Cefcapene
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| Category | Antibiotics |
| Catalog number | BBF-04114 |
| CAS | 135889-00-8 |
| Molecular Weight | 453.49 |
| Molecular Formula | C17H19N5O6S2 |
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Description
Cefbuperazone is a third-generation cephalosporin antibiotic.
Specification
| Synonyms | (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-carboxylic acid |
| IUPAC Name | (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-carboxylic acid |
| Canonical SMILES | CCC=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O |
| InChI | InChI=1S/C17H19N5O6S2/c1-2-3-8(9-6-30-16(18)20-9)12(23)21-10-13(24)22-11(15(25)26)7(4-28-17(19)27)5-29-14(10)22/h3,6,10,14H,2,4-5H2,1H3,(H2,18,20)(H2,19,27)(H,21,23)(H,25,26)/b8-3-/t10-,14-/m1/s1 |
| InChI Key | HJJRIJDTIPFROI-NVKITGPLSA-N |
Properties
| Antibiotic Activity Spectrum | bacteria |
| Boiling Point | 936°C at 760 mmHg |
| Density | 1.63 g/cm3 |
Reference Reading
1. Cefcapene inactivates chromosome-encoded class C beta-lactamases
Yoshikazu Ishii, Moreno Galleni, Keizo Yamaguchi, Masahiko Ito, Jean-Marie Frère, Jimena Alba J Infect Chemother . 2002 Sep;8(3):207-10. doi: 10.1007/s10156-002-0177-7.
The stability of cefcapene and cefpodoxime, oral antibacterial cephalosporins, toward different classes of beta-lactamases was evaluated. For the class A beta-lactamases, TEM-1, SHV-1, and NMC-A, only the steady-state kinetic parameter ( k(cat)/ Km) values were calculated (3100 - 1.1 x 10(7) M(-1) x s(-1)), because these enzymes have very high Km values for cefpodoxime and cefotaxime. As for class B beta-lactamases L1, IMP-1, and CcrA, in general, similar k(cat)/ Km values were obtained. However, regarding class C beta-lactamases from Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa, and Citrobacter freundii, we found major differences in stability between the two compounds. Cefpodoxime acted as a good substrate for the class C beta-lactamases, except for the enzyme from E. cloacae; its k(cat) and Km values were successfully calculated ( k(cat)/ Km, 1.8 x 10(5) - 1.2 x 10(7) M(-1) x s(-1)). On the other hand, cefcapene acted as a poor substrate or an inactivator for class C beta-lactamases; its k(2)/ K value was successfully calculated (8.7 x 10(5) - 7.0 x 10(6) M(-1) x s(-1)). In addition, k(3) values were determined for beta-lactamases from P. aeruginosa (2.3 x 10(-2) x s(-1)) and C. freundii (2.1 x 10(-1) x s(-1)). Even though these values could be calculated, transient inactivation as an enzyme reactivation reaction for all these enzymes was observed. These findings suggest the potential of cephem compounds as inhibitors of class C beta-lactamases.
2. Cefcapene Pivoxil Hydrochloride Is a Potentially New Treatment for Palmoplantar Pustulosis with Pustulotic Arthro-Osteitis
Kana Masuda, Chika Namba, Fumiko Oda, Masamoto Murakami, Koji Sayama, Ryo Utsunomiya Dermatology . 2015;231(4):304-11. doi: 10.1159/000439401.
Pustulosis palmaris et plantaris or palmoplantar pustulosis (PPP) is a refractory pustular eruption of the palms and soles with unknown etiology. In addition to skin lesions, PPP patients may present with severe joint pain and pustulotic arthro-osteitis (PAO), especially of the sternoclavicular joint. PAO is sometimes regarded as a variant of synovitis, acne, pustulosis, hyperostosis and osteitis (SAPHO) syndrome. Hence, macrolide and tetracycline antibiotics are used for the treatment of PPP with PAO. We report 3 cases of PPP with PAO that did not improve upon administration of macrolide antibiotics with NSAIDs. After administration of cefcapene pivoxil hydrochloride (CFPN-PI), a third-generation cephalosporin, the swelling and sternoclavicular joint pain were promptly reduced and dramatically improved in all 3 cases. We review the conventional antibiotic treatments used currently and propose CFPN-PI as a potentially new therapy for PPP or PPP + PAO.
3. Poor penetration of cefcapene into aqueous humor after oral administration of cefcapene pivoxil to patients undergoing cataract surgery
Tetsuya Toyono, Yuta Okada, Hiroshi Suzuki, Shotaro Asano, Shu Okugawa, Makoto Aihara, Ryo Yamaguchi, Takehito Yamamoto, Koh Okamoto, Kyoji Moriya J Infect Chemother . 2020 Feb;26(2):312-315. doi: 10.1016/j.jiac.2019.08.004.
Objectives:Studies on the penetration of orally administered cephalosporins to the aqueous humor are scarce. Therefore, in this study, we determined the concentration of cefcapene, a third-generation cephalosporin administrated orally as pivalate ester (cefcapene pivoxil), in the aqueous humor of patients undergoing cataract surgery to assess its potential for preventing postoperative endophthalmitis.Methods:Forty-four patients were administered a single dose of 100 mg cefcapene pivoxil preoperatively. Blood and aqueous humor samples were obtained at the time of surgery, and cefcapene concentrations were measured using ultra-performance liquid chromatography with tandem mass spectrometric detection.Results:The samples were obtained from 41 eyes of 39 patients (two patients underwent surgery in both eyes). The median cefcapene concentrations in the aqueous humor after 1-2 h, 2-3 h, and later than 3 h were 8.3, 18.4, and 23.7 ng/mL, respectively. The median cefcapene concentrations in serum after 1-2 h, 2-3 h, and later than 3 h were 198.5, 287.2, and 170.3 ng/mL, respectively. Aqueous humor penetration of cefcapene after 1-2 h, 2-3 h, and later than 3 h was 4.1, 7.9, and 13.5% respectively.Conclusions:Aqueous humor penetration of orally-administered cefcapene pivoxil in patients undergoing cataract surgery was poor. Therefore, cefcapene pivoxil was unlikely to be effective for preventing endophthalmitis after cataract surgery.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
