Midecamycin

Midecamycin is a macrolide antibiotic[1] that is synthesized from Streptomyces mycarofaciens.[2]

Midecamycin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-{[(4R,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-(propanoyloxy)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl propanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.047.784
Chemical and physical data
FormulaC41H67NO15
Molar mass813.979 g·mol−1
3D model (JSmol)
Melting point155 to 156 °C (311 to 313 °F)
Solubility in waterSoluble in acidic/low pH water; Very soluble in methanol, chloroform, ethyl acetate, benzene, ethyl ether; Almost completely in ethanol(>95.5) mg/mL (20 °C)
SMILES
  • O=CC[C@H]3C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)CC)[C@H](OC)[C@H]3O[C@@H]2O[C@@H]([C@@H](O[C@@H]1O[C@H]([C@H](OC(=O)CC)[C@](O)(C1)C)C)[C@H](N(C)C)[C@H]2O)C)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 Y
  • Key:DMUAPQTXSSNEDD-QALJCMCCSA-N Y
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Physical Properties

Its melting point may vary depending on the compound type and the source consulted. For example, the Merck Index gives a melting point of 155-156 Celsius for the A1 type while the Japanese Pharmacopoeia reports 153-158 Celsius. The Merck Index also gives a melting point of 122-125 Celsius for the A3 type.

References
  1. Salhi A, Vindel JA, Brunaud M, Berceaux G, Marin A, Wuatelet C (1977). "Properties of midecamycin, a new macrolide antibiotic". Giornale Italiano Di Chemioterapia. 24 (1–2): 67–76. PMID 308022.
  2. Wang YG, Hutchinson CR (1989). "Cloning of midecamycin biosynthetic genes from Streptomyces mycarofaciens 1748". Chinese Journal of Biotechnology. 5 (4): 191–201. PMID 2491329.
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