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MedKoo Cat#: 100136 | Name: Carmofur
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Carmofur is a 5-fluorouracil (5-FU) derivative and prodrug with antitumor activity. It inhibits thymidylate synthase (TS) by releasing 5-FU intracellularly, disrupting DNA and RNA synthesis. Additionally, Carmofur inhibits acid ceramidase (AC) with an IC₅₀ of ~30 nM, leading to ceramide accumulation and apoptosis in cancer cells. It has demonstrated cytotoxicity against various cancer cell lines, including colorectal, breast, and glioblastoma, with IC₅₀ values in the low micromolar range. In vivo studies show significant tumor growth inhibition in xenograft models. Carmofur also exhibits anti-inflammatory properties and potential antiviral activity, including inhibition of SARS-CoV-2 main protease (Mpro) with an IC₅₀ of 1.82 µM.

Chemical Structure

Carmofur
Carmofur
CAS#61422-45-5

Theoretical Analysis

MedKoo Cat#: 100136

Name: Carmofur

CAS#: 61422-45-5

Chemical Formula: C11H16FN3O3

Exact Mass: 257.1176

Molecular Weight: 257.26

Elemental Analysis: C, 51.36; H, 6.27; F, 7.38; N, 16.33; O, 18.66

Price and Availability

Size Price Availability Quantity
200mg USD 250.00 2 Weeks
500mg USD 450.00 2 Weeks
1g USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
HCFU; 1hexylcarbamoyl5fluorouracil.
IUPAC/Chemical Name
5-fluoro-N-hexyl-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxamide
InChi Key
AOCCBINRVIKJHY-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(N(C(N1)=O)C=C(F)C1=O)NCCCCCC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Carmofur (INN) or HCFU (1-hexylcarbamoyl-5-fluorouracil) is a pyrimidine analogue used as an antineoplastic agent. It is a derivative of fluorouracil. 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.     

