Cefteram pivoxil

Cefteram pivoxil

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Cefteram pivoxil
Category Antibiotics
Catalog number BBF-00745
CAS 82547-81-7
Molecular Weight 593.64
Molecular Formula C22H27N9O7S2
Purity 90%

Ordering Information

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BBF-00745 100 mg $999 In stock

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Description

It is produced by the strain of Semisynthetic third generation cephalosporin. Ceftrium Pivoxil is a prevalent of ceftrium, which is a semi-synthetic, broad-spectrum antibiotic with antibacterial activity.

Specification

Synonyms Ro 19-5248; T 2588; Tomir; Tomiron; T-2588; Cefteram pivaloyloxymethyl ester; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((5-methyl-2H-tetrazol-2-yl)methyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6R-(6-alpha,7-beta(Z)))-
Storage −20 °C under inert atmosphere
IUPAC Name 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Canonical SMILES CC1=NN(N=N1)CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
InChI InChI=1S/C22H27N9O7S2/c1-10-26-29-30(27-10)6-11-7-39-18-14(25-16(32)13(28-36-5)12-8-40-21(23)24-12)17(33)31(18)15(11)19(34)37-9-38-20(35)22(2,3)4/h8,14,18H,6-7,9H2,1-5H3,(H2,23,24)(H,25,32)/b28-13-/t14-,18-/m1/s1
InChI Key UIYAXIPXULMHAI-JLGRZTKVSA-N
Source Synthetic

Properties

Appearance White to Pale Yellow Solid
Application Anti-Bacterial Agents
Melting Point 127-128 °C (dec.)
Density 1.66 g/cm3
Solubility Soluble in Methanol, anhydrous Ethanol, Acetone, Chloroform; Insoluble in Ether; Hardly soluble in Water

Reference Reading

1. New sensitization to house dust mites in cefteram-induced occupational asthma: a case report
Hyun Jung Jin, Jeong-Eun Kim, Joo-Hee Kim, Young-Min Ye, Hae-Sim Park Allergy Asthma Immunol Res. 2011 Apr;3(2):132-4. doi: 10.4168/aair.2011.3.2.132. Epub 2011 Feb 14.
Occupational asthma (OA) can improve after cessation of exposure; however, some patients suffer from persistence or aggravation of their asthmatic symptoms. Here we report a case of a new sensitization to house dust mites during the follow-up period in a 37-year-old female patient with OA induced by cefteram pivoxil powder (cefteram powder). She was previously diagnosed with OA caused by inhalation of cefteram powder. Consequently, she left her job and had been well for 9 subsequent years. She began to experience aggravation of her rhinitis and asthmatic symptoms again several months prior to presentation. Her skin-prick test results had converted to strongly positive responses to two types of house dust mites. The serum levels of eosinophil cationic protein (ECP) and the total and specific immunoglobulin (Ig)E levels against the two types of house dust mites were elevated. An inhalation challenge test with Dermatophagoides farinae was performed, and significant bronchoconstriction (21.1% reduction in the forced expiratory volume in the first second) with asthma symptoms was observed at 10 minutes. To our knowledge, this is the first case demonstrating a new sensitization to house dust mites in a patient with OA caused by cefteram powder. Regular monitoring, including skin-prick tests and measurement of specific serum IgE/ECP levels, may help to screen potential cases.
2. Pharmacokinetics and bioequivalence studies of cefteram pivoxil in healthy Chinese volunteers
Fangmi Wei, Rong Zhu, Wenhui Zhao, Jing Yang, Zheng Cai, Qin Hu Eur J Drug Metab Pharmacokinet. 2009 Jul-Sep;34(3-4):157-62. doi: 10.1007/BF03191167.
A simple, sensitive and specific method has been developed for the determination of cefteram in human plasma. Sample preparation was accomplished through protein precipitation with 20% trichloroacetic acid (v/v) and chromatographic separation was performed on a C18 column at 25 degrees C. The mobile phase consisted of methanol-aqueous 20 mM ammonium acetate (18:82, v/v) at flow rate of 1.0 mL/min. Wavelength was set at 235 nm. The lower limit of quantification was 0.04 microg/mL and the assay exhibited a linear range of 0.04-3.2 microg/mL (r=0.9996). The relative recoveries of cefteram from human plasma at three different concentrations were more than 90%. The method was successfully applied to investigate the bioequivalence between two kinds of cefteram pivoxil preparations (test vs reference) in 24 healthy Chinese volunteers. After a single 100 mg dose for the test and reference product, the resulting means of major pharmacokinetic parameters such as AUC(0-t), AUC(0-infinity), Cmax and Tmax of cefteram pivoxil were 4.75 +/- 1.35 vs 4.76 +/- 1.29 microg h/mL, 4.89 +/- 1.36 vs 4.91 +/- 1.29 microg h/mL, 1.65 +/- 0.45 vs 1.73 +/- 0.45 microg/mL and 1.48 +/- 0.59 vs 1.73 +/- 0.45 h, respectively, indicating that these two kinds of preparations were bioequivalent.
3. Impurity profiling of Cefteram pivoxil based on Fourier transform ion cyclotron resonance MS
Yiqiang Yue, Jiahong Wang, Yanhong Zhao, Siqi Li, Jing Han, Yu Zhang, Qingyu Zhang, Fei Han J Pharm Biomed Anal. 2020 Nov 30;191:113591. doi: 10.1016/j.jpba.2020.113591. Epub 2020 Aug 29.
Profiling impurities for the active pharmaceutical ingredients (APIs) is an indispensable step in drug development process. Nowadays, high resolution mass spectrometry is the first choice for determining the chemical formula of organic impurities. However, merely base on the accurate mass to screen the formula is obviously not a flawless method. In this paper, a reliable strategy based on Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) was presented to profile the related impurities. Firstly, Cefteram pivoxil was subjected to forced degration under hydrolytic (acidic and basic), oxidative, photolytic and thermal conditions according to ICH guidelines. Then, a highly specific and efficient HPLC-FT-ICR MS compatible method was developed and it was used to separate and characterize the process related substances and the major degradation products in Cefteram pivoxil. Next, isotopic fine structures (IFSs) of all impurities were acquired to decisively determine their elemental composition. Finally, the possible chemical structures of impurities were predicted by combining the information of accurate mass, retention time, IFSs and characteristic fragmentation ions. As a result, a total of 20 related substances including 6 process related substances and 14 degradation products were identified and characterized. To the best of our knowledge, 13 of these related substances were not reported in the previous literature. It indicates that the developed strategy is accurate and standard independent to determine the chemical formulae of organic impurities in APIs. In conclusion, the impurity profiles obtained in this study are critical to the quality control and stability study of Cefteram pivoxil. Moreover, the developed method can be used as a versatile workflow to profile the impurities in APIs in the future, especially for the unknown impurities.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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