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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRoxithromycin
Identification
- Name
- Roxithromycin
- Accession Number
- DB00778 (APRD01305)
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Description
Roxithromycin is a semi-synthethic macrolide antibiotic that is structurally and pharmacologically similar to erythromycin, azithromycin, or clarithromycin. It was shown to be more effective against certain Gram-negative bacteria, particularly Legionella pneumophila. Roxithromycin exerts its antibacterial action by binding to the bacterial ribosome and interfering with bacterial protein synthesis. It is marketed in Australia as a treatment for respiratory tract, urinary and soft tissue infections.
- Structure
Structure for Roxithromycin (DB00778)
- Synonyms
- (9E)-erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime)
- Roxithromycin
- Roxithromycine
- Roxithromycinum
- Roxitromicina
- External IDs
- RU 28965 / RU 965
- International/Other Brands
- Acevor (Help) / Actirox (Active HC) / Ai Luo Xin (Huashen Pharmaceutical) / Allolide (Roman Industries) / Ammirox (MacroPhar) / Anti-Bio (Kon/Nos Leon) / Ao Ge Shen (Jianfa Pharmaceutical) / Aparox (Siza) / Arbid (Hetero) / Aroxe (Global) / Asmetic (Farmilia) / Assoral (Savio I.B.N.) / Aswad (Robins) / Azuril (Pharmanel) / Bazuctril (Chrispa) / BD-Rox (Panacea) / Bei Ke (Aoda Pharmaceuticals) / Bei Sha (Huipusen Medical Biological Technology) / Bi Ai Di (Siping Aimo Pharmaceutical) / Biaxsig (Sanofi-Aventis) / Bicofen (Pharmex) / Biostatik (Pharos) / Claramid (Pfizer) / Coroxin / Delitroxin (Pharmathen) / Delos (Dallas) / Dorolid (Domesco) / Elrox (Biopharm M.J.) / Erybros (Bros) / Eslid (Shin Poong) / Guamil (P T Interbat) / Heng Te (Hanson Pharmaceutical) / Hycin (Saga) / I-Throcin (T.C. Pharma-Chem) / Infectoroxit (Infectopharm) / Inrox (Intra) / Ixor (Soho) / Klomicina (Klonal) / Ladlid (Choseido Pharmaceutical) / Lang Su (Shandong Dayin Yanghai Bio-Pharmaceutical Co.) / Le Er Tai (Tianji Biological Pharmaceutical) / Le Xi Qing (Zhangshu Santai Pharmaceutical) / Li Fu (Suzhou Chung-Hwa Chemical & Pharmaceutical Industrial) / Lizhuxing (Livzon Zhuhai) / Ludin (Vellpharm) / Luo Jun Qing (Fusen Pharmaceutical) / Luo Shi Li (Xi'an Detian Pharmaceutical Co.) / Luo Si Mei (Yabo Pharmaceutical Co.) / Luprex (Lupin) / Macrol (UAP) / Macrolid (Rafarm) / Marulide (Pasteur) / Neo-Suxigal (Anfarm) / Nirox (Gabriel Health) / Odirox (Cipla) / Overal (Lusofarmaco) / Pedilid (Incepta) / Pedrox (Beximco) / Pinsheng (Xincat) / Plethirox (Sel-J) / Poliroxin (Polipharm) / Pu Hong (Shyndec) / Pymeroxitil (PMP) / Qi Wei (Lanling Pharmaceutical Production) / Ramivan (Medipharm) / Redotrin (Coup) / Remora (Nobel) / Ren Su (Yangtze River Pharma) / Renicin (Sandoz) / Ridinfect (Medicraft) / Ritosin (Münir Sahin) / Rocin (Pasteur) / Rokithrid (Taiyo Pharmaceutical) / Roksimin (Il-Ko) / Rolexit (Nufarindo) / Rolicyn (Polfa Tarchomin) / Romac (Saiph) / Romicin (Dae Woo) / Romycin (Livzon Zhuhai) / Romyk (Lindopharm) / Ropit (Epitome) / Rossitrol (Sanofi-Aventis) / Rothricin (Siam Bheasach) / Rotram (Ranbaxy) / Rovenal (Leciva) / Roxamed (Dar Al Dawa) / Roxar (Sigma) / Roxcin (Biolab) / Roxemicin (Han Mi) / Roxeptin (Ipca Laboratories Ltd.) / Roxetomin (Sun) / Roxi (Dae Won) / Roxi-Fatol (Riemser) / Roxi-Puren (Actavis) / Roxi-Q (Juta) / Roxi-saar (MIP) / Roxibest (Blue Cross) / Roxibeta (Betapharm) / Roxibron (Viofar) / Roxicin (Atlantic Lab) / Roxicur (Velka) / Roxicure (Pharmaceutical) / Roxid (Alembic) / Roxide (Sandoz) / Roxidura (Mylan dura) / Roxigamma (Wörwag Pharma) / Roxigrün (Grünenthal) / Roxihexal (Salutas) / Roxikid (Ahn-Gook) / Roxil (YSS) / Roxilan (Olan-Kemed) / Roximac (Ram Pharmaceutical) / Roximain (Towa Yakuhin) / Roximax (Pharmaghreb) / Roximed (Medhaus) / Roximerck (Mylan Seiyaku) / Roximic (Acto) / Roximin (Novis