Natural and semi-synthetic antibiotics

<p>Stability Very unstable<br>Applications Cefixime Impurity is an impurity of Cefixime (C242800); an orally active third generation cephalosporin antibiotic.<br>References Kamimura, T., et al.: Antimicrob. Agents Chemother., 25, 98 (1984); Yamanaka, H., et al.: J. Antibiot., 38, 1738 (1985); Guay, D.R.P., et al.: Antimicrob. Agents Chemother., 30, 485 (1986)<br></p>

<p>Applications The minor glucuronide metabolite of Chloramphenicol (C325030).<br>References Simons, P., et al.: Xenobiotica, 22, 1267 (1992), Kaji, H., et al.: Drug Metab. Dispos., 33, 60 (2005),<br></p>

<p>Applications An antibiotic derived from Tetracycline. Studies have shown that this derivative can have a 250-fold higher toxicity depending on the system under study. This compound is a contaminant of emerging concern (CECs).<br>References Simmons, D., et al.: J. Pharm. Sci., 55, 1313 (1966), Paemen, L., et al.: Biochem. Pharmacol., 52, 105 (1996),<br></p>

<p>Applications (6R,7S)-Cefoperazone Sodium Salt is the enantiomer of Cefoperazone (C242900) as an impurity.<br>References Fabre, H., et al.: J. Pharm. Sci., 73, 611 (1984), Strasters, J., et al.: Anal. Chem., 63, 2503 (1991), Chen, Z., et al.: World Notes Antibiot., 25, 249 (2004),<br></p>

<p>Impurity Amoxicillin EP Impurity J<br>Applications Amoxicillin Dimer Sodium Salt is an impurity of Amoxicillin (A634235), a β-lactam family antibiotic that is commonly used in conjunction with clavulanic acid (C56370) to the treat bacterial infections.<br>References Gurwith, M., et al.: Antimicrob. Agents Ch., 24, 716 (1983); Kumar, A., et al.: J. Mater. Chem., 20, 10152 (2010);<br></p>

<p>Applications Mitomycin (M371900) impurity.<br>References Siegel, D., et al.: Biochemistry, 31, 7879 (1992), Kontou, M., et al.: Oncogene, 21, 2406 (2002),<br></p>

<p>Impurity Terbinafine EP Impurity B<br>Applications cis-Terbinafine Hydrochloride (Terbinafine EP Impurity B) is an impurity in the production of Terbinafine hydrochloride.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Petranyi, G., et al.: Science, 224, 1239 (1984), Stutz, A., et al.: J. Med. Chem., 27, 1539 (1984),<br></p>

<p>Applications Tigecycline pentacyclic analog is an impurity of Tigecycline (T440015), one of the very few glycylcycline antimicrobials that exhibit activity against Gram-negative bacteria and also one of the few that also circumvent around the major resistance mechanisms of tetracycline.<br>References Grosse, E., et al.: Clin. Infect. Dis. (Supplement 5), 41, S341 (2005); Livermore, D.: J. Antimicrob. Chemoth., 56, 611 (2005); Stein, G. &amp; Craig, W.: Clin. Infect. Dis., 43, 518 (2006)<br></p>

<p>Stability Light Sensitive<br>Applications Di-2-(Hydroxyphenyl)acetamido Cefprozil is an impurity in the synthesis of Cefprozil (C243910), semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial.<br>References Jones, R.N., et al.: Diagn. Microb. Infect. Dis., 9, 11 (1988), Barbhaiya, R.H., et al.: Antimicrob. Agents Chemother., 34, 1204 (1990)<br></p>

<p>Impurity Erythromycin EP Impurity B<br>Applications N-Demethyl Erythromycin A (Erythromycin EP Impurity B) is a metabolite of Erythromycin (E649950).<br>References Rich, D.H., et al.: J. Med. Chem., 18, 1004 (1975), Itoh, Z,. et al.: Antimicrob. Agents Chemother., 26, 863 (1984), Omura, S., et al.: J. Antibiotics 38, 1631 (1985),<br></p>

<p>Impurity Ciprofloxacin Impurity E<br>Applications Ciprofloxacin impurity. Ciprofloxacin Impurity E<br>References Borner, K, et al.: J. Clin. Chem. Clin. Biochem., 24, 325 (1986), Lacroix, P., et al.: J. Pharm. Biomed. Anal., 14, 641 (1996), Barron, D., et al.: Anal. Chim. Acta, 415, 83 (2000,<br></p>

<p>Applications Ixabepilone is an anti-tumor agent used in the treatment of patients suffering from solid tumors, such as metastatic breast cancer.<br>References Duska, L. et al.: Gynecol. Oncol., 135, 44 (2014); Deeken, J. et al.: Cancer Chemother. Pharmacol., 73, 1071 (2014);<br></p>

<p>Applications 5-Bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine is an intermediate in the synthesis of Tedizolid (T013750), an known oral and intravenous antibiotic.<br>References Xin, Q. S., et al.: J. Med. Chem., 54, 7493 (2011);<br></p>

