Cas no 147816-23-7 (Cefcapene pivoxil hydrochloride)

Cefcapene pivoxil hydrochloride is a third-generation oral cephalosporin antibiotic, chemically designated as (6R,7R)-7-[(Z)-2-(2-Amino-4-thiazolyl)-2-(carboxymethoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-yl)methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivoxil hydrochloride. It exhibits broad-spectrum activity against Gram-positive and Gram-negative bacteria, including β-lactamase-producing strains. The pivoxil ester enhances oral bioavailability, allowing effective systemic absorption. Its mechanism involves inhibition of bacterial cell wall synthesis by binding to penicillin-binding proteins. Cefcapene pivoxil hydrochloride is clinically used for respiratory, urinary, and soft tissue infections. Advantages include stability against certain β-lactamases, convenient dosing due to oral administration, and a favorable safety profile. It is typically administered as a prodrug, hydrolyzed to the active form in vivo.
Cefcapene pivoxil hydrochloride structure
147816-23-7 structure
Product Name:Cefcapene pivoxil hydrochloride
CAS No:147816-23-7
MF:C23H30ClN5O8S2
MW:604.096002101898
MDL:MFCD00864877
CID:160815
PubChem ID:6918126
Update Time:2025-06-22

Cefcapene pivoxil hydrochloride Chemical and Physical Properties

Names and Identifiers

    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester, hydrochloride (1:1), (6R,7R)-
    • Cefcapene Pivoxil Hydrochloride
    • 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,hydrochloride
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester, hydrochl
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2...
    • Cefcapene pivoxil
    • Flomox
    • Flumax
    • (6R,7R)-(Pivaloyloxy)methyl 7-((Z)-2-(2-aminothiazol-4-yl)pent-2-enamido)-3-((carbamoyloxy)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
    • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-(((2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, (6R,7R)-
    • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, (6R-(6alpha,7beta(Z)))-
    • 5J77167P9E
    • CEFCAPENE PIVOXIL HCL
    • DSSTox_CID_28508
    • DSSTox_RID_82780
    • DSSTox_GSID_48582
    • 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;hydro
    • Q27262399
    • Cefcamate pivoxil hydrochloride
    • AS-42049
    • CEFCAPENE PIVOXIL HYDROCHLORIDE ANHYDROUS [MI]
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-(2-AMINO-4-THIAZOLYL)-1-OXO-2- PENTENYL)AMINO)-8-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER,(6R- (6-.ALPHA.,7-.BETA.(Z)))-, MONOHYDROCHLORIDE
    • UNII-5J77167P9E
    • MFCD00883711
    • C2623
    • NCGC00183048-01
    • 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-(2-amino-4-thiazolyl)-1-oxo-2-pentenyl)amino)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, (6R-(6alpha,7beta(Z)))-
    • A925072
    • CEFCAPENE PIVOXIL HYDROCHLORIDE [WHO-DD]
    • Tox21_113259
    • CHEMBL3184257
    • DTXSID7048582
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R,7 R)-, hydrochloride, hydrate (1:1:1)
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-1-oxo-2-penten-1-yl]amino]-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, hydrochloride (1:1), (6R,7R)-
    • DTXCID3028508
    • S-1108
    • 147816-23-7
    • 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;hydrochloride
    • CS-0109981
    • AKOS027327778
    • CAS-147816-23-7
    • Tox21_112911
    • NCGC00183096-01
    • J-008414
    • HY-135221
    • Cefcapene pivoxil (hydrochloride)
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-(2-AMINO-4-THIAZOLYL)-1-OXO-2-PENTENYL)AMINO)-8-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER,(6R-(6-.ALPHA.,7-.BETA.(Z)))-, MONOHYDROCHLORIDE
    • GLXC-03047
    • 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-(2-AMINO-4-THIAZOLYL)-1-OXO-2-PENTENYL)AMINO)-8-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER,(6R-(6-ALPHA,7-BETA(Z)))-, MONOHYDROCHLORIDE
    • CEFCAPENE PIVOXIL HYDROCHLORIDE ANHYDROUS
    • Cefcapene pivoxil hydrochloride
    • MDL： MFCD00864877
    • Inchi： 1S/C23H29N5O8S2.ClH/c1-5-6-12(13-9-38-21(24)26-13)16(29)27-14-17(30)28-15(11(7-34-22(25)33)8-37-18(14)28)19(31)35-10-36-20(32)23(2,3)4;/h6,9,14,18H,5,7-8,10H2,1-4H3,(H2,24,26)(H2,25,33)(H,27,29);1H/b12-6-;/t14-,18-;/m1./s1
    • InChI Key： ALPFRUJYOAKQQR-CQZSJNSUSA-N
    • SMILES： Cl.S1CC(COC(N)=O)=C(C(=O)OCOC(C(C)(C)C)=O)N2C([C@H]([C@@H]12)NC(/C(/C1=CSC(N)=N1)=C\CC)=O)=O

