Roxithromycin

Identification

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Name

Roxithromycin

Accession Number

DB00778  (APRD01305)

Type

Small Molecule

Groups

Approved, Investigational, Withdrawn

Description

Roxithromycin is a semi-synthethic macrolide antibiotic that is structurally and pharmacologically similar to erythromycin, azithromycin, or clarithromycin. It was shown to be more effective against certain Gram-negative bacteria, particularly Legionella pneumophila. Roxithromycin exerts its antibacterial action by binding to the bacterial ribosome and interfering with bacterial protein synthesis. It is marketed in Australia as a treatment for respiratory tract, urinary and soft tissue infections.

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Roxithromycin (DB00778)

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Synonyms

• (9E)-erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime)
• Roxithromycin
• Roxithromycine
• Roxithromycinum
• Roxitromicina

External IDs

RU 28965 / RU 965

International/Other Brands

Acevor (Help) / Actirox (Active HC) / Ai Luo Xin (Huashen Pharmaceutical) / Allolide (Roman Industries) / Ammirox (MacroPhar) / Anti-Bio (Kon/Nos Leon) / Ao Ge Shen (Jianfa Pharmaceutical) / Aparox (Siza) / Arbid (Hetero) / Aroxe (Global) / Asmetic (Farmilia) / Assoral (Savio I.B.N.) / Aswad (Robins) / Azuril (Pharmanel) / Bazuctril (Chrispa) / BD-Rox (Panacea) / Bei Ke (Aoda Pharmaceuticals) / Bei Sha (Huipusen Medical Biological Technology) / Bi Ai Di (Siping Aimo Pharmaceutical) / Biaxsig (Sanofi-Aventis) / Bicofen (Pharmex) / Biostatik (Pharos) / Claramid (Pfizer) / Coroxin / Delitroxin (Pharmathen) / Delos (Dallas) / Dorolid (Domesco) / Elrox (Biopharm M.J.) / Erybros (Bros) / Eslid (Shin Poong) / Guamil (P T Interbat) / Heng Te (Hanson Pharmaceutical) / Hycin (Saga) / I-Throcin (T.C. Pharma-Chem) / Infectoroxit (Infectopharm) / Inrox (Intra) / Ixor (Soho) / Klomicina (Klonal) / Ladlid (Choseido Pharmaceutical) / Lang Su (Shandong Dayin Yanghai Bio-Pharmaceutical Co.) / Le Er Tai (Tianji Biological Pharmaceutical) / Le Xi Qing (Zhangshu Santai Pharmaceutical) / Li Fu (Suzhou Chung-Hwa Chemical & Pharmaceutical Industrial) / Lizhuxing (Livzon Zhuhai) / Ludin (Vellpharm) / Luo Jun Qing (Fusen Pharmaceutical) / Luo Shi Li (Xi'an Detian Pharmaceutical