Natural and semi-synthetic antibiotics

<p>Applications Linezolid Dimer is an impurity of the antibacterial agent Linezolid (L466500).<br></p>

<p>Applications Imipenem intermediate.<br></p>

<p>Applications tert-Butyl N-[2-[2-(6-chlorohexyloxy)ethoxy]ethyl]carbamate is an intermediate in the synthesis of HaloTag O2 Tobramycin (H103850). HaloTag O2 Tobramycin is a derivative compound of Tobramycin (T524000), a single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. An Antibacterial.<br>References Koch, K.F., et al.: Antimicrob. Agents Chemother., 309 (1970); Welles, J.S., et al.: Toxicol. Appl. Pharmacol., 22, 332 (1972); Dash, A.K., et al.: Anal. Profiles Drug Subs. Excip., 24, 579 (1996)<br></p>

<p>Applications Pipecolic Acid (P479760) derivative. Found in wheat, rye and barley.<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>Stability Hygroscopic<br>Applications 2-Chloroethoxy Roxithromycin is an impurity of Roxithromycin (R700850); a semisynthetic Erythromycin (E649950) derivative and antibacterial.<br>References Jones, R.N., et al.: Antimicrob. Agents Chemother., 24, 209 (1983); Barry, A.L., et al.: Eur. J. Clin. Microbiol., 5, 536 (1986); Grassi, C., et al.: Chemioterapia, 6, 41 (1987); Gasc, J.C., et al.: J. Antibiot., 44, 313 (1991);<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 Lovastatin-d9, is the labeled analogue of Lovastatin (L472225), an antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase.<br>References Bilheimer, D.W., et al.: Proc. Nat. Acad. Sci. USA, 80, 4124 (1983),<br></p>

<p>Applications Pseudoerythromycin A Hemiketal is an impurity of Erythromycin (E649950), an antibiotic.This compound is a contaminant of emerging concern (CECs).<br>References Koch, W.L., et al.: Anal. Profiles Drug Subs., 8, 157 (1979),<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>Impurity Amoxicillin EP Impurity B ; Amoxicillin USP Related Compound B<br>Applications L-Amoxicillin (Amoxicillin EP Impurity B) is an isomer of Amoxicillin (A634235), a semi-synthetic antibiotic related to penicillin.<br>References Brogden, R.N., et al.: Drugs, 18, 169 (1979), Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1994),<br></p>

<p>Applications Intermediate in the preparation of Cycloserine (C988800).<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>Applications 2-(5-Mercaptotetrazole-1-yl)ethanolis a mercaptotetrazole derivative used as an intermediate in the preparation of beta-lactam antibiotic Flomoxef (F401850) as well one of its metabolite. 2-(5-Mercaptotetrazole-1-yl)ethanol also shows vitamin K-dependent glutamylcarboxylase inhibitory activity.<br>References Oka, T. et al.: Jap. J. Pharmacol., 46, 165 (1988); Konaka, R. et al.: Chemotherapy, 35, 137 (1987);<br></p>

<p>Stability Hygroscopic, Temperature Sensitive, Very Unstable<br>Applications Thienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.<br>References Kahan, J., et al.: J. Antibiot., 32, 1 (1979); Bradley, J., et al.: Int. J. Antimicrob. Agents, 11, 93 (1999); Spratt, B., et al.: Antimcrob. Agents Chemother., 12, 406 (1977);<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>Impurity Linezolid USP Related Compound B<br>Applications Deacetyl Linezolid Thioacetamide is an impurity of Linezolid (L466500), an oxazolidinone antimicrobial which inhibits bacterial mRNA translation. Linezolid USP Related Compound B.<br>References Brickner, S.J., et al.: J. Med. Chem., 39, 673 (1996); Ford, C.W., et al.: Antimicrob. Agents Chemother., 40, 1508 (1996); Rybak, M.J., et al.: Pharmacotherapy, 18, 456 (1998); Stevens, D.L., et al.: Clin. Infect. Dis., 34, 1481 (2002);<br></p>

<p>Applications 3,6-Methylene-2,5-piperazinedione is an impurity of Cycloserine (C988800), an antibacterial agent.<br>References Ajo, D., et al.: J. Molec. Structure.,141, 415 (1986); Gentry-Weeks, C., et al.: J. Biol. Chem., 268, 7298 (1993); Alexander, F., et al.: Eur. J. Biochem., 219, 953 (1994); Auger, S., et al.: Biochimie, 87, 231 (2005)<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 Protected rac Zearalenone-d6<br></p>

