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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/04 16:55:12」(JST)

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Roxithromycin is a semi-synthetic macrolide antibiotic. It is used to treat respiratory tract, urinary and soft tissue infections. Roxithromycin is derived from erythromycin, containing the same 14-membered lactone ring. However, an N-oxime side chain is attached to the lactone ring. It is also currently undergoing clinical trials for the treatment of male-pattern hair loss.^[1]

Roxithromycin is available under several brandnames. Roxithromycin is not available in the United States. Roxithromycin is available in Australia. Roxithromycin has also been tested to possess antimalarial activity.

History

German pharmaceutical company Hoechst Uclaf brought out roxithromycin in 1987.

Available forms

Roxithromycin is commonly available as tablets or oral suspension.

Mechanism of action

Roxithromycin prevents bacteria from growing, by interfering with their protein synthesis. Roxithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translocation of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila.

Pharmacokinetics

When taken before a meal, roxithromycin is very rapidly absorbed, and diffused into most tissues and phagocytes. Due to the high concentration in phagocytes, roxithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations of roxithromycin are released.

Metabolism

Only a small portion of roxithromycin is metabolised. Most of roxithromycin is secreted unchanged into the bile and some in expired air. Under 10% is excreted into the urine. Roxithromycin's half-life is 12 hours.

Side effects

Most common side effects are gastrointestinal; diarrhoea, nausea, abdominal pain and vomiting. Less common side effects include central or peripheral nervous system events such as headaches, dizziness, vertigo, and also the rarely seen rashes, abnormal liver function values and alteration in senses of smell and taste.

Drug interactions

Roxithromycin has fewer interactions than erythromycin as it has a lower affinity for cytochrome P450.

Roxithromycin does not interact with hormonal contraceptives, prednisolone, carbamazepine, ranitidine or antacids.

When roxithromycin is administered with theophylline, some studies have shown an increase in the plasma concentration of theophylline. A change in dosage is usually not required but patients with high levels of theophylline at the start of the treatment should have their plasma levels monitored.

Roxithromycin appears to interact with warfarin. This is shown by an increase in prothrombin time and/or international normalised ratio (INR) in patients taking roxithromycin and warfarin concurrently. As a consequence, severe bleeding episodes have occurred.

References

^ "The Effect of 0.5% Roxithromycin Lotion for Androgenetic Alopecia - ClinicalTrials.gov". Retrieved 2007-09-22.

External links

Roxithromycin bound to proteins in the PDB

UpToDate Contents

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1. 無症候性腹部大動脈瘤のマネージメント management of asymptomatic abdominal aortic aneurysm
2. 小児における急性肝不全：病因および評価 acute liver failure in children etiology and evaluation
3. 跛行の内科的マネージメント medical management of claudication
4. 慢性鼻副鼻腔炎のマネージメント management of chronic rhinosinusitis
5. 慢性副鼻腔炎の微生物学的および抗菌薬によるマネージメント microbiology and antibiotic management of chronic rhinosinusitis

English Journal

Efficacy and safety of long-term antibiotics (macrolides) for the treatment of chronic rhinosinusitis.

Cervin A, Wallwork B.Author information Royal Brisbane & Women's Hospital, School of Medicine, University of Queensland, Level 9, Room 915, UQ Health Science Building, Herston, QLD, 4029, Australia, a.cervin@uq.edu.au.AbstractLong-term treatment of airway inflammation/infection with macrolide antibiotics has now been in use for almost 30 years. Whereas the beneficial clinical effect in cystic fibrosis and COPD have been backed up by randomized controlled trials, the evidence from the upper airways is not as strong. We have identified 22 open studies in chronic rhinosinusitis, with and without polyps, but only 2 randomized controlled trials. Of the controlled trials, the one including CRS patients just without polyps, showed a significant effect in sino-nasal outcome test, saccharine transit time, nasal endoscopy, and IL-8 levels in lavage fluid after 12 weeks of roxithromycin, whereas, in the other RCT with a mixed study group of CRS patients with and without polyps, 12 weeks of azithromycin showed no effect compared to placebo. Concerns regarding the risk of macrolides to induce arrhythmia have been raised. Recent FDA guidelines changes has recommended caution in patients with risk factors such as long QT syndrome, bradycardia, hypokalemia, or hypomagnesemia. Ototoxicity is another concern. Long-term macrolide antibiotics in the treatment of CRS patients is still a viable option in a select group of patients.
Current allergy and asthma reports.Curr Allergy Asthma Rep.2014 Mar;14(3):416. doi: 10.1007/s11882-013-0416-2.
Long-term treatment of airway inflammation/infection with macrolide antibiotics has now been in use for almost 30 years. Whereas the beneficial clinical effect in cystic fibrosis and COPD have been backed up by randomized controlled trials, the evidence from the upper airways is not as strong. We ha
PMID 24429901

Antimicrobial resistance and prevalence of resistance genes of obligate anaerobes isolated from periodontal abscesses.