<p>Applications E-Ceftazidime is an impurity of Ceftazidime Pentahydrate (C244100); which is a third generation cephalosporin antibiotic.<br>References Brodie, A., et al.: Antimicrob. Agents Chemother., 17, 876 (1980); Richards, D.M., et al.: Drugs, 29, 105 (1985); Abounassif, M.A., et al.: Anal. Profiles Drug Subs., 19, 95 (1990)<br></p>

<p>Applications Protected Penicillamin.<br>References Klingstroem, J., et al.: Eur. J. Immunol., 36, 2649 (2006), Atyabi, F., et al.: J. Nanosci. Nanotechnol., 9, 4593 (2009), Yip, K., et al.: Brit. J. Pharmacol., 156, 1279 (2009),<br></p>

<p>Applications Erythromycin (E649950) derivative.<br></p>

<p>Applications (Z)-7-(((2R)-2-Carboxy-2-((4-oxopentan-2-yl)amino)ethyl)thio)-2-((S)-2,2-dimethylcyclopropanecarboxamido)hept-2-enoic Acid is an impurity of Cilastatin (C441100), prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct.<br>References Finlay, K.R., et al.: Invest. Ophthalmol. Visual Sci., 24, 1147 (1983), Norrby, S.R., et al.: Antimicrob. Agents Chemother., 23, 300 (1983), Washburn, D.E., et al.: J. Antimicrob. Chemother., 12, 39 (1983),<br></p>

<p>Impurity Posaconazole Impurity;<br>Applications 2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxymethyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol is building block to synthesize key intermediates towards synthesis of highly active azole antifungals Sch 51048, Sch 56592 and Sch 45012. It is also an impurity/intermediate for posaconazole (P689600).<br>References Saksena, A., et al.: Tetrahedron Lett., 37, 5657 (1996); Lovey, R., et al.: Tetrahedron Lett., 35, 6047 (1994); Saksena, A., et al.: Tetrahedron Lett., 36, 1787 (1995)<br></p>

<p>Impurity Ceftazidime EP Impurity H<br>Applications Ceftazidime Methyl Ester (Ceftazidime EP Impurity H) is an impurity of Ceftazidime (C244100). Ceftazidime impurity G.<br>References Miyake, A., et al.: Antimicrob. Agents Chemother., 486, 182 (1989), Seibert, G., et al.: Arzneim.-Forsch., 33, 1084 (1983),<br></p>

<p>Impurity Clarithromycin EP Impurity E<br>Applications 6,11-Di-O-methyl Erythromycin (Clarithromycin EP Impurity E) is a Di-O-alkyl Erythromycin (E649950) is an impurity of Clarithromycin (C559750). Clarithromycin impurity E per British Pharmacopoeia.<br>References Morimoto, S. et al.: J. Antibiot., 43, 286 (1990); Kohno, Y. et al.: J. Antimicrob. Chemother., 26, 503 (1990);<br></p>

<p>Stability Hygroscopic<br>Applications Streptidine is a metabolite derivative of Streptomycin (S687500), an antibiotic (antimycobacterial) drug, used for patients suffering from tuberculosis or other infectious diseases.<br>References Granados, O., et al.: Histology and Histopathology, 20, 357 (2005)<br></p>

<p>Applications The epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.<br>References Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995), Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (2001), Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)<br></p>

<p>Applications Erythromycin Glucoheptonate is a derivative of Erythromycin (E649950), an antibiotic.<br>References Delaforge, M. et al.: Biochem. Pharm., 32, 2309 (1983); Niederau, W. et al.: Chemother., 26, 121 (1980);<br></p>

<p>Impurity Potassium Clavulanate EP Impurity K<br>Applications tert-Octylamine (Potassium Clavulanate EP Impurity K) is used in the synthesis of aminomethyltetracycline dericatives as novel antibacterial agents. Also used in the preparation of carbonyl or sulfonylpyrrolidine containing uracil derivatives which have potent effect in the inhibitoon of deoxyuridine triphosphatase inhibitors.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Clark, R. et al.: J. Med. Chem., 56, 8112 (2013); Miyakoshi, H. et al.: J. Med. Chem., 55, 2960 (2012);<br></p>

<p>Applications 7-Chloro-6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid is a 1-arylated derivative of 1,4-dihydro-4-oxoquinoline-3-carboxylic acid with antibacterial activity.<br>References Radl, S. et al.: Coll. Czech. Chem. Comm., 54, 2181 (1989):<br></p>

<p>Applications Produced concentration-related relaxations of mouse anococcygeus, in a range similar to that already found for NO and other nitrovasodilators. A potent relaxant of non-vascular smooth muscle. Serves as an NO donor.<br>References Bauer &amp; Fung: J. Pharmacol. Exp. Ther., 256, 249 (1991), Gibson, A., et al.: Brit. J. Pharm., 107, 715 (1992), Shaffer, et al.: J. Pharm. Exper. Ther., 260, 286 (1992), Jansen, A., et al.: J. Pharmacol. Exp. Ther., 261, 154 (1992), Lander, H.M. et al.: J. Immunol., 150, 1509 (1993)<br></p>

