Bacterial cell wall synthesis; β-lactam
Cefetamet pivoxil hydrochloride targets bacterial penicillin-binding proteins (PBPs) involved in cell wall synthesis. As a cephalosporin antibiotic, the active form cefetamet inhibits bacterial cell wall synthesis by binding to PBPs, leading to bacterial cell lysis and death. The compound is active against a broad spectrum of aerobic gram-positive and gram-negative organisms including Streptococcus pneumoniae, Moraxella catarrhalis, Haemophilus influenzae, Group A hemolytic streptococci, Neisseria gonorrhoeae, and Enterobacteriaceae.

In vitro, cefetamet pivoxil hydrochloride is a prodrug and is not directly active as an antibiotic. However, its active metabolite cefetamet shows broad-spectrum antibacterial activity against many aerobic gram-positive and gram-negative organisms. Cefetamet is stable against bacterial beta-lactamases, making it effective against beta-lactamase-producing strains. The compound is active against Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, and various Enterobacteriaceae.

Cefetamet pivoxil is an oral third-generation cephalosporin that is hydrolyzed in vivo to release the active moiety, cefetamet. Cefetamet demonstrates excellent in vitro activity against major respiratory pathogens, including Streptococcus pneumoniae, Haemophilus influenzae, Moraxella (Branhamella) catarrhalis, and group A beta-hemolytic streptococci. It is active against beta-lactamase-producing strains of H. influenzae and M. catarrhalis, but exhibits poor activity against penicillin-resistant S. pneumoniae. Cefetamet shows marked activity against Neisseria gonorrhoeae and possesses a broad spectrum of activity against Enterobacteriaceae. Staphylococci and Pseudomonas species are resistant to cefetamet. Cefetamet pivoxil has been investigated for the treatment of both upper and lower community-acquired respiratory tract infections and has demonstrated efficacy equivalent to several established agents, including cefaclor, amoxicillin, and cefixime. In patients with group A beta-hemolytic streptococcal pharyngotonsillitis, a 7-day course of cefetamet pivoxil was as effective as a 10-day course of the standard agent, phenoxymethylpenicillin. In complicated urinary tract infections, cefetamet pivoxil showed similar efficacy to cefadroxil, cefaclor, and cefuroxime axetil. Cefetamet pivoxil was also effective in the treatment of otitis media, pneumonia, pharyngotonsillitis, and urinary tract infections in children. Preliminary data indicate that a single dose of cefetamet pivoxil can effectively eradicate N. gonorrhoeae in both men and women. The tolerability profile of cefetamet pivoxil is similar to that of other oral cephalosporins, with gastrointestinal effects being the most commonly reported adverse events. To date, no symptoms of carnitine deficiency have been reported with cefetamet pivoxil. Cefetamet pivoxil offers an effective oral alternative for the outpatient management of community-acquired respiratory tract infections, with the advantages of enhanced activity against H. influenzae and increased stability against beta-lactamases. However, its use in regions with a high prevalence of penicillin-resistant S. pneumoniae may be limited. Cefetamet pivoxil is also effective in treating urinary tract infections, although further trials are needed to establish any comparative advantages over other oral agents.
In vivo, cefetamet pivoxil hydrochloride is an orally active cephalosporin prodrug. Following oral administration, it is rapidly absorbed and metabolized to the active antibiotic cefetamet. The prodrug is used clinically for the treatment of community-acquired respiratory and urinary tract infections. It shows strong clinical efficacy against susceptible pathogens. The compound's oral bioavailability and tissue penetration allow effective treatment of systemic infections.

For non-cell enzyme/receptor binding assays, cefetamet pivoxil hydrochloride activity is assessed through its active metabolite cefetamet. Antibacterial susceptibility testing is performed using standard methods such as broth microdilution or agar dilution according to CLSI guidelines. Minimum inhibitory concentrations (MICs) are determined for various bacterial strains. The compound's stability against beta-lactamases can be assessed using enzyme inhibition assays. PBP binding affinity can be measured using radiolabeled penicillin competition assays.

For in vitro cell-based assays, cefetamet pivoxil hydrochloride is typically tested as its active metabolite cefetamet in antibacterial susceptibility assays. Bacterial cultures are incubated with various concentrations of the compound, and bacterial growth is monitored spectrophotometrically. MIC values are determined as the lowest concentration that inhibits visible bacterial growth. Time-kill studies can be performed to assess bactericidal activity. The compound's activity against clinical isolates is evaluated in susceptibility testing panels.

