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Dirithromycin (Standard)

CAT: 0804-HY-B0643R-02Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0643R-02Size:25 mg
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Description
Dirithromycin (Standard) is the analytical standard of Dirithromycin. This product is intended for research and analytical applications. Dirithromycin (LY237216), a derivative of Erythromycin, is a potent and orally active semi-synthetic macrolide antibiotic. Dirithromycin is active against gram-positive bacteria, Legionella spp., Helicobacter pylori, and Chlamydia trachomatis[1][2].
CAS Number
62013-04-1
Product Name Alternative
LY237216 (Standard)
UNSPSC
12352005
Target
Antibiotic; Bacterial; Reference Standards
Type
Reference Standards
Related Pathways
Anti-infection; Others
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/dirithromycin-standard.html
Smiles
CC1[C@@]([C@](O)([C@H](OC([C@@H]2C)=O)CC)C)([H])O[C@H](COCCOC)N[C@@]1([H])[C@](C[C@@](O)([C@@H]([C@@H](C)[C@]2([H])O[C@@](O[C@@H](C)[C@@H]3O)([H])C[C@@]3(C)OC)O[C@@](O[C@H](C)C[C@@H]4N(C)C)([H])[C@@H]4O)C)([H])C
Molecular Formula
C42H78N2O14
Molecular Weight
835.07
References & Citations
[1]Wasilewski MM, et, al. Five-day dirithromycin therapy is as effective as seven-day erythromycin therapy for acute exacerbations of chronic bronchitis. J Antimicrob Chemother. 1999 Apr;43 (4) :541-8.|[2]Counter FT, et, al. Synthesis and antimicrobial evaluation of dirithromycin (AS-E 136; LY237216), a new macrolide antibiotic derived from erythromycin. Antimicrob Agents Chemother. 1991 Jun;35 (6) :1116-26.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Dirithromycin

Dirithromycin is the hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms. It has a role as a prodrug.

CAS Number62013-04-1
PubChem CID6473883
IUPAC Name(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Molecular FormulaC42H78N2O14
Molecular Weight835.1
XLogP4.2
Topological Polar Surface Area196
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count16
Rotatable Bond Count12
Heavy Atom Count58
Formal Charge0
Complexity1300
SMILES
CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O
InChI
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
InChIKey
WLOHNSSYAXHWNR-DWIOZXRMSA-N
Chemical Structure
2D Structure
2D structure of Dirithromycin
CAS: 62013-04-1
CID: 6473883
Formula: C42H78N2O14
MW: 835.1
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight835.1
XLogP34.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count16
Rotatable Bond Count12
Exact Mass834.54530517
Monoisotopic Mass834.54530517
Topological Polar Surface Area196 Ų
Heavy Atom Count58
Formal Charge0
Complexity1300
Isotope Atom Count0
Defined Atom Stereocenter Count20
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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