8018. Pyrrolnitrin

Nomenclature

CAS number: 1018-71-9
3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole; 3-chloro-4-(2′-nitro-3′-chlorophenyl)pyrrole; PN; Pyroace (Fujisawa).
C10H6Cl2N2O2; mol wt 257.07.
C 46.72%, H 2.35%, Cl 27.58%, N 10.90%, O 12.45%.

Description and references

Antifungal antibiotic isolated from Pseudomonas pyrrocinia n. sp.: K. Arima et al., Agric. Biol. Chem. 28, 575 (1964); eidem, J. Antibiot. 18, 201 (1965). Structure: Imanaka et al., ibid. 207. Synthesis: S. Umio et al., BE 670427; eidem, US 3428648 (1964, 1969 both to Fujisawa); Nakano et al., Tetrahedron Lett. 1966, 737; S. Umio et al. (10 publications) Chem. Pharm. Bull. 17, 559-628 (1969); Gosteli, Helv. Chim. Acta 55, 451 (1972). Pharmacological studies: M. Nishida et al., J. Antibiot. 18, 211 (1965).

Chemical structure

Properties

Pale yellow crystals from hot cyclohexane, mp 124.5°. Gradually changes to a red or brown color on exposure to sunlight and loses antibiotic activity. uv max: 252 nm (ε 7500). Slightly sol in water, petr ether, cyclohexane; sol in methanol, ethanol, butanol, acetone, ethyl acetate, benzene, ether, chloroform, carbon tetrachloride, pyridine, acetic acid. LD50 in rats, rabbits (mg/kg): 68, 105 i.p. (Nishida).

Therapeutic Category

Antifungal.

Keywords

Antifungal (Antibiotics)