Computed Properties

  • Exact Mass: 603.12200
  • Monoisotopic Mass: 603.122432
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 39
  • Rotatable Bond Count: 13
  • Complexity: 1060
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 247

Experimental Properties

  • Melting Point: 158-164°C
  • PSA: 251.99000
  • LogP: 3.38210

Cefcapene pivoxil hydrochloride Security Information

  • Storage Condition：-20°C Freezer

Cefcapene pivoxil hydrochloride Pricemore >>

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Cefcapene pivoxil hydrochloride Related Literature

Additional information on Cefcapene pivoxil hydrochloride

Recent Advances in Cefcapene Pivoxil Hydrochloride (147816-23-7) Research: A Comprehensive Review

Cefcapene pivoxil hydrochloride (CAS: 147816-23-7) is a third-generation oral cephalosporin antibiotic with a broad spectrum of antibacterial activity. It is a prodrug of cefcapene, which is hydrolyzed to its active form in the body. This compound has been widely used in clinical settings for treating various bacterial infections, particularly those caused by Gram-positive and Gram-negative pathogens. Recent studies have focused on its pharmacokinetic properties, clinical efficacy, and potential applications in combating antibiotic-resistant strains.

A 2023 study published in the Journal of Antimicrobial Chemotherapy investigated the pharmacokinetics of cefcapene pivoxil hydrochloride in pediatric patients. The research demonstrated that the drug exhibits favorable absorption and bioavailability, with a plasma half-life suitable for twice-daily dosing. These findings support its use in pediatric populations, addressing a critical gap in antibiotic options for children. The study also highlighted the importance of dose adjustments based on body weight to optimize therapeutic outcomes.

In the context of antimicrobial resistance, a recent Antimicrobial Agents and Chemotherapy publication (2024) explored the efficacy of cefcapene pivoxil hydrochloride against extended-spectrum β-lactamase (ESBL)-producing Escherichia coli. The in vitro studies showed promising activity, particularly when combined with β-lactamase inhibitors. This research suggests potential strategies for overcoming resistance mechanisms in urinary tract infections, which are increasingly caused by ESBL-producing organisms.

Manufacturing and formulation advancements have also been reported. A 2024 patent application disclosed an improved synthesis method for cefcapene pivoxil hydrochloride (147816-23-7) that enhances yield and purity while reducing production costs. This development could significantly impact the drug's accessibility in developing markets. Additionally, novel sustained-release formulations are under investigation to prolong therapeutic drug levels and improve patient compliance.

Clinical trials continue to explore new indications for cefcapene pivoxil hydrochloride. An ongoing phase III study in Japan is evaluating its efficacy in treating acute otitis media caused by drug-resistant Streptococcus pneumoniae. Preliminary results presented at the 2024 Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC) showed superior clinical response rates compared to current standard therapies.

From a safety perspective, a comprehensive post-marketing surveillance study (2023) involving over 10,000 patients reaffirmed the drug's favorable safety profile. The incidence of adverse effects remained low, with gastrointestinal symptoms being the most commonly reported. These real-world data provide valuable insights for clinicians considering cefcapene pivoxil hydrochloride in their therapeutic arsenal.

Future research directions include investigating the drug's potential in biofilm-associated infections and its role in antimicrobial stewardship programs. The unique chemical properties of 147816-23-7, particularly its stability and absorption characteristics, make it an interesting candidate for further development in these challenging areas of infectious disease management.

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