For in vivo animal experiments, cefetamet pivoxil hydrochloride is typically administered orally to rodent models of infection. Efficacy is assessed by measuring bacterial clearance from infected tissues. Pharmacokinetic studies in animals determine the absorption, distribution, metabolism, and elimination of the prodrug and its active metabolite. Dose-response studies are conducted to determine the effective dose for treating various infections. The compound's efficacy against specific pathogens is evaluated in infection models.

Cefetamet pivoxil hydrochloride has a molecular weight of 548.03 g/mol and molecular formula C₂₀H₂₆ClN₅O₇S₂. The compound is an ester prodrug with enhanced lipophilicity for oral absorption. It is rapidly metabolized to the active antibiotic cefetamet. The prodrug has low plasma protein binding (approximately 22%) and an elimination half-life of about 2.2 hours, with the drug being excreted primarily unchanged in the urine. The compound should be stored at 2-8°C.

5489410 rat LD50 subcutaneous >2 gm/kg SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION; SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE; KIDNEY, URETER, AND BLADDER: OTHER CHANGES Yakuri to Chiryo. Pharmacology and Therapeutics., 18(Suppl
5489410 dog LD oral >1 gm/kg Gekkan Yakuji. Pharmaceuticals Monthly., 35(803), 1993
5489410 rat LD50 oral >2 gm/kg SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION; SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE; KIDNEY, URETER, AND BLADDER: OTHER CHANGES Yakuri to Chiryo. Pharmacology and Therapeutics., 18(Suppl
Cefetamet pivoxil hydrochloride is generally well-tolerated at therapeutic doses. Common adverse effects include gastrointestinal disturbances such as nausea, diarrhea, and abdominal pain. Allergic reactions may occur in penicillin-allergic patients. The compound should be used with caution in patients with renal impairment as dose adjustment may be needed. Serious adverse effects are rare but include hypersensitivity reactions and Clostridium difficile-associated diarrhea.

[1]. Cefetamet pivoxil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1993;45(4):589-621.

Cefetamet Pivoxil hydrochloride is the hydrochloride form of cefotaxime, which is the pentvalerate prodrug form of cefotaxime. After oral administration of cefotaxime hydrochloride, the ester bond breaks, releasing the active ingredient cefotaxime.
Cefetamet pivoxil hydrochloride is an oral prodrug of cefetamet, a third-generation cephalosporin antibiotic approved for the treatment of community-acquired respiratory and urinary tract infections. The compound is a pivaloyloxymethyl ester that enhances oral bioavailability. It is converted to the active antibiotic cefetamet in the body. The drug is approved in various countries for clinical use. It is effective against a broad spectrum of pathogens and is stable against many beta-lactamases. It is available as a pharmaceutical product for oral administration.

C20H26CLN5O7S2

548.0327

547.096

111696-23-2

Cefetamet;65052-63-3;Cefetamet pivoxyl;65243-33-6 Cefetamet pivoxil hydrochloride;111696-23-2;Cefetamet hydrochloride;724438-16-8; 65243-25-6 (sodium)

5485221

White to off-white solid powder

732.3ºC at 760 mmHg

396.7ºC

9.78E-22mmHg at 25°C

2.551

3

12

10

35

933

2

Cl[H].S1C([H])([H])C(C([H])([H])[H])=C(C(=O)OC([H])([H])OC(C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])=O)N2C([C@]([H])([C@@]12[H])N([H])C(/C(/C1=C([H])SC(N([H])[H])=N1)=N/OC([H])([H])[H])=O)=O

XAAOHMIKXULDKJ-LZRHLYMTSA-N

InChI=1S/C20H25N5O7S2.ClH/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4;/h7,12,16H,6,8H2,1-5H3,(H2,21,22)(H,23,26);1H/b24-11+;/t12-,16-;/m1./s1

2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride

Cefetamet pivoxil hydrochloride; 111696-23-2; Globocef; 2YE9732GFU; Ro 15-8075;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 100 mg/mL (~182.47 mM)
H2O : ~0.67 mg/mL (~1.22 mM)

Solubility in Formulation 1: ≥ 2.75 mg/mL (5.02 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.75 mg/mL (5.02 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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 (Please use freshly prepared in vivo formulations for optimal results.)