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Cefazolin

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Identification
Molecular formula
C14H14N8O4S3
CAS number
25953-19-9
IUPAC name
(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

The compound is a crystalline solid at room temperature, commonly found in its sodium salt form for medical applications.

Melting point (Celsius)
198.00
Melting point (Kelvin)
471.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
454.51g/mol
Molar mass
454.5070g/mol
Density
1.6480g/cm3
Appearence

Cefazolin typically appears as a white to off-white powder and is provided as a sodium salt for intravenous or intramuscular administration. It is used as an antibiotic in its sodium form, which makes it highly soluble in aqueous solutions.

Comment on solubility

Solubility of (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility characteristics of this compound can be intriguing due to its complex structure, which includes multiple functional groups. Generally, the solubility of such compounds can be influenced by factors such as:

  • Polarity: The presence of polar functional groups, like the carboxylic acid and sulfonamide, often increases solubility in polar solvents, such as water.
  • Hydrogen Bonding: Functional groups capable of hydrogen bonding, such as amines and carboxylic acids, may enhance solubility in aqueous solutions.
  • Size and Shape: The overall molecular geometry and the steric hindrance caused by bulky substituents can impact the solubility; generally, smaller molecules tend to be more soluble.

As a result, this compound may exhibit:

  • Moderate solubility in water: Owing to its polar carboxylic acid and amide functionalities.
  • Higher solubility in organic solvents: Such as dimethyl sulfoxide (DMSO) or ethanol, which can better accommodate non-polar regions of the molecule.

In summary, the solubility of (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is likely to be influenced by its functional groups and structural configuration. This could provide useful insight for its applications in various fields, including medicinal chemistry.

Interesting facts

Interesting Facts about (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This compound, a member of the β-lactam antibiotic family, exhibits fascinating chemical and biological properties. Here are some intriguing aspects:

  • Structure & Function: The complex bicyclic structure of this compound contributes to its antibiotic activity. The presence of a β-lactam ring, known for its role in disrupting bacterial cell wall synthesis, highlights its significance in combating bacterial infections.
  • Thiadiazole Moiety: The inclusion of a 5-methyl-1,3,4-thiadiazole group enhances the compound's antimicrobial efficacy. This heterocyclic unit is known to offer a diverse range of biological activities, from anti-infective to anticancer.
  • Tetrazole Substituent: The tetrazole ring is notable for its ability to mimic carboxylic acids in biological systems, allowing the compound to effectively bind to target proteins. This feature often leads to improved bioactivity compared to compounds lacking this structural element.
  • Therapeutic Potential: Due to its unique structure, this compound is being researched for its potential use in treating various bacterial infections, especially those resistant to conventional antibiotics. Its combination of different functional groups could open new avenues in pharmacology.

Researchers continue to explore the mechanisms of action and potential modifications of this compound to enhance its antibiotic properties. As we delve further into its capabilities, it stands as a promising candidate in the fight against antibiotic resistance.

Synonyms
cefazolin
25953-19-9
Cephazolin
Cefazoline
Cephamezine
Cephazoline
Cefamezin
Cephazolidin
Cefazolina
Cefazolinum
Elzogram
(6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEBI:474053
IHS69L0Y4T
DTXSID2022753
J01DB04
SK&F-41558
DTXCID302753
(6R,7R)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)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-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl)methyl)-8-oxo-7-((1H-tetrazol-1-ylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl)methyl)-8-oxo-7-(2-(1H-1,2,3,4-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
(6R,7R)-3-((5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl)-8-oxo-7-((2-(tetrazol-1-yl)acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
RefChem:54731
247-362-8
Cefazolin acid
CEZ
C14H14N8O4S3
Cefazina
Firmacef
Liviclina
Atirin
Acef
NCGC00159465-02
Cefazoline [INN-French]
Cefazolinum [INN-Latin]
(6R,7R)-7-(2-(1H-tetrazol-1-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefazolina [INN-Spanish]
Cephamezine;Cephazoline
Cefazolin (USP)
SMR000387025
CAS-25953-19-9
HSDB 3213
EINECS 247-362-8
UNII-IHS69L0Y4T
BRN 4169371
Cefazolin [USP:INN:BAN]
Cefazolin; (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefazolin (Standard)
(6R-trans)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)-amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
7-(1-(1H-)-Tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic acid
Spectrum_000106
CEFAZOLIN [INN]
CEFAZOLIN [MI]
CEFAZOLIN [HSDB]
Prestwick0_000736
Prestwick1_000736
Prestwick2_000736
Prestwick3_000736
Spectrum2_001140
Spectrum3_000330
Spectrum4_000267
Spectrum5_000665
CEFAZOLIN [VANDF]
CEFAZOLIN [MART.]
Epitope ID:116197
EC 247-362-8
CEFAZOLIN [USP-RS]
CEFAZOLIN [WHO-DD]
SCHEMBL2841
CHEMBL1435
Lopac0_000274
BSPBio_000692
BSPBio_001939
KBioGR_000734
KBioSS_000546
MLS001032060
MLS001049010
DivK1c_000014
SPBio_001039
SPBio_002631
BPBio1_000762
orb1298974
GTPL10935
HY-B1892R
KBio1_000014
KBio2_000546
KBio2_003114
KBio2_005682
KBio3_001159
CEFAZOLIN [USP MONOGRAPH]
MSK7014
NINDS_000014
GLXC-10539
HMS2268D15
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-, (6R,7R)-
HY-B1892
Tox21_111691
BDBM50370587
MFCD00243010
s5936
AKOS015962265
Tox21_111691_1
DB01327
SDCCGSBI-0050262.P005
IDI1_000014
NCGC00022653-09
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7beta-[(1H-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic acid
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)amino)-, (6R-trans)-
AC-16010
AC172185
BS-52943
Cefazolin 1000 microg/mL in Acetonitrile
SBI-0050262.P004
CS-0013954
C06880
D02299
F87674
EN300-6731073
953C199
Q415739
BRD-K99750640-236-18-7
BRD-K99750640-236-19-5
(6R, 7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2- yl)thio]methyl]-8-oxo-7-[[1H-tetrazol-1- yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2- ene-2-carboxylic acid
(6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]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-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-8-OXO-7-(((1H-TETRAZOL-1-YL)ACETYL)AMINO)-(6R-TRANS)