Midecamycins
Title: Midecamycins
Literature 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 Type: Midecamycin A1
CAS Registry Number: 35457-80-8
Additional Names: Leucomycin V 3,4B-dipropanoate; espinomycin A; mydecamycin; turimycin P3
Manufacturers' Codes: SF-837; YL-704B1
Trademarks: Aboren (Promeco); Medemycin (Meiji); Midecin (Farmaka); Momicine (Morrith); Myoxam (Menarini); Normicina (Meiji Seika); Rubimycin (Nikken)
Molecular Formula: C41H67NO15
Molecular Weight: 813.97
Percent Composition: C 60.50%, H 8.30%, N 1.72%, O 29.48%
Properties: Colorless needles from benzene, mp 155-156° (after drying at 80° for 8 hrs in vacuo). [a]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.
Melting point: mp 155-156° (after drying at 80° for 8 hrs in vacuo)
pKa: pKa¢ 6.9 in 50% aq ethanol
Optical Rotation: [a]D23 -67° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 232 nm (E1%1cm 325)
 
Derivative Type: Midecamycin A3
CAS Registry Number: 36025-69-1
Additional Names: 9-Deoxy-9-oxoleucomycin V 3,4B-dipropanoate; antibiotic SF-837A3
Molecular Formula: C41H65NO15
Molecular Weight: 811.95
Percent Composition: C 60.65%, H 8.07%, N 1.73%, O 29.56%
Properties: White powder, mp 122-125°. [a]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.
Melting point: mp 122-125°
pKa: pKa¢ 7.0 in 50% aq ethanol
Optical Rotation: [a]D22 -44° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 280 nm (E1%1cm 295)
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Macrolides.

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