Midecamycin
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| Category | Antibiotics |
| Catalog number | BBF-01905 |
| CAS | 35457-80-8 |
| Molecular Weight | 813.97 |
| Molecular Formula | C41H67NO15 |
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Description
Midecamycin is a main component of YL-704, a macrolide antibiotic complex isolated from Streptomyces platensis subsp. malvinus. It is active against gram-positive bacteria.
Specification
| Synonyms | YL-704B1; YL 704B1; YL 704 B1; Rubimycin; Espinomycin A; Mydecamycin |
| Storage | 2-8°C |
| IUPAC Name | [(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-4-(dimethylamino)-3-hydroxy-5-[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate |
| Canonical SMILES | CCC(=O)OC1CC(=O)OC(CC=CC=CC(C(CC(C(C1OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C |
| InChI | InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1 |
| InChI Key | DMUAPQTXSSNEDD-QALJCMCCSA-N |
| Source | Streptomyces mycarofaciens |
Properties
| Appearance | White or Off-White Powder |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 131-133°C |
| Solubility | Insoluble |
Reference Reading
1. [Acylation specificity of midecamycin 3-O-acyltransferase within Streptomyces spiramyceticus F21]
Hongxia Zhou, Jingyan Li, Chunyan Ma, Kan Zhang, Xiaochun Sun, Yiguang Wang, Jianlu Dai, Huanzhang Xia, Linzhuan Wu Sheng Wu Gong Cheng Xue Bao . 2008 Dec;24(12):2086-92.
Spiramycin and midecamycin are 16-membered macrolide antibiotics with very similar chemical structures. Spiramycin has three components, namely spiramycin I, II and III. Spiramycin II and III are, respectively, the O-acetyl and propionyl derivatives at C3-hydroxyl group of spiramycin I. Midecamycin has four components, and the C3-hydroxyl group of midecamycin is all O-propionylated. The enzyme adding acyl group(s) at the C3-hydroxyl group during the biosynthesis of spiramycin and midecamycin is 3-O-acyltransferase. The 3-O-acyltransferases for spiramycin and midecamycin are also very similar, and presume to function when exchanged. To explore whether the 3-O-acyltransferase for midecamycin biosynthesis hold still the character of selective and efficient propionylation for spiramycin I at its C3-hydroxyl group, we inserted mdmB, the 3-O-acyltransferase gene from Streptomyces mycarofaciens ATCC 21454 for midecamycin biosynthesis, into a mutant strain of S. spiramyceticus F21, in which the 3-O-acyltransferase gene for spiramycin biosynthesis, sspA, was deleted; and the mdmB was integrated exactly into the chromosomal site where the sspA was deleted. We name this "hybrid" strain as SP-mdmB. HPLC analysis of the spiramycin produced by SP-mdmB showed that spiramycin I was still the major component, although the relative proportions of both spiramycin II and III increased significantly. We thus conclude that MdmB from Streptomyces mycarofaciens ATCC 21454 for midecamyicn biosynthesis do not hold the character of selective and efficient propionylation for spiramycin I within S. spiramyceticus F21, and this character is possibly limited in Streptomyces mycarofaciens ATCC 21454 for midecamycin biosynthesis.
2. [Diagnosis and treatment of acute tonsillopharyngitis. Consensus document update]
Juan Carlos Silva Rico, Alicia Berghezan Suárez, Begoña Carazo Gallego, Ana María Borrull Senra, César García Vera, Marta Cruz Cañete, Jorge Sotoca Fernández, Francisco Hijano Bandera, Antonio Conejo Fernández, Leticia Martínez Campos, Santiago Alfayate Miguélez, Josep de la Flor I Bru, Carlos Pérez Cánovas, Cristina Calvo Rey, Pilar Lupiani Castellanos, Fernando Álvez González, Gonzalo Cabrera Roca, Josefa Ares Álvarez, Roi Piñeiro Pérez, Fernando Baquero-Artigao, Ana Fernández Landaluce, Javier López Ávila, Grupo Colaborador de Faringoamigdalitis Aguda en Pediatría, María José Cilleruelo Ortega An Pediatr (Engl Ed) . 2020 Sep;93(3):206.e1-206.e8. doi: 10.1016/j.anpedi.2020.05.004.
An update of the Spanish consensus document on the diagnosis and treatment of acute tonsillopharyngitis is presented. Clinical scores should not be used to prescribe antibiotics, unless microbiological tests are not available or there is a child at risk of rheumatic fever. There is no score better than those set out in the previous consensus. Microbiological tests are recommended in proposed cases, regardless of the result of the scores. Penicillin is the treatment of choice, prescribed twice a day for 10 days. Amoxicillin is the first alternative, prescribed once or twice a day for the same time. First-generation cephalosporins are the treatment of choice in children with non-immediate reaction to penicillin or amoxicillin. Josamycin and midecamycin are the best options for children with immediate penicillin allergic reactions, when non-beta-lactam antibiotics should be used. In microbiological treatment failure, and in streptococcal carriers, the treatments proposed in the previous consensus are still applicable.
3. Bacteriological evaluation of midecamycin acetate and its metabolites
S Someya, Y Kazuno, T Watanabe, K Miyauchi, T Yoshida, R Okamoto, S Ishihara, T Shomura Jpn J Antibiot . 1982 Jun;35(6):1462-74.
In vitro midecamycin acetate was shown to have broad spectrum of antibacterial activities similar to those of other macrolides (midecamycin, josamycin, 9-propionyl josamycin and 2'-ethylsuccinyl erythromycin), which include Gram-positive organisms, a part of Gram-negative organisms and anaerobes. Metabolites of midecamycin acetate also showed certain degree of antibacterial activities although they gave higher MIC values than midecamycin acetate. The antibacterial activities of midecamycin acetate were potentiated in the medium with pH 7 or pH 8 and little affected by inoculum size or addition of human serum into the medium. Both midecamycin acetate and its metabolites were found to have relatively high protein binding rates. In vivo therapeutic experiments in experimental infections in mice, midecamycin acetate was shown to be much superior to other drugs tested in the therapeutic efficacy against intraperitoneal infections caused by Staph. aureus, Strept. pyogenes, Strept. pneumoniae and Cl. perfringens. In infections transnasally induced by Strept. pneumoniae, midecamycin acetate showed therapeutic efficacy 2 or 5 times greater than that of josamycin or midecamycin, despite that MICs of midecamycin acetate were equal to josamycin or midecamycin. Moreover, midecamycin acetate showed high therapeutic efficacy for subcutaneous infections due to Staph. aureus, suggesting that it exerts pronounced antibacterial activities against not only systemic infections but also local infections.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