Preparing Stock Solutions

The following data is based on the product molecular weight 257.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Islam MM, Mirza SP. Versatile use of Carmofur: A comprehensive review of its chemistry and pharmacology. Drug Dev Res. 2022 Nov;83(7):1505-1518. doi: 10.1002/ddr.21984. Epub 2022 Aug 28. PMID: 36031762. 2: Du X, Peng Y, Zhao C, Xing J. Temperature/pH-responsive carmofur-loaded nanogels rapidly prepared via one-pot laser-induced emulsion polymerization. Colloids Surf B Biointerfaces. 2022 Sep;217:112611. doi: 10.1016/j.colsurfb.2022.112611. Epub 2022 Jun 6. PMID: 35679736. 3: Hemati N, Hadidi S, Shiri F, Farzaei MH. Structural modification of antineoplastic drug carmofur designed to the inhibition of SARS-CoV-2 main protease: A theoretical investigation. Results Chem. 2022 Jan;4:100259. doi: 10.1016/j.rechem.2021.100259. Epub 2021 Dec 9. PMID: 34904062; PMCID: PMC8656244. 4: Gessner EE, Shah MH, Ghent BN, Westbrook NE, van den Hurk P, Baldwin WS. The reproductive effects of the cancer chemotherapy agent, Carmofur, on Daphnia magna are mediated by its metabolite, 5-Fluorouracil. Ecotoxicology. 2022 Jul;31(5):860-872. doi: 10.1007/s10646-022-02551-5. Epub 2022 May 17. PMID: 35579761; PMCID: PMC9233140. 5: Kuzuhara S, Ohkoshi N, Kanemaru K, Hashimoto H, Nakanishi T, Toyokura Y. Subacute leucoencephalopathy induced by carmofur, a 5-fluorouracil derivative. J Neurol. 1987 Aug;234(6):365-70. doi: 10.1007/BF00314079. PMID: 3309192. 6: Suzuki T, Koizumi J, Uchida K, Shiraishi H, Hori M. Carmofur-induced organic mental disorders. Jpn J Psychiatry Neurol. 1990 Dec;44(4):723-7. doi: 10.1111/j.1440-1819.1990.tb01650.x. PMID: 2096243. 7: Islam MM, Kub EF, Rajaratnam V, Mirza SP. The development and validation of sensitive LC-MS/MS method for quantitative bioanalysis of carmofur in mouse plasma and its application to pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2022 Dec 1;1212:123516. doi: 10.1016/j.jchromb.2022.123516. Epub 2022 Oct 29. PMID: 36332509. 8: Shahabi M, Raissi H. A new insight into the transfer and delivery of anti- SARS-CoV-2 drug Carmofur with the assistance of graphene oxide quantum dot as a highly efficient nanovector toward COVID-19 by molecular dynamics simulation. RSC Adv. 2022 May 11;12(22):14167-14174. doi: 10.1039/d2ra01420c. PMID: 35558858; PMCID: PMC9092566. 9: Gröhn P, Heinonen E, Kumpulainen E, Länsimies H, Lantto A, Salmi R, Pyrhönen S, Numminen S. Oral carmofur in advanced gastrointestinal cancer. Am J Clin Oncol. 1990 Dec;13(6):477-9. doi: 10.1097/00000421-199012000-00005. PMID: 2239802. 10: Yamada T, Okamura S, Okazaki T, Ushiroyama T, Yanagawa Y, Ueki M, Sugimoto O, Yamazaki H, Sugino M, Masui Y. Leukoencephalopathy following treatment with carmofur: a case report and review of the Japanese literature. Asia Oceania J Obstet Gynaecol. 1989 Jun;15(2):161-8. doi: 10.1111/j.1447-0756.1989.tb00171.x. PMID: 2667512. 11: Matsumoto S, Nishizawa S, Murakami M, Noma S, Sano A, Kuroda Y. Carmofur- induced leukoencephalopathy: MRI. Neuroradiology. 1995 Nov;37(8):649-52. doi: 10.1007/BF00593382. PMID: 8748897. 12: Ma C, Hu Y, Townsend JA, Lagarias PI, Marty MT, Kolocouris A, Wang J. Ebselen, disulfiram, carmofur, PX-12, tideglusib, and shikonin are non-specific promiscuous SARS-CoV-2 main protease inhibitors. bioRxiv [Preprint]. 2020 Sep 16:2020.09.15.299164. doi: 10.1101/2020.09.15.299164. Update in: ACS Pharmacol Transl Sci. 2020 Oct 09;3(6):1265-1277. PMID: 32995786; PMCID: PMC7523112. 13: Ma C, Hu Y, Townsend JA, Lagarias PI, Marty MT, Kolocouris A, Wang J. Ebselen, Disulfiram, Carmofur, PX-12, Tideglusib, and Shikonin Are Nonspecific Promiscuous SARS-CoV-2 Main Protease Inhibitors. ACS Pharmacol Transl Sci. 2020 Oct 9;3(6):1265-1277. doi: 10.1021/acsptsci.0c00130. PMID: 33330841; PMCID: PMC7571300. 14: Dementiev A, Joachimiak A, Nguyen H, Gorelik A, Illes K, Shabani S, Gelsomino M, Ahn EE, Nagar B, Doan N. Molecular Mechanism of Inhibition of Acid Ceramidase by Carmofur. J Med Chem. 2019 Jan 24;62(2):987-992. doi: 10.1021/acs.jmedchem.8b01723. Epub 2018 Dec 19. PMID: 30525581; PMCID: PMC6863082. 15: Jin Z, Zhao Y, Sun Y, Zhang B, Wang H, Wu Y, Zhu Y, Zhu C, Hu T, Du X, Duan Y, Yu J, Yang X, Yang X, Yang K, Liu X, Guddat LW, Xiao G, Zhang L, Yang H, Rao Z. Structural basis for the inhibition of SARS-CoV-2 main protease by antineoplastic drug carmofur. Nat Struct Mol Biol. 2020 Jun;27(6):529-532. doi: 10.1038/s41594-020-0440-6. Epub 2020 May 7. PMID: 32382072. 16: Wu K, Xiu Y, Zhou P, Qiu Y, Li Y. A New Use for an Old Drug: Carmofur Attenuates Lipopolysaccharide (LPS)-Induced Acute Lung Injury via Inhibition of FAAH and NAAA Activities. Front Pharmacol. 2019 Jul 19;10:818. doi: 10.3389/fphar.2019.00818. PMID: 31379583; PMCID: PMC6659393. 17: Giudetti G, Polyakov I, Grigorenko BL, Faraji S, Nemukhin AV, Krylov AI. How Reproducible Are QM/MM Simulations? Lessons from Computational Studies of the Covalent Inhibition of the SARS-CoV-2 Main Protease by Carmofur. J Chem Theory Comput. 2022 Aug 9;18(8):5056-5067. doi: 10.1021/acs.jctc.2c00286. Epub 2022 Jul 7. PMID: 35797455. 18: Furuya A, Shiroyama H, Yano Y, Kishida S, Okeda R. [Report on an autopsy of a cancer patient with Carmofur (HCFU) leukoencephalopathy]. Rinsho Shinkeigaku. 1987 Nov;27(11):1430-40. Japanese. PMID: 3329075. 19: Fujikawa A, Tsuchiya K, Katase S, Kurosaki Y, Hachiya J. Diffusion-weighted MR imaging of Carmofur-induced leukoencephalopathy. Eur Radiol. 2001;11(12):2602-6. doi: 10.1007/s003300100955. Epub 2001 Jun 22. PMID: 11734966. 20: Ota K, Kishida S. [Drug-induced leukoencephalopathy]. Nihon Naika Gakkai Zasshi. 2007 Aug 10;96(8):1641-5. Japanese. doi: 10.2169/naika.96.1641. PMID: 17802714.