, 61422-45-5, UNII-HA82M3RAB2, CCRIS 2759, C11H16FN3O3, Uracil, 5-fluoro-1-hexylcarbamoyl-, BRN 0888898, HA82M3RAB2, 1(2H)-Pyrimidinecarboxamide, 5-fluoro-N-hexyl-3,4,
::

| tradename = | Drugs.com = | pregnancy_US = | routes_of_administration = Oral

| C=11 | H=16 | F=1 | N=3 | O=3 | smiles = CCCCCCNC(=O)N1C=C(C(=O)NC1=O)F | synonyms = 1-hexylcarbamoyl-5-fluorouracil, HCFU, N-hexylcarbamoyl-5-fluorouracil, Yamaful, NCGC00095165-01, Hexylcarbamoyl fluorouracil, 61422-45-5, UNII-HA82M3RAB2, CCRIS 2759, C11H16FN3O3, Uracil, 5-fluoro-1-hexylcarbamoyl-, BRN 0888898, HA82M3RAB2, 1(2H)-Pyrimidinecarboxamide, 5-fluoro-N-hexyl-3,4,

Carmofur (INN) or HCFU (1-hexylcarbamoyl-5-fluorouracil) is a pyrimidine analogue used as an antineoplastic agent. It is a derivative of fluorouracil, being a lipophilic-masked analog of 5-FU that can be administered orally.

Biology

Carmofur prodrug is ingested and taken up in the intestine, overcoming the problem of 5-FU degradation by dihydropyrimidine dehydrogenase. Once inside a cell, the carmofur prodrug is converted into 5-FU.

Mechanism of action

The mechanism of action of carmofur prodrug is traditionally thought to be the generation of 5–FU. Carmofur, much more effective than temozolomide, has been reported as the small-molecule drug capable of killing adult and pediatric glioblastomas.

Medicinal uses

Product marketing for carmofur started in 1981. Carmofur has also been used as adjuvant chemotherapy for curatively resected colorectal cancer patients in China, Japan, and Finland for many years. Trials and meta-analyses have confirmed that the drug is effective on patients with this cancer type, extending their survival.

Carmofur has been shown to inhibit the SARS-CoV-2 main protease, and is therefore a promising lead compound to develop new antiviral treatment for COVID-19.

Adverse effects

As fluorouracil, carmofur has been known to induce leukoencephalopathy, characterized by progressive damage to white matter in the brain with stroke-like symptoms.

A clinical trial for small hepatocellular carcinoma was stopped prematurely because 56% of the treated patients had unacceptable side effects. Moreover, the treatment had no survival advantage for stage 1 and 2 cancer patients. This may be a reason why carmofur was never pursued for FDA-approval in the US.

Chemical synthesis

Ozaki et al. have reported a synthesis by treating 5-FU with phosgene and hexylamine. Xiong et al. reported an alternative approach for the synthesis of carmofur . Chemical preparations and structures can be found here.

References

(December 2016). "Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs". Chemical Reviews.
(Jan 2013). "Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity". Scientific Reports.
(April 2017). "Acid ceramidase is a novel drug target for pediatric brain tumors". Oncotarget.
(December 2017). "Acid ceramidase and its inhibitors: a ''de novo'' drug target and a new class of drugs for killing glioblastoma cancer stem cells with high efficiency". Oncotarget.
(October 2006). "Efficacy of oral anticancer agents for colorectal cancer". Diseases of the Colon and Rectum.
(September 2005). "An individual patient data meta-analysis of adjuvant therapy with carmofur in patients with curatively resected colon cancer". Japanese Journal of Clinical Oncology.
(June 2020). "Structural basis for the inhibition of SARS-CoV-2 main protease by antineoplastic drug carmofur". Nature Structural & Molecular Biology.
(June 1989). "Leukoencephalopathy following treatment with carmofur: a case report and review of the Japanese literature". Asia-Oceania Journal of Obstetrics and Gynaecology.
(February 2008). "[Leukoencephalopathy caused by antineoplastic drugs]". Brain and Nerve = Shinkei Kenkyu No Shinpo.
(May 2008). "Delayed leukoencephalopathy with stroke-like presentation in chemotherapy recipients". Journal of Neurology, Neurosurgery, and Psychiatry.
(March 1996). "Adjuvant oral chemotherapy to prevent recurrence after curative resection for hepatocellular carcinoma". The British Journal of Surgery.
(1987). "Synthesis and antitumor activity of 1- or 3-(alpha-hetero substituted)alkyl-5-fluorouracil derivatives". Nucleic Acids Symposium Series.

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