Antibiotiques Naturels et Semi-Synthétiques

<p>Cefazolin is a semi-synthetic cephalosporin that has a broad spectrum of antibacterial activity and inhibits the synthesis of bacterial cell walls.</p>

<p>Homoharringtonine (HHT) is an alkaloid combatting myeloid cancers and potentially some myelodysplastic syndromes, may treat leukemia and resistant NSC-LC.</p>

<p>Biapenem (CLI 86815), a carbapenem antibiotic, has broad antibacterial effects, stable kidney enzyme resistance, and low neurotoxicity.</p>

<p>Ceftobiprole medocaril: injectable prodrug; its active form fights broad-range infections including MRSA.</p>

<p>Tulathromycin A (CP 472295) is a macrolide antibiotic.</p>

<p>Tedizolid (DA-7157)is a novel oxazolidinone-class antibiotic that inhibits bacterial protein synthesis by binding to the 23S ribosomal RNA of the 50S subunit of</p>

<p>Ceftezole sodium (Falomesin) is a broad-spectrum cephalosporin antibiotic active gram-negative and gram-positive bacteria except for Proteus vulgaris,</p>

<p>Flucloxacillin sodium (floxacillin sodium) is a highly active antibiotic against Gram-negative and Gram-positive bacteria.</p>

<p>Retapamulin (SB-275833), a Pleuromutilin Antibacterial, binds to both E. coli and S. aureus ribosomes with similar potencies (Kd: 3 nM).</p>

<p>Clindamycin is a semisynthetic antibiotic that blocks bacterial protein synthesis by detaching peptidyl-tRNA from ribosomes.</p>

<p>Ticarcillin sodium: a semisynthetic, broad-spectrum antibiotic effective against various aerobic and anaerobic bacteria.</p>

<p>Aspoxicillin, a broad-spectrum antimicrobial agent, demonstrates efficacy against 68 isolates of Actinobacillus pleuropneumoniae, with a minimum inhibitory</p>

<p>Cadazolid (ACT-179811) is an oxazolidinone-type antibiotic, with activity against gram-positive bacteria, including Clostridium difficile.</p>

<p>Fidaxomicin (Tiacumicin B) is a semisynthetic macrolide antibiotic used to treat Clostridium difficile-associated diarrhea in adults.</p>

<p>Tacrolimus monohydrate (LCP-Tacro) is a macrolide from the culture broth of a strain of Streptomyces tsukubaensis, binds to FKBP to form a complex.</p>

<p>Faropenem sodium: Oral penem antibiotic for tuberculosis, pneumonia.</p>

<p>Amdinocillin pivoxil, an oral prodrug of amdinocillin, targets gram-negative bacteria.</p>

<p>Fumagillin (Amebacilin) is a selective and potent irreversible inhibitor of Methionine aminopeptidase 2 (MetAP2), used as an antibiotic to treat</p>

<p>Tilmicosin phosphate, a macrolide antibiotic, is used to treat cattle for pathogens that cause Bovine Respiratory Disease.</p>

<p>Delafloxacin (WQ-3034, RX-3341, ABT-492) is a potent antibiotic for levofloxacin-resistant S. pneumoniae (MIC: 0.0078-0.125 μg/ml).</p>

<p>Oritavancin diphosphate, a novel semisynthetic glycopeptide antibiotic, targets serious Gram-positive infections.</p>

<p>Lumefantrine, an antimalarial, treats malaria with artemether, effective against Plasmodium spp. including in chloroquine-resistant areas.</p>

<p>Ivermectin B1a is the major (80%) component of commercially available ivermectin and a derivative of Avermectin B1a.</p>

<p>Mecillinam, an antibiotic, targets Gram-negative bacteria, mainly for urinary infections and some fevers.</p>

<p>Pipecolic acid is a lysine metabolite in urine, plasma, CSF, and regulates immunity in plants and humans.</p>

<p>Stability Hygroscopic, Light Sensitive<br>Applications Polyene antifungal antibiotic.<br>References Levinskas, G.J., et al.: Toxicol. Appl. Pharmacol., 8, 97 (1966), Pandey, R.C., et al.: J. Antibiot., 29, 1035 (1976), Brik, H., et al.: Anal. Profiles Drug Subs. Excip., 23, 399 (1994),<br></p>

