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Approved, Investigational, Withdrawn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
Thumb
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

Pharmacology

Indication

Used to treat respiratory tract, urinary and soft tissue infections.

Structured Indications
Not Available
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.

TargetActionsOrganism
A50S ribosomal protein L10
inhibitor
Shigella flexneri
UMultidrug resistance protein 1Not AvailableHuman
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
PathwayCategory
Roxithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmiodaroneThe metabolism of Roxithromycin can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Roxithromycin can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Roxithromycin can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Roxithromycin can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Roxithromycin is combined with Atorvastatin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Roxithromycin.Investigational
BoceprevirThe metabolism of Roxithromycin can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Roxithromycin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Roxithromycin can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Roxithromycin.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Roxithromycin.Approved, Investigational
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Roxithromycin.Approved
CarbamazepineThe metabolism of Roxithromycin can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Roxithromycin can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Roxithromycin.Withdrawn
CisaprideThe metabolism of Cisapride can be decreased when combined with Roxithromycin.Approved, Investigational, Withdrawn
ClarithromycinThe metabolism of Roxithromycin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Roxithromycin can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Roxithromycin can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Roxithromycin can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Roxithromycin can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Roxithromycin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Roxithromycin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Roxithromycin can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Roxithromycin can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Roxithromycin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Roxithromycin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Roxithromycin can be decreased when combined with Delavirdine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Roxithromycin.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Roxithromycin.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Roxithromycin.Experimental
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Roxithromycin.Approved
DiltiazemThe metabolism of Roxithromycin can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Roxithromycin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Roxithromycin can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Roxithromycin can be decreased when it is combined with Enzalutamide.Approved
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Roxithromycin.Approved
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Roxithromycin.Approved
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Roxithromycin.Approved
ErythromycinThe metabolism of Roxithromycin can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Roxithromycin can be decreased when combined with Fluconazole.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Roxithromycin.Approved
FluvoxamineThe metabolism of Roxithromycin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Roxithromycin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Roxithromycin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Roxithromycin can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Roxithromycin can be increased when it is combined with Fusidic Acid.Approved
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Roxithromycin.Approved
IdelalisibThe metabolism of Roxithromycin can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Roxithromycin can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Roxithromycin can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Roxithromycin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Roxithromycin can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Roxithromycin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Roxithromycin can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Roxithromycin can be decreased when combined with Ketoconazole.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Roxithromycin.Approved, Investigational
LopinavirThe metabolism of Roxithromycin can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Roxithromycin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Roxithromycin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Roxithromycin can be increased when combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Roxithromycin.Illicit, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Roxithromycin.Experimental
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Roxithromycin.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Roxithromycin.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Roxithromycin.Experimental
MifepristoneThe serum concentration of Roxithromycin can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Roxithromycin can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Roxithromycin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Roxithromycin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Roxithromycin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Roxithromycin can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Roxithromycin.Approved, Investigational
NilotinibThe metabolism of Roxithromycin can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Roxithromycin can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Roxithromycin can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Roxithromycin can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Roxithromycin can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Roxithromycin.Approved, Investigational, Vet Approved, Withdrawn
PhenobarbitalThe metabolism of Roxithromycin can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Roxithromycin can be increased when combined with Phenytoin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Roxithromycin.Approved
PimozideRoxithromycin may increase the QTc-prolonging activities of Pimozide.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Roxithromycin.Approved
PosaconazoleThe metabolism of Roxithromycin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Roxithromycin.Approved
PrimidoneThe metabolism of Roxithromycin can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Roxithromycin can be decreased when combined with Ranolazine.Approved, Investigational
RibociclibThe risk or severity of QTc prolongation can be increased when Ribociclib is combined with Roxithromycin.Approved
RifabutinThe metabolism of Roxithromycin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Roxithromycin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Roxithromycin can be increased when combined with Rifapentine.Approved
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Roxithromycin.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Roxithromycin.Approved
RucaparibThe metabolism of Roxithromycin can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Roxithromycin can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Roxithromycin can be decreased when used in combination with Sarilumab.Approved
SildenafilThe metabolism of Roxithromycin can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Roxithromycin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Roxithromycin can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Roxithromycin.Approved
St. John's WortThe serum concentration of Roxithromycin can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Roxithromycin can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Roxithromycin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Roxithromycin can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Roxithromycin can be decreased when combined with Telithromycin.Approved
TerfenadineRoxithromycin may increase the QTc-prolonging activities of Terfenadine.Withdrawn
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Roxithromycin.Experimental
TiclopidineThe metabolism of Roxithromycin can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Roxithromycin can be decreased when it is combined with Tocilizumab.Approved
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Roxithromycin.Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Roxithromycin.Approved, Investigational, Nutraceutical
VemurafenibThe serum concentration of Roxithromycin can be decreased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Roxithromycin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Roxithromycin can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Roxithromycin can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe 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
  1. 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]
  2. 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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentRheumatoid Arthritis1
Not AvailableCompletedTreatmentReactive Arthritis1
Not AvailableUnknown StatusTreatmentHair Thinning1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.0189 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))Not Available
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.187 mg/mLALOGPS
logP2.9ALOGPS
logP3ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area216.89 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity211.24 m3·mol-1ChemAxon
Polarizability91.84 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8875
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.5625
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8339
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.708
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9615
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8676
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9728 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9792
hERG inhibition (predictor II)Inhibitor0.6433
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00xr-0000493040-58979c13aa08aabece66
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0000090010-6a8aec8cf2250a61f51e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0000095000-b6d63d80187aeea8a81f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00b9-0000159000-4d5697a33fe979ce33e3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2911101000-e3794cff943215a188cb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0aor-3911000000-4cbf211b5d9e86f931c0

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. 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]
  2. 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
Substrate
Inhibitor
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
  1. 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
  1. 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
  1. 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 December 01, 2017 14:34