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Polymyxin B1

Names

[ CAS No. ]:
4135-11-9

[ Name ]:
Polymyxin B1

[Synonym ]:
(6S)-N-[(2S)-4-Amino-1-{[(2S,3R)-1-{[(2S)-4-amino-1-oxo-1-({(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-isobutyl-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl}amino)-2-butanyl]amino}-3-hydroxy-1-oxo-2-butanyl]amino}-1-oxo-2-butanyl]-6-methyloctanamide
polymyxin B
Octanamide, N-[(1S)-3-amino-1-[[[(1S,2R)-1-[[[(1S)-3-amino-1-[[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-15-(phenylmethyl)-1,4,7,10,13,16,19-heptaazacyclotricos-21-yl]amino]carbonyl]propyl]amino]carbonyl]-2-hydroxypropyl]amino]carbonyl]propyl]-6-methyl-, (6S)-
Polymyxin B1
polymixin B1

Biological Activity

[Description]:

Polymyxin B1 is a potent antimicrobial lipopeptide first derived from Bacilus polymyxa. Polymyxin B1 is the major component in Polymyxin B (HY-A0248). Polymyxin B1 can induce lysis of bacterial cells through interaction with their membranes. Polymyxin B1 has the potential for multidrug-resistant Gram-negative bacterial infections treatment[1][2].

[Related Catalog]:

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

[In Vitro]

Polymyxin B1 has antimicrobial activity that againsts Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii ATCC BAA 747, Klebsiella pneumoniae ATCC 13883, P. aeruginosa 9019, A. baumannii 1261 and K. pneumoniae VM9 isolates with MIC values of 4 μg/mL, 2 μg/mL, 2 μg/mL, 4 μg/mL, 4 μg/mL and 2 μg/mL, respectively[3]. Polymyxin B1 strongly inhibits protein synthesis in yeast, and in E. coli and S. aureus[4].

[In Vivo]

The pharmacokinetics of Polymyxin B1 is investigated in a rat model following intravenous administration (0.8 mg/kg). The area under the concentration-time curve for Polymyxins B1 is greater than those of colistins A and B. Colistin A colistin B. The clearance value of Polymyxins B1 is 2.39 mL/min/kg, the plasma protein binding is 82.3%, the elimination half-life is 79.5 min and the AUC0-∞ is 365 mg•min/L[5].

[References]

[1]. Kwa AL, et al. Pharmacokinetics of polymyxin B1 in patients with multidrug-resistant Gram-negative bacterial infections. Diagn Microbiol Infect Dis. 2008 Feb;60(2):163-7.

[2]. Berglund NA, et al. Interaction of the antimicrobial peptide polymyxin B1 with both membranes of E. coli: a molecular dynamics study. PLoS Comput Biol. 2015 Apr 17;11(4):e1004180.

[3]. Tam VH, et al. In vitro potency of various polymyxin B components. Antimicrob Agents Chemother. 2011 Sep;55(9):4490-1.

[4]. Alonso MA, et al. Compounds affecting membranes that inhibit protein synthesis in yeast. Antimicrob Agents Chemother. 1979 Dec;16(6):750-6.

[5]. Sivanesan S, et al. Pharmacokinetics of the Individual Major Components of Polymyxin B and Colistin in Rats. J Nat Prod. 2017 Jan 27;80(1):225-229.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
1571.6±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C56H98N16O13

[ Molecular Weight ]:
1203.477

[ Flash Point ]:
904.2±34.3 °C

[ Exact Mass ]:
1202.749878

[ PSA ]:
490.66000

[ LogP ]:
-2.87

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.592

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TR1055000
CHEMICAL NAME :
Polymyxin B1
CAS REGISTRY NUMBER :
4135-11-9
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C56-H98-N16-O13
MOLECULAR WEIGHT :
1203.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
19 mg/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: 4(1),334,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
80 mg/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: 4(1),334,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1500 ug/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: 4(1),334,1980

Precursor & DownStream

Precursor

DownStream

Related Compounds