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MedKoo Cat#: 584247 | Name: Emitefur

Description:

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

Emitefur, also known as BOF-A2, is a 5-fluorouracil derivative antitumor drug.

Chemical Structure

Emitefur
Emitefur
CAS#110690-43-2

Theoretical Analysis

MedKoo Cat#: 584247

Name: Emitefur

CAS#: 110690-43-2

Chemical Formula: C28H19FN4O8

Exact Mass: 558.1187

Molecular Weight: 558.48

Elemental Analysis: C, 60.22; H, 3.43; F, 3.40; N, 10.03; O, 22.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Emitefur; BOF-A2; BOFA2; BOF A2
IUPAC/Chemical Name
Benzoic acid, 3-((3-(ethoxymethyl)-5-fluoro-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl)carbonyl)-, 6-(benzoyloxy)-3-cyano-2-pyridinyl ester
InChi Key
WTSKMKRYHATLLL-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H19FN4O8/c1-2-39-16-32-15-21(29)25(35)33(28(32)38)24(34)18-9-6-10-19(13-18)27(37)41-23-20(14-30)11-12-22(31-23)40-26(36)17-7-4-3-5-8-17/h3-13,15H,2,16H2,1H3
SMILES Code
O=C(OC1=NC(OC(C2=CC=CC=C2)=O)=CC=C1C#N)C3=CC=CC(C(N(C(N(COCC)C=C4F)=O)C4=O)=O)=C3
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
Shelf Life
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 558.48 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: Shibahara T, Kaneko E, Itoh T, Awogi T, Tsushimoto G, Takahashi N, Marshall RR, Kirkland DJ. Mutagenic and clastogenic properties of (3-[3-(6-benzoyloxy-3-cyano-2- pyridyloxycarbonyl) benzoyl]-1-ethoxymethyl-5-fluorouracil) (BOF-A2), a new 5-fluorouracil derivative with anti-tumour activity. J Toxicol Sci. 1993 Aug;18 Suppl 3:11-9. PubMed PMID: 8258847. 2: Sugimachi K, Maehara Y. A phase II trial of a new 5-fluorouracil derivative, BOF-A2 (Emitefur), for patients with advanced gastric cancer. Surg Today. 2000;30(12):1067-72. PubMed PMID: 11193737. 3: Shibamoto Y, Murata R, Miyauchi S, Hirohashi M, Takagi T, Sasai K, Shibata T, Oya N, Takahashi M. Combined effect of clinically relevant doses of emitefur, a new 5-fluorouracil derivative, and radiation in murine tumours. Br J Cancer. 1996 Dec;74(11):1709-13. PubMed PMID: 8956782; PubMed Central PMCID: PMC2077217. 4: Fujita F, Fujita M, Sakamoto Y, Taguchi T. [Antitumor activity of combination treatment of BOF-A2 with CDDP against human lung cancers xenografted in nude mice]. Gan To Kagaku Ryoho. 1993 Feb;20(2):215-21. Japanese. PubMed PMID: 8382036. 5: Miyauchi S, Imaoka T, Okada T, Motoyama M, Kawaguchi T, Akiyama H, Odomi M. Leukopenia-inducing effect of a combination of a new 5-fluorouracil (5-FU)-derived drug, BOF-A2 (emitefur), with other 5-FU-derived drugs or BV-araU (sorivudine) in rats. Jpn J Pharmacol. 1996 Feb;70(2):139-48. PubMed PMID: 8866751. 6: Miyauchi S, Imaoka T, Utsunomiya T, Hayashi K, Kubo M, Kawaguchi T, Matsui Y. Oral administration of BOF-A2 to rats with lung transplanted tumors results in increased 5-fluorouracil levels. Jpn J Cancer Res. 1994 Jun;85(6):665-8. PubMed PMID: 8063621. 