4609. Hamycin

Nomenclature

CAS number: 1403-71-0
Primamycin.

Description and references

Polyene antibiotic complex produced by Streptomyces pimprina: M. J. Thirumalachar et al., Hind. Antibiot. Bull. 3, 136 (1961), C.A. 55, 27515i (1961); M. J. Thirumalachar, US 3261751 (1966 to Hindustan Antibiot.). Formerly believed to be identical to trichomycin and candicidin, q.q.v.: H. Burrows, D. Calam, J. Chromatogr. 53, 566 (1970). Subsequent HPLC studies have shown the three polyene antibiotics to be different entities: P. Helboe et al., ibid. 189, 249 (1980). Structural study showing hamycin to be a mixture of components A, B, C, D: R. C. Pandey, K. L. Rinehart, 16th Interscience Conference on Antimicrob. Ag. Chemother., Chicago, 1976, Abstracts of Papers, no. 41. Absorption, excretion, tissue concentration: M. G. Phatak et al., Indian J. Exp. Biol. 12, 284 (1974), C.A. 82, 118703j (1975). Toxicity studies: Williams et al., Antimicrob. Agents Chemother. 1964, 737; antifungal activity: A. C. Parekh, C. V. Dave, Life Sci. 19, 1737 (1976). HPLC study: W. Mechlinski, C. P. Schaffner, J. Antibiot. 33, 591 (1980). Review of clinical use in mycoses: M. J. Thirumalachar, J. Sci. Ind. Res. 31, 542-544 (1972), C.A. 79, 13308 (1973).

Properties

Yellow amorphous powder, no definite mp, decomp 160°. [α]D25+216°. uv max (80% methanol): 383 nm (E1%1cm 916). An amphoteric compd. Almost insol in water, benzene, chloroform, dry lower aliphatic alcohols, ether. Sol in basic solvents such as pyridine, collidine, and in aq lower alcohols. In concd H2SO4 gives stable blue color; no coloration with ferric chloride or with HCl. LD50 i.v. in mice (using sodium carboxymethyl cellulose as a vehicle): 6.16 mg/kg (Williams). Also reported as LD50 i.v. in Swiss mice (using a colloidal suspension): 1.20 mg/kg (Parekh, Dave).

Derivative

Hamycin A.

Properties

mp >300° (dec), [α]D24 +181.1° (c = 0.6 in DMF). uv max: 380 nm (E1%1cm 989).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Antibiotics); Polyenes