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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-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Penicillin G is usually in solid form at room temperature and is often available as a powder or crystals for use in various pharmaceutical formulations.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.15
Boiling point (Celsius)
150.00
Boiling point (Kelvin)
423.15
General information
Molecular weight
334.39g/mol
Molar mass
334.3900g/mol
Density
1.4100g/cm3
Appearence

Penicillin G is typically a white or off-white crystalline powder. The appearance may vary slightly depending on formulation and purity. It is generally a solid at room temperature.

Comment on solubility

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

This compound presents an intriguing profile in terms of solubility, which can be influenced by several factors, including its unique structural features. Here are some important aspects to consider:

  • Polarity: The presence of functional groups such as the amino and carboxylic acid moieties suggests that this compound is likely to form hydrogen bonds with water, which enhances its solubility in polar solvents.
  • Hydrophobic regions: The dimethyl groups and the bicyclic structure may introduce hydrophobic characteristics, potentially leading to lower solubility in non-polar solvents.
  • pH dependency: As a carboxylic acid, solubility may vary with pH levels. At lower pH, the compound is likely to exist mainly in its protonated form, possibly affecting its solubility in aqueous solutions.

To summarize, the solubility of (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid can be characterized as follows:

  1. Good solubility in polar solvents (e.g., water)
  2. Lower solubility in non-polar solvents (e.g., hexane)
  3. Variation in solubility based on pH conditions

Understanding these solubility patterns is crucial for applications in pharmaceuticals and materials science, where the bioavailability and transport of the compound can significantly impact its function.

Interesting facts

Interesting Facts About (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

This intriguing compound, often referred to in the context of medicinal chemistry, showcases a unique bicyclic structure that is pivotal in its biological activity. Here are some engaging insights about this compound:

  • Bicyclic Framework: The bicyclic nature of this compound comprises both nitrogen and sulfur elements, making it a member of a class of compounds known as thiazolidines. This unique architecture contributes to its potential as a pharmaceutical agent.
  • Biological Activity: Compounds resembling this structure are often explored for their activity against various diseases, particularly in antibiotic development, due to their interaction with bacterial enzymes.
  • Stereochemistry: The specified stereochemistry (2S, 5R, 6R) plays a crucial role in determining the compound's reactivity and interaction with biological targets. Chirality is vital in drug design, influencing efficacy and safety profiles.
  • Research Significance: Ongoing research delves into the optimization of such compounds. Small modifications to the structure can lead to dramatically different pharmacological properties. This is why chemists emphasize the importance of structure-activity relationships (SAR).

As a fascinating example of how organic chemistry intersects with biology, this compound highlights the intricacies of compound design and discovery in the field of pharmaceuticals. The understanding of these complex structures not only advances drug development but also enhances our appreciation of chemical diversity.


Synonyms
6-Aminopenicillanic acid
551-16-6
6-Apa
Penicin
Penin
Aminopenicillanic acid
6-Aps
(+)-6-Aminopenicillanic acid
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Phenacyl 6-aminopenicillinate
6-Aminopenicillamine acid
AI3-52557
MFCD00005176
CHEBI:16705
6-amino-penicillanic acid
QR0C4R7XVN
6beta-aminopenicillanic acid
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
CHEMBL1236749
DTXSID7046097
6-amino-2,2-dimethylpenam-3alpha-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
SR-01000640154-1
(2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
EINECS 208-993-4
UNII-QR0C4R7XVN
NSC 50071
NSC-50071
NCGC00160198-01
(2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
amino penicillanic acid
6-aminopenicillanic-acid
6-aminopenici llanic acid
bmse000312
Epitope ID:117703
EC 208-993-4
SCHEMBL66332
DTXCID5026097
09070_FLUKA
6-aminopenicillinic acid (6-APA)
BCP13375
HY-W013549R
STR03060
6-Aminopenicillanic acid (Standard)
Tox21_111749
BDBM50420257
CCG-50809
s5035
(+)-6-Aminopenicillanic acid, 96%
6-AMINOPENICILLANIC ACID [MI]
AKOS015907713
CS-W014265
FA36389
HY-W013549
KS-5277
s12351
AC-11282
CAS-551-16-6
PD014430
AMPICILLIN IMPURITY A [EP IMPURITY]
PIPERACILLIN SODIUM IMPURITY H [EP]
A0800
NS00011463
C02954
EN300-114057
(+)-6-Aminopenicillanic acid, analytical standard
SULBACTAM SODIUM IMPURITY B [EP IMPURITY]
AMOXICILLIN SODIUM IMPURITY A [EP IMPURITY]
CLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
Q2823234
6beta-amino-2,2-dimethylpenam-3alpha-carboxylic acid
AMOXICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
AMPICILLIN TRIHYDRATE IMPURITY A [EP IMPURITY]
BRD-K30284967-001-01-8
DICLOXACILLIN SODIUM IMPURITY C [EP IMPURITY]
BENZYLPENICILLIN SODIUM IMPURITY A [EP IMPURITY]
PHENOXYMETHYLPENICILLIN IMPURITY C [EP IMPURITY]
Z1269203097
(3S,5R,6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
BENZYLPENICILLIN POTASSIUM IMPURITY A [EP IMPURITY]
(3S, 5R, 6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
OXACILLIN SODIUM MONOHYDRATE IMPURITY A [EP IMPURITY]
FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE IMPURITY C [EP IMPURITY]
FLUCLOXACILLIN SODIUM MONOHYDRATE IMPURITY C [EP IMPURITY]
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY]
Flucloxacillin impurity C, European Pharmacopoeia (EP) Reference Standard
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY C [EP IMPURITY]
(2S,5R,6R)-(+)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
[2S-(2alpha,5alpha,6beta)]-6-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-amino-3,3-dimethyl-7-oxo-, (2S,6R)-
6-APA (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Penicin Penin
rel-(2R,6S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
X1E