Carmofur

Carmofur
Clinical data
Other names	1-hexylcarbamoyl-5-fluorouracil
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	L01BC04 (WHO) ;
Identifiers
	IUPAC name 5-fluoro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide;
CAS Number	61422-45-5 ;
PubChem CID	2577;
DrugBank	DB09010 ;
ChemSpider	2479 ;
UNII	HA82M3RAB2;
ChEMBL	ChEMBL460499 ;
CompTox Dashboard (EPA)	DTXSID2045941 ;
ECHA InfoCard	100.216.315
Chemical and physical data
Formula	C11H16FN3O3
Molar mass	257.261 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCNC(=O)N1C=C(C(=O)NC1=O)F;
	InChI 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) ; Key:AOCCBINRVIKJHY-UHFFFAOYSA-N ;
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Carmofur (INN) or HCFU (1-hexylcarbamoyl-5-fluorouracil) is a pyrimidine analogue used as an antineoplastic agent. It is a derivative of fluorouracil.

Mechanism of action

The mechanism of action of carmofur is traditionally thought to be the generation of 5–FU.^[1] However, carmofur is a highly potent acid ceramidase (AC) inhibitor.^[1] Ceramide influences cancer cell survival, growth and death.^[1] Inhibition of AC activity sensitizes tumor cells to the effects of antineoplastic agents and radiation.^[1]

Uses

Carmofur, in its oral form, has also been used as adjuvant chemotherapy for curatively resected colorectal cancer patients. Trials and meta-analyses have confirmed that the drug is effective on patients with this cancer type, extending their survival.^[2]

Adverse effects

As fluorouracil, carmofur has been known to induce leukoencephalopathy.^[3]^[4]^[5]

References

^ ^a ^b ^c ^d Realini, Natalia; Solorzano, Carlos; Pagliuca, Chiara; Pizzirani, Daniela; Armirotti, Andrea; Luciani, Rosaria; Paola Costi, Maria; Bandiera, Tiziano; Piomelli, Daniele (8 January 2013). "Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity". Scientific Reports. 3 (1035). doi:10.1038/srep01035.
^ Sakamoto, J; Hamada, C; Rahman, M; Kodaira, S; Ito, K; Nakazato, H; Ohashi, Y; Yasutomi, M (2005). "An Individual Patient Data Meta-analysis of Adjuvant Therapy with Carmofur in Patients with Curatively Resected Colon Cancer". Japanese Journal of Clinical Oncology. 35 (9): 536–544. doi:10.1093/jjco/hyi147. PMID 16155120.
^ Yamada T, Okamura S, Okazaki T, et al. (June 1989). "Leukoencephalopathy following treatment with carmofur: a case report and review of the Japanese literature". Asia Oceania J Obstet Gynaecol. 15 (2): 161–8. PMID 2667512.
^ Mizutani T (February 2008). "[Leukoencephalopathy caused by antineoplastic drugs]". Brain Nerve (in Japanese). 60 (2): 137–41. PMID 18306661.
^ Baehring JM, Fulbright RK (May 2008). "Delayed leukoencephalopathy with stroke-like presentation in chemotherapy recipients". J Neurol Neurosurg Psychiatr. 79 (5): 535–9. doi:10.1136/jnnp.2007.123737. PMID 17682013.

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[Realini2013-1] Realini, Natalia; Solorzano, Carlos; Pagliuca, Chiara; Pizzirani, Daniela; Armirotti, Andrea; Luciani, Rosaria; Paola Costi, Maria; Bandiera, Tiziano; Piomelli, Daniele (8 January 2013). "Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity". Scientific Reports. 3 (1035). doi:10.1038/srep01035.

[2] Sakamoto, J; Hamada, C; Rahman, M; Kodaira, S; Ito, K; Nakazato, H; Ohashi, Y; Yasutomi, M (2005). "An Individual Patient Data Meta-analysis of Adjuvant Therapy with Carmofur in Patients with Curatively Resected Colon Cancer". Japanese Journal of Clinical Oncology. 35 (9): 536–544. doi:10.1093/jjco/hyi147. PMID 16155120.

[3] Yamada T, Okamura S, Okazaki T, et al. (June 1989). "Leukoencephalopathy following treatment with carmofur: a case report and review of the Japanese literature". Asia Oceania J Obstet Gynaecol. 15 (2): 161–8. PMID 2667512.

[4] Mizutani T (February 2008). "[Leukoencephalopathy caused by antineoplastic drugs]". Brain Nerve (in Japanese). 60 (2): 137–41. PMID 18306661.

[5] Baehring JM, Fulbright RK (May 2008). "Delayed leukoencephalopathy with stroke-like presentation in chemotherapy recipients". J Neurol Neurosurg Psychiatr. 79 (5): 535–9. doi:10.1136/jnnp.2007.123737. PMID 17682013.

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