Xie Y, Chen J, He J, Miao X, Xu M, Wu X, Xu B, Yu L, Zhang W.Author information Department of Stomatology, Hua Shan Hospital, Fudan University, Yangpu, Shanghai, China.AbstractBackground: This study attempts to determine the antimicrobial resistance profiles of obligate anaerobic bacteria that were isolated from a periodontal abscess and to evaluate the prevalence of resistance genes in these bacteria. Methods: Forty-one periodontal abscess samples were cultivated on selective and non-selective culture media to isolate the oral anaerobes. Their antibiotic susceptibilities to clindamycin, doxycycline, amoxicillin, imipenem, cefradine, cefixime, roxithromycin, and metronidazole were determined using the agar dilution method, and polymerase chain reaction assays were performed to detect the presence of the ermF, tetQ, nim, and cfxA drug resistance genes. Results: A total of 60 different bacterial colonies was isolated and identified. All of the isolates were sensitive to imipenem. Of the strains, 6.7%, 13.3%, 16.7%, and 25% were resistant to doxycycline, metronidazole, cefixime, and amoxicillin, respectively. The resistance rate for both clindamycin and roxithromycin was 31.7%. Approximately 60.7% of the strains had the ermF gene, and 53.3% of the amoxicillin-resistant strains were found to have the cfxA gene. Two nim genes that were found in eight metronidazole-resistant strains were identified as nimB. Conclusions: In the present study, the Prevotella species are the most frequently isolated obligate anaerobes from periodontal abscesses. The current results show their alarmingly high resistance rate against clindamycin and roxithromycin; thus, the use of these antibiotics is unacceptable for the empirical therapy of periodontal abscesses. A brief prevalence of four resistance genes in the anaerobic bacteria that were isolated was also demonstrated.
Journal of periodontology.J Periodontol.2014 Feb;85(2):327-34. doi: 10.1902/jop.2013.130081. Epub 2013 May 9.
Background: This study attempts to determine the antimicrobial resistance profiles of obligate anaerobic bacteria that were isolated from a periodontal abscess and to evaluate the prevalence of resistance genes in these bacteria. Methods: Forty-one periodontal abscess samples were cultivated on sele
PMID 23659425

Photodegradation of antibiotics under simulated solar radiation: Implications for their environmental fate.

Batchu SR1, Panditi VR2, O'Shea KE3, Gardinali PR4.Author information 1Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA; Southeast Environmental Research Center, Florida International University, Miami, FL 33199, USA. Electronic address: sbatc001@fiu.edu.2Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA; Southeast Environmental Research Center, Florida International University, Miami, FL 33199, USA. Electronic address: vpand001@fiu.edu.3Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA. Electronic address: osheak@fiu.edu.4Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA; Southeast Environmental Research Center, Florida International University, Miami, FL 33199, USA. Electronic address: gardinal@fiu.edu.AbstractRoxithromycin, erythromycin, ciprofloxacin and sulfamethoxazole are frequently detected antibiotics in environmental waters. Direct and indirect photolysis of these problematic antibiotics were investigated in pure and natural waters (fresh and salt water) under irradiation of different light sources. Fundamental photolysis parameters such as molar absorption coefficient, quantum yield and first order rate constants are reported and discussed. The antibiotics are degraded fastest under ultraviolet 254nm, followed by 350nm and simulated solar radiation. The composition of the matrix (pH, dissolved organic content, chloride ion concentration) played a significant role in the observed photodegradation. Under simulated solar radiation, ciprofloxacin and sulfamethoxazole degrade relatively quickly with half-lives of 0.5 and 1.5h, respectively. However, roxithromycin and erythromycin, macrolides are persistent (half-life: 2.4-10days) under solar simulation. The transformation products (15) of the targeted antibiotics produced under irradiation experiments were identified using high resolution mass spectrometry and degradation pathways were proposed.
The Science of the total environment.Sci Total Environ.2014 Feb 1;470-471:299-310. doi: 10.1016/j.scitotenv.2013.09.057. Epub 2013 Oct 18.
Roxithromycin, erythromycin, ciprofloxacin and sulfamethoxazole are frequently detected antibiotics in environmental waters. Direct and indirect photolysis of these problematic antibiotics were investigated in pure and natural waters (fresh and salt water) under irradiation of different light source
PMID 24144935

