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MedKoo Cat#: 329202 | Name: Cefatrizine

Description:

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

Cefatrizine, also known as BL-S-640 and S-640P, is a eukaryotic elongation factor-2 kinase inhibitor with an anti-proliferative activity toward breast cancer cells. Eukaryotic elongation factor-2 kinase, a unique calcium/calmodulin-dependent protein kinase, is well known to regulate apoptosis, autophagy and ER stress in many types of human cancers.

Chemical Structure

Cefatrizine
Cefatrizine
CAS#51627-14-6

Theoretical Analysis

MedKoo Cat#: 329202

Name: Cefatrizine

CAS#: 51627-14-6

Chemical Formula: C18H18N6O5S2

Exact Mass: 462.0780

Molecular Weight: 462.50

Elemental Analysis: C, 46.75; H, 3.92; N, 18.17; O, 17.30; S, 13.86

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Synonym
Cefatrizine; BL-S-640; BL S 640; BLS640; Cephatriazine; S 640P; S-640P; S640P
IUPAC/Chemical Name
(6R,7R)-3-(((1H-1,2,3-triazol-4-yl)thio)methyl)-7-(2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
UOCJDOLVGGIYIQ-QQGYXAEISA-N
InChi Code
InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12?,13-,17-/m1/s1
SMILES Code
O=C(C(N12)=C(CSC3=CNN=N3)CS[C@]2([H])[C@H](NC(C(N)C4=CC=C(O)C=C4)=O)C1=O)O
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 462.50 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: Pan J, Wang L, Li D, Ye L. [Synthesis of cefatrizine by recombinant alpha-amino acid ester hydrolase]. Sheng Wu Gong Cheng Xue Bao. 2013 Apr;29(4):501-9. Chinese. PubMed PMID: 23894823. 2: Papantoniou N, Ismailos G, Daskalakis G, Karabinas C, Mesogitis S, Papapanagiotou A, Antsaklis A. Pharmacokinetics of oral cefatrizine in pregnant and non-pregnant women with reference to fetal distribution. Fetal Diagn Ther. 2007;22(2):100-6. PubMed PMID: 17135753. 3: Choi HG, Jun HW, Kim DD, Sah H, Yoo BK, Yong CS. Simultaneous determination of cefatrizine and clavulanic acid in dog plasma by HPLC. J Pharm Biomed Anal. 2004 Apr 1;35(1):221-31. PubMed PMID: 15030898. 4: Sultana N, Arayne MS. In vitro activity of cefadroxil, cephalexin, cefatrizine and cefpirome in presence of essential and trace elements. Pak J Pharm Sci. 2007 Oct;20(4):305-10. PubMed PMID: 17604254. 5: Yao Z, Li J, Liu Z, Zheng L, Fan N, Zhang Y, Jia N, Lv J, Liu N, Zhu X, Du J, Lv C, Xie F, Liu Y, Wang X, Fei Z, Gao C. Integrative bioinformatics and proteomics-based discovery of an eEF2K inhibitor (cefatrizine) with ER stress modulation in breast cancer cells. Mol Biosyst. 2016 Mar;12(3):729-36. doi: 10.1039/c5mb00848d. PubMed PMID: 26776155. 6: Matsuda K, Yuasa H, Watanabe J. Dose dependency in the gastrointestinal absorption of cefatrizine: correlation between in vivo and in situ. Biol Pharm Bull. 1998 Jun;21(6):604-9. PubMed PMID: 9657046. 7: Yu LX, Amidon GL. Saturable small intestinal drug absorption in humans: modeling and interpretation of cefatrizine data. Eur J Pharm Biopharm. 1998 Mar;45(2):199-203. PubMed PMID: 9704917. 8: Brambilla C, Benhamou D, Guérin JC, Kelkel E, Muir JF, Prud'homme A, Taytard A, Fauche A. [Comparative trial of the clinical efficacy and tolerance of cefatrizine (Cefaperos) and cefpodoxime proxetil (Orelox) in superinfections of chronic obstructive bronchopneumopathies in adults in urban practice]. Pathol Biol (Paris). 1995 Nov;43(9):815-24. French. PubMed PMID: 8746104. 9: Couet W, Fauvel JP, Laville M, Pozet N, Fourtillan JB. Pharmacokinetics of oral cefatrizine in patients with impaired renal function. Int J Clin Pharmacol Ther Toxicol. 1991 Jun;29(6):213-7. PubMed PMID: 1869342. 10: Couet W, Reigner BG, Lefebvre MA, Bizouard J, Fourtillan JB. [Pharmacokinetics of cefatrizine administered in repeated doses]. Pathol Biol (Paris). 1988 May;36(5):513-6. French. PubMed PMID: 3043350. 11: Neu HC, Fu KP. Cefatrizine activity compared with that of other cephalosporins. Antimicrob Agents Chemother. 1979 Feb;15(2):209-12. PubMed PMID: 426514; PubMed Central PMCID: PMC352634. 12: Pfeffer M, Gaver RC, Ximenez J. Human intravenous pharmacokinetics and absolute oral bioavailability of cefatrizine. Antimicrob Agents Chemother. 1983 Dec;24(6):915-20. PubMed PMID: 6660858; PubMed Central PMCID: PMC185407. 13: Mastrandrea V, Ripa S, La Rosa F, Ghezzi A. Pharmacokinetics of cefatrizine after oral administration in human volunteers. Int J Clin Pharmacol Res. 1985;5(5):319-23. PubMed PMID: 4066082. 14: Reigner BG, Couet W, Guedes JP, Fourtillan JB, Tozer TN. Saturable rate of cefatrizine absorption after oral administration to humans. J Pharmacokinet Biopharm. 1990 Feb;18(1):17-34. PubMed PMID: 2329468. 15: Cremonesi G, Tarantino V, Stura M, Ciampini M. Comparison of cefatrizine and erythromycin for pediatric ear, nose, and throat infections. Clin Ther. 1987;9(3):263-6. PubMed PMID: 3300988.