Pharmaceutical) / Roximisan (Slaviamed) / Roximol (Torrent) / Roximycin (Alphapharm) / Roxinga (Roxinga) / Roxinox (Charoen Bhaesaj) / Roxiratio (ratiopharm) / Roxirocin (Korea Arlico) / Roxisara (Abbott) / Roxistad (Aliud) / Roxitas (Intas) / Roxitazon (Alice Loren) / Roxithrin (Kuk Je) / Roxithro (Millimed) / Roxithrostad (STADA) / Roxitil (Kolon) / Roxitin (T P Drug) / Roxitis (Medley) / Roxitop (Farmaline) / Roxitran (Neo Quimica) / Roxitrom (Biolab) / Roxitromycine (Sandoz) / Roxitron (ICN) / Roxivar (Zota) / Roxivinol (Pheracon) / Roxivista (Cadila) / Roxl-150 / Roxo / Roxomycin / Roxy (Ind-Swift) / Roxy-150 (Cipla) / Rulid / Rulide (Sanofi-Aventis) / Rulide D (Sanofi-Aventis) / Surlid (Sanofi-Aventis) / Tirabicin / Xthrocin
- Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Erythromycin and similars
- Lactones
- Macrolides
- Macrolides, Lincosamides and Streptogramins
- Moderate Risk QTc-Prolonging Agents
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Polyketides
- QTc Prolonging Agents
- UNII
- 21KOF230FA
- CAS number
- 80214-83-1
- Weight
- Average: 837.0465
Monoisotopic: 836.524569772 - Chemical Formula
- C41H76N2O15
- InChI Key
- RXZBMPWDPOLZGW-XMRMVWPWSA-N
- 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
- 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
- SMILES
- CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=NOCOCCOC)[C@H](C)[C@@H](O)[C@]1(C)O
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Pharmacology
- Indication
Used to treat respiratory tract, urinary and soft tissue infections.
- Pharmacodynamics
Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.
- Mechanism of action
Roxithromycin prevents bacterial growth by interfering with their protein synthesis. It binds to the 50S subunit of bacterial ribosomes and inhibits the translocation of peptides.
Target Actions Organism A50S ribosomal protein L10 inhibitorShigella flexneri UP-glycoprotein 1 Not Available Humans - Absorption
Very rapidly absorbed and diffused into most tissues and phagocytes.
- Volume of distribution
- Not Available
- Protein binding
96%, mainly to alpha1-acid glycoproteins
- Metabolism
Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.
- Route of elimination
- Not Available
- Half life
12 hours
- Clearance
- Not Available
- Toxicity
Roxithromycin primarily causes gastrointestinal adverse events, such as diarrhoea, nausea, abdominal pain and vomiting. Less common adverse events include headaches, rashes, abnormal liver function values and alteration in senses of smell and taste.
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
Pathway Category Roxithromycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data(R)-warfarin The serum concentration of (R)-warfarin can be increased when it is combined with Roxithromycin. (S)-Warfarin The serum concentration of (S)-Warfarin can be increased when it is combined with Roxithromycin. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Roxithromycin. 9-aminocamptothecin The metabolism of 9-aminocamptothecin can be decreased when combined with Roxithromycin. Abexinostat The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Abexinostat. Acebutolol The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Acebutolol. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Roxithromycin. Aceprometazine The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Aceprometazine. Acetyldigoxin The risk or severity of adverse effects can be increased when Roxithromycin is combined with Acetyldigoxin. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Roxithromycin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- Synthesis Reference
Murali Krishna Madala, Suresh Babu Meduri, Ketan Dhansukhlal Vyas, Ashok Krishna Kulkarni, "Process for preparing erythromycin derivative, such as roxithromycin, from the corresponding oxime." U.S. Patent US6051695, issued September, 1998.
