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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 of ROXITHROMYCIN

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

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

CNS Non-penetrant
1014
Curator's Comment: Roxithromycin traverses the blood-brain barrier poorly. One study found no detectable roxithromycin in the CSF of volunteers with normal meninges who received 150 mg every 12 hours. Others have stated that roxithromycin exhibits excellent penetration through the blood-brain barrier; however, there is no evidence to substantiate this claim.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Not Provided
504
ROXITHROMYCIN SANDOZ

Approved Use

Unknown
Curative
Not Provided
504
ROXITHROMYCIN SANDOZ

Approved Use

Unknown
Curative
Not Provided
504
ROXITHROMYCIN SANDOZ

Approved Use

Unknown
Curative
Not Provided
504
ROXITHROMYCIN SANDOZ

Approved Use

Unknown
Curative
Not Provided
504
ROXITHROMYCIN SANDOZ

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vivo synergism of roxithromycin (RU 965) and interferon against Toxoplasma gondii.
1987 Feb
In vitro susceptibility of Mycobacterium tuberculosis to a new macrolide antibiotic: RU-28965.
1987 Jun
In vitro activities of several new macrolide antibiotics against Mycobacterium avium complex.
1989 Sep
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
Roxithromycin-induced digoxin toxicity.
1996 Oct 21
Immediate reaction to roxithromycin and prick test cross-sensitization to erythromycin and clarithromycin.
1998
In-vitro activity of lytic peptides alone and in combination with macrolides and inhibitors of dihydrofolate reductase against Pneumocystis carinii.
1998 Oct
In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials.
2000 Jan
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Reversible anosmia after amikacin therapy.
2003 Dec
In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis.
2005 Apr
Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin.
2006 Apr
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction.
2006 Oct
Inhibition of sulfur mustard-induced cytotoxicity and inflammation by the macrolide antibiotic roxithromycin in human respiratory epithelial cells.
2007 May 24
Patents

Patents

20010020147
5
JP3292732B2
20

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
Curator's Comment: It was investigated the antitumor effects of roxithromycin and clarithromycin, alone and in combination with several cytotoxic drugs, on mouse B16BL6 melanoma cells. Neither roxithromycin nor clarithromycin, altered the cytotoxicity of 4-hydroperoxycyclophosphamide, cis-diamminedichloroplatinum(II), Adriamycin or vindesine in an in vitro cell proliferation assay. It was shown the antiangiogenic activity of roxithromycin might provide beneficial effects in combination with cytotoxic therapies against solid tumors.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:07 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:07 UTC 2023
Record UNII
21KOF230FA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROXITHROMYCIN
JAN   INN   USAN  
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
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
WHO-ATC J01FA06
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
NCI_THESAURUS C261
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
Code System Code Type Description
CHEBI
48935
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
IUPHAR
1465
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
WIKIPEDIA
ROXITHROMYCIN
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID8041117
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL1214185
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
RXCUI
9478
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
2410
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
LACTMED
Roxithromycin
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
CAS
80214-83-1
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
NSC
758443
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
NCI_THESAURUS
C818
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
INN
5815
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
MESH
D015575
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
EVMPD
SUB10400MIG
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
CHEBI
32109
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
MERCK INDEX
m9679
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY Merck Index
USAN
X-56
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
SMS_ID
100000092081
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
DRUG BANK
DB00778
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
FDA UNII
21KOF230FA
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
PUBCHEM
6915744
Created by admin on Fri Dec 15 15:24:07 UTC 2023 , Edited by admin on Fri Dec 15 15:24:07 UTC 2023
PRIMARY
Related Record Type Details
Structure of ROXITHROMYCIN
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