(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

• ChemBase ID: 339
• Molecular Formular: C16H16N2O6S2
• Molecular Mass: 396.43804
• Monoisotopic Mass: 396.04497824
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)Cc2sccc2)C(=C(C1)COC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1cccs1
• 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
• InChIKey: XIURVHNZVLADCM-IUODEOHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: cefalotin; cephalothin; (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
• Brand Name: Averon-1; Cemastin; Coaxin; Keflin; Seffin
• Synonyms: Cefalotina [INN-Spanish]; Cefalotine [INN-French]; Cefalotinum [INN-Latin]; Cephalothin Sodium; Cephalothinum; Cephalothin; Cephalotin; CLS; Cefalothin; Cefalotin; (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; 7-(2-Thiopheneacetamido)cephalosporanic acid; Cephalosporin 871; Cefalotin

Database IDs

• CAS Number: 153-61-7
• MDL Number: MFCD00242614
• PubChem SID: 46509079; 160963802
• PubChem CID: 6024

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.625907
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.8540871
• LogD (pH = 7.4): -3.3175669
• Log P: 0.016272906
• Molar Refractivity: 93.794 cm^3
• Polarizability: 36.38155 Å^3
• Polar Surface Area: 113.01 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.63
• LOG S: -3.88
• Solubility (Water): 5.21e-02 g/l

PROPERTIES

Physical Property

• Solubility: 158 mg/L
• Hydrophobicity(logP): -0.2

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: Mucopeptide synthesis inhibitor

Product Information

• Purity: 95+%; 97%
• Application(s): Parenteral antibiotic

DETAILS

DrugBank - DB00456

• Drug Groups: approved
• Description: A cephalosporin antibiotic. [PubChem]
• Indication: Used to prevent infection during surgery and to treat many kinds of infections of the blood, bone or joints, respiratory tract, skin, and urinary tract.
• Pharmacology: Cefalotin (INN) or cephalothin (USAN) is a semisynthetic first generation cephalosporin having a broad spectrum of antibiotic activity that is administered parenterally.
• Toxicity: Rat intravenous LD₅₀ is 4000 mg/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Metabolized to a less active desacetyl metabolite, although 50-75% of the drug is eliminated unchanged in the urine.
• Half Life: 30 minutes
• Protein Binding: 65-80%
• External Links: Wikipedia

REFERENCES

• Chauvette, R.R. et al., J.A.C.S., 1962, 84, 3401, (synth)
• Woodward, R.B. et al., J.A.C.S., 1966, 88, 852, (synth)
• Simmons, R.J., Anal. Profiles Drug Subst., 1972, 1, 319, (rev)
• Welles, J.S., Cephalosporins Penicillins: Chem. Biol., (Flynn, E.H., Ed.), Academic Press, 1972, 583, (rev)
• Ratcliffe, R. et al., Tet. Lett., 1973, 4649
• Nishikawa, J. et al., J. Antibiot., 1982, 35, 1724, (ir, cmr)
• Cowley, B.R. et al., Tetrahedron, 1983, 39, 461, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3941, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 138
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCX250; SFQ500