Bacterial cell wall synthesis; β-lactam

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.

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

[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.

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.)