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Cefepime

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Identification
Molecular formula
C19H24N6O5S2
CAS number
88040-23-7
IUPAC name
7-[[2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, cefepime is in a solid state. It is usually handled as a powder for reconstitution in clinical and pharmaceutical applications. Given its pharmaceutical application, cefepime is stable as a solid and typically requires dissolution in sterile water or other solvents just prior to administration.

Melting point (Celsius)
156.00
Melting point (Kelvin)
429.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
480.57g/mol
Molar mass
480.5730g/mol
Density
1.1503g/cm3
Appearence

Cefepime is a white to pale yellow crystalline powder. It is highly soluble in water, forming a clear, colorless to light yellow solution, due to its formulation as a hydrochloride salt for medical use.

Comment on solubility

Solubility of 7-[[2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility of the compound C19H24N6O5S2 can be influenced by several factors, given its complex structure. Key points to consider include:

  • Polarity: This compound contains both polar and non-polar functional groups. The presence of carboxylic acid (-COOH), hydroxyl (-OH), and amine (-NH₂) groups suggests some degree of polarity, which may lead to enhanced solubility in polar solvents like water.
  • Hydrophobic regions: The ethyl and tetrazole components contribute to hydrophobic characteristics, which may hinder solubility in polar solvents, creating a balance that could lead to variable solubility.
  • Interaction with solvents: The ability of the compound to form hydrogen bonds with water will enhance its solubility. Compounds with functional groups capable of such interactions generally show greater solubility in aqueous environments.
  • Temperature dependence: Like many chemical species, the solubility of this compound may vary with temperature, potentially increasing at higher temperatures due to greater molecular motion.

In summary, while the presence of polar functional groups suggests a tendency towards solubility in water, the compound's overall hydrophobic characteristics may limit its solubility. Understanding the specific interactions that occur within different solvent environments will be essential to predict its behavior in practical applications.

Interesting facts

Exploring the Compound: 7-[[2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This compound is a prime example of the complexity in modern medicinal chemistry. With a structure that combines multiple functional groups, it showcases the exquisite *design* often required for therapeutic agents. Here are some interesting aspects:

  • Multi-functional Architecture: The presence of both piperazine and tetrazole rings highlights its potential for varied biological activity, making it a fascinating subject of study for drug development.
  • Structure-Activity Relationship: The intricate arrangement of substituents around the bicyclic core can significantly influence the compound's interactions with biological targets. This is key for optimizing its efficacy and reducing side effects.
  • Potential Pharmacological Applications: Researchers are particularly interested in compounds like this for their possible *antimicrobial*, *anti-inflammatory*, and *antitumor* properties. The incorporation of various moieties enhances the likelihood of achieving unique biological effects.
  • Innovation in Synthesis: The synthetic methodologies employed to construct such complex structures often push the boundaries of traditional chemistry, driving advancements in organic synthesis techniques.

As one expert in the field noted, "The fusion of diverse structural components reflects the creativity and challenge in developing novel therapeutics." This compound serves not just as a potential drug candidate, but also as a *laboratory for chemical innovation*, illustrating how intricate molecular designs can lead to groundbreaking discoveries in health sciences.

Synonyms
1315481-36-7
(6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
Cefoperazone Impurity F
SR-05000001802
Cefoperazonedihydrate
Spectrum_001439
Spectrum2_001764
Spectrum3_000746
Spectrum4_000322
Spectrum5_001140
ChemDiv1_024737
BSPBio_002332
KBioGR_000663
KBioSS_001919
MLS006011828
DivK1c_000128
SPBio_001627
CHEMBL1331919
SCHEMBL18061225
KBio1_000128
KBio2_001919
KBio2_004487
KBio2_007055
KBio3_001552
DTXSID50860777
NINDS_000128
Pharmakon1600-01502042
BCP28874
NSC758173
STL451014
CCG-212989
IDI1_000128
7-{[{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMR001550017
AB01562952_01
SR-05000001802-5
BRD-A73079885-001-01-1
CEFOPERAZONE, cefoperazone sodium, Cefoperazone dihydrate, Cefoperazone sodium salt
(6R,7S)-Cefoperazone;(6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]aMino]-2-(4-hydroxyphenyl)acetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]
7-{2-[(4-Ethyl-2,3-dioxopiperazine-1-carbonyl)amino](4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
sodium,(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate