Cefcapene pivoxil
Basic information
- CAS
105889-45-0- Standard SMILES
CC/C=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=C(COC(N)=O)CS[C@H]12)c1csc(N)n1- InChIKey
WVPAABNYMHNFJG-QDVBXLKVSA-N- Molecular formula
- C23H29N5O8S2
- Average molar mass
- 567.6 g/mol
- Monoisotopic mass
- 567.14575525
Overview
Cefcapene Pivoxil is the pivalate ester prodrug form of cefcapene, a semi-synthetic third-generation cephalosporin with antibacterial activity. After oral administration of cefcapene pivoxil, the ester bond is cleaved, releasing active cefcapene.
Names & identifiers
- Preferred name
- Cefcapene pivoxil
- IUPAC
- 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- Cefcapene pivoxil
- Molecular formula
- C23H29N5O8S2
- Molecular weight
- 567.64
Names & synonyms
Cefcapene pivoxil105889-45-0cefcapene-pivoxil2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate8I8MJ56XFQCefcapene piroxilCefcamate pivoxilCefcamateCHEMBL3184257UNII-8I8MJ56XFQ2,2-DIMETHYLPROPANOYLOXYMETHYL (6R,7R)-7-(((Z)-2-(2-AMINO-1,3-THIAZOL-4-YL)PENT-2-ENOYL)AMINO)-3-(CARBAMOYLOXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATESCHEMBL155121
Show more names
FumaxS-1108FlumaxCefcapene Impurity 3Cefcapene pivoxil USP/EP/BPCefcapene Pivoxil ImpuritiesCefcapene Pivoxil See C242555Cefcapene pivoxil Impurity 13
Cefcapene; Cefcapene pivoxil free acid; S 1006; S 1006 (pharmaceutical)CHEMBL2431072DTXSID7049134WVPAABNYMHNFJG-QDVBXLKVSA-NCEFCAPENE PIVOXIL [WHO-DD]BDBM50655503AKOS015841961AKOS015896113
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 247 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 13
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 1,060
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 158 · 158-164°C
- Boiling point
- 888.4 · 888.4±65.0 °C(Predicted)
- Density
- 1.47 · 1.47±0.1 g/cm3(Predicted)
- solubility
- DMSO, Water( warm)
- form
- Solid
- pka
- 11.33 · 11.33±0.60(Predicted)
- color
- Off-White
- FDA UNII
- 8 I8MJ56XFQ · 8I8MJ56XFQ
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
DescriptionFlomox was launched in Japan as an orally active cephalosporin for respiratory and urinary tract infections, heptatic infections, ophthalmological and otorhinolarynological infections, skinkoft tissue infections, and for use in gynacology, dentistry and oral surgery. It can be prepared by condesation of 2(Z)-(2-(t-butoxycarbonylamino) thiazol-4-yl)-2-pentenoic acid with 7-amino-3-(carbanoyloxymethyl)- 3-cephem-4-carboxylic acid pivaloyl methyl ester followed by deprotection. Flomox is highly active against a wide variety of Gram-positive and Gram-negative bacteria, except for several strains such as Pseudomonas aeruginosa and enterococci, by acting as a cell wall synthesis inhibitor (β-lactamase stability against TEM-1 type β-lactamases) and is more effective than cefaclor and cefdinir. Absorption is improved by the pivaloyloxymethyl ester group which is easily lost by deesterification during GI absorption to produce the biologically active form. The pivalic acid generated quickly conjugates with carnitine and is excreted in the urine. The drop in plasma levels of carnitine was dose dependent and returned to normal levels upon termination of treatment.
UsesAntibacterial. Orally absorbed cephalosporin; ester prodrug of the active free acid metabolite, Cefcapene.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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