<p>Stability Unstable in Solution<br>Applications Meropenem-d6 is the labeled analogue of Meropenem, a carbapenem antibiotic. Antibacterial.<br>References Adams, M.D., et al.: J. Bacteriol., 190, 8053 (2008); Pattanaik, P., et al.: J. Biol. Chem., 284, 945 (2009); Mendes, R., et al.: J. Antimicrob. Chemother., 63, 55 (2009)<br></p>

<p>Applications Terbinafine is used to treat infections caused by a fungus.<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></p>

<p>Applications N-[(2R)-3-[[3-Fluoro-4-(4-morpholinyl)phenyl]amino]-2-hydroxypropyl]acetamide is an impurity of Linezolid (L466500).<br>References Gregory, W., et al.: J. Med. Chem., 32, 1673 (1989), Shinabarger, D., et al.: J. Antimicrob. Agents Chemother., 41, 2132 (1997),<br></p>

<p>Applications Erythromycin B is a co-metabolite of Erythromycin A (E649950), an antibacterial agent.<br>References Minh, N. et al.: Int. Food. Res. J., 18, 95 (2011); Koch, W.L. et al.: Anal. Profiles Drug Subs., 8, 157 (1979);<br></p>

<p>Stability Hygroscopic<br>Applications Avilamycin is an antimicrobial agent used against methicillin resistant Staphylococcus.<br>References Flora, D. et al.: J. Coastal Life Med., 3, 193 (2015);<br></p>

<p>Impurity Tacrolimus Diene Impurity (USP)<br>Applications Δ23-FK 506 is an impurity of FK-506 (Tacrolimus) (F370000), an immunosuppressant macrolactam.<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 Namiki, Y., et al.: J. Antibiot 1993, 46, 1149,,Akashi, T; J Pharm Biomed Anal 1996, 14, 339,,,,Wiedeman, P; J Med Chem 1999, 42, 4456,,,<br></p>

<p>Stability Hygroscopic<br>Applications 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 Semi-synthetic antibiotic related to Penicillin. Antimicrobial.<br>References Robinson, B., et al.: Biochem. Med. Metab. Biol., 48, 122 (1992), Lesnefsky, E., et al.: J. Biol. Chem., 279, 47961 (2004), Marroquin, L., et al.: Toxicol. Sci., 97, 539 (2007),<br></p>

<p>Applications Azithromycin Dihydrate is a semi-synthetic macrolide antibiotic; related to Erythromycin A. Antibacterial.<br>References Langtry, H.D., et al.: Drugs, 56, 273 (1998),<br></p>

<p>Impurity Clarithromycin EP Impurity N<br>Applications (10E)-10,11-Didehydro-11-deoxy-6-O-methylerythromycin (Clarithromycin EP Impurity N) is a Erythromycin (E649950) derivative.<br></p>

<p>Applications Ledipasvir is most commonly used in combination with sofosbuvir for treatment in chronic hepatitis C genotype 1 patients. It inhibits an important viral phosphoprotein, NS5A, which is involved in viral replication, assembly, and secretion.<br>References Lawitz, E., et al.: J. Hepatol., 57, 24 (2012); Afdhal, N., et al.: New England J. Med., 370, 1889 (2014)<br></p>

<p>Impurity Linezolid USP Related Compound D<br>Applications (5R)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone (Linezolid USP Related Compound D) is an intermediate in the synthesis of Linezolid Dimer (L466520), an impurity of the antibacterial agent Linezolid (L466500).<br>References Xu, Heteroatom, Chem., 19, 316 (2008); Wang, J.W., et al.: Lett. Org. Chem., 5, 336 (2008);<br></p>

<p>Impurity Lovastatin EP Impurity C<br>Stability Light Sensitive<br>Applications Dehydro Lovastatin (Lovastatin EP Impurity C) is a Lovastatin impurity.<br>References Duggan, D., et al.: Drug Metab. Dispos., 17, 166 (1989), Wang-Iverson, D., et al.: Drugs, 23, 127 (1994), Wu, Y., et al.: J. Pharm. Biomed. Anal., 20, 471 (1999),<br></p>

