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P1382

Sigma-Aldrich

Phenoxymethylpenicillinic acid potassium salt

potency: 1444-1536 units per mg

Synonym(s):

Penicillin V potassium salt

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About This Item

Empirical Formula (Hill Notation):
C16H17N2O5SK
Molecular Weight:
388.48
EC Number:
205-086-5
MDL number:
MFCD00051771
UNSPSC Code:
12352106
PubChem Substance ID:
24898194
NACRES:
NA.85

form

solid

potency

1444-1536 units per mg

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell wall synthesis | interferes

SMILES string

[K+].CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C([O-])=O

InChI

1S/C16H18N2O5S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1

InChI key

HCTVWSOKIJULET-LQDWTQKMSA-M

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General description

Chemical structure: ß-lactam

Application

Phenoxymethylpenicillinic acid, also known as Penicillin V, is a narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V is a penicillin β-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. It is commonly used in cell culture in combination with streptomcyin and other antibiotics. It is used to study penicillin-binding protein 2, molecular cloning of the Bacillus sphaericus penicillin V amidase gene, and gastrointestinal persistence and bile tolerance of Listeria monocytogenes.

Biochem/physiol Actions

Phenoxymethylpenicillinic acid binds to specific penicillin-binding proteins (PBPs) and inhibits the synthesis of bacterial cell walls by preventing cell wall peptidoglycan chain cross-linking. This causes cell lysis, which is mediated by autolytic enzymes such as autolysins. Phenoxymethylpenicillnic acid may interfere with autolysin inhibitors.

Other Notes

10mu,100mu
Keep container tightly closed in a dry and well-ventilated place.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Olsson et al.
Applied and environmental microbiology, 49(5), 1084-1089 (1985-05-01)
The Bacillus sphaericus gene coding for penicillin V amidase, which catalyzes the hydrolysis of penicillin V to yield 6-aminopenicillanic acid and phenoxyacetic acid, has been isolated by molecular cloning in Escherichia coli. The gene is contained within a 2.2-kilobase HindIII-PstI
Máire Begley et al.
Infection and immunity, 73(2), 894-904 (2005-01-25)
Listeria monocytogenes must resist the deleterious actions of bile in order to infect and subsequently colonize the human gastrointestinal tract. The molecular mechanisms used by the bacterium to resist bile and the influence of bile on pathogenesis are as yet
Susumu Ochiai et al.
The Journal of antimicrobial chemotherapy, 60(1), 54-60 (2007-06-02)
In Neisseria gonorrhoeae, the mosaic structure of penicillin-binding protein 2 (PBP 2), composed of fragments of PBP 2 from Neisseria cinerea and Neisseria perflava, was significantly associated with decreased susceptibility to cephalosporins, particularly oral cephalosporins. The aim of this study
Adel Ben Salem et al.
Bioorganic & medicinal chemistry, 19(24), 7534-7540 (2011-11-15)
Two well-known antibiotic heterocycles, the 'quinolone' nalidixic acid and the β-lactam penicillin V, active at different levels of the bacterial growth process, have been attached via an ether-ester junction to the p-tert-butylcalix[4]arene lower rim, in alternate position. The resulting hydrophobic

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