ROXITHROMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C41H76N2O15
Molecular Weight	837.0465
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]2(O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)\C(=N\OCOCCOC)[C@H](C)C[C@@](C)(O)[C@]([H])(O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@H]2C

InChI

InChIKey=RXZBMPWDPOLZGW-XMRMVWPWSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets

Roxithromycin is a semi-synthetic macrolide antibiotic, which was developed by Roussel Uclaf and is available in Australia. 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. It can treat respiratory tract, urinary and soft tissue infections.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15386112	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute pharyngitis 2 Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets	Curative	Not Provided 504	ROXITHROMYCIN SANDOZ Approved Use Unknown
Acute bronchitis 10 Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets	Curative	Not Provided 504	ROXITHROMYCIN SANDOZ Approved Use Unknown
Pneumonia 90 Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets	Curative	Not Provided 504	ROXITHROMYCIN SANDOZ Approved Use Unknown
Skin and soft tissue infections 33 Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets	Curative	Not Provided 504	ROXITHROMYCIN SANDOZ Approved Use Unknown
Non gonococcal urethritis 1 Sources: http://www.nps.org.au/medicines/infections-and-infestations/antibiotics/for-individuals/antibiotics-for-respiratory-tract-infections/for-individuals/active-ingredients/roxithromycin/for-individuals/brands/roxithromycin-sandoz-tablets	Curative	Not Provided 504	ROXITHROMYCIN SANDOZ Approved Use Unknown

PubMed

Title	Date	PubMed
Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview.	1987 Nov	3323166
In vitro activity of antimicrobial agents against mycobacteria.	1988	3150951
In vitro activity of roxithromycin against 16 species of atypical mycobacteria and effect of pH on its radiometric MICs.	1993 Jul	8363393
Activities of roxithromycin used alone and in combination with ethambutol, rifampin, amikacin, ofloxacin, and clofazimine against Mycobacterium avium complex.	1994 Jun	8092850
Roxithromycin alone and in combination with either ethambutol or levofloxacin for disseminated Mycobacterium avium infections in beige mice.	1996 Apr	8849223
In-vitro activity of fluorinated quinolones and macrolides against drug-resistant Mycobacterium tuberculosis.	1997 Dec	9462443
[Macrolide antibiotic-induced vasculitis (Churg-Strauss syndrome)].	1998 Feb	9555706
Possible roxithromycin-induced fulminant hepatic failure in a child.	2001 Jul	11444584
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Roxithromycin promotes lymphocyte apoptosis in Dermatophagoides-sensitive asthma patients.	2003 Aug 8	12921874
Reversible anosmia after amikacin therapy.	2003 Dec	14676161
Acute renal failure and hepatotoxicity associated with roxithromycin.	2004 Apr	14766998
Effects of eight antibacterial agents on cell survival and expression of epithelial-cell- or cell-adhesion-related genes in human gingival epithelial cells.	2004 Feb	14687228
In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis.	2005 Apr	15793125
Roxithromycin inhibits constitutive activation of nuclear factor {kappa}B by diminishing oxidative stress in a rat model of hepatocellular carcinoma.	2005 Aug 1	16061884
Quantitative prediction of macrolide drug-drug interaction potential from in vitro studies using testosterone as the human cytochrome P4503A substrate.	2006 Mar	16416302
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.	2006 Oct	16837568

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage for adults is 300mg per day. You may take this according to one of the following dosage regimens: one 300mg tablet once a day, or one 150mg tablet twice a day, or two 150 mg tablets once a day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ROXITHROMYCIN

Official Name

English

RU 965

Code

English

ROXITHROMYCIN [MART.]

Common Name

English

RU-965

Code

English

(E)-ERYTHROMYCIN-9-(O-((2-METHOXYETHOXY)METHYL)OXIME)

Common Name

English

roxithromycin [INN]

Common Name

English

ERYTHROMYCIN 9-(E)-(O-((2-METHOXYETHOXY)METHYL)OXIME)

Common Name

English

ERYTHROMYCIN A, 9-(O-(2-METHOXYETHOXYMETHYL)-OXIME)

Common Name

English

ROXITHROMYCIN [JAN]

Common Name

English

ROXITHROMYCIN [MI]

Common Name

English

ROXITHROMYCIN [USAN]

Common Name

English

RU 28965

Code

English

ROXITHROMYCIN [EP IMPURITY]

Common Name

English

NSC-758443

Code

English

RU-28965

Code

English

Roxithromycin [WHO-DD]

Common Name

English

(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-4-((2,6DIDEOXY-3-C-METHYL-3-O-METHYL-.ALPHA.-L-RIBO-HEXOPYRANOSYL)OXY)-14-ETHYL-7,12,13-TRIHYDROXY-10-((E)((2-METHOXYETHOXY)METHOXY)IMINO)-3,5,7,9,11,13HEXAMETHYL-6-((3,4,6-TRIDEOXY-3-(DIMETHYLAMINO)-.BETA.-D-XYLOHEXOP

Systematic Name

English

Erythromycin 9-[O-[(2-methoxyethoxy)methyl]oxime]

Common Name

English

ROXITHROMYCIN [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01FA06