Jump to section
IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRoxithromycin
Identification
- Name
- Roxithromycin
- Accession Number
- DB00778 (APRD01305)
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Description
Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. 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. It can treat respiratory tract, urinary and soft tissue infections. It is not available in the United States, but is available in Australia.
- Structure
Structure for DB00778 (Roxithromycin)
- 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
- 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
Pharmacology
- Indication
Used to treat respiratory tract, urinary and soft tissue infections.
- Pharmacodynamics
Roxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. 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 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.
Target Actions Organism A50S ribosomal protein L10 inhibitorShigella flexneri UMultidrug resistance protein 1 Not Available Human - 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
Most common side-effects are gastrointestinal; diarrhoea, nausea, abdominal pain and vomiting. Less common side-effects 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
Drug Interaction Drug group Acetyl sulfisoxazole The metabolism of Roxithromycin can be decreased when combined with Acetyl sulfisoxazole. Approved, Vet Approved Amiodarone The metabolism of Roxithromycin can be decreased when combined with Amiodarone. Approved, Investigational Apalutamide The serum concentration of Roxithromycin can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Roxithromycin can be increased when it is combined with Aprepitant. Approved, Investigational Asunaprevir The serum concentration of Asunaprevir can be increased when it is combined with Roxithromycin. Approved, Investigational, Withdrawn Atazanavir The metabolism of Roxithromycin can be decreased when combined with Atazanavir. Approved, Investigational Atomoxetine The metabolism of Roxithromycin can be decreased when combined with Atomoxetine. Approved Atorvastatin The risk or severity of adverse effects can be increased when Roxithromycin is combined with Atorvastatin. Approved BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Roxithromycin. Investigational Boceprevir The metabolism of Roxithromycin can be decreased when combined with Boceprevir. Approved, Withdrawn Bortezomib The metabolism of Roxithromycin can be decreased when combined with Bortezomib. Approved, Investigational Bosentan The serum concentration of Roxithromycin can be decreased when it is combined with Bosentan. Approved, Investigational Bosutinib The serum concentration of Bosutinib can be increased when it is combined with Roxithromycin. Approved Bromocriptine The risk or severity of adverse effects can be increased when Bromocriptine is combined with Roxithromycin. Approved, Investigational Cabergoline The risk or severity of adverse effects can be increased when Cabergoline is combined with Roxithromycin. Approved Carbamazepine The metabolism of Roxithromycin can be increased when combined with Carbamazepine. Approved, Investigational Ceritinib The serum concentration of Roxithromycin can be increased when it is combined with Ceritinib. Approved Cerivastatin The serum concentration of Cerivastatin can be increased when it is combined with Roxithromycin. Approved, Withdrawn Cisapride The serum concentration of Cisapride can be increased when it is combined with Roxithromycin. Approved, Investigational, Withdrawn Clarithromycin The metabolism of Roxithromycin can be decreased when combined with Clarithromycin. Approved Clemastine The metabolism of Roxithromycin can be decreased when combined with Clemastine. Approved, Investigational Clotrimazole The metabolism of Roxithromycin can be decreased when combined with Clotrimazole. Approved, Vet Approved Cobicistat The metabolism of Roxithromycin can be decreased when combined with Cobicistat. Approved Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Roxithromycin. Approved, Investigational Crizotinib The metabolism of Roxithromycin can be decreased when combined with Crizotinib. Approved Curcumin The metabolism of Roxithromycin can be decreased when combined with Curcumin. Approved, Investigational Cyclosporine The metabolism of Roxithromycin can be decreased when combined with Cyclosporine. Approved, Investigational, Vet Approved Dabrafenib The serum concentration of Roxithromycin can be decreased when it is combined with Dabrafenib. Approved, Investigational Darunavir The metabolism of Roxithromycin can be decreased when combined with Darunavir. Approved Dasatinib The serum concentration of Roxithromycin can be increased when it is combined with Dasatinib. Approved, Investigational Deferasirox The serum concentration of Roxithromycin can be decreased when it is combined with Deferasirox. Approved, Investigational Delamanid Roxithromycin may increase the QTc-prolonging activities of Delamanid. Approved, Investigational Delavirdine The metabolism of Roxithromycin can be decreased when combined with Delavirdine. Approved Deutetrabenazine Roxithromycin may increase the QTc-prolonging activities of Deutetrabenazine. Approved, Investigational Dihydroergocornine The risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Roxithromycin. Approved Dihydroergocristine The risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Roxithromycin. Approved, Experimental Dihydroergocryptine The risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Roxithromycin. Experimental Dihydroergotamine The risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Roxithromycin. Approved, Investigational Diltiazem The metabolism of Roxithromycin can be decreased when combined with Diltiazem. Approved, Investigational Doxycycline The metabolism of Roxithromycin can be decreased when combined with Doxycycline. Approved, Investigational, Vet Approved Dronedarone The metabolism of Roxithromycin can be decreased when combined with Dronedarone. Approved Enzalutamide The serum concentration of Roxithromycin can be decreased when it is combined with Enzalutamide. Approved Ergoloid mesylate The serum concentration of Ergoloid mesylate can be increased when it is combined with Roxithromycin. Approved Ergonovine The risk or severity of adverse effects can be increased when Ergonovine is combined with Roxithromycin. Approved Ergotamine The risk or severity of adverse effects can be increased when Ergotamine is combined with Roxithromycin. Approved Erythromycin The metabolism of Roxithromycin can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Fluconazole The metabolism of Roxithromycin can be decreased when combined with Fluconazole. Approved, Investigational Fluvastatin The serum concentration of Fluvastatin can be increased when it is combined with Roxithromycin. Approved Fluvoxamine The metabolism of Roxithromycin can be decreased when combined with Fluvoxamine. Approved, Investigational Fosamprenavir The metabolism of Roxithromycin can be decreased when combined with Fosamprenavir. Approved Fosaprepitant The serum concentration of Roxithromycin can be increased when it is combined with Fosaprepitant. Approved Fosphenytoin The metabolism of Roxithromycin can be increased when combined with Fosphenytoin. Approved, Investigational Fusidic Acid The serum concentration of Roxithromycin can be increased when it is combined with Fusidic Acid. Approved, Investigational Ibrutinib The serum concentration of Ibrutinib can be increased when it is combined with Roxithromycin. Approved Idelalisib The metabolism of Roxithromycin can be decreased when combined with Idelalisib. Approved Imatinib The metabolism of Roxithromycin can be decreased when combined with Imatinib. Approved Indinavir The metabolism of Roxithromycin can be decreased when combined with Indinavir. Approved Isavuconazole The serum concentration of Roxithromycin can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Roxithromycin can be decreased when combined with Isavuconazonium. Approved, Investigational Isradipine The metabolism of Roxithromycin can be decreased when combined with Isradipine. Approved, Investigational Itraconazole The metabolism of Roxithromycin can be decreased when combined with Itraconazole. Approved, Investigational Ivacaftor The serum concentration of Roxithromycin can be increased when it is combined with Ivacaftor. Approved Ketoconazole The metabolism of Roxithromycin can be decreased when combined with Ketoconazole. Approved, Investigational Lisuride The risk or severity of adverse effects can be increased when Lisuride is combined with Roxithromycin. Approved, Investigational Lopinavir The metabolism of Roxithromycin can be decreased when combined with Lopinavir. Approved Lorpiprazole The serum concentration of Roxithromycin can be increased when it is combined with Lorpiprazole. Approved Lovastatin The serum concentration of Lovastatin can be increased when it is combined with Roxithromycin. Approved, Investigational Luliconazole The serum concentration of Roxithromycin can be increased when it is combined with Luliconazole. Approved Lumacaftor The metabolism of Roxithromycin can be increased when combined with Lumacaftor. Approved Lysergic Acid Diethylamide The risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Roxithromycin. Illicit, Investigational, Withdrawn Macimorelin Roxithromycin may increase the QTc-prolonging activities of Macimorelin. Approved, Investigational Metergoline The risk or severity of adverse effects can be increased when Metergoline is combined with Roxithromycin. Experimental Methylergometrine The risk or severity of adverse effects can be increased when Methylergometrine is combined with Roxithromycin. Approved Methysergide The risk or severity of adverse effects can be increased when Methysergide is combined with Roxithromycin. Approved Mevastatin The serum concentration of Mevastatin can be increased when it is combined with Roxithromycin. Experimental Mifepristone The serum concentration of Roxithromycin can be increased when it is combined with Mifepristone. Approved, Investigational Mitotane The serum concentration of Roxithromycin can be decreased when it is combined with Mitotane. Approved Nefazodone The metabolism of Roxithromycin can be decreased when combined with Nefazodone. Approved, Withdrawn Nelfinavir The metabolism of Roxithromycin can be decreased when combined with Nelfinavir. Approved Netupitant The serum concentration of Roxithromycin can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Roxithromycin can be increased when combined with Nevirapine. Approved Nicergoline The risk or severity of adverse effects can be increased when Nicergoline is combined with Roxithromycin. Approved, Investigational Nilotinib The metabolism of Roxithromycin can