<p>Impurity Simvastatin EP Impurity F<br>Applications Epi Lovastatin (Simvastatin EP Impurity F) is a Lovastatin impurity; an antihypercholesterolemic compound.<br>References Hoffman, W.F., et al.: J. Med. Chem., 29, 849 (1986),<br></p>

<p>Stability Light and Temperature Sensitive<br>Applications Δ2-Cefadroxil is a derivative of Cefadroxil (C235750), a semi-synthetic cephalosporin antibiotic. Antibacterial.<br>References Buck, R.E., et al.: Antimicrob. Agents Chemother., 11, 324 (1977)<br></p>

<p>Stability Unstable in Solution<br>Applications Cefathiamidine is an antibacterial agent that exhibits a broad spectrum of bactericidal activity against gram-positive bacteria.<br>References Chen, H.Y., et al.: J. Antimicrob. Chemother., 12, 19 (1983); Philpott-Howard, J., et al.: Scand. J. Infect. Dis. Suppl., 39, 109 (1983); Chen, H.Y., et al.: J. Med. Microbiol., 23, 141 (1987);<br></p>

<p>Applications A semi-synthetic cephalosporin antibiotic. Antibacterial.<br>References Goodhart, F., et al.: J. Pharamac. Sci., 62, 133 (1973), Maier, H., et al.: Arzneim.-Forsch., 42, 980 (1992),<br></p>

<p>Impurity Tacrolimus Methylacryl Aldehyde (USP)<br>Applications Tacrolimus Methyl Acryl Aldehyde is the degradation product of Tacrolimus (F370000), a novel macrocyclic lactone isolated from Streptomyces tsukubaensis, having immunosuppressant activity.<br>References Asano, K., et al.: In Vivo, 10, 537 (1996), McCall, E., et al.: Circ. Res., 79, 1110 (1996), Raufman, J.P., et al.: J. Biol. Chem., 271, 19877 (1996), Rokaw, M.D., et al.: Am. J. Physiol., 271, C194 (1996), Knoll, G.A., and Bell, R.C.: Brit. Med. J., 318, 1104 (1999),<br></p>

<p>Applications Protected form of FK-506 (Tacrolimus)<br>References Rokaw, M.D., et al.: Am. J. Physiol., 271, C194 (1996), Knoll, G.A., et al.: Brit. Med. J., 318, 1104 (1999),<br></p>

<p>Applications Intermediate in the preparation of Azamulin<br></p>

<p>Impurity Flucloxacillin EP Impurity D<br>Applications 3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylic Acid (Flucloxacillin EP Impurity D) is an impurity of Flucloxacillin (F419200), a new semisynthetic penicillin with broad spectrum of antibacterial activity.<br>References Macsari, I., et al.: Bioorg. Med. Chem. Lett., 21, 3871 (2011); Cui, Y., et al.: Curr. Sci., 89, 531 (2005);<br></p>

<p>Impurity Flucloxacillin EP Impurity B<br>Applications Flucloxacillin Penilloic Acid (Flucloxacillin EP Impurity B) is a degradation product/impurity of Flucloxacillin (F419200).<br>References Aboul K.A., et al.: Anal. Lett., 17, 1667 (1984),<br></p>

<p>Applications Amoxicillin sodium (Amox) (cas# 34642-77-8) is a useful research chemical.<br></p>

<p>Impurity Cefixime EP Impurity F<br>Applications Cefixime Ethyl Ester is an ester impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).<br>References Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010);<br></p>

<p>Cefixime is a broad-spectrum oral antibiotic used to treat bacterial infections, including respiratory tract and ear infections. Cefixime is the prodrug of cefixime acid, which is hydrolyzed in vivo to cefixime. This impurity is an analytical standard that can be used for research and development, high purity drug product, API impurity, HPLC standard and niche drugs. It can also be used as a metabolite and an impurity standard. The CAS number for this compound is 1335475-08-5. This chemical has natural or synthetic origins but is not specified.</p>

<p>Azithromycin impurity J, also known as Azithromycin P-Toluenesulfonate, is an impurity of the drug azithromycin. It is an antibiotic that has been shown to be effective in the treatment of protozoal infections, cancer and parasites. Azithromycin impurity J has been shown to bind to DNA gyrase and topoisomerase IV enzymes, which are necessary for bacterial replication. Azithromycin impurity J is a protozoan inhibitor that acts by blocking the synthesis of RNA and DNA. This impurity binds to DNA gyrase and topoisomerase IV enzymes, which are necessary for bacterial replication. Azithromycin impurity J is a protozoan inhibitor that acts by blocking the synthesis of RNA and DNA.</p>