<p>Impurity Cefadroxil EP Impurity B<br>Applications 7-Aminodesacetoxycephalosporanic Acid (Cefadroxil EP Impurity B) is a metabolite of Cephalexin (C256800).<br>References Dantzig, A., et al.: Biochim. Biophys. Acta, 1027, 211 (1990), Shen, H., et al.: J. Biol. Chem., 278, 4786 (2003), Watanabe, C., et al.: Drug Metab. Pharmacokinet., 20, 443 (2005)<br></p>

<p>Applications 25-Deacetyl-21-acetyl Rifampicin is a structural isomer, and impurity, of Rifampicin (R508000), a semisynthetic antibiotic. Antibacerial (tuberculostatic).<br>References Furesz, et al.: Antibiot. Chemother., 16, 316 (1970), Gallo, G.G., et al.: Anal. Profiles Drug Subs., 5, 467 (1976),<br></p>

<p>Applications Third generation cephalosporin antibiotic. Antibacterial.<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>Stability Light Sensitive<br>Applications (Z)-Desbutyl Lumefantrine is a metabolite of Lumefantrine (L474000).<br>References Lefevre, G., et al.: Br. J. Clin. Pharmacol., 54, 485 (2002); Schepers, U., et al.: J. Pharm. Biomed. Anal., 310 (2005)<br></p>

<p>Applications Labelled Cycloserine. Antibacterial (tuberculostatic).<br>References Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972), 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 3-Chloro-D-alanine Methyl Ester Hydrochloride is an intermediate in the preparation of antibiotic D-Cycloserine (C988815) which inhibits cell wall biosynthesis in bacteria.<br>References Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972); 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); Chem and Eng. News p. 12, Dec. 7/14 (2015);<br></p>

<p>Applications Azithromycin is an azalide macrolide antibiotic.<br>References Hunter, R., et al.: J. Vet. Pharmacol. Ther., 26, 117 (2003);<br></p>

<p>Impurity Mupirocin EP impurity C<br>Stability Hygroscopic<br>Applications An antibiotic isolated from Pseudomonas fluorescens.<br>References Banks, R.M., et al.: J. Antibiot., 41, 609 (1988),<br></p>

<p>Applications Non-absorbable semisynthetic Rifamycin antibiotic.<br>References Brufani, M., et al.: J. Antibiot., 37, 1611 (1984), Gillis, J.C., et al.: Drugs, 49, 467 (1995), Huang, D.B., et al.: J. Infection, 50, 97 (2005),<br></p>

<p>Applications Ivermectin B1a is a major component of Ivermectin (I940800), a semi-synthetic derivative of Abamectin; consists of a mixture of not less than 80% component B1a and not more than 20% component B1b. Antihelmintic (Onchocerca). An invitro inhibitor of SARS-CoV-2/ Covid-19.<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 Chabala, J.C., et al.: J. Med. Chem., 23, 1134 (1980); Campbell, W.C., et al.: Science, 221, 823 (1983); Bennett, J.L., et al.: Parasitol. Today, 4, 226 (1988); Plaisier, A.P., et al.: J. Infect. Dis., 172, 204 (1995);; Caly, L., et al.: Antivir. Res., 178<br></p>

<p>Applications Inhibits hemozoin formation. Antimalarial.<br>References Kumar, N., et al.: Parasitol Res., 76, 214 (1990), Pradines, B., et al.: Antimicrob. Agents Chemother., 43, 418 (1999), Chotivanich, K., et al.: J. Infect. Dis., 182, 629 (2000), Mutabingwa, T., et al.: Lancet, 365, 1474 (2005),<br></p>

<p>Applications Erythromycin Lactobionate is an antibiotic used to reduce the prevalence of drug resistant bacteria as well as keeping constant the efficacy of other antibacterial drugs.<br>References Kiso, S. et al.: Anticanc. Res., 20, 2827 (2000); Broad, J. et al.: Brit. J. Pharm., 168,1859 (2013); Itoh, Z., et al.: Antimicrob. Agents Chemother., 26, 863(1984)<br></p>

<p>Impurity Fosfomycin EP-Impurity A<br>Applications P-[(1R,2R)-1,2-Dihydroxypropyl]-phosphonic Acid is a Fosfomycin (F727500) impurity. Fosfomycin is an antibiotic that exerts a broad spectrum of antibacterial activity.<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 McGrath, J.W., et al.: Org. Biomolec. Chem., 7, 9 (1944); Goto, M., et al.: Antimicrob. Agents Chemother., 20, 393 (1981);<br></p>

