Midecamycin | CAS#35457-80-8

MedKoo Cat#: 341151 | Name: Midecamycin

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Description:

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

Midecamycin is a naturally occurring 16-membered macrolide that fits under the category of acetoxy-substituted macrolide antibiotics. In this molecule, an acetoxy group is substituted on the position 9 of the 16-member ring and on position 4 of the terminal sugar.

Chemical Structure

Midecamycin

CAS#35457-80-8 (free base)

Theoretical Analysis

MedKoo Cat#: 341151

Name: Midecamycin

CAS#: 35457-80-8 (free base)

Chemical Formula: C41H67NO15

Exact Mass: 813.4511

Molecular Weight: 813.98

Elemental Analysis: C, 60.50; H, 8.30; N, 1.72; O, 29.48

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 350.00	2 Weeks
100mg	USD 600.00	2 Weeks

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Related CAS #

55881-07-7 (acetate) 35457-80-8 (free base)

Synonym

Midecamycin; SF 837; SF-837; SF837;

IUPAC/Chemical Name

7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4',4''-dipropionate (ester)

InChi Key

DMUAPQTXSSNEDD-QALJCMCCSA-N

InChi Code

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

SMILES Code

CCC(=O)O[C@@H]1CC(=O)O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C

Appearance

Solid powder

Purity

>90% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Midecamycin, an acetoxy-substituted macrolide antibiotic, is tested against gram-positive and gram-negative bacteria.

In vitro activity:

Midecamycin, an acetoxy-substituted macrolide antibiotic, was tested against gram-positive and gram-negative bacteria. It inhibited the majority of streptococci, staphylococci, and strains of Haemophilus and Listeria at concentrations of less than 3.1 micrograms/ml. Reference: Antimicrob Agents Chemother. 1983 Sep;24(3):443-4. https://pubmed.ncbi.nlm.nih.gov/6639001/

In vivo activity:

TBD

	Solvent	mg/mL	mM	comments
Solubility
	Ethanol	100.0	122.85

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 813.98 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.

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

Formulation protocol:

1. Poachanukoon O, Koontongkaew S, Monthanapisut P, Pattanacharoenchai N. Macrolides attenuate phorbol ester-induced tumor necrosis factor-α and mucin production from human airway epithelial cells. Pharmacology. 2014;93(1-2):92-9. doi: 10.1159/000358366. Epub 2014 Feb 18. PMID: 24556631. 2. Neu HC. In vitro activity of midecamycin, a new macrolide antibiotic. Antimicrob Agents Chemother. 1983 Sep;24(3):443-4. doi: 10.1128/AAC.24.3.443. PMID: 6639001; PMCID: PMC185343.

In vitro protocol:

In vivo protocol:

