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Key Documents

PENK

Sigma-Aldrich

Penicillin G potassium salt

95.0 - 102.0%

Synonym(s):

Benzylpenicillin potassium salt

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About This Item

Empirical Formula (Hill Notation):
C16H17KN2O4S
CAS Number:
Molecular Weight:
372.48
Beilstein:
3832841
EC Number:
MDL number:
UNSPSC Code:
51283424
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Assay

95.0 - 102.0%

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

SMILES string

[K+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)Cc3ccccc3)C([O-])=O

InChI

1S/C16H18N2O4S.K/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/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

IYNDLOXRXUOGIU-LQDWTQKMSA-M

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Application

Penicillin G is a narrow spectrum antibiotic derived from Streptococcus pneumoniae. It is the drug of choice for groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridians group streptococci, and non-penicillinase producing staphylococcus. The potassium salt has been used to study murosomes of staphylococci† and the penicillin-induced lysis of Streptococcus mutans.

Biochem/physiol Actions

Mode of Action: Penicillin G acts by inhibiting cell wall synthesis through binding to penicillin binding proteins (PBPs), inhibiting peptidoglycan chain cross-linking.

Antimicrobial spectrum: This product is active against gram-positive and gram-negative bacteria.

Packaging

1mu,10mu,100mu

Caution

Solutions should be filter sterilized and stored at 2-8°C for 1 week or at -20°C for more lengthy periods. Solutions are stable at 37°C for 3 days.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Handle and store under inert gas. Keep in a dry place.Very soluble in water, slightly soluble in ethanol (96%), practically insoluble in methylene chloride

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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T A Kral et al.
Infection and immunity, 46(2), 442-447 (1984-11-01)
Treatment of Streptococcus mutans GS-5 cells with concentrations of penicillin G within a relatively narrow range resulted in substantial lysis. This penicillin-induced lysis was dependent upon cell density and pH of the lysis medium. Other oral streptococci (Streptococcus sobrinus, Streptococcus
P Giesbrecht et al.
Journal of bacteriology, 174(7), 2241-2252 (1992-04-01)
Electron microscopic research into the murosomes of staphylococci has shown that the number of murosomes involved in penicillin-induced death varies depending on the experimental conditions employed. With 0.1 micrograms of penicillin G per ml, only 1 of a total of
Mariagrazia Perilli et al.
Antimicrobial agents and chemotherapy, 57(2), 1047-1049 (2012-11-28)
Two laboratory mutant forms, TEM-149(H240) and TEM-149(H164-H240), of the TEM-149 extended-spectrum β-lactamase enzyme were constructed by site-directed mutagenesis. TEM-149(H240) and TEM-149(H164-H240) were similar in kinetic behavior, except with respect to benzylpenicillin and ceftazidime. Molecular modeling of the two mutant enzymes
Lemierre's syndrome in systemic lupus erythematosus: a report of two cases.
J C Rødgaard et al.
Scandinavian journal of rheumatology, 42(2), 167-168 (2013-01-15)
Congenital syphilis: the story of a greek tragedy.
Sarah Hawkes
Sexually transmitted diseases, 40(2), 95-96 (2013-01-17)

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