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D2880000

Dirithromycin

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

[9S(R)]-9-Deoxo-11-deoxy-9,11-[imino[2-(2-methoxy)ethylidene]oxy]erthromycin; LY-237216

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About This Item

Empirical Formula (Hill Notation):
C42H78N2O14
CAS Number:
62013-04-1
Molecular Weight:
835.07
MDL number:
MFCD00865041
UNSPSC Code:
41116107
PubChem Substance ID:
329798757
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

dirithromycin

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

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]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C4N[C@@H](COCCOC)OC([C@H]4C)[C@]1(C)O

InChI

1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41+,42-/m1/s1

InChI key

WLOHNSSYAXHWNR-KZYCBHIHSA-N

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Dirithromycin EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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R N Brogden et al.
Drugs, 48(4), 599-616 (1994-10-01)
Dirithromycin is a new macrolide with a spectrum and degree of in vitro antimicrobial activity similar to that of erythromycin. Compared with erythromycin, dirithromycin has a long elimination half-life enabling once-daily administration, and it also achieves a greater cellular:extracellular concentration
Macrolide - induced clinically relevant drug interactions with cytochrome P-450A (CYP) 3A4: an update focused on clarithromycin, azithromycin and dirithromycin.
J F Westphal
British journal of clinical pharmacology, 50(4), 285-295 (2000-09-30)
G D Sides et al.
The Journal of antimicrobial chemotherapy, 31 Suppl C, 65-75 (1993-03-01)
Dirithromycin is a new member of the macrolide class of antibiotics and has been developed for oral administration. Dirithromycin is a 14-membered lactone ring macrolide and is the C9-oxazine derivative of erythromycylamine. The human pharmacokinetics and clinical pharmacology of dirithromycin
M T Labro et al.
The Journal of antimicrobial chemotherapy, 31 Suppl C, 51-64 (1993-03-01)
Polymorphonuclear neutrophils (PMN) play a prominent role in the host response to infectious diseases. One major bactericidal mechanism used by these cells is the production of reactive oxygen species during what is referred to as the oxidative burst. However, excessive
S M Wintermeyer et al.
The Annals of pharmacotherapy, 30(10), 1141-1149 (1996-10-01)
To review the clinical microbiology and therapeutic use of dirithromycin, emphasizing comparative data between dirithromycin and the standard macrolide erythromycin, as well as clarithromycin and azithromycin. A MEDLINE search of English-language literature during the years 1966-1996, and an extensive review
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