Cefminox sodium
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| Category | Antibiotics |
| Catalog number | BBF-04041 |
| CAS | 75498-96-3 |
| Molecular Weight | 541.56 |
| Molecular Formula | C16H20N7O7S3Na |
| Purity | ≥98% |
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Description
Cefminox is a broad-spectrum, bactericidal cephalosporin antibiotic. It is especially effective against Gram-negative and anaerobic bacteria. Cefminox Sodium is the sodium salt form of cefminox, which is a semi-synthetic, second-generation and beta-lactamase-stable cephalosporin with antibacterial activity. It is also known as Meicelin and MT-141, which is a penicillin binding protein inhibitor used to treat bacterial infection.
Specification
| Related CAS | 75481-73-1 (free acid) |
| Synonyms | MT-141; MT 141; Meicelin |
| Storage | Store at -20°C |
| IUPAC Name | sodium;(6R,7S)-7-[[2-[(2S)-2-amino-2-carboxyethyl]sulfanylacetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| Canonical SMILES | CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC(C(=O)O)N)OC)SC2)C(=O)[O-].[Na+] |
| InChI | InChI=1S/C16H21N7O7S3.Na/c1-22-15(19-20-21-22)33-4-7-3-32-14-16(30-2,13(29)23(14)10(7)12(27)28)18-9(24)6-31-5-8(17)11(25)26;/h8,14H,3-6,17H2,1-2H3,(H,18,24)(H,25,26)(H,27,28);/q;+1/p-1/t8?,14-,16+;/m1./s1 |
| InChI Key | SBIDXLKJYJVQOE-ZMUPEPPLSA-M |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Solubility | Soluble in DMSO |
Reference Reading
1. Antibacterial activity of cefminox against anaerobes
K Watanabe,M Bunai,K Sawa,K Ueno J Antibiot (Tokyo) . 1985 May;38(5):649-60. doi: 10.7164/antibiotics.38.649.
The antibacterial activity of cefminox (CMNX) against anaerobic bacteria was studied in vitro. The results are as follows: 1. CMNX exerted antibacterial activity against a wide range of anaerobes, excluding Clostridium innocuum. The antibacterial activity of CMNX against Bacteroides fragilis was comparable to that of latamoxef and superior to cefoxitin, but CMNX's activity against anaerobic cocci was slightly inferior to cefoxitin's; 2. A comparison of the MICs and MBCs of CMNX indicated that this drug exerts a complete bactericidal effect at a concentration which inhibits the growth of bacteria; 3. CMNX was found to be stable to the beta-lactamases produced by B. fragilis; 4. CMNX exerted an antibacterial activity against C. difficile.
2. Synthesis of cefminox by cell-free extracts of Streptomyces clavuligerus
Y H Park,Y J Choi,J S Chae,H Kang,J K Kim FEMS Microbiol Lett . 2000 Jan 15;182(2):313-7. doi: 10.1111/j.1574-6968.2000.tb08914.x.
In vitro synthesis of cefminox by cell-free extracts of Streptomyces clavuligerus was investigated using alpha-ketoglutarate, L-ascorbic acid, FeSO(4), S-adenosyl-L-methionine, and 7alpha-demethoxycefminox as the substrates. The formation of cefminox was detected both by a biological assay with Proteus vulgaris GN 76/C-1 and by high performance liquid chromatography. Although the conversion rate of 7alpha-demethoxycefminox to cefminox was observed to be quite low, it still demonstrated the potential for an enzymatic process to replace the chemical steps which are currently in use for the production of cefminox.
3. [Study on the concentration of cefminox sodium in serum and prostatic tissue]
I Sasagawa Hinyokika Kiyo . 1990 Jun;36(6):737-9.
The concentration of cefminox sodium (CMNX) in serum and prostatic tissue was determined in 25 patients with benign prostatic hypertrophy. One gram of CMNX was intravenously administered prior to transurethral prostatectomy. Blood and prostatic tissue were obtained 1 hour after the administration of CMNX. The concentration of CMNX was 69.17 +/- 17.47 micrograms/ml (mean +/- SD) in serum and 5.33 +/- 2.33 micrograms/g (mean +/- SD) in the prostatic tissue. The ratio of the prostatic tissue concentration/serum concentration was 8.18 +/- 4.45% (mean +/- SD). There was no correlation between serum and prostatic tissue level of CMNX.
4. In vitro activities of cefminox against anaerobic bacteria compared with those of nine other compounds
D B Hoellman,P C Appelbaum,S K Spangler,M R Jacobs Antimicrob Agents Chemother . 1998 Mar;42(3):495-501. doi: 10.1128/AAC.42.3.495.
The agar dilution MIC method was used to test the activity of cefminox, a beta-lactamase-stable cephamycin, compared with those of cefoxitin, cefotetan, moxalactam, ceftizoxime, cefotiam, cefamandole, cefoperazone, clindamycin, and metronidazole against 357 anaerobes. Overall, cefminox was the most active beta-lactam, with an MIC at which 50% of isolates are inhibited (MIC50) of 1.0 microg/ml and an MIC90 of 16.0 microg/ml. Other beta-lactams were less active, with respective MIC50s and MIC90s of 2.0 and 64.0 microg/ml for cefoxitin, 2.0 and 128.0 microg/ml for cefotetan, 2.0 and 64.0 microg/ml for moxalactam, 4.0 and > 128.0 microg/ml for ceftizoxime, 16.0 and > 128.0 microg/ml for cefotiam, 8.0 and >128.0 microg/ml for cefamandole, and 4.0 and 128.0 microg/ml for cefoperazone. The clindamycin MIC50 and MIC90 were 0.5 and 8.0 microg/ml, respectively, and the metronidazole MIC50 and MIC90 were 1.0 and 4.0 microg/ml, respectively. Cefminox was especially active against Bacteroides fragilis (MIC90, 2.0 microg/ml), Bacteroides thetaiotaomicron (MIC90, 4.0 microg/ml), fusobacteria (MIC90, 1.0 microg/ml), peptostreptococci (MIC90, 2.0 microg/ml), and clostridia, including Clostridium difficile (MIC90, 2.0 microg/ml). Time-kill studies performed with six representative anaerobic species revealed that at the MIC all compounds except ceftizoxime were bactericidal (99.9% killing) against all strains after 48 h. At 24 h, only cefminox and cefoxitin at 4x the MIC and cefoperazone at 8x the MIC were bactericidal against all strains. After 12 h, at the MIC all compounds except moxalactam, ceftizoxime, cefotiam, cefamandole, clindamycin, and metronidazole gave 90% killing of all strains. After 3 h, cefminox at 2 x the MIC produced the most rapid effect, with 90% killing of all strains.
5. Cefminox, a Dual Agonist of Prostacyclin Receptor and Peroxisome Proliferator-Activated Receptor-Gamma Identified by Virtual Screening, Has Therapeutic Efficacy against Hypoxia-Induced Pulmonary Hypertension in Rats
Gulinuer Wumaier,Li Yang,Mengjie Niu,Liang Dong,Zhiwei Yang,Shengli Zhang,Jingwen Xia,Xiaomin Wei,Yi Gong,Shengqing Li,Ying Li,Ning Zhu Front Pharmacol . 2018 Feb 23;9:134. doi: 10.3389/fphar.2018.00134.
Prostacyclin receptor (IP) and peroxisome proliferator-activated receptor-gamma (PPARγ) are both potential targets for treatment of pulmonary arterial hypertension (PAH). Expression of IP and PPARγ decreases in PAH, suggesting that screening of dual agonists of IP and PPARγ might be an efficient method for drug discovery. Virtual screening (VS) of potential IP-PPARγ dual-targeting agonists was performed in the ZINC database. Ten of the identified compounds were further screened, and cefminox was found to dramatically inhibit growth of PASMCs with no obvious cytotoxicity. Growth inhibition by cefminox was partially reversed by both the IP antagonist RO113842 and the PPARγ antagonist GW9662. Investigation of the underlying mechanisms of action demonstrated that cefminox inhibits the protein kinase B (Akt)/mammalian target of rapamycin (mTOR) signaling pathway through up-regulation of the expression of phosphatase and tensin homolog (PTEN, which is inhibited by GW9662), and enhances cyclic adenosine monophosphate (cAMP) production in PASMCs (which is inhibited by RO113842). In a rat model of hypoxia-induced pulmonary hypertension, cefminox displayed therapeutic efficacy not inferior to that of the prostacyclin analog iloprost or the PPARγ agonist rosiglitazone. Our results identified cefminox as a dual agonist of IP and PPARγ that significantly inhibits PASMC proliferation by up-regulation of PTEN and cAMP, suggesting that it has potential for treatment of PAH.
6. Cefminox sodium penetration into prostatic tissue with and without inflammation
I Sasagawa,Y Shiraiwa,O Yamaguchi Int Urol Nephrol . 1991;23(6):569-72. doi: 10.1007/BF02549847.
The concentrations of cefminox sodium (CMNX) in serum and prostatic tissue were determined in 36 cases of prostatic hyperplasia with and without inflammation. Mean ratios of CMNX in tissue over concentration in serum were 0.11 +/- 0.07 for patients with inflammation and 0.09 +/- 0.06 for those without inflammation. There was no significant difference between the two groups. These data suggest that CMNX penetration into prostatic tissue is not influenced by the presence of inflammation.
