Cephalothin
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| Category | Antibiotics |
| Catalog number | BBF-00511 |
| CAS | 153-61-7 |
| Molecular Weight | 396.44 |
| Molecular Formula | C16H16N2O6S2 |
| Purity | 98% |
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Description
It is produced by the strain of Semisynthetic first generation cephalosporin for injection.
Specification
| Related CAS | 58-71-9 (sodium) |
| Synonyms | Cefalotin; Cephalotin; Cefalothin; Cephalothinum; Cefalonium Impurity A; Keflin; Cemastin; Cefalotina; Cefalotine; 7-(2-Thienylacetamido)cephalosporanic acid; 6R-trans-3-((Acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic acid |
| Storage | −20 °C |
| IUPAC Name | (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 |
| Canonical SMILES | CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O |
| InChI | InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 |
| InChI Key | XIURVHNZVLADCM-IUODEOHRSA-N |
Properties
| Appearance | White Crystal Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 757.2±60.0 °C (Predicted) |
| Melting Point | 160-160.5 °C |
| Density | 1.416 g/cm3 (Predicted) |
| Solubility | Soluble in Acetonitrile, DMSO, Dioxane, Methanol |
Reference Reading
1. Square-wave Voltammetric Behaviour and Automated Determination of Cephalothin by a Novel Sample Handling Approach
Dorit Peled, Chaim Yarnitzky, W. Franklin Smyth*. ANALYST, JULY 1987, VOL. 112
These antibiotics, commonly used for the treatment of infections caused by Gram-positive cocci and Gram-negative bacilli, were each found to exhibit one reduction wave and were used for qualitative and quantitative analysis. Hall et a1.2 have carried out a more exhaustive electrochemical study on cephalosporin C derivatives which included cephalothin. They found a d.c. current at 10-4 M concentrations which was constant in height over the pH range 0-4 and decreased to zero by pH 7-8. They reported that there was no observable reduction wave for the cephalothin anion in buffered solutions up to pH 8 but that a wave at -1.80 V existed in 0.1 M Et4NC1O4 supporting electrolyte
2. Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications
Paul C. Trippier*, Christopher McGuigan. Med. Chem. Commun., 2010, 1, 183–198
The group of Shoichet has published extensively in the field of boronic acid based b-lactamase inhibitors and based upon this previous experience, set out to identify a new, more potent inhibitor. Cephalothin, a widely used Cephalosporin antibiotic, possess a Ki of 320 nM versus AmpC type b-lacta-mases. Shoichet et al. illustrated that the closer the boronic acid resembles the natural substrate, the better the potency. The more the structure mimics the b-lactam of cephalothin, the greater the inhibition, with boronic acid 32 (Ki = 0.32 μM) the weakest. Addition of a stereogenic phenyl group 33, mimicking the dihydrothiazine of cephalothin, provides a 10-fold increase in potency (Ki = 0.035 μM). The insertion of a meta-carboxyphenyl moiety further improved the affinity for AmpC type b-lactamase to provide the most potent inhibitor yet described, boronic acid 34 (Ki = 0.001 μM).
3. β-Lactam-host defence peptide conjugates as antibiotic prodrug candidates targeting resistant bacteria
Stephane Desgranges, Carol C. Ruddle, Marc Devocelle*. RSC Adv., 2012, 2, 2480–2492
The cephalosporin and peptide candidates selected for the synthesis of a prototypical conjugate were cephalothin and Bac8c, respectively. Cephalothin 1, containing a 39-acetate substituent and a thienyl side-chain, is a first generation cephalosporin with a broad spectrum of activity. Bac8c is a peptide amide of sequence RIWVIWRR-NH2, obtained by optimisation of the bovine dodecapeptide bactenecin. The asset of this short 8-mer candidate is an activity against both Gram-negative and Gram-positive bacteria in the low micromolar range. Also, its number of residues, which remains close to the minimal length of a continuous epitope for an antigen, should prevent its immunogenicity and limit its production cost.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
