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

Molecular Formula	C41H76N2O15
Molecular Weight	837.0465
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	1
Optical Activity	UNSPECIFIED

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 effects of four macrolides (roxithromycin, spiramycin, azithromycin [CP-62,993], and A-56268) on Toxoplasma gondii.	1988 Apr	2837140
In vitro activities of several new macrolide antibiotics against Mycobacterium avium complex.	1989 Sep	2817858
[Activity of azithromycin and roxithromycin alone or in combination against Mycobacterium avium and Mycobacterium xenopi].	1990 May	2164181
In vitro activity of roxithromycin against 16 species of atypical mycobacteria and effect of pH on its radiometric MICs.	1993 Jul	8363393
Intracellular activities of roxithromycin used alone and in association with other drugs against Mycobacterium avium complex in human macrophages.	1995 Apr	7786006
Activities of roxithromycin against Mycobacterium avium infections in human macrophages and C57BL/6 mice.	1995 Apr	7785988
International Congress on Chemotherapy.	1995 Sep	11362904
Spectrum of activity of levofloxacin against nontuberculous mycobacteria and its activity against the Mycobacterium avium complex in combination with ethambutol, rifampin, roxithromycin, amikacin, and clofazimine.	1996 Nov	8913450
Roxithromycin-induced digoxin toxicity.	1996 Oct 21	8913245
In-vitro activity of fluorinated quinolones and macrolides against drug-resistant Mycobacterium tuberculosis.	1997 Dec	9462443
Immediate reaction to roxithromycin and prick test cross-sensitization to erythromycin and clarithromycin.	1998	9621142
[Macrolide antibiotic-induced vasculitis (Churg-Strauss syndrome)].	1998 Feb	9555706
In-vitro activity of lytic peptides alone and in combination with macrolides and inhibitors of dihydrofolate reductase against Pneumocystis carinii.	1998 Oct	9818742
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 induced torsade de pointes in a patient with complex congenital heart disease and complete atrioventricular block.	2003 Jun	12822762
Acute renal failure and hepatotoxicity associated with roxithromycin.	2004 Apr	14766998
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
Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin.	2006 Dec	17164692
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.	2006 Oct	16837568
Inhibition of sulfur mustard-induced cytotoxicity and inflammation by the macrolide antibiotic roxithromycin in human respiratory epithelial cells.	2007 May 24	17524151
Macrolides attenuate mucus hypersecretion in rat airways through inactivation of NF-kappaB.	2008 Jan	18197913

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:24:07 GMT 2023` Edited by `admin` on `Fri Dec 15 15:24:07 GMT 2023`
Record UNII	21KOF230FA
Record Status	`Validated (UNII)`
Record Version

Download

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