TBD

1: Zhang X, Li J, Wang C, Song D, Hu C. Identification of impurities in macrolides by liquid chromatography-mass spectrometric detection and prediction of retention times of impurities by constructing quantitative structure-retention relationship (QSRR). J Pharm Biomed Anal. 2017 Oct 25;145:262-272. doi: 10.1016/j.jpba.2017.06.069. Epub 2017 Jul 6. PubMed PMID: 28700970. 2: Zhang J, Zhong J, Dai J, Wang Y, Xia H, He W. [Expression of 4"-O-isovaleryltransferase gene from Streptomyces thermotolerans in Streptomyces lividans TK24]. Sheng Wu Gong Cheng Xue Bao. 2014 Sep;30(9):1390-400. Chinese. PubMed PMID: 25720154. 3: Hao D, Xing X, Li G, Wang X, Zhang M, Zhang W, Xia X, Meng J. Prevalence, toxin gene profiles, and antimicrobial resistance of Staphylococcus aureus isolated from quick-frozen dumplings. J Food Prot. 2015 Jan;78(1):218-23. doi: 10.4315/0362-028X.JFP-14-100. PubMed PMID: 25581200. 4: Poachanukoon O, Koontongkaew S, Monthanapisut P, Pattanacharoenchai N. Macrolides attenuate phorbol ester-induced tumor necrosis factor-α and mucin production from human airway epithelial cells. Pharmacology. 2014;93(1-2):92-9. doi: 10.1159/000358366. Epub 2014 Feb 18. PubMed PMID: 24556631. 5: Zhu P, Chen D, Liu W, Zhang J, Shao L, Li JA, Chu J. Hydroxylation and hydrolysis: two main metabolic ways of spiramycin I in anaerobic digestion. Bioresour Technol. 2014 Feb;153:95-100. doi: 10.1016/j.biortech.2013.11.073. Epub 2013 Dec 1. PubMed PMID: 24345568. 6: Chatterjee S, Richert L, Augustijns P, Annaert P. Hepatocyte-based in vitro model for assessment of drug-induced cholestasis. Toxicol Appl Pharmacol. 2014 Jan 1;274(1):124-36. doi: 10.1016/j.taap.2013.10.032. Epub 2013 Nov 7. PubMed PMID: 24211272. 7: Belov BS. [Pharyngeal A-streptococcal infection encountered in the practical work of an internal medicine specialist]. Vestn Otorinolaringol. 2013;(3):39-43. Review. Russian. PubMed PMID: 23887373. 8: Armenta S, Alcalà M, Blanco M, González JM. Ion mobility spectrometry for the simultaneous determination of diacetyl midecamycin and detergents in cleaning validation. J Pharm Biomed Anal. 2013 Sep;83:265-72. doi: 10.1016/j.jpba.2013.05.016. Epub 2013 May 20. PubMed PMID: 23770781. 9: Wan H, Zhao F, Zeng B. Direct electrochemistry and voltammetric determination of midecamycin at a multi-walled carbon nanotube coated gold electrode. Colloids Surf B Biointerfaces. 2011 Aug 1;86(1):247-50. doi: 10.1016/j.colsurfb.2011.03.037. Epub 2011 Apr 12. PubMed PMID: 21543194. 10: Chernomortseva ES, Pokrovskiĭ MV, Titareva LV, Pokrovskaia TG, Gureev VV. [Integrated assessment of endothelio- and cardioprotective activity of macrolide antibiotics in nitric oxide deficiency model]. Eksp Klin Farmakol. 2010 Sep;73(9):20-3. Russian. PubMed PMID: 21086648. 11: Burnell KJ, Boyce N, Hunt N. A Good War? Exploring British veterans' moral evaluation of deployment. J Anxiety Disord. 2011 Jan;25(1):36-42. doi: 10.1016/j.janxdis.2010.07.003. Epub 2010 Jul 15. PubMed PMID: 20688466. 12: Chernomortseva ES, Pokrovskiĭ MV, Pokrovskaia TG, Artiushkova EB, Gureev VV. [Experimental study of cardioprotective and endothelioprotective action of macrolides and azalides]. Eksp Klin Farmakol. 2009 Mar-Apr;72(2):29-31. Russian. PubMed PMID: 19441724. 13: Ma C, Wu L, Dai J, Zhou H, Li J, Sun X, Zhang K, Xia H, Wang Y. [Acylation specificity of midecamycin 3-O-acyltransferase within Streptomyces spiramyceticus F21]. Sheng Wu Gong Cheng Xue Bao. 2008 Dec;24(12):2086-92. Chinese. PubMed PMID: 19306580. 14: Araújo L, Demoly P. Macrolides allergy. Curr Pharm Des. 2008;14(27):2840-62. Review. PubMed PMID: 18991703. 15: Xia H, Wang Y. A ketoreductase gene from Streptomyces mycarofaciens 1748 DNA involved in biosynthesis of a spore pigment. Sci China C Life Sci. 1997 Dec;40(6):636-41. doi: 10.1007/BF02882694. PubMed PMID: 18726288. 16: Liu YQ, Chen QY, Chen BM, Liu SG, Deng FL, Zhou P. Quantitative determination of erythromycylamine in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study of dirithromycin. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Mar 15;864(1-2):1-8. doi: 10.1016/j.jchromb.2007.12.021. Epub 2008 Jan 4. PubMed PMID: 18296129. 17: Miura T, Kurihara K, Furuuchi T, Yoshida T, Ajito K. Novel 16-membered macrolides modified at C-12 and C-13 positions of midecamycin A1 and miokamycin. Part 1: Synthesis and evaluation of 12,13-carbamate and 12-arylalkylamino-13-hydroxy analogues. Bioorg Med Chem. 2008 Apr 1;16(7):3985-4002. doi: 10.1016/j.bmc.2008.01.027. Epub 2008 Jan 19. PubMed PMID: 18258437. 18: Mazzariol A, Koncan R, Vitali LA, Cornaglia G. Activities of 16-membered ring macrolides and telithromycin against different genotypes of erythromycin-susceptible and erythromycin-resistant Streptococcus pyogenes and Streptococcus pneumoniae. J Antimicrob Chemother. 2007 Jun;59(6):1171-6. Epub 2007 Apr 3. PubMed PMID: 17405779. 19: Cong L, Piepersberg W. Cloning and characterization of genes encoded in dTDP-D-mycaminose biosynthetic pathway from a midecamycin-producing strain, Streptomyces mycarofaciens. Acta Biochim Biophys Sin (Shanghai). 2007 Mar;39(3):187-93. PubMed PMID: 17342257. 20: Sugiyama K, Shirai R, Mukae H, Ishimoto H, Nagata T, Sakamoto N, Ishii H, Nakayama S, Yanagihara K, Mizuta Y, Kohno S. Differing effects of clarithromycin and azithromycin on cytokine production by murine dendritic cells. Clin Exp Immunol. 2007 Mar;147(3):540-6. PubMed PMID: 17302905; PubMed Central PMCID: PMC1810497.