be decreased when combined with Nilotinib. Approved, Investigational Olaparib The metabolism of Roxithromycin can be decreased when combined with Olaparib. Approved Osimertinib The serum concentration of Roxithromycin can be increased when it is combined with Osimertinib. Approved Palbociclib The serum concentration of Roxithromycin can be increased when it is combined with Palbociclib. Approved, Investigational Pentobarbital The metabolism of Roxithromycin can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Pergolide The risk or severity of adverse effects can be increased when Pergolide is combined with Roxithromycin. Approved, Investigational, Vet Approved, Withdrawn Phenobarbital The metabolism of Roxithromycin can be increased when combined with Phenobarbital. Approved, Investigational Phenytoin The metabolism of Roxithromycin can be increased when combined with Phenytoin. Approved, Vet Approved Picosulfuric acid The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Roxithromycin. Approved Pitavastatin The serum concentration of Pitavastatin can be increased when it is combined with Roxithromycin. Approved Pitolisant The serum concentration of Roxithromycin can be decreased when it is combined with Pitolisant. Approved, Investigational Posaconazole The metabolism of Roxithromycin can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Pravastatin The serum concentration of Pravastatin can be increased when it is combined with Roxithromycin. Approved Primidone The metabolism of Roxithromycin can be increased when combined with Primidone. Approved, Vet Approved Ranolazine The metabolism of Roxithromycin can be decreased when combined with Ranolazine. Approved, Investigational Ribociclib The risk or severity of QTc prolongation can be increased when Ribociclib is combined with Roxithromycin. Approved, Investigational Rifabutin The metabolism of Roxithromycin can be increased when combined with Rifabutin. Approved, Investigational Rifampicin The metabolism of Roxithromycin can be increased when combined with Rifampicin. Approved Rifapentine The metabolism of Roxithromycin can be increased when combined with Rifapentine. Approved, Investigational Rilpivirine The serum concentration of Rilpivirine can be increased when it is combined with Roxithromycin. Approved Rosuvastatin The serum concentration of Rosuvastatin can be increased when it is combined with Roxithromycin. Approved Rucaparib The metabolism of Roxithromycin can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Roxithromycin can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Roxithromycin can be decreased when used in combination with Sarilumab. Approved, Investigational Sildenafil The metabolism of Roxithromycin can be decreased when combined with Sildenafil. Approved, Investigational Siltuximab The serum concentration of Roxithromycin can be decreased when it is combined with Siltuximab. Approved, Investigational Simeprevir The serum concentration of Roxithromycin can be increased when it is combined with Simeprevir. Approved Simvastatin The serum concentration of Simvastatin can be increased when it is combined with Roxithromycin. Approved St. John's Wort The serum concentration of Roxithromycin can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Roxithromycin can be increased when it is combined with Stiripentol. Approved Sulfisoxazole The metabolism of Roxithromycin can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Telaprevir The metabolism of Roxithromycin can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Roxithromycin can be decreased when combined with Telithromycin. Approved Terfenadine The serum concentration of Terfenadine can be increased when it is combined with Roxithromycin. Approved, Withdrawn Terguride The risk or severity of adverse effects can be increased when Terguride is combined with Roxithromycin. Experimental Ticlopidine The metabolism of Roxithromycin can be decreased when combined with Ticlopidine. Approved Tocilizumab The serum concentration of Roxithromycin can be decreased when it is combined with Tocilizumab. Approved Tolvaptan The serum concentration of Tolvaptan can be increased when it is combined with Roxithromycin. Approved Vemurafenib The risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Roxithromycin. Approved Venlafaxine The metabolism of Roxithromycin can be decreased when combined with Venlafaxine. Approved Verapamil The metabolism of Roxithromycin can be decreased when combined with Verapamil. Approved Voriconazole The metabolism of Roxithromycin can be decreased when combined with Voriconazole. Approved, Investigational Ziprasidone The metabolism of Roxithromycin can be decreased when combined with Ziprasidone. Approved - 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 4 Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1 4 Completed Treatment Rheumatoid Arthritis 1 Not Available Completed Treatment Reactive Arthritis 1 Not Available Not Yet Recruiting Diagnostic Hyperaldosteronism 1 Not Available Unknown Status Treatment Hair Thinning 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
- Human
- 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
- Human
- 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
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Kind
- Protein
- Organism
- Human
- 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
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:40