<p>Applications An intermediate in the preparation of detoxification inhibitors of the crucifer phytoalexin Brassinin, as potential fungicides against Leptosphaeria maculans.<br>References Gaspari, P., et al.: J. Med. Chem., 49, 684 (2006), Pedras, M., et al.: Bioorg. Med. Chem., 14, 714 (2006),<br></p>

<p>Stability Hygroscopic<br>Applications Delactamimipenem Monosodium is an impurity found in imipenem (I465200).<br>References Ratcliffe, R.W., et. al.: J. Org. Chem., 54, 653 (1989)<br></p>

<p>Applications Third generation, orally active cephalosporin antibiotic. Antibacterial.<br>References Wise, R., et al.: Antimicrob. Agents Chemother., 29, 1067 (1986), Hirai, S., et al.: Jpn. J. Antibiot., 39, 958 (1986), Lentz, K., et al.: Int. J. Pharm., 200, 41 (2000), Takagi, T., et al.: Mol. Pharmaceutics, 3, 631 (2006), Gu, C., et al.: Pharm. Res., 24, 1118 (2007),<br></p>

<p>Impurity Linezolid USP Related Compound C<br>Applications An impurity of Linezolid (L466500), as antimycobacterial agent. Linezolid USP Related Compound C.<br>References Sato, K., et al.: Eur. J. Pharmacol., 347, 231 (1998), Maignan, S., et al.: J. Med. Chem., 43, 3226 (2000), Tokuyama, R., et al.: Chem. Pharm. Bull., 49, 353 (2001),<br></p>

<p>Stability Temperature Sensitive<br>Applications Amoxicilloic Acid Dimer is an impurity of Amoxicillin (A634528), 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>Stability Hygroscopic<br>Applications Kanamycin (K137500) derivative as synthetic byproduct of Amikacin (A578500).<br>References Kawaguchi, H., et al.: J. Antibiotics, 25, 695 (1972), Naito, T., et al.: J. Antibiotics, 26, 297 (1973),<br></p>

<p>Applications Sisomicin is an Antibacterial. Gentamicin-like aminoglycoside antibiotic; has broad spectrum antibiotic activity.<br>References Weinstein, M.J., et al.: J. Antibiot., 23, 551 (1970), Sculier, J.P., et al.: J. Antimicrob. Chemother., 9, 63 (1982), Noone, P., et al.: Drugs, 27, 548 (1984),<br></p>

<p>Impurity Clarithromycin EP Impurity F<br>Applications 12-O-Methyl Clarithromycin (Clarithromycin EP Impurity F) is a methylated impurity of the semi-synthetic macrolide antibiotic Clarithromycin (C559750). 12-O-Methyl Clarithromycin was shown to inhibit uptake of Clarithromycin into the lung cells.<br>References Chen, X. et al.: Zhong. Yao., 17, 32 (2008); Yoshida, H. et al.: Jap. J. Antibiot., 53, 615 (2000); Omura, S. et al.: Yakug. Zas., 112, 593 (1992);<br></p>

<p>Applications Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.<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>Stability Hygroscopic<br>Applications Cefbuperazone is a second-generation cephalosporin antibiotic.<br>References Izumi, K., et al.: J. Chemother., 7 Suppl 4, 173 (1995)<br></p>

<p>Stability Hygroscopic<br>Applications Vancomycin Hydrochloride is an antibiotic used against gram-positive bacterial strains.<br>References Yao, N., et al.: Biopolymers, 90, 421 (2008); Lai, H., et al.: ACS Appl. Mater. Interfaces, 7, 2046 (2015);<br></p>

<p>Applications Bacitracin is a peptide antibiotic effective against gram-postive bacteria. Bacitracin is an inhibitor of peptidoglycan synthesis. Bacitracin disrupts bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate. Bacitracin also strongly inhibits proline endopeptidase from human muscle.<br>References Ward, J.B. et al.: Biochem. J., 141, 227 (1974); Anastasi, A. et al.: Biochem. J., 290, 601 (1993); Daly, D.J. et al.: Biochem. Soc. Trans., 13, 1161 (1985); Weinberg, E.D. et al.: Antibiot. Ber., 90, (1967);<br></p>

<p>Applications Erythromycin is 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>