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Penicillin G

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Identification
Molecular formula
C16H18N2O4S
CAS number
61-33-6
IUPAC name
(2S,5R,6R)-6-[(2-carboxy-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Penicillin G is typically stable as a solid at room temperature, appearing as a crystalline powder. It is generally stored in this solid form to maintain its stability and efficacy.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.00
Boiling point (Celsius)
298.00
Boiling point (Kelvin)
571.00
General information
Molecular weight
334.39g/mol
Molar mass
334.3900g/mol
Density
1.4000g/cm3
Appearence

Penicillin G is typically a white or off-white crystalline powder. It can vary in form from needle-like crystals to amorphous powder, depending on its processing.

Comment on solubility

Solubility of (2S,5R,6R)-6-[(2-carboxy-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

The solubility of this complex compound can be influenced by several factors, particularly due to its structural characteristics and functional groups. Here are some key points to consider:

  • Polarity: The presence of polar functional groups such as carboxylic acids can enhance water solubility. In this compound, the two carboxylic acid groups may contribute significantly to its solubility in water.
  • Hydrogen bonding: The ability to form hydrogen bonds with water molecules will likely improve its solubility, making it more compatible in aqueous solutions.
  • Solvent interactions: The solubility may vary in different solvents, with potential greater solubility in organic solvents due to its aromatic and aliphatic components.
  • Concentration: As with many compounds, solubility can also be concentration-dependent; thus, higher concentrations might affect the solubility limit.

Overall, while this compound may exhibit reasonable solubility in water due to its polar characteristics, it is essential to consider various environmental factors and the specific medium used to determine its precise solubility behavior. As a rule of thumb, like dissolves like, meaning polar solvents are better suited for dissolving polar compounds, while nonpolar solvents will be less effective.


In summary, the combination of functional groups and the molecular structure of (2S,5R,6R)-6-[(2-carboxy-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid suggests moderate to high solubility in polar solvents, particularly water.

Interesting facts

Interesting Facts about (2S,5R,6R)-6-[(2-carboxy-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound is known for its intricate structure and significant biological activity, making it an intriguing subject of study in the field of chemistry. Here are some fascinating points about this compound:

  • Complex Structure: It features a bicyclic framework combined with a thiazolidine ring, showcasing nature's ability to create intricate molecular architectures.
  • Biological Significance: Many compounds in this class exhibit antibiotic properties, providing potential avenues for drug development and therapeutic applications.
  • Mechanism of Action: It is believed to inhibit specific bacterial enzymes, a mechanism that could offer insights for combating antibiotic resistance.
  • Pharmacophore Characteristics: The presence of both a carboxylic acid and an amine group in its structure allows for numerous interactions with biological targets, enhancing its effectiveness.
  • Research Applications: The unique properties of this compound make it valuable for medicinal chemistry studies, particularly in the synthesis of new derivatives with improved bioactivity.

As noted by researchers, “the challenge lies not only in the synthesis but also in understanding the compound’s interaction with biological systems.” This highlights the ongoing exploration needed in the study of such complex molecules.

In summary, (2S,5R,6R)-6-[(2-carboxy-2-phenyl-acetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid stands as a testament to the intricate relationships within chemical structures and their potential for practical applications in medicine.

Synonyms
carbenicillin
Carboxybenzylpenicillin
4697-36-3
Carbenicilina
Carbenicilline
Carbenicillinum
alpha-Carboxybenzylpencillin
Carboxybenzylpenicillin acid
Carbenicillina [DCIT]
alpha-Phenyl(carboxymethylpenicillin)
Carbenicillina
Carbenicilina [INN-Spanish]
Carbenicilline [INN-French]
Carbenicillinum [INN-Latin]
Carbenicillin [INN:BAN]
Carbenicillin (INN)
CHEBI:3393
HSDB 3020
EINECS 225-171-0
6-(alpha-Carboxyphenylacetamido)penicillanic acid
G42ZU72N5G
(2S,5R,6R)-6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CARBENICILLIN [MI]
CARBENICILLIN [INN]
CARBENICILLIN [HSDB]
CARBENICILLIN [VANDF]
CARBENICILLIN [WHO-DD]
N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid
N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-azabicyclo(3.2.0)hept-6-yl)-2-phenylmalonamic acid
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
DTXSID6048464
BRL2064
Malonamic acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenyl-
(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CP-156392
Carboxybenzyl Penicillin
6beta-(2-carboxy-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Carbenicilina (INN-Spanish)
Carbenicilline (INN-French)
Carbenicillinum (INN-Latin)
Penicillin, Carboxybenzyl
(2S,5R,6R)-6-((2-carboxy-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-((carboxy(phenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
CARBANICILLIN
DTXCID2028438
J01CA03
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-(2.alpha.,5.alpha.,6.beta.)]-
225-171-0
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((CARBOXYPHENYLACETYL)AMINO-3,3-DIMETHYL-7-OXO-, (2S-(2ALPHA,5ALPHA,6BETA))-
Pyopen
CBPC
Carbenicillin (disodium)
CP 15639-2
UNII-G42ZU72N5G
NSC111071
(2S,5R,6R)-6-[(3-hydroxy-3-oxo-2-phenyl-propanoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Carbenicillin solution
Spectrum_000098
Spectrum2_000120
Spectrum3_000326
Spectrum4_000263
Spectrum5_000900
Epitope ID:116648
SCHEMBL3375
CHEMBL1214
BSPBio_001931
KBioGR_000726
KBioSS_000518
DivK1c_000735
SPBio_000140
GTPL10768
KBio1_000735
KBio2_000518
KBio2_003086
KBio2_005654
KBio3_001151
NINDS_000735
BCP28512
HY-B0525
DB00578
IDI1_000735
DA-71923
SBI-0051303.P003
NS00011609
C06869
D07614
Klebsiella Selective Supplement, for microbiology
EN300-19748910
Q1050019
BRD-A13078313-304-05-7
BRD-A13078313-304-06-5
BRD-A13078313-304-07-3
BRD-A13078313-304-08-1
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-