US6051695- General References
- Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. [PubMed:3323166]
- Link [Link]
- External Links
- KEGG Drug
- D01710
- KEGG Compound
- C13173
- PubChem Compound
- 6915744
- PubChem Substance
- 46507676
- ChemSpider
- 5291557
- ChEBI
- 48935
- ChEMBL
- CHEMBL1214185
- Therapeutic Targets Database
- DAP000885
- PharmGKB
- PA164750505
- HET
- ROX
- Wikipedia
- Roxithromycin
- ATC Codes
- J01FA06 — Roxithromycin
- PDB Entries
- 1jzz
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Quality of Life / Respiratory Function Tests 1 4 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 4 Completed Treatment Rheumatoid Arthritis 1 4 Not Yet Recruiting Prevention Bacterial Infections / Pacemaker Complication 1 4 Recruiting Prevention Premature Rupture of Membranes 1 Not Available Completed Treatment Reactive Arthritis 1 Not Available Not Yet Recruiting Diagnostic Hyperaldosteronism 1 Not Available Unknown Status Treatment Alopecia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 0.0189 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996)) Not Available logP 1.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.187 mg/mL ALOGPS logP 2.9 ALOGPS logP 3 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 12.45 ChemAxon pKa (Strongest Basic) 9.08 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 216.89 Å2 ChemAxon Rotatable Bond Count 13 ChemAxon Refractivity 211.24 m3·mol-1 ChemAxon Polarizability 91.84 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.8875 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Inhibitor 0.5625 Renal organic cation transporter Non-inhibitor 0.8178 CYP450 2C9 substrate Non-substrate 0.8339 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.708 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9615 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.8676 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.9728 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9792 hERG inhibition (predictor II) Inhibitor 0.6433
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Aminoglycosides
- Alternative Parents
- Macrolides and analogues / O-glycosyl compounds / Monosaccharides / Oxanes / Tertiary alcohols / Secondary alcohols / Amino acids and derivatives / Carboxylic acid esters / Lactones / Trialkylamines show 11 more
- Substituents
- Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester show 22 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- erythromycin derivative, semisynthetic derivative, macrolide (CHEBI:48844)
Targets
- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Structural constituent of ribosome
- Specific Function
- Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a cent...
- Gene Name
- rplJ
- Uniprot ID
- P0A7J6
- Uniprot Name
- 50S ribosomal protein L10
- Molecular Weight
- 17711.38 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Bertho G, Gharbi-Benarous J, Delaforge M, Girault JP: Transferred nuclear Overhauser effect study of macrolide-ribosome interactions: correlation between antibiotic activities and bound conformations. Bioorg Med Chem. 1998 Feb;6(2):209-21. [PubMed:9547944]
- Yam WK, Wahab HA: Molecular insights into 14-membered macrolides using the MM-PBSA method. J Chem Inf Model. 2009 Jun;49(6):1558-67. doi: 10.1021/ci8003495. [PubMed:19469526]
- Mabe S, Eller J, Champney WS: Structure-activity relationships for three macrolide antibiotics in Haemophilus influenzae. Curr Microbiol. 2004 Oct;49(4):248-54. [PubMed:15386112]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Beltinger J, Haschke M, Kaufmann P, Michot M, Terracciano L, Krahenbuhl S: Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin. Ann Pharmacother. 2006 Apr;40(4):767-70. Epub 2006 Mar 7. [PubMed:16595573]
- Kaufmann P, Haschke M, Torok M, Beltinger J, Bogman K, Wenk M, Terracciano L, Krahenbuhl S: Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin. Ther Drug Monit. 2006 Dec;28(6):766-74. [PubMed:17164692]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Yamazaki H, Shimada T: Comparative studies of in vitro inhibition of cytochrome P450 3A4-dependent testosterone 6beta-hydroxylation by roxithromycin and its metabolites, troleandomycin, and erythromycin. Drug Metab Dispos. 1998 Nov;26(11):1053-7. [PubMed:9806945]
- Yamazaki H, Hiroki S, Urano T, Inoue K, Shimada T: Effects of roxithromycin, erythromycin and troleandomycin on their N-demethylation by rat and human cytochrome P450 enzymes. Xenobiotica. 1996 Nov;26(11):1143-53. doi: 10.3109/00498259609050259. [PubMed:8948090]
- Ohno Y, Hisaka A, Suzuki H: General framework for the quantitative prediction of CYP3A4-mediated oral drug interactions based on the AUC increase by coadministration of standard drugs. Clin Pharmacokinet. 2007;46(8):681-96. doi: 10.2165/00003088-200746080-00005. [PubMed:17655375]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Kaufmann P, Haschke M, Torok M, Beltinger J, Bogman K, Wenk M, Terracciano L, Krahenbuhl S: Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin. Ther Drug Monit. 2006 Dec;28(6):766-74. [PubMed:17164692]
Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 05:34