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Pyrrolnitrin

Names

[ CAS No. ]:
1018-71-9

[ Name ]:
Pyrrolnitrin

[Synonym ]:
Pyrrolnitrine
Pyrrolnitrin
Pirrolnitrina
Pyroace
3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Pyrrolnitrinum

Biological Activity

[Description]:

Pyrrolnitrin is an antibiotic isolated from Pseudomonas pyrrocinia. Pyrrolnitrin shows a broad spectrum of antibiotic activity against fungi, yeast and gram-positive bacteria[1].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Fungal
Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Target: fungi, yeast and gram-positive bacteria[1]


[In Vitro]

Pyrrolnitrin (0-100 μg/ml) shows antibiotic activities against various bacteria and fungi with different MIC values. It against Staphylococcus aureus, Mycobacterium, Bacillus subtillis, Candida albicans, Aspergillus niger, and Trichophyton rubrum with MIC values of 50 μg/ml, 100 μg/ml, 0.78 μg/ml, 10 μg/ml, 12.5 μg/ml, and 1 μg/ml, respectively[1]. Pyrrolnitrin (0-100 μg/ml) exhibits antimicrobial effect in a microtitre plate assay. It against Arthrobacter oxydans ATCC 14358, Bacillus coagulans ATCC 7050, Bacillus licheniformis ATCC 14580, Bacillus subtilis ATCC 6051, and Bacillus thuringiensis ATCC 10792 with MIC of 6.25 μg/ml[2].

[References]

[1]. K H van Pée, et al. Biosynthesis of Pyrrolnitrin and Other Phenylpyrrole Derivatives by Bacteria. Nat Prod Rep. 2000 Apr;17(2):157-64.

[2]. N el-Banna, et al. Pyrrolnitrin From Burkholderia Cepacia: Antibiotic Activity Against Fungi and Novel Activities Against Streptomycetes.J Appl Microbiol. 1998 Jul;85(1):69-78.

[3]. R S Gordee, et al.Systemic Antifungal Activity of Pyrrolnitrin.Appl Microbiol. 1969 May;17(5):690-4.

Chemical & Physical Properties

[ Density]:
1.523g/cm3

[ Boiling Point ]:
410.5ºC at 760mmHg

[ Molecular Formula ]:
C10H6Cl2N2O2

[ Molecular Weight ]:
257.07300

[ Flash Point ]:
202.1ºC

[ Exact Mass ]:
255.98100

[ PSA ]:
61.61000

[ LogP ]:
4.41990

[ Vapour Pressure ]:
1.42E-06mmHg at 25°C

[ Index of Refraction ]:
1.65

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UX9450000
CHEMICAL NAME :
Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)-
CAS REGISTRY NUMBER :
1018-71-9
BEILSTEIN REFERENCE NO. :
1287646
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C10-H6-Cl2-N2-O2
MOLECULAR WEIGHT :
257.08
WISWESSER LINE NOTATION :
T5MJ CG DR CG BNW

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue)
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
68 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue)
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue)
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
86 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue)
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,44,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
105 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue)
REFERENCE :
JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%


Related Compounds

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