Carmofur

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Carmofur

Systematic (IUPAC) name
5-fluoro-N-hexyl-2,4-dioxo-pyrimidine-1-carboxamide
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Routes	Oral
Identifiers
CAS number	61422-45-5^Y
ATC code	L01BC04
PubChem	CID 2577
ChemSpider	2479^N
UNII	HA82M3RAB2^N
Synonyms	1-hexylcarbamoyl-5-fluorouracil
Chemical data
Formula	C₁₁H₁₆F N₃O₃
Mol. mass	257.261 g/mol
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)^N Key:AOCCBINRVIKJHY-UHFFFAOYSA-N^N
N (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

Uses

Breast Cancer

Colorectal Cancer

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.^[1]

Adverse effects

As fluorouracil, carmofur has been known to induce leukoencephalopathy.^[2]^[3]^[4]

References

↑ 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.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vinflunine^§ Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine^#) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin Topotecan Irinotecan Rubitecan^‡ Belotecan)

II	Podophyllum (Etoposide^# Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin^# Doxorubicin^# Epirubicin Idarubicin Amrubicin^† Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide^# (Ifosfamide Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Platinum-based	Carboplatin Cisplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Photosensitizers/PDT

Aminolevulinic acid / Methyl aminolevulinate
Efaproxiral
Porphyrin derivatives (Porfimer sodium
Talaporfin
Temoporfin
Verteporfin)

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Alvocidib^† Seliciclib^†) PrI (Bortezomib Carfilzomib) PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib^§) HDAC (Panobinostat Vorinostat Romidepsin)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Celecoxib Demecolcine Elesclomol^§ Elsamitrucin Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

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