Pyrrolnitrin

Title: Pyrrolnitrin
CAS Registry Number: 1018-71-9
CAS Name: 3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole
Additional Names: 3-chloro-4-(2¢-nitro-3¢-chlorophenyl)pyrrole; PN
Trademarks: Pyroace (Fujisawa)
Molecular Formula: C10H6Cl2N2O2
Molecular Weight: 257.07
Percent Composition: C 46.72%, H 2.35%, Cl 27.58%, N 10.90%, O 12.45%
Literature 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).
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 (e 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).
Melting point: mp 124.5°
Absorption maximum: uv max: 252 nm (e 7500)
Toxicity data: LD50 in rats, rabbits (mg/kg): 68, 105 i.p. (Nishida)
Therap-Cat: Antifungal.
Keywords: Antifungal (Antibiotics).
Pyrrolysine Pyruvate Decarboxylase Pyruvic Acid Pyrvinium Pamoate Q-Enzyme

Pyrrolnitrin
Pyrrolnitrin.svg
Identifiers
CAS number 1018-71-9
PubChem 13916
KEGG D01094 YesY
ATC code D01AA07
Jmol-3D images Image 1
Properties
Molecular formula C10H6Cl2N2O2
Molar mass 257.07284
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Pyrrolnitrin is an antifungal antibiotic.[1] Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite.[2][3]