CAS 80214-83-1|(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-dimethyl...

General Information

Structure

Molecular Formula

C₄₁H₇₆N₂O₁₅

Molecular Mass

837.04654

Exact Mass

836.52456974

Charge

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

InChIKey

RXZBMPWDPOLZGW-HEWSMUCTSA-N

Canonic Smiles

COCCOCO/N=C\1/[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C

Isomeric Smiles

[C@@H]1([C@@](C[C@H](/C(=N/OCOCCOC)/[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]1C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C)CC)(C)O)O)C)C)(O)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O

Calculated Properties

JChem

LogD (pH = 7.4)

1.32

LogD (pH = 5.5)

-0.24

Log P

3.00

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.08

Polar Surface Area

216.89

Polarizability

92.54

Molar Refractivity

211.24

LOG S

-1.40

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Roxithromycin(Z)-roxithromycinRoxithromycin

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 (3R,4S,5S,6R,7R,9R,10Z,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

IUPAC Traditional name

roxiβ (Z)-roxithromycin roxithromycin

Brand Name

SurlidRulideROXRulid

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

Chemspider ID

CHEBI ID

Wikipedia Title

Unique Ingredient Identifier

ATC CODE

DrugBank ID

KEGG ID

CHEMBL

SureChEMBL Database

KEGG DRUG Database

Registration numbers

Properties

Physical Property

Solubility

0.0189 mg/L at 25 oC (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))

Hydrophobicity(logP)

1.7

Pharmacology Properties

Pregnancy Category

? (USA)
B1 (Aus)

Metabolism

Liver, peak concentration averaging 2 hours after ingestion.

Half Life

11 hours

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00778

Drug Groups

approved

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.

Indication

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

Pharmacology

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.

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

Biotransformation

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.

Absorption

Very rapidly absorbed and diffused into most tissues and phagocytes.

Half Life

12 hours

Protein Binding

96%, mainly to alpha1-acid glycoproteins

References

• [Link]

• 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]

External Links

• [Wikipedia]

A minor geometrical isomer of roxithromycin.

Molecule Details

References

PubChem Literature

From Data Sources

• Link

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

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Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

Names and Identifiers