Cefotiam
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| Category | Antibiotics |
| Catalog number | BBF-00733 |
| CAS | 61622-34-2 |
| Molecular Weight | 525.63 |
| Molecular Formula | C18H23N9O4S3 |
| Purity | ≥ 95% |
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Description
It is produced by the strain of Semisynthetic second generation cephalosporin. Cefotiam is active against a broad spectrum of both Gram positive and Gram negative bacteria. Cefotiam binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted.
Specification
| Related CAS | 66309-69-1 (dihydrochloride) |
| Synonyms | Cefotiamum; Ceradon; Ceradolan; Haloapor; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)acetyl)amino)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-trans)- |
| IUPAC Name | (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CN(C)CCN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)CC4=CSC(=N4)N)SC2)C(=O)O |
| InChI | InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1 |
| InChI Key | QYQDKDWGWDOFFU-IUODEOHRSA-N |
Properties
| Boiling Point | 843.0 °C |
| Density | 1.80±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water |
Reference Reading
1. Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses
S Shimizu, K R Chen, S Miyakawa Dermatology. 1996;192(2):174-6. doi: 10.1159/000246352.
A case of occupational contact urticaria syndrome caused by cefotiam dihydrochloride (CTM) in a Japanese nurse is reported. The patient had become sensitized to CTM through the process of preparing antibiotics 8 months before she developed symptoms. A review of the literature revealed 13 similar cases, all involving Japanese nurses, reported since CTM became available in Japan.
2. Study on Isomeric Impurities in Cefotiam Hydrochloride
Ye Tian, Xiao-Meng Chong, Ying Liu, Ying Han, Chang-Qin Hu, Shang-Chen Yao, Ming-Zhe Xu Front Chem. 2021 Jan 15;8:619307. doi: 10.3389/fchem.2020.619307. eCollection 2020.
In this study, two isomeric impurities were identified in cefotiam hydrochloride injection preparation and were characterized. Column-switching HPLC-MS and NMR techniques were used to identify the impurity 1 as the Δ3(4) isomers of cefotiam. Using software-based calculations, it was predicted that neither of the isomeric impurities was embryotoxic. This study provides a reference for the production, storage, and quality control of cefotiam and related cephalosporin antibiotics.
3. Cefotiam Treatment in Children: Evidence of Subtherapeutic Levels
Min Kan, Ling Wu, Xin-Wei Zhou, Yong-Fang Jiang, Yue-E Wu, Hai-Yan Shi, Guo-Xiang Hao, Yi Zheng, Le-Qun Su, Xin Huang, Wei Zhao Ther Drug Monit. 2020 Oct;42(5):733-736. doi: 10.1097/FTD.0000000000000759.
Background: Cefotiam, a second-generation cephalosporin, is a broad-spectrum antibiotic with good antibacterial action against both gram-negative and gram-positive bacteria. It is used widely in clinical practice, although bacterial drug resistance makes its clinical use problematic. The authors hypothesized that subtherapeutic concentrations of cefotiam leads to bacterial resistance. The present study was conducted to evaluate whether the standard cefotiam dosing regimen resulted in a subtherapeutic concentrations in children. Method: Data were prospectively collected from pediatric patients with suspected or confirmed community-acquired pneumonia who were receiving cefotiam at the standard dosing regimen (40-80 mg/kg, 2 or 3 times daily). A blood sample was collected after 70%-100% of the dosing interval, and plasma concentrations were determined by high-performance liquid chromatography using an ultraviolet detector. Results: The data from 88 patients (age, 3.0 ± 2.8 years; weight, 15.4 ± 8.3 kg) were used for analysis. The average of cefotiam concentrations was 0.06 mcg/mL (range: <0.05-0.79 mcg/mL). Most patients (n = 72, 81.8%) had concentrations below 0.1 mcg/mL; only 2 patients had concentrations higher than 0.4 mcg/mL. Conclusions: The standard dosing regimen for cefotiam resulted in extremely low plasma concentrations in children; such low concentrations may lead to antimicrobial drug resistance. Thus, an increase in cefotiam dosage in children to 80 mg/kg 4 times daily is recommended (maximum dose on the label).
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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 ╳
