Carmofur

Carmofur
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code L01BC04 (WHO)
Identifiers
Synonyms 1-hexylcarbamoyl-5-fluorouracil
CAS Number 61422-45-5 YesY
PubChem (CID) 2577
DrugBank DB09010 N
ChemSpider 2479 N
UNII HA82M3RAB2 N
ChEMBL CHEMBL460499 N
ECHA InfoCard 100.216.315
Chemical and physical data
Formula C11H16FN3O3
Molar mass 257.261 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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

  1. 1 2 3 4 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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