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Penicillin G

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Identification
Molecular formula
C16H18N2O4S
CAS number
61-33-6
IUPAC name
(6R,7R)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, Penicillin G is typically in a solid state as a crystalline powder.

Melting point (Celsius)
114.00
Melting point (Kelvin)
387.15
Boiling point (Celsius)
770.00
Boiling point (Kelvin)
1 043.15
General information
Molecular weight
334.39g/mol
Molar mass
334.3890g/mol
Density
1.3300g/cm3
Appearence

Penicillin G appears as a white to off-white crystalline powder. It is often odorless or may have a faint odor. The compound is known for being slightly soluble in water and more soluble in organic solvents.

Comment on solubility

Solubility of (6R,7R)-7-[[[2R]-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility of the compound (6R,7R)-7-[[[2R]-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid can be influenced by several factors:

  • Polarity: The presence of polar functional groups such as carboxylic acid and amine groups suggests that this compound may have some level of solubility in polar solvents, particularly water.
  • Hydrogen Bonding: The ability of the compound to form hydrogen bonds enhances its solubility in aqueous solutions, which is crucial for its bioavailability.
  • pH Sensitivity: Given that this compound has acidic and basic functionalities, its solubility might vary with changes in pH, being more soluble in basic conditions where the carboxylic acid could be deprotonated.
  • Solvent Choice: It may also show variable solubility in organic solvents, depending on their polarity. For instance, it can be more soluble in solvents such as DMSO or methanol.

In summary, the solubility of this compound can be described as dependent on its chemical structure and the solvent environment. It illustrates how complex molecular arrangements can affect the overall behavior of chemical compounds in solution, leading to unique challenges and considerations in pharmaceutical applications. As the saying goes, "Solubility is more than a number; it's a reflection of molecular interaction."

Interesting facts

Interesting Facts about (6R,7R)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This compound is well-known in the realm of medicinal chemistry, particularly as a key player in the development of antibiotics. The structure reveals its complex nature, featuring both thiazolidine rings and a bicyclic framework which contribute to its biological activity. Here are some intriguing facts:

  • Antibiotic Properties: Known for its effectiveness against bacterial infections, this compound belongs to a class of antibiotics that disrupts bacterial cell wall synthesis.
  • Mechanism of Action: The compound functions primarily by inhibiting enzymes involved in the peptidoglycan biosynthesis, an essential component for bacterial cell wall integrity.
  • Synthetic Approaches: Scientists have developed various synthetic methods to create this compound, showcasing its structural complexity and the challenges associated with its synthesis.
  • Pharmacokinetics: Understanding how this compound is metabolized in the body is crucial for optimizing its therapeutic effects and minimizing side effects. Studies into its bioavailability and half-life continue to be a focus in pharmacology.
  • Drug Design: The structure serves as a template for creating semi-synthetic derivatives, enhancing potency and broadening spectrum of activity against resistant strains of bacteria.

As stated by a prominent chemist, "The intricacies of antibiotic design are like solving a puzzle where every piece matters towards the goal of eradicating bacterial infections." This compound exemplifies the intersection of chemistry and medicine, representing both challenges and breakthroughs in the fight against infectious diseases.