7. Cefminox versus Cefoxitin in Hysterectomy Prophylaxis : Clinical Efficacy and Serum and Tissue Concentrations
M Vargas,M A Macía,J M Romo,M Maciá,R Garrido,M Sánchez,P Coronet,M Gimeno,L Carrasco,A Novo,S Quintana,F Lapuente,A J Carcas,Y Mieza,J Frías,V Caballero Fernández,M J de Dios Clin Drug Investig . 1997 Jun;13(6):317-25. doi: 10.2165/00044011-199713060-00004.
This phase III, prospective, randomised, open, controlled clinical trial compared the efficacy of single-dose cefminox (2g) versus triple-dose cefoxitin (2g every 4 hours) as antibiotic prophylaxis in 112 women undergoing gynaecological surgery (vaginal or abdominal hysterectomy). Peak, intraoperative and trough serum concentrations were determined for both antibiotics, as well as their concentrations in myometrial tissue in a subset of patients from the study (22 patients from the cefminox group and 18 from the cefoxitin group). Clinical response was satisfactory in all women treated with cefminox (59 of 59) and in 52 of 53 patients treated with cefoxitin. Fever-related morbidity, hospital stay and adverse reactions were similar in both groups. Peak serum concentrations were 132.3 mg/L for cefminox and 82.2 mg/L for cefoxitin. 12-hour concentrations were 2.82 mg/L for cefminox and 2.17 mg/L for cefoxitin, and were higher than the respective minimum inhibitory concentrations (MICs) for pathogens commonly associated with this pathology. Uterine tissue concentrations were 24.5 and 41.6 mg/L for cefminox and cefoxitin, respectively, and also clearly exceeded MIC. It was shown that the use of a single preoperative dose of cefminox was similar in efficacy to 3 doses of cefoxitin administered every 4 hours, and that the serum and tissue concentrations attained provide adequate antibiotic coverage. In view of the general trend towards the use of a single dose for prophylaxis, cefminox offers a new alternative for antibiotic prophylaxis in gynaecological surgery.
8. Severe coagulopathy caused by cefminox sodium in a liver cirrhosis patient: a case report
Yao Xie,Shuling Wu,Minghui Li,Xiaoyue Bi,Yanjie Lin,Liu Yang Infect Agent Cancer . 2022 Jun 16;17(1):30. doi: 10.1186/s13027-022-00446-y.
Cefminox sodium is an antimicrobial agent with broad-spectrum antibacterial activity against Gram-positive and Gram-negative bacteria. Cefminox sodium has high security in clinical practice for its few adverse effects such as coagulation dysfunction, which is rare in clinical treatment. Even in patients suffering from chronic liver disease with coagulation dysfunction, it rarely leads to further deterioration of coagulation function. Therefore, patients with chronic liver disease develop severe coagulation dysfunction during the application of cefminox sodium, which is often mistaken for worsening of liver disease other than considered to be the side effect of the drug. Therefore, we report a 55-year-old female patient with liver cirrhosis and hepatocellular carcinoma treated with cefminox sodium intravenously twice for peritonitis. During the treatments, severe coagulopathy occurred, and the coagulation function quickly recovered after drug withdrawal. The diagnosis and treatment of this patient provides us with ideas for dealing with similar problems in clinical practice in the future.
9. Separation and Characterization of Unknown Impurities and Isomers in Cefminox Sodium and Study of the Forming Mechanisms of Impurities by Liquid Chromatography Coupled with Ion Trap/Time-Of-Flight Mass Spectrometry
Yu Xu,Jian Wang,Dandan Wang,Lan Tang J Chromatogr Sci . 2019 Mar 1;57(3):204-212. doi: 10.1093/chromsci/bmy101.
Thirteen unknown impurities and isomers in cefminox sodium were separated and characterized by liquid chromatography coupled with high-resolution ion trap/time-of-flight mass spectrometry (LC-IT-TOF-MS) with the positive mode of electrospray ionization (ESI) method. New HPLC-gradient elution method was developed for the detection of impurities in cefminox sodium. And the ESI ion trap multiple-stage tandem mass spectrometry had been applied successfully to the direct investigation of impurities and isomers in cefminox sodium. The fragmentation patterns and structural assignment of these impurities were studied. Full scan liquid chromatography-mass spectrometry (LC-MS) was first performed to obtain the m/z value of the protonated molecules and formulas of all detected peaks, LC-MSn (n = 1-6) were then carried out on the compounds of interest. Structures of 13 degradation products in cefminox sodium were deduced based on the high-resolution MSn (n = 1-6) data, assisted by the UV spectra and stress testing. And the forming mechanisms of degradation products in cefminox were also studied. The method of LC-IT-TOF-MSn (n = 1-6) was worthy of widespread use and application for the further improvement of official monographs in pharmacopoeias with the advantages of stability and repeatability.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
