Cephalexin hydrate

Cephalexin hydrate

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Cephalexin hydrate
Category Antibiotics
Catalog number BBF-03856
CAS 23325-78-2
Molecular Weight 365.40
Molecular Formula C16H19N3O5S
Purity >98%

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Description

Cephalexin hydrate is an semisynthetic cephalosporin antibiotic. It is effective against both gram-positive and gram-negative organisms.

Specification

Related CAS 15686-71-2 (anhydrous) 59695-59-9 (hydrochloride)
Synonyms Cephacillin hydrate; Keflex hydrate
Storage Store at -20°C
IUPAC Name (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate
Canonical SMILES CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O.O
InChI InChI=1S/C16H17N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15-;/m1./s1
InChI Key AVGYWQBCYZHHPN-CYJZLJNKSA-N
Source Semi-synthetic

Properties

Appearance White Crystalline Powder
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 727.4°C at 760 mmHg
Density 1.5 g/cm3

Reference Reading

1.Ionization constants and solubility of compounds involved in enzymatic synthesis of aminopenicillins and aminocephalosporins
V. B. Kurochkina • A. V. Sklyarenko • J. E. Satarova • S. V. Yarotsky. Bioprocess Biosyst Eng (2011) 34:1103–1117
Under the development of a sorption method of aminocephalosporin, isolation data on solubility are used for choice of the conditions for antibiotic desorption from a sorbent. For example, under desorption of cephalexin from nonionic sorbents high-concentrated eluates (120 g/l and more, regarding to anhydrous substance), suitable for following effective precipitation of cephalexin monohydrate, have to be produced. Possible pH values of eluates calculated on the basis of Eqs. 11 and 12 using data on antibiotic solubility from Table 1 are pH B 1.9 and pH C 8.1.
2.Investigation on the endothermic event of cephalexin monohydrate in differential scanning calorimetric curve
Monica C. Chuong • Ravi Varanasi • Daniel Seniuk • Neha Aggarwal. J Therm Anal Calorim (2016) 123:2165–2172
The phase change (melting) of cephalexin monohydrate was not typical when observed through the scope of a Melt-Temp apparatus. Neither 196–198 ℃ nor 326.8 ℃is the melting temperature of cephalexin BP, USP. More correctly, 196–198 ℃ is the decomposition temperature. Since pharmaceutical operations are frequently time courses, DSC and melting point study alone may not be sufficient to determine an optimal operation temperature in the required process time duration. Application of heat stress test on a drug of interest at different temperatures for different durations and then analyze with HPLC may be the best approach to identifying the safe operation temperature and process duration. It is advised that the results obtained from DSC, MEL-TEMP® apparatus, visual inspection and HPLC analysis should also be incorporated into a decision making. Small quantity of cephalexin monohydrate BP, USP may be degraded as early as 80 ℃ if the heating process is 90 min or greater. The results of this study suggested that the bound water in cephalexin is not just there to fill the voids in the crystal, but exhibits the interaction with the crystal structure. The evidences are (1) the UV and HPLC studies found that there was a [3% decomposition when cephalexin monohydrate was heated at 100 ℃ for 90 min (n = 7, Table 4d), (2) the MEL-TEMP apparatus identifies decomposition began at 98 ℃, small bubble formation occurred at 140–148 ℃(n = 8, Fig. 3b), and (3) DSC displayed a large sharp exothermic event (102.9 mJ mg-1, n = 4. Table 1) from 173 to 208 ℃ with the apex temperature at 196.9 ℃(n = 6, Table 5).

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