Co.) / Luo Si Mei (Yabo Pharmaceutical Co.) / Luprex (Lupin) / Macrol (UAP) / Macrolid (Rafarm) / Marulide (Pasteur) / Neo-Suxigal (Anfarm) / Nirox (Gabriel Health) / Odirox (Cipla) / Overal (Lusofarmaco) / Pedilid (Incepta) / Pedrox (Beximco) / Pinsheng (Xincat) / Plethirox (Sel-J) / Poliroxin (Polipharm) / Pu Hong (Shyndec) / Pymeroxitil (PMP) / Qi Wei (Lanling Pharmaceutical Production) / Ramivan (Medipharm) / Redotrin (Coup) / Remora (Nobel) / Ren Su (Yangtze River Pharma) / Renicin (Sandoz) / Ridinfect (Medicraft) / Ritosin (Münir Sahin) / Rocin (Pasteur) / Rokithrid (Taiyo Pharmaceutical) / Roksimin (Il-Ko) / Rolexit (Nufarindo) / Rolicyn (Polfa Tarchomin) / Romac (Saiph) / Romicin (Dae Woo) / Romycin (Livzon Zhuhai) / Romyk (Lindopharm) / Ropit (Epitome) / Rossitrol (Sanofi-Aventis) / Rothricin (Siam Bheasach) / Rotram (Ranbaxy) / Rovenal (Leciva) / Roxamed (Dar Al Dawa) / Roxar (Sigma) / Roxcin (Biolab) / Roxemicin (Han Mi) / Roxeptin (Ipca Laboratories Ltd.) / Roxetomin (Sun) / Roxi (Dae Won) / Roxi-Fatol (Riemser) / Roxi-Puren (Actavis) / Roxi-Q (Juta) / Roxi-saar (MIP) / Roxibest (Blue Cross) / Roxibeta (Betapharm) / Roxibron (Viofar) / Roxicin (Atlantic Lab) / Roxicur (Velka) / Roxicure (Pharmaceutical) / Roxid (Alembic) / Roxide (Sandoz) / Roxidura (Mylan dura) / Roxigamma (Wörwag Pharma) / Roxigrün (Grünenthal) / Roxihexal (Salutas) / Roxikid (Ahn-Gook) / Roxil (YSS) / Roxilan (Olan-Kemed) / Roximac (Ram Pharmaceutical) / Roximain (Towa Yakuhin) / Roximax (Pharmaghreb) / Roximed (Medhaus) / Roximerck (Mylan Seiyaku) / Roximic (Acto) / Roximin (Novis Pharmaceutical) / Roximisan (Slaviamed) / Roximol (Torrent) / Roximycin (Alphapharm) / Roxinga (Roxinga) / Roxinox (Charoen Bhaesaj) / Roxiratio (ratiopharm) / Roxirocin (Korea Arlico) / Roxisara (Abbott) / Roxistad (Aliud) / Roxitas (Intas) / Roxitazon (Alice Loren) / Roxithrin (Kuk Je) / Roxithro (Millimed) / Roxithrostad (STADA) / Roxitil (Kolon) / Roxitin (T P Drug) / Roxitis (Medley) / Roxitop (Farmaline) / Roxitran (Neo Quimica) / Roxitrom (Biolab) / Roxitromycine (Sandoz) / Roxitron (ICN) / Roxivar (Zota) / Roxivinol (Pheracon) / Roxivista (Cadila) / Roxl-150 / Roxo / Roxomycin / Roxy (Ind-Swift) / Roxy-150 (Cipla) / Rulid / Rulide (Sanofi-Aventis) / Rulide D (Sanofi-Aventis) / Surlid (Sanofi-Aventis) / Tirabicin / Xthrocin

