CAS 69-57-8|PENICILLIN G SODIUM SALT U.S.P.|sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate|sodium benzylpenicillin(1-)|Benzylpenicillin|PE...

General Information

Structure

Molecular Formula

C₁₆H₁₇N₂NaO₄S

Molecular Mass

356.37195

Exact Mass

356.08067232

Charge

InChI

InChI=1S/C16H18N2O4S.Na/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

InChIKey

FCPVYOBCFFNJFS-LQDWTQKMSA-M

Canonic Smiles

O=C(Cc1ccccc1)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[Na+]

Isomeric Smiles

[Na+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)Cc3ccccc3)[C@H]2SC1(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

-2.29

LogD (pH = 5.5)

-0.88

Log P

1.08

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.53

Polar Surface Area

89.54

Polarizability

33.02

Molar Refractivity

95.36

LOG S

-4.56

Data Source

Names and Identifiers

Synonyms

PENICILLIN G SODIUM SALT U.S.P.BenzylpenicillinPENICILLIN G SODIUM SALTBenzylpenicillin sodium saltBenzylpenicillin sodium salt 钠盐Penicillin G sodium salt 钠盐Penicillin G sodium saltbenzylpenicillinic acid sodium saltAmerican penicillinmonosodium benzylpenicillinsodium benzylpenicillinatepenicillin G sodiumsodium penicillin Gbenzylpenicillin sodium saltbenzylpenicillin sodium

IUPAC name

sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

IUPAC Traditional name

sodium benzylpenicillin(1-) penicillin g sodium

Brand Name

Crystapen

Names and Identifiers

Registration numbers

CAS Number

69-57-8

EC Number

200-710-2

PubChem CID

23668834

PubChem SID

162089932248983842489906857269794

Beilstein Number

MDL Number

CompTox Database

BKMS React Database

ACToR Database

BRENDA Database

3.5.1.884.6.1.181.4.3.33.4.11.143.5.1.112.4.1.1293.5.2.63.5.1.23.4.16.43.4.17.82.7.8.12

SureChEMBL Database

SCHEMBL34218

BRENDA Ligand Database

2664

CHEMBL

CHEMBL1126

CHEBI ID

CHEBI:51765

Registration numbers

Properties

Product Information

Grade

USP

Certificate of Analysis

Download link

Potency

≥1477 units per mg

Suitability

suitable for cell culture

Physical Property

Apperance

powder

Solubility

H2O: soluble100 mg/mL (Solutions should be filter sterilized and stored at 2-8°C for 1 week or at -20°C for extended periods. Solutions are stable at 37°C for 3 days.)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02100548

Sodium Salt
(Not less than 1,500 units per mg)
Meets or exceeds U.S.P. specifications

02156065

Sodium Salt
Approx. 1650 units per mg.

Sigma Aldrich

PENNA

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria.
Penicillin G is active against gram-positive and gram-negative aerobic and anaerobic bacteria. Penicillin G inhibits cell wall synthesis by binding to penicillin binding proteins (PBPs), which inhibits peptidoglycan chain cross-linking. Penicillin G is stable against hydrolysis by β-lactamases, such as penicillinases and cephalosporinases.
Application
Penicillin G is narrow spectrum antibiotic. It is the drug of choice for Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Penicillin G sodium salt is used to study the diagnostic and therapeutic implications of gentamicin-resistant Enterococcus faecalis sequence type 6 with reduced penicillin susceptibility 1. It is used in cell culture alone as well as in combination with streptomcyin and other antibiotics2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

P3032

Biochem/physiol Actions
Mode of Action: Inhibits bacterial cell wall synthesis.Antimicrobial spectrum: Gram-positive bacteria.
Reconstitution
Recommended for use in cell culture media at 100,000 units/L. Solutions should be filter sterilized and stored at 2-8 °C for up to 1 week, -20 °C for extended periods. Solutions are stable at 37 °C for 3 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Molecule Details

References

PubChem Literature

No Data Available

Click here to submit data

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

IUPAC Traditional name

sodium benzylpenicillin(1-) penicillin g sodium

Brand Name

Crystapen

Registration numbers

CAS Number

69-57-8

EC Number

200-710-2

PubChem CID

23668834

PubChem SID

162089932248983842489906857269794

Beilstein Number

MDL Number

CompTox Database

BKMS React Database

ACToR Database

BRENDA Database

3.5.1.884.6.1.181.4.3.33.4.11.143.5.1.112.4.1.1293.5.2.63.5.1.23.4.16.43.4.17.82.7.8.12

SureChEMBL Database

SCHEMBL34218

BRENDA Ligand Database

2664

CHEMBL

CHEMBL1126

CHEBI ID

CHEBI:51765

Properties

Product Information

Grade

USP

Certificate of Analysis

Download link

Potency

≥1477 units per mg

Suitability

suitable for cell culture

Physical Property

Apperance

powder

Solubility

H2O: soluble100 mg/mL (Solutions should be filter sterilized and stored at 2-8°C for 1 week or at -20°C for extended periods. Solutions are stable at 37°C for 3 days.)

Molecule Details

MP Biomedicals

02100548

Sodium Salt
(Not less than 1,500 units per mg)
Meets or exceeds U.S.P. specifications

02156065

Sodium Salt
Approx. 1650 units per mg.

Sigma Aldrich

PENNA

P3032

References

PubChem Literature

No Data Available

Click here to submit data

Bioactivity

PubChem BioAssay

Molecule

ID:102198