Roxithromycin - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)Enzymes (3)

Targets (2)Enzymes (3)Biointeractions (5)

Identification

Name

Roxithromycin

Accession Number

DB00778 (APRD01305)

Type

Small Molecule

Groups

Approved, Withdrawn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

MOL SDF PDB SMILES InChI

Synonyms

(9e)-Erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime)

Roxithromycin

Roxithromycine

Roxithromycinum

Roxitromicina

External IDs

RU 28965 / RU 965

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
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	Not Available
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	Not Available
Roxo	Not Available
Roxomycin	Not Available
Roxy	Ind-Swift
Roxy-150	Cipla
Rulid	Not Available
Rulide	Sanofi-Aventis
Rulide D	Sanofi-Aventis
Surlid	Sanofi-Aventis
Tirabicin	Not Available
Xthrocin	Not Available

Brand mixtures

Not Available

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[[email protected]]1OC(=O)[[email protected]](C)[C@@H](O[[email protected]]2C[C@@](C)(OC)[C@@H](O)[[email protected]](C)O2)[[email protected]](C)[C@@H](O[C@@H]2O[[email protected]](C)C[C@@H]([[email protected]]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=NOCOCCOC)[[email protected]](C)[C@@H](O)[C@]1(C)O

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
50S ribosomal protein L10	Protein	yes	inhibitor	Shigella flexneri	P0A7J6	details
Multidrug resistance protein 1	Protein	unknown	Not Available	Human	P08183	details

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.

Substrate	Enzymes	Product
Roxithromycin	Not Available	descladinose roxithromycin	Details
Roxithromycin	Not Available	N-di-demethyl roxithromycin	Details
Roxithromycin	Not Available	N-mono roxithromycin	Details

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	SMPDB ID
Roxithromycin Action Pathway	Drug action	SMP00251

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Amiodarone	The metabolism of Roxithromycin can be decreased when combined with Amiodarone.	Approved, Investigational
Aprepitant	The serum concentration of Roxithromycin can be increased when it is combined with Aprepitant.	Approved, Investigational
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
BCG vaccine	The therapeutic efficacy of Bcg can be decreased when used in combination with Roxithromycin.	Investigational
Bexarotene	The serum concentration of Roxithromycin can be decreased when it is combined with Bexarotene.	Approved, Investigational
Boceprevir	The metabolism of Roxithromycin can be decreased when combined with Boceprevir.	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
Bromocriptine	The serum concentration of Bromocriptine can be increased when it is combined with Roxithromycin.	Approved, Investigational
Cabergoline	The serum concentration of Cabergoline can be increased when it 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
Cisapride	The metabolism of Cisapride can be decreased when 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
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 Roxithromycin can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	The metabolism of Roxithromycin can be decreased when combined with Crizotinib.	Approved
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
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
Delavirdine	The metabolism of Roxithromycin can be decreased when combined with Delavirdine.	Approved
Dexamethasone	The serum concentration of Roxithromycin can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dihydroergotamine	The serum concentration of Dihydroergotamine can be increased when it is combined with Roxithromycin.	Approved
Diltiazem	The metabolism of Roxithromycin can be decreased when combined with Diltiazem.	Approved
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
Efavirenz	The serum concentration of Roxithromycin can be decreased when it is combined with Efavirenz.	Approved, Investigational
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 serum concentration of Ergonovine can be increased when it is combined with Roxithromycin.	Approved
Ergotamine	The serum concentration of Ergotamine can be increased when it is combined with Roxithromycin.	Approved
Erythromycin	The metabolism of Roxithromycin can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Roxithromycin can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Etravirine	The serum concentration of Roxithromycin can be decreased when it is combined with Etravirine.	Approved
Fluconazole	The metabolism of Roxithromycin can be decreased when combined with Fluconazole.	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
Fusidic Acid	The serum concentration of Roxithromycin can be increased when it is combined with Fusidic Acid.	Approved
Idelalisib	The serum concentration of Roxithromycin can be increased when it is 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
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
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
Lopinavir	The metabolism of Roxithromycin can be decreased when combined with Lopinavir.	Approved
Lovastatin	The metabolism of Roxithromycin can be decreased when combined with Lovastatin.	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
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
Modafinil	The serum concentration of Roxithromycin can be decreased when it is combined with Modafinil.	Approved, Investigational
Nafcillin	The serum concentration of Roxithromycin can be decreased when it is combined with Nafcillin.	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
Nevirapine	The metabolism of Roxithromycin can be increased when combined with Nevirapine.	Approved
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
Pentobarbital	The metabolism of Roxithromycin can be increased when combined with Pentobarbital.	Approved, Vet Approved
Phenobarbital	The metabolism of Roxithromycin can be increased when combined with Phenobarbital.	Approved
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
Pimozide	Roxithromycin may increase the QTc-prolonging activities of Pimozide.	Approved
Posaconazole	The metabolism of Roxithromycin can be decreased when combined with Posaconazole.	Approved, Investigational, Vet 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
Rifabutin	The metabolism of Roxithromycin can be increased when combined with Rifabutin.	Approved
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
Ritonavir	The metabolism of Roxithromycin can be decreased when combined with Ritonavir.	Approved, Investigational
Saquinavir	The metabolism of Roxithromycin can be decreased when combined with Saquinavir.	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
Simeprevir	The serum concentration of Roxithromycin can be increased when it is combined with Simeprevir.	Approved
St. John's Wort	The serum concentration of Roxithromycin can be decreased when it is combined with St. John's Wort.	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.	Withdrawn
Telithromycin	The metabolism of Roxithromycin can be decreased when combined with Telithromycin.	Approved
Terfenadine	Roxithromycin may increase the QTc-prolonging activities of Terfenadine.	Withdrawn
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
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

Resource	Link
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

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

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	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00xr-0000493040-58979c13aa08aabece66	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0000090010-6a8aec8cf2250a61f51e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00fr-0000095000-b6d63d80187aeea8a81f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00b9-0000159000-4d5697a33fe979ce33e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0aor-3911000000-4cbf211b5d9e86f931c0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organic oxygen compounds

Sub Class

Organooxygen compounds

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

Substituents

Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

erythromycin derivative, semisynthetic derivative, macrolide (CHEBI:48844 )

Targets

Details

1. 50S ribosomal protein L10

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 central role in the interaction of the ribosome with GTP-bound translation factors.
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 ]

Details

2. Multidrug resistance protein 1

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

Details

1. Cytochrome P450 3A4

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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
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 ]

Details

2. Cytochrome P450 1A2

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
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 ]

Details

3. Cytochrome P450 2B6

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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
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 July 18, 2017 16:52

Get DrugBank to go!

Structure for DB00778 (Roxithromycin)

Targets

References

References

Enzymes

References

References

References