Categories

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (weak)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Erythromycin and similars
• Lactones
• Macrolides
• Macrolides, Lincosamides and Streptogramins
• Moderate Risk QTc-Prolonging Agents
• OATP1B1/SLCO1B1 Inhibitors
• OATP1B3 inhibitors
• Polyketides
• QTc Prolonging Agents

UNII

21KOF230FA

CAS number

80214-83-1

Weight

Average: 837.0465
Monoisotopic: 836.524569772

Chemical Formula

C₄₁H₇₆N₂O₁₅

InChI Key

RXZBMPWDPOLZGW-XMRMVWPWSA-N

InChI

InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1

IUPAC Name

(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

SMILES

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

Pharmacology

Indication

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

Pharmacodynamics

Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.

Mechanism of action

Roxithromycin prevents bacterial growth by interfering with their protein synthesis. It binds to the 50S subunit of bacterial ribosomes and inhibits the translocation of peptides.

Target	Actions	Organism
A50S ribosomal protein L10	inhibitor	Shigella flexneri
UP-glycoprotein 1	Not Available	Humans

Absorption

Very rapidly absorbed and diffused into most tissues and phagocytes.

Volume of distribution

Not Available

Protein binding

96%, mainly to alpha1-acid glycoproteins

Metabolism

Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.

• Roxithromycin
  descladinose roxithromycin
• Roxithromycin
  N-di-demethyl roxithromycin
• Roxithromycin
  N-mono roxithromycin

Route of elimination

Not Available

Half life

12 hours

Clearance

Not Available

Toxicity

Roxithromycin primarily causes gastrointestinal adverse events, such as diarrhoea, nausea, abdominal pain and vomiting. Less common adverse events include headaches, rashes, abnormal liver function values and alteration in senses of smell and taste.

Affected organisms

• Enteric bacteria and other eubacteria

Pathways

Pathway	Category
Roxithromycin Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The serum concentration of (R)-warfarin can be increased when it is combined with Roxithromycin.
(S)-Warfarin	The serum concentration of (S)-Warfarin can be increased when it is combined with Roxithromycin.
9-aminocamptothecin	The metabolism of 9-aminocamptothecin can be decreased when combined with Roxithromycin.
Abexinostat	The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Abexinostat.
Acebutolol	The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Acebutolol.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Roxithromycin.
Aceprometazine	The risk or severity of QTc prolongation can be increased when Roxithromycin is combined with Aceprometazine.
Acetyldigoxin	The risk or severity of adverse effects can be increased when Roxithromycin is combined with Acetyldigoxin.
Acrivastine	The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Roxithromycin.
Adenosine	The risk or severity of QTc prolongation can be increased when Adenosine is combined with Roxithromycin.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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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

• J01FA — Macrolides
• J01F — MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

PDB Entries

1jzz

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Quality of Life / Respiratory Function Tests	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Treatment	Rheumatoid Arthritis	1
4	Not Yet Recruiting	Prevention	Bacterial Infections / Pacemaker Complication	1
4	Recruiting	Prevention	Premature Rupture of Membranes	1
Not Available	Completed	Treatment	Reactive Arthritis	1
Not Available	Not Yet Recruiting	Diagnostic	Hyperaldosteronism	1
Not Available	Unknown Status	Treatment	Alopecia	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	0.0189 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))	Not Available
logP	1.7	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.187 mg/mL	ALOGPS
logP	2.9	ALOGPS
logP	3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	216.89 Å2	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	211.24 m3·mol-1	ChemAxon
Polarizability	91.84 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	-	0.5
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.8957
P-glycoprotein substrate	Substrate	0.8875
P-glycoprotein inhibitor I	Inhibitor	0.8564
P-glycoprotein inhibitor II	Inhibitor	0.5625
Renal organic cation transporter	Non-inhibitor	0.8178
CYP450 2C9 substrate	Non-substrate	0.8339
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.708
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9615
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.8676
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.9728 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9792
hERG inhibition (predictor II)	Inhibitor	0.6433

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00xr-0000493040-58979c13aa08aabece66
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00di-0000090010-6a8aec8cf2250a61f51e
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00fr-0000095000-b6d63d80187aeea8a81f
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00b9-0000159000-4d5697a33fe979ce33e3
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-2911101000-e3794cff943215a188cb
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0aor-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 / Trialkylamines1,2-aminoalcohols / Oxime ethers / Polyols / Monocarboxylic acids and derivatives / Dialkyl ethers / Oxacyclic compounds / Acetals / Carbonyl compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

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 esterLactone / Oxime ether / Secondary alcohol / Tertiary aliphatic amine / Tertiary amine / Acetal / Monocarboxylic acid or derivatives / Polyol / Organoheterocyclic compound / Oxacycle / Ether / Dialkyl ether / Carboxylic acid derivative / Carbonyl group / Alcohol / Organopnictogen compound / Organonitrogen compound / Amine / Organic oxide / Hydrocarbon derivative / Organic nitrogen compound / Aliphatic heteromonocyclic compound

show 22 more

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

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

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Drug created on June 13, 2005 07:24 / Updated on November 02, 2019 00:34