5348. Laidlomycin

Nomenclature

CAS number: 56283-74-0
16-Deethyl-3-O-demethyl-16-methyl-3-O-(1-oxopropyl)monensin.
C37H62O12; mol wt 698.88.
C 63.59%, H 8.94%, O 27.47%.

Description and references

Polyether ionophore antibiotic; structurally related to monensin, q.v. Isoln from Streptomyces spp. and antimicrobial activity: F. Kitame et al., J. Antibiot. 27, 884 (1974). Structure determn: F. Kitame, N. Ishida, ibid. 29, 759 (1976). Prepn of esters: A. F. Kluge, R. D. Clark, EP 24189 (1981 to Syntex). 13C-NMR study and enhancement of biological activities: R. D. Clark et al., J. Antibiot. 35, 1527 (1982). Mechanism of action study: U. Grfe et al., J. Basic Microbiol. 29, 391 (1989). HPLC determn in fermentation broth: M. Beran et al., Chromatographia 31, 603 (1991). Effect on cattle growth: M. T. Van Koevering et al., 1991 Animal Science Research Report (Agricultural Experiment Station, Oklahoma State University, Stillwater, OK, 1991) 241; M. L. Galyean et al., J. Anim. Sci. 70, 2950 (1992).

Chemical structure

Properties

Colorless prisms from chloroform-ethyl acetate. mp 151-153°. [α]D22 +51.3° (c=0.2 in CHCl3). Sol in CHCl3, acetone, alcohols. Insol in water, n-hexane. LD50 in mice (mg/kg): 5 i.p.; 1 i.v.; 2.5 s.c. (Kitame).

Derivative

Propionate potassium.

Nomenclature

CAS number: 84799-02-0
RS-11988; Cattlyst (Syntex).
C40H65KO13; mol wt 793.03.
C 60.58%, H 8.26%, K 4.93%, O 26.23%.

Properties

mp 190-192°.

Therapeutic Category (Veterinary)

Growth promotant.