<p>Applications 3-Methyl-2,5-bis-(2-hydroxyethyl)pyrazine is a degradation product of Clavulanic Acid (C563750), a β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.<br>References Reading, C. and Cole, M.: Antimicrob. Ag. Chemother., 11, 852 (1977), Ball, A.P., et al.: Lancet, 1, 620 (1980), Brogden, R.N., et al. Drugs, 22, 337 (1981); Haginaka, J. et al.: Chem. Pharm. Bull., 33, 218 (1985);<br></p>

<p>Applications N-t-Butyl Linezolid is a derivative of Linezolid (L466500), prototype of the oxazolidinone antimicrobials; inhibits bacterial mRNA translation.<br>References Brickner, S.J., et al.: J. Med. Chem., 39, 673 (1996), Ford, C.W., et al.: Antimicrob. Agents Chemother., 40, 1508 (1996), Rybak, M.J., et al.: Pharmacotherapy, 18, 456 (1998), Stevens, D.L., et al.: Clin. Infect. Dis., 34, 1481 (2002),<br></p>

<p>Applications A labelled impurity of Gatifloxacin.<br>References Naber, C., et al.: Antimicrob. Agents Chemother., 45, 293 (2001), Herzler, M., et al.: J. Anal. Toxicol., 27, 233(2003), Pragst, F., et al.: Clin. Chem. Lab. Med., 42, 1325 (2004),<br></p>

<p>Impurity Lovastatin EP Impurity D<br>Applications Lovastatin Dimer (Lovastatin EP Impurity D) is an impurity in Lovastatin (L472225) bulk drug.<br>References Houck, A., et al.: Talanta, 40, 491 (1993),<br></p>

<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>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>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 The Δ2-isomer of Cefotean (C242970). It is useful as intermediate in the preparation of cephalesorin compounds.<br>References Sugioka, T., et al.: Chem. Pharm. Bull., 38, 1998 (1990),<br></p>

<p>Applications Reagent used in the preparation of Cephalosporin antibiotics.<br>References Choi, K., et al.: J. Antibiotics, 50, 279 (1997), Bharathi, C., et al.: J. Pharm. Biomed. Anal., 43, 733 (2007),<br></p>

<p>Applications cis-1-Hydroxy-2,7-diamino Mitosene is derived from Mitomycin C (M371900), which is an antitumor antibiotic. It is antineoplastic. Also, it is an oxazolidinone derivative resulting from a cyclization reaction of bicarbonate with the aziridine ring of aziridinomitosene.<br>References Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971); Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1986); Paz, M. M.: Bioorg. Med. Chem. Lett., 20, 31-34 (2010)<br></p>

<p>Impurity Terbinafine EP Impurity D; Terbinafine USP Related Compound D; Terbinafine BP Impurity D<br>Applications N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N,4-dimethyl-1-naphthalenemethanamine (Terbinafine EP Impurity D; Terbinafine USP Related Compound D; Terbinafine BP Impurity D) is an impurity of Terbinafine (T107500), an orally active, antimycotic allylamine and a specific inhibitor of squalene epoxidase.<br>References Petranyi, G., et al.: Science, 224, 1239 (1984); Ryder, N.S., et al.: Antimicrob. Agents Chemother., 27, 252 (1985); Evans, E.G.V., et al.: Br. Med. J., 318, 1031 (1999);<br></p>

<p>Stability Hygroscopic<br>Applications Clindamycin (C580000) impurity in bulk drug.<br>References Zhou, H., et al.: J. Pharma. Biomed. Anal., 41, 1116 (2006),<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 Tiamulin Hydrogen Fumarate Impurity C<br>Applications Reagent used in the addition of Thiobistriethylamine.<br>References Evers, M., et al.: Bioorg. Med. Chem. Lett., 13, 4415 (2003),<br></p>

<p>Applications 3-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylic Acid-13C4 Ethyl Ester is an isotope labelled derivative in the synthesis 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>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>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>Applications Intermediate in the production of labelled Posaconazole.<br></p>

<p>Applications 4-(2-Fluoro-4-nitrophenyl)morpholine is a reactant in the synthesis of 5-​substituted oxazolidinone derivatives with high antimicrobial activity.<br>References De Rosa, M., et. al.: Eur. J. Med. Chem., 69, 779 (2013)<br></p>

<p>Applications Bis-clindamycinyl Phosphate is an impurity of Clindamycin (C580000), which is an antibiotic prepared from Lincomycin (L466200), used to treat various infections.<br>References Birkenmeyer, R.D., et al.: J. Med. Chem., 13, 616 (1970); Oesterling, et al.: J. Pharm. Sci., 59, 63 (1970); Gray, J.E., et al.: Toxicol. Appl. Pharmacol., 21, 516 (1972); Brown, L.W., et al.: Anal. Profiles Drug Subs., 10, 75 (1981);<br></p>