7049. Partricin

Nomenclature

CAS number: 11096-49-4
Ayfactin; SPA-S-132.

Description and references

Heptaene macrolide antibiotic complex produced by Streptomyces aureofaciens NRRL 3878. Isoln: T. Bruzzese, R. Ferrari, US 3773925 (1973 to SPA). Recovery and purification process: S. Magnaghi et al., GB 1462442 (1977 to SPA), C.A. 87, 66588a (1977). In vitro activity: W. Ritzerfeld, Farmaco Ed. Sci. 27, 235 (1972); G. A. Meloni et al., ibid. 34, 183 (1979). Use in treatment of benign prostatic hypertrophy: T. Bruzzese, L. Ferrari, US 4237117 (1980 to SPA). Separation, characterization and structure of components A and B: R. C. Tweit et al., J. Antibiot. 35, 997 (1982).

Chemical structure

Derivative

Partricin A.
C59H86N2O19.4H2O; mol wt 1199.38.
C 59.08%, H 7.90%, N 2.34%, O 30.68%.

Properties

Greenish-yellow powder, mp >300° (dec). uv max (75% methanol in DMF): 232, 240, 247, 288, 342, 358, 378, 400 nm (ε 33476, 32237, 22936, 15493, 58282, 76883, 102308, 89280). pKa's (70% aq DMF): 6.07, 8.91.

Derivative

Partricin B.
C58H84N2O19.2 1/2 H2O; mol wt 1158.33.
C 60.14%, H 7.74%, N 2.42%, O 29.70%.

Properties

Brownish-yellow powder, mp >300° (dec). uv max (75% methanol in DMF): 232, 240, 247, 288, 342, 358, 378, 400 nm (ε 34761, 32826, 23174, 20594, 50207, 73392, 100425, 87558). pKa's (70% aq DMF): 6.31, 8.95. [α]D26 +87.2° (c = 0.06 in DMF).

Derivative

Complex.

Properties

Amphoteric yellow crystals. uv max (ethanol): 401, 379, 359, 341 nm. Sol in DMF, DMSO, dimethyl acetamide, pyridine. Practically insol in water, common organic solvents. LD50 in mice (mg/kg): 300 orally; 0.5 i.p. (Bruzzese).

Derivative

Methyl ester see Mepartricin.