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Cefixime

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Identification
Molecular formula
C16H15N5O7S2
CAS number
79350-37-1
IUPAC name
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, cefixime is in a solid state.

Melting point (Celsius)
220.50
Melting point (Kelvin)
493.65
Boiling point (Celsius)
291.80
Boiling point (Kelvin)
564.95
General information
Molecular weight
453.45g/mol
Molar mass
453.4500g/mol
Density
1.7000g/cm3
Appearence

Cefixime appears as a white to off-white powder.

Comment on solubility

Solubility of (6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility of this complex compound, commonly referred to as a thiazolidine derivative, is influenced by several factors due to its intricate structure. Here are some key points regarding its solubility:

  • Polarity: The presence of functional groups such as acetoxymethyl and carboxylic acid can enhance polarity, potentially increasing solubility in polar solvents like water.
  • Hydrophobic Regions: Conversely, the bicyclic structure may introduce hydrophobic characteristics, which could decrease solubility in aqueous solutions.
  • pH Dependency: Solubility might vary significantly with changes in pH, especially given the presence of a carboxylic acid, which can ionize to form carboxylate anions.
  • Solvent Compatibility: The compound may demonstrate varying solubility in organic solvents due to its diverse functional groups, with better solubility generally expected in polar aprotic solvents.

In conclusion, while the solubility profile of this compound is likely complex and context-dependent, its interaction with both polar and non-polar solvents opens avenues for further exploration and application in pharmaceutical formulations. A thorough understanding of its solubility characteristics can greatly enhance its practical utility and therapeutic efficacy.

Interesting facts

Interesting Facts about (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

This intriguing compound is a member of a class of molecules that possess both biological significance and synthetic utility. It combines a bicyclic structure with various functional groups, making it a fascinating subject of study in medicinal chemistry.

Key Features:

  • Structural Complexity: The bicyclic framework presents them as unique scaffolds for developing pharmaceuticals.
  • Biological Activity: The presence of the pyridine and thia groups suggests potential interaction with biological systems, possibly leading to new therapeutic agents.
  • Acetoxy Group: The acetoxymethyl moiety enhances the compound's lipophilicity, which is often desirable in drug design as it may improve membrane permeability.
  • 7-Amino Functionality: The amino group can engage in hydrogen bonding, potentially enhancing interactions with biological targets.
  • Enzyme Interactions: The oxo and carboxylic acid functionalities may interact with various enzymes, making it a candidate for exploring enzyme inhibition.

As with many compounds in this category, the implications for research can be vast. The unique combination of sulfur and nitrogen heteroatoms adds additional avenues for exploration, particularly in the realm of complex biological pathways.

Quotes from leading researchers shed light on the potential impact of such compounds: "The search for more effective therapeutic agents requires us to look at complex structures and their interactions in unprecedented ways." This statement emphasizes the compelling nature of exploring molecules like this one.

In conclusion, the study of (6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid not only enriches our understanding of chemical diversity but also fuels innovation in drug discovery.

Synonyms
cephapirin
Cefapirin
21593-23-7
Cephapirine
Cefaprin
Cefapirina
Cefapirine
Cefapirinum
CEPR
CHEBI:554446
7-(2-(4-Pyridylthio)acetamido)cephalosporanic acid
89B59H32VN
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-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, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6R-trans)-
DTXSID9022784
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester)
Cephalosporanic acid, 7-(2-(4-pyridylthio)acetamido)-
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-((acetyloxy)methyl)-8-oxo-7-(2-(pyridin-4-ylsulfanyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(((pyridin-4-ylsulfanyl)acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-((2-pyridin-4-ylsulfanylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
RefChem:54749
DTXCID602784
244-466-5
Cefapirine [INN-French]
Cefapirinum [INN-Latin]
Cefapirina [INN-Spanish]
Cefatrexyl
Ambrocef
Cefatrex
Cefa
MFCD00864868
Cefaprin sodium
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefapirin [INN:BAN]
ANTIBIOTIC BL-P1322
Cefapirin (BAN)
Metricure (TN)
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
356C603
Cefa-Lak
HSDB 3215
C17H17N3O6S2
Cefa -ak
EINECS 244-466-5
BRN 1095157
Spectrum_000112
CEFAPIRIN [INN]
CEPHAPIRIN [MI]
CEFAPIRIN [HSDB]
Prestwick0_000851
Prestwick1_000851
Prestwick2_000851
Spectrum2_000103
Spectrum3_000333
Spectrum4_000270
Spectrum5_000671
CEPHAPIRIN [VANDF]
Epitope ID:116226
CEFAPIRIN [WHO-DD]
SCHEMBL3205
CHEMBL1599
Lopac0_000279
BSPBio_001965
KBioGR_000740
KBioSS_000552
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
3-(Hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamidol-5-thia-1-azabicyclo(4.2.0)oct-2-en-2carbonsaeure acetat
DivK1c_000042
UNII-89B59H32VN
SPBio_000086
SPBio_002782
GTPL12191
KBio1_000042
KBio2_000552
KBio2_003120
KBio2_005688
KBio3_001185
NINDS_000042
HY-A0153
MSK12001
BDBM50370592
AKOS015896499
DB01139
IDI1_000042
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylthio)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic acid
AS-86280
DA-51742
SBI-0050267.P004
CS-0017478
NS00084098
C06896
D07636
G92112
EN300-25916814
Q549803
BRD-K49880111-236-09-2
7-(.ALPHA.-(4-PYRIDYLTHIO)ACETAMIDO)CEPHALOSPORANIC ACID
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
(6R,7R)-3-(HYDROXYMETHYL)-8-OXO-7-(2-(4-PYRIDYLTHIO)ACETAMIDO)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE ACETATE (ESTER)
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-, (6R,7R)-