7: Motoyama M, Imaoka T, Ichihara N, Miyauchi S. [Effect of BOF-A2 on experimental and spontaneous metastasis model of mouse colon 26]. Gan To Kagaku Ryoho. 1994 Jul;21(8):1209-14. Japanese. PubMed PMID: 8031163. 8: Shirasaka T, Fukushima M, Shimamoto Y, Kimura Y, Ohshimo H, Imaoka T, Kimura A, Utsunomiya T, Fujii S. [Metabolic characteristics and antitumor activity of BOF-A2, a new 5-fluorouracil derivative]. Gan To Kagaku Ryoho. 1990 May;17(5):1051-8. Japanese. PubMed PMID: 2334171. 9: Fujii S, Fukushima M, Shimamoto Y, Ohshimo H, Imaoka T, Shirasaka T. Antitumor activity of BOF-A2, a new 5-fluorouracil derivative. Jpn J Cancer Res. 1989 Feb;80(2):173-81. PubMed PMID: 2498252. 10: Yoneda K, Yamamoto T, Ueta E, Osaki T. The inhibitory action of BOF-A2, a 5-fluorouracil derivative, on squamous cell carcinoma. Cancer Lett. 1999 Mar 22;137(1):17-25. PubMed PMID: 10376790. 11: Murata R, Shibamoto Y, Miyauchi S, Hirohashi M, Takagi T, Sasai K, Oya N, Hiraoka M. The combined antitumour effect of a new 5-fluorouracil derivative, BOF-A2, and radiation in vivo. Br J Cancer Suppl. 1996 Jul;27:S114-6. PubMed PMID: 8763861; PubMed Central PMCID: PMC2150011. 12: Fujita F, Fujita M, Inaba H, Taguchi T. [Antitumor activity of BOF-A2, a new 5-fluorouracil derivative, against human cancers xenografted in nude mice by intermittent administration]. Gan To Kagaku Ryoho. 1993 Feb;20(2):223-8. Japanese. PubMed PMID: 8434959. 13: Fujita F, Fujita M, Fujita M, Sakamoto Y. [Combination chemotherapy of BOF-A2, a new 5-FU derivative, with various anticancer agents against human cancer xenografts in nude mice]. Gan To Kagaku Ryoho. 1994 Aug;21(10):1619-25. Japanese. PubMed PMID: 8060137. 14: Fujii S. [BOF-A1 and BOF-A2, new 5-FU degradation-inhibitory agents]. Gan To Kagaku Ryoho. 1987 Jul;14(7):2244-50. Japanese. PubMed PMID: 2955745. 15: Macdonald JS. Oral fluoropyrimidines: a closer look at their toxicities. Am J Clin Oncol. 1999 Oct;22(5):475-80. Review. PubMed PMID: 10521062. 16: Shirasaka T, Fujita F, Fujita M, Fukushima M, Taguchi T, Fujii S. [Antitumor activity and metabolism of BOF-A2, a new 5-fluorouracil derivative, with human cancers xenografted in nude mice]. Gan To Kagaku Ryoho. 1990 Sep;17(9):1871-6. Japanese. PubMed PMID: 2393305. 17: Sakata Y, Takemori H, Suzuki H. [Chemotherapy for pancreatic cancer]. Gan To Kagaku Ryoho. 1996 Oct;23(12):1647-50. Review. Japanese. PubMed PMID: 8886035. 18: Eng C, Kindler HL, Schilsky RL. Oral fluoropyrimidine treatment of colorectal cancer. Clin Colorectal Cancer. 2001 Aug;1(2):95-103. Review. PubMed PMID: 12445367. 19: Okayasu T, Sugiyama K, Miyauchi S. Inhibition of catabolic pathway of 5-fluorouracil by 3-cyano-2,6-dihydroxypyridine in human lung cancer tissues. Jpn J Cancer Res. 1994 Jan;85(1):101-5. PubMed PMID: 8106287. 20: Sasaki T. [New anti-cancer drugs for gastrointestinal cancers]. Gan To Kagaku Ryoho. 1997 Oct;24(13):1925-31. Review. Japanese. PubMed PMID: 9350237.