Synonyms
cephalexin
Cefalexin
15686-71-2
Keflex
Cephacillin
Ceporexin
Cepexin
Carnosporin
Cefaleksin
Cefalexina
Cefalexine
Cephalexine
Cephalexinum
Ceporexine
Mamalexin
Sinthecillin
Uphalexin
Alsporin
Celexin
Cepastar
Ceporex
Durantel
Felexin
Pyassan
Keflet
Cefalexinum
Cefaloto
Cefaseptin
Lexibiotico
Madlexin
Neolexina
Sencephalin
Larixin
Syncl
Cephalexin anhydrous
Novolexin
Biocef
Keforal
Panixine Disperdose
Lilly 66873
Cefalexin anhydrous
Anhydrous cephalexin
7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acid
Rilexine
CHEBI:3534
S 6437
7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid
DTXSID9022780
5SFF1W6677
7-(D-2-Amino-2-phenylacetamido)-3-methyl-delta3-cephem-4-carboxylic acid
(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
NSC-758162
DTXCID002780
(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((aminophenylacetyl)amino)-3-methyl-8-oxo-, (6R-(6alpha,7beta(R*)))-
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-aminophenylacetyl)amino)-3-methyl-8-oxo-, (6R,7R)-
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-amino-2-phenylacetamido)-3-methyl-8-oxo-, D-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-aminophenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)-
(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Kiflone
Tenkorex
Cephalexin USP
(6R,7R)-7-(((2R)-2-amino-2-phenylacetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-7-((2R)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
Cephalexin Monohydrochloride, Monohydrate
Rilexine Chewable Tablets
(6R,7R)-7-(((2R)-2-azaniumyl-2-phenylacetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate
(6R,7R)-7-((2R)-2-Amino-2-phenylacetylamino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
239-773-6
Cefalexin monohydrate
Cefanex
LY-66873
OBN7UDS42Y
Alcephin
Cefablan
Cefadin
Tepaxin
Palitrex
Cefalessina [DCIT]
Cefalexine [INN-French]
Cefalexinum [INN-Latin]
Cefalexina [INN-Spanish]
Cephalexin hydrate
Taicelexin
Cefalexin [INN]
Ceffanex
Cephanasten
CEFADROS
CEPHAMASTEN
EFALEXIN
GARASIN
IWALEXIN
KEFLORIDINA
ORACOCIN
Ceforal
Cophalexin
Factagard
Kefalospes
Lopilexin
Ortisporina
Sartosona
Servispor
Tokiolexin
Cefadal
Cefadina
Cefalin
Cefovit
Cephaxin
Erocetin
Ibrexin
Inphalex
Kefolan
Kekrinal
Kidolex
Lafarine
Lenocef
Lonflex
Mamlexin
Medoxine
MFCD00056877
Oriphex
Ospexin
Pectril
Sanaxin
Sepexin
Sialexin
Sporicef
Sporidex
Zozarine
Alexin
Cefax
Cephin
Cepol
Check
Fexin
Ibilex
Neokef
Nufex
Oracef
Oroxin
Roceph
Syncle
Synecl
Voxxim
Winlex
Cefa-iskia
Ceporex Forte
Ceporexin-E
SQ 20248
CHEMBL1727
Durantel DS
L-Keflex
Cefalessina
CEX
Ed A-Ceph
LILLY-66873
Roceph Distab
NCGC00159522-02
Ceflax
S-6437
(6R,7R)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cephalexin 1-hydrate
Cerexin
Optocef
Cephalexin [USAN:BAN]
(6R,7R)-7-((R)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMR000338536
CAS-15686-71-2
Keflex (TN)
HSDB 3022
EINECS 239-773-6
BRN 0965503
Cerexins
Amplex
UNII-5SFF1W6677
Anhydrous cefalexin
(6R,7R)-7-((R)-2-AMINO-2-PHENYLACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Cefalexin (JP18)
Cephalexin (Standard)
Cephalexin (Cefalexin)
CEFALEXIN [JAN]
CEPHALEXIN [MI]
Prestwick0_000358
Prestwick1_000358
Prestwick2_000358
Prestwick3_000358
CEPHALEXIN [HSDB]
Epitope ID:117132
CEFALEXIN [WHO-DD]
SCHEMBL2961
7-(D-2-Amino-2-phenylacetamido)-3-methyl-delta (sup 3)-cephem-4- carboxylic acid
BSPBio_000455
(6R,7R)-7-((R)-2-Amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
MLS000759527
MLS001424036
SPBio_002376
BPBio1_000501
GTPL4832
orb1310065
HY-B0200R
MSK7013
BCPP000289
HMS2051A04
HY-B0200
Tox21_111740
BDBM50139896
AKOS004119846
Tox21_111740_1
BCP9000509
CCG-100831
CS-2137
DB00567
NC00081
NSC 758162
NCGC00159522-03
NCGC00159522-05
DS-11971
NS00098606
Cefalexin, VETRANAL(TM), analytical standard
C06895
D00263
H10995
Cefalexin 1000 microg/mL in Acetonitrile:Water
Q411417
BRD-K90733503-001-05-3
BRD-K90733503-001-06-1
BRD-K90733503-001-07-9
BRD-K90733503-002-03-6
Cefalexin, British Pharmacopoeia (BP) Reference Standard
Z1880962282
7-(D-alpha-amino-phenylacetamido)-3-methyl-3-cepheme-4-carboxylic acid
Cephalexin, Pharmaceutical Secondary Standard; Certified Reference Material
7-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID
7beta-[(2R)-2-amino-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic acid
(6R,7R)-7-((R)-2-Amino-2-phenyl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-((R)-2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINOPHENYLACETYL)AMINO)-3-METHYL-8-OXO-,(6R-(6.ALPHA.,7.BETA.(R*)))-