Clarithromycin related compound I
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| Category | Others |
| Catalog number | BBF-04329 |
| CAS | 118058-74-5 |
| Molecular Weight | 589.77 |
| Molecular Formula | C30H55NO10 |
| Purity | ≥90.0% |
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Description
An impurity found in the macrolide antibiotic, Clarithromycin.
Specification
| Synonyms | De(cladinosyl) Clarithromycin; 3-O-De(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)-6-O-methylerythromycin; 5-O-Desosaminyl-6-O-methylerythronolide A; 3-O-Decladinosyl-6-O-methylerythronolide A; Clarithromycin EP Impurity I |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-4,12,13-trihydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione |
| Canonical SMILES | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)O)C)OC2C(C(CC(O2)C)N(C)C)O)(C)OC)C)C)O)(C)O |
| InChI | InChI=1S/C30H55NO10/c1-12-21-30(8,37)25(35)17(4)22(32)15(2)14-29(7,38-11)26(18(5)23(33)19(6)27(36)40-21)41-28-24(34)20(31(9)10)13-16(3)39-28/h15-21,23-26,28,33-35,37H,12-14H2,1-11H3/t15-,16?,17+,18+,19-,20?,21-,23+,24?,25-,26-,28?,29-,30-/m1/s1 |
| InChI Key | QTLYNHBYTKOXTE-LOOUJMBSSA-N |
Properties
| Appearance | White to Off-white Solid |
| Boiling Point | 708.6±60.0°C (Predicted) |
| Melting Point | 154-157°C |
| Density | 1.17±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Chloroform, Methanol |
Reference Reading
1. Clarithromycin-induced neurotoxicity in adults
Daniela Audenino, Alberto Primavera, M Bandettini di Poggio, Sandra Anfosso J Clin Neurosci . 2011 Mar;18(3):313-8. doi: 10.1016/j.jocn.2010.08.014.
Clarithromycin is a relatively new antibiotic of the macrolide family heralded for an improved side effect profile, dosing schedule, and microbiological activity relative to its parent compound, erythromycin. We review the literature on clarithromycin-induced neurotoxicity in adults and present an illustrative case. A total of 38 patients with clarithromycin-induced neurotoxicity have been reported. The average age of patients was 51.3 years (range: 19-87 years) with females comprising 52.6% of patients. Psychiatric illness was the most common comorbidity, while only two patients had renal failure. Clarithromycin had been prescribed for respiratory infections in most patients, and only two patients were receiving more than 1000 mg/day of antibiotic. The symptoms started 1 day to 10 days after starting clarithromycin (mean: 5 days). A total of 71% of patients were under treatment with concomitant medication, and eight patients were undergoing treatment with psychoactive drugs. Patients had a very good outcome after clarithromycin was discontinued, but medication with neuroleptics or benzodiazepine was required for 58% of patients in the acute phase. Only four patients underwent an electroencephalogram (EEG). Our illustrative patient was a 74-year-old woman with clarithromycin-induced delirium due to non-convulsive status epilepticus (NCSE). Her clinical symptoms and electroencephalogram (EEG) readings dramatically improved after discontinuation of clarithromycin. The mechanism underlying the central nervous system side effects remains unclear. We suggest including an EEG in the diagnostic procedures of patients under treatment with clarithromycin who develop features of neurotoxicity because an EEG can help to differentiate patients with psychiatric illness from those with encephalopathy or epilepsy. Because of the widespread use of clarithromycin, clinicians should be aware of its neurotoxicity. Early detection of clarithromycin-induced neurotoxicity and discontinuation of the drug may result in full recovery.
2. Helicobacter pylori infection--current treatment practice
N J Talley, S K Lam, H H Xia, B C Yu Wong Expert Opin Pharmacother . 2001 Feb;2(2):253-66. doi: 10.1517/14656566.2.2.253.
Helicobacter pylori infection, which is present in 30 - 60% of the population in developed countries and in more than 60% in developing countries, is established to be a major cause of gastritis, peptic ulcer disease and gastric cancer. Eradication therapy has been incorporated into clinical practice over the past 15 years. Treatment regimens include a 2 week bismuth-based triple therapy (a bismuth compound plus metronidazole, tetracycline or amoxycillin), a 1 week proton-pump inhibitor (PPI)-based triple therapy and a 1 week ranitidine bismuth citrate (RBC)-based triple therapy (a PPI or RBC plus any two of the three antibiotics, metronidazole, amoxycillin and clarithromycin). These regimens achieve eradication rates of >> 80%. H. pylori resistance to metronidazole and clarithromycin decreases the clinical efficacy of most regimens, despite the high eradication rates for resistant strains achieved by the RBC-triple therapy in some recent trials. The dose of antibiotics (especially clarithromycin) and the duration of treatment may also influence the eradication rate. Doctors' beliefs impact on clinical practice and, thus, influence the clinical application of eradication therapy. Whereas peptic ulcer disease and primary gastric low-grade B-cell mucosa-associated lymphoid tissue lymphoma (MALToma) have become established as definite indications for eradication therapy, there remain controversies surrounding non-ulcer dyspepsia, gastro-oesophageal reflux disease, atrophic gastritis, intestinal metaplasia, use of non-steroidal anti-inflammatory drugs (NSAIDs) and H. pylori-related extradigestive diseases.
3. Daphnetin: A Novel Anti- Helicobacter pylori Agent
Xue Li, Xiukun Wang, Xinyi Yang, Xuefu You, Tongying Nie, Genzhu Wang, Jiandong Jiang, Yan Q Xiong, Xinxin Hu, Yun Lu, Congran Li, Xi Lu, Jing Pang Int J Mol Sci . 2019 Feb 15;20(4):850. doi: 10.3390/ijms20040850.
Background:Antibiotic-resistantH. pyloriwas increasingly found in infected individuals, which resulted in treatment failure and required alternative therapeutic strategies. Daphnetin, a coumarin-derivative compound, has multiple pharmacological activities.Methods:The mechanism of daphnetin onH. pyloriwas investigated focusing on its effect on cell morphologies, transcription of genes related to virulence, adhesion, and cytotoxicity to human gastric epithelial (GES-1) cell line.Results:Daphnetin showed good activities against multidrug resistant (MDR)H. pyloriclinical isolates, with minimal inhibitory concentration (MIC) values ranging from 25 to 100 μg/mL. In addition, daphnetin exposure resulted inH. pylorimorphological changes. Moreover, daphnetin caused increased translocation of phosphatidylserine (PS), DNA damage, andrecAexpression, and RecA protein production vs. control group. Of great importance, daphnetin significantly decreasedH. pyloriadhesion to GES-1 cell line vs. control group, which may be related to the reduced expression of colonization related genes (e.g.,babAandureI).Conclusions:These results suggested that daphnetin has good activity against MDRH. pylori.The mechanism(s) of daphnetin againstH. pyloriwere related to change of membrane structure, increase of DNA damage and PS translocation, and decrease ofH. pyloriattachment to GES-1 cells.
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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 ╳
