6183. Midecamycins
Description and references
Macrolide antibiotic complex produced by Streptomyces mycarofaciens nov. sp. Isoln and characterization of the major component, midecamycin A1: T. Tsuruoka et al., JP 71 28834; eidem, US 3761588 (1971, 1973 both to Meiji); eidem, J. Antibiot. 24, 319, 452 (1971). Structure: I. Shigeharu et al., ibid. 460. Isoln, properties, structures of the minor components, midecamycins A2, A3, A4: T. Tsuruoka et al., ibid. 476, 526. Enzymatic interconversion of A1 and A3: Y. Matsuhashi et al., ibid. 32, 777 (1979). Metabolism: T. Shomura et al., Chem. Pharm. Bull. 22, 2427 (1974). Pharmacokinetics: K. Fukaya et al., Chemotherapy (Tokyo) 21, 692 (1973). Pharmacology: K. Mashimo et al., ibid. 729. Antibacterial activity: T. Watanabe et al., ibid. 25, 1624 (1977). Toxicity and teratogenicity study in mice: M. Moriguchi et al., Jpn. J. Antibiot. 15, 187, 193 (1972), C.A. 78, 11652a, 11653b (1973).
Derivative
Midecamycin A1.Nomenclature
Properties
Colorless needles from benzene, mp 155-156° (after drying at 80° for 8 hrs in vacuo). [α]D23 67° (c = 1 in ethanol). uv max (ethanol): 232 nm (E1%1cm 325). Weakly basic; pKa′ 6.9 in 50% aq ethanol. Sol in methanol, ethanol, acetone, chloroform, ethyl acetate, benzene, ethyl ether, acidic water. Practically insol in n-hexane, petr ether, water.Derivative
Midecamycin A3.Nomenclature
Properties
White powder, mp 122-125°. [α]D22 44° (c = 1 in ethanol). uv max (ethanol): 280 nm (E1%1cm 295). pKa′ 7.0 in 50% aq ethanol. Solubilities similar to midecamycin A1.Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); Macrolides