Japanese Journal

Inhibition of P-glycoprotein–Mediated Efflux of Digoxin and Its Metabolites by Macrolide Antibiotics

Hughes Jeff,Crowe Andrew
Journal of Pharmacological Sciences 113(4), 315-324, 2010
… In contrast, clarithromycin and roxithromycin almost eliminated basolateral targeted efflux. … In contrast, clarithromycin and roxithromycin were 10-fold greater P-gp inhibitors. … Clarithromycin and roxithromycin are likely to exhibit drug interactions with digoxin via inhibition of efflux mechanisms. …
NAID 130000301208

Effects of oral antibiotic roxithromycin on quality of life in acne patients

KOBAYASHI Miwa,KABASHIMA Kenji,NAKAMURA Motonobu,TOKURA Yoshiki
Journal of dermatology 36(7), 383-391, 2009-07-01
NAID 10027063873

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★リンクテーブル★

リンク元	「マクロライド系抗菌薬」「ロキシスロマイシン」

「マクロライド系抗菌薬」

Roxithromycin
Systematic (IUPAC) name
	(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B1; ;
Pharmacokinetic data
Metabolism	Liver, peak concentration averaging 2 hours after ingestion.
Biological half-life	11 hours
Identifiers
CAS Number	80214-83-1
ATC code	J01FA06
PubChem	CID: 6915744
IUPHAR/BPS	1465
DrugBank	DB00778
ChemSpider	5291557
UNII	21KOF230FA
KEGG	D01710
ChEBI	CHEBI:48935
ChEMBL	CHEMBL1214185
Chemical data
Formula	C41H76N2O15
Molecular mass	837.047 g/mol
	SMILES O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](\C(=N\OCOCCOC)[C@H](C)C[C@](O)(C)[C@H](O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H]3C)C)C ;
	InChI InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1 ; Key:RXZBMPWDPOLZGW-XMRMVWPWSA-N ;
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　　[★]

英: macrolide antibiotic macrolide antibiotics, macrolides, MLs
同: マクロライド系抗生物質　←厳密には違うが、多くの人が間違って使っている
関: 抗菌薬

特徴

抗菌スペクトルが広い
静菌的に作用
大きな環状構造を有する。14員環-16員環
タンパク質合成阻害薬
抗生物質としての作用の他に、抗炎症作用を有するらしい

炎症の抑制 ex.びまん性汎細気管支炎

構造

http://www.sigmaaldrich.com/life-science/life-science-catalog/product-catalog.html?TablePage=14572877
Macrolide antibiotics contain a many-membered lactone ring (14-membered rings for erythromycin and clarithromycin and a 15-membered ring for azithromycin) to which are attached one or more deoxy sugars. Clarithromycin differs from erythromycin only by methylation of the hydroxyl group at the 6 position, and azithromycin differs by the addition of a methyl-substituted nitrogen atom into the lactone ring. These structural modifications improve acid stability and tissue penetration and broaden the spectrum of activity.(GOO. chapter 46)

作用機序

50Sリボソームに結合してタンパク質合成を阻害

inhibit bacterial protein synthesis by reacting with the 50s ribosomal subunit and preventing the release of the uncharged tRNA.

薬理作用

動態

経口で吸収される

抗菌スペクトル

ペニシリンより広い抗菌スペクトル
グラム陽性球菌、グラム陰性球菌、グラム陰性桿菌、スピロヘータ、一部のリケッチア、ウイルス

適応

マイコプラズマ肺炎、クラミジア感染症、カンピロバクター腸炎、レジオネラ症
びまん性汎細気管支炎：14員環マクロライドのみ
URIs, pneumonias, STD

グラム陽性球菌(ペニシリンアレルギー), Mycoplasma, Legionella, Chlamydia, Neisseria

注意

禁忌

副作用

肝障害
消化器障害
QT延長、心室性不整脈

悪心、嘔吐、消化器の蠕動を促進

薬物相互作用

テオフィリン

喘息の治療薬。CYP3A4で代謝される。中毒域と治療域がちかいので注意する