Skip to main content

Cephalothin

ADVERTISEMENT
Identification
Molecular formula
C16H16N2O6S2
CAS number
153-61-7
IUPAC name
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, cephalothin is typically a solid in the form of crystals or a crystalline powder.

Melting point (Celsius)
218.00
Melting point (Kelvin)
491.15
Boiling point (Celsius)
285.00
Boiling point (Kelvin)
558.15
General information
Molecular weight
396.45g/mol
Molar mass
396.4470g/mol
Density
1.4600g/cm3
Appearence

Cephalothin is a white or cream-colored crystalline powder. It is generally odorless, but it may have a faint, characteristic medicinal smell.

Comment on solubility

Solubility Analysis

The solubility of the compound (6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, represented by the formula C16H16N2O6S2, presents some intriguing characteristics. Understanding the solubility of this compound can be crucial for its applications in various fields.

Factors Influencing Solubility

The solubility of this compound can be largely influenced by several factors:

  • Polarity: The presence of polar functional groups, such as carboxylic acid and ester groups, suggests that the compound may exhibit moderate to high solubility in polar solvents like water and methanol.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvents can enhance solubility; the carboxylic acid group enhances potential interactions.
  • Molecular Structure: The bicyclic structure and thiophenyl group might reasonably impact the spatial orientation and stacking in solution, affecting solubility.

Expected Solubility

Due to the compound's diverse functional groups:

  • It is likely to exhibit good solubility in polar organic solvents.
  • In aqueous environments, the acid functionality may aid solubility, depending on pH.
  • Solubility might decrease in less polar solvents due to increased hydrophobic character from the thienyl group.

As a rule of thumb, compound solubility can vary widely across different solvents and conditions. A systematic approach to solubility testing in various environments would provide a clearer understanding of this compound's behavior in practical applications.

Interesting facts

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

This complex compound represents a fascinating blend of organic chemistry and pharmacology, showcasing the intricacies involved in the design of bioactive molecules.

Structural Insights

The compound features a unique bicyclic structure, which is essential for its biological activity. The thia and azabicyclo components contribute to its ability to interact with biological macromolecules.

Biological Relevance

One of the notable aspects of this compound is its potential medicinal applications. It is part of a class of molecules known as beta-lactams, which are crucial in antibiotic development. Here are some highlighted uses:

  • Antibacterial Activity: The compound's structure may enhance its ability to combat bacterial infections.
  • Enzymatic Inhibition: It may function by inhibiting essential enzymes within bacteria, disrupting their growth and replication.

Functional Groups

The presence of acetoxymethyl and thienyl groups is particularly interesting. These functional groups are known for:

  • Increasing lipophilicity, which may improve cell membrane penetration.
  • Facilitating interactions with specific receptors or enzymes due to steric and electronic properties.

Research and Development

Research into compounds like this is critical, especially in the context of drug resistance. Scientists continuously explore modified derivatives to enhance effectiveness against resistant strains of bacteria, reflecting the ongoing need for innovative therapeutic strategies.

In summary, the compound (6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid stands as a valuable subject of study, illustrating the interconnectedness of chemical structure and biological function. Its intricacies offer a rich avenue for exploration in the realm of medicinal chemistry.

Synonyms
cephalothin
Cefalotin
153-61-7
Cephalotin
Cefalothin
Cephalothinum
Cefalotina
Cefalotine
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefalotinum
Cemastin
7-(2-Thienylacetamido)cephalosporanic acid
Coaxin
Keflin
Cefalotine [INN-French]
Cefalotinum [INN-Latin]
Cefalotina [INN-Spanish]
Averon-1
7-(Thiophene-2-acetamido)cephalosporin
Cephalotin acid
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefalotin [INN]
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEBI:124991
MLS001048966
7-(2'-thienylacetamido)cephalosporanic acid
DTXSID4022783
R72LW146E6
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-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, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6R-trans)-
NCGC00159332-02
SMR000386987
DTXCID202783
C16H16N2O6S2
Cefalotin (BAN)
7-(Thiophene-2-acetamido)cephalosporanic acid
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS-153-61-7
7-(2-(2-Thienyl)acetylamido)cephalosporanic acid
HSDB 3024
Cefalotina fabra (TN)
EINECS 205-815-7
BRN 0945586
UNII-R72LW146E6
6R-trans-3-((Acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic acid
4kox
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6R,7R)-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)-
(+-)-Cephalothin
MFCD00242614
3-(Acetoxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
3-(Hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid acetate
Cephalothin (Standard)
Spectrum_000110
CEPHALOTHIN [MI]
Prestwick0_000719
Prestwick1_000719
Prestwick2_000719
Prestwick3_000719
Spectrum2_000121
Spectrum3_000332
Spectrum4_000269
Spectrum5_000669
CEPHALOTHIN [HSDB]
CHEMBL617
Epitope ID:116207
CEPHALOTHIN [VANDF]
CEFALOTIN [WHO-DD]
cid_6024
SCHEMBL2990
Lopac0_000283
BSPBio_000937
BSPBio_001963
KBioGR_000738
KBioSS_000550
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-, acetate (ester)
DivK1c_000097
SPBio_000162
SPBio_002858
BPBio1_001031
GTPL8798
HY-B1275AR
CEPHALOTHIN [GREEN BOOK]
SCHEMBL20477170
BDBM82898
HY-B1275A
KBio1_000097
KBio2_000550
KBio2_003118
KBio2_005686
KBio3_001183
NINDS_000097
HMS2267P23
Tox21_111579
s5294
AKOS015920120
Tox21_111579_1
CCG-268605
CS-W008776
DB00456
FA32097
GS-3577
SDCCGSBI-0050271.P005
7beta-(thiophen-2-ylacetamido)-3-acetoxymethyl-3,4-didehydrocepham-4-carboxylic acid
IDI1_000097
NCGC00023699-09
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
DA-51778
SBI-0050271.P004
7-(2-thienylacetamido) cephalosporanic acid
7-(2-thienylacetamido)-cephalosporanic acid
C2769
NS00126621
C07761
D07635
EN300-267043
SR-01000003118
Q2736126
SR-01000003118-3
BRD-K28210218-236-05-7
BRD-K28210218-236-08-1
Z1741977144
CEPHALOTHIN 7-(2-THIENYLACETAMIDO)CEPHALOSPORANIC ACID
3-acetoxymethyl-7beta-(2-thienylacetamido) ceph-3-em-4-carboxylic acid
3-acetoxymethyl-7beta-(2-thienylacetamido)-3-cephem-4-carboxylic acid
3-Acetoxymethyl-7beta-(2-thienylacetamido)ceph-3-em-4-carboxylic acid
(6R,7R)-3-(acetoxymethyl)-8-keto-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-(acetyloxymethyl)-8-oxidanylidene-7-(2-thiophen-2-ylethanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
51098-29-4