Dirithromycin
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| Category | Antibiotics |
| Catalog number | BBF-03919 |
| CAS | 62013-04-1 |
| Molecular Weight | 835.07 |
| Molecular Formula | C42H78N2O14 |
| Purity | >98% |
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Description
Dirithromycin is a macrolide glycopeptide antibiotic by binding to the 50S subunit of the 70S bacterial ribosome to inhibit the translocation of peptides. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and thus inhibits the translocation of peptides.
Specification
| Synonyms | LY-237216; LY 237216; LY237216; Antibiotic AS-E 136 |
| Storage | Store at -20°C |
| 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 |
| Canonical SMILES | CCC1C(C2C(C(C(CC(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C)O)(C)O)C)NC(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 |
| InChI Key | WLOHNSSYAXHWNR-JFSYMESMSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 871.8°C at 760 mmHg |
| Melting Point | 185-189°C |
| Density | 1.19 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO; Limited water solubility. |
Reference Reading
1.Quantitative determination of erythromycylamine in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study of dirithromycin.
Liu YQ1, Chen QY, Chen BM, Liu SG, Deng FL, Zhou P. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Mar 15;864(1-2):1-8. doi: 10.1016/j.jchromb.2007.12.021. Epub 2008 Jan 4.
A sensitive, rapid liquid chromatographic-electrospray ionization mass spectrometric method for determination of erythromycylamine in human plasma was developed and validated. Erythromycylamine in plasma (0.2 mL) was extracted with ethyl acetate, the organic phase was transferred to another clear 1.5 mL Eppendorf tube and evaporated to dryness under gentle nitrogen stream at 45 degrees C, and the residue was dissolved in 100 microL of mobile phase. The samples were separated using a Thermo Hypersil HyPURITY C18 reversed-phase column (150 mm x 2.1 mm I.D., 5 microm). A mobile phase containing 10 mM of ammonium acetate (pH = 6.4)-acetonitrile-methanol (50:10:40, v/v/v) was used isocratically eluting at a flow rate of 0.2 mL/min. Erythromycylamine and its internal standard (IS), midecamycin, were measured by electrospray ion source in positive selective ion monitoring mode. The method demonstrated that good linearity ranged from 4.5 to 720 ng/mL with r = 0.
2.Long-acting erythromycins: assessing their role in treating outpatient odontogenic infections.
Alexander RE1, Grogan DM. Tex Dent J. 2009 Apr;126(4):326-33.
Erythromycins have been part of our armamentarium against selected bacterial infections since they were discovered in 1952 and approved by the Food and Drug Administration (FDA) in 1964. In 1991, two newer, long-acting erythromycin analogues, azythromycin (brand name: Zithromax) and clarithromycin (brand name: Biaxin) were approved by the FDA. They were joined a few years later by a third long-acting form, dirithromycin (brand name: Dynabac).
3.Structural Correspondence of the Oriented Attachment Growth Mechanism of Crystals of the Pharmaceutical Dirithromycin.
Liang Z1, Wang Y1, Wang W1, Han X1, Chen JF1, Xue C1, Zhao H1. Langmuir. 2015 Dec 29;31(51):13802-12. doi: 10.1021/acs.langmuir.5b02901. Epub 2015 Dec 15.
The oriented attachment (OA) mechanism is promising for designing novel nanomaterials, yet an intensive understanding of the relationship between the crystal structure and attachment orientation is still lacking. In this work, we report layered hexagonal crystals of the pharmaceutical dirithromycin (DIR) containing multiple layers fabricated via a solvothermal method for a certain period of time at 40 °C. These elongated hexagonal crystals experience an OA that is preferentially on the face (001) of the initial crystals to assemble the final crystals into layered stacks. Through agreement with molecular modeling calculations, we predicted the final crystal growth morphology and confirmed the favored attachment surface based on the energy change ΔE following an OA event. These simulation results at the molecular level yielded good agreement with the crystal growth experiments. This study demonstrates the critical importance of combining experiments with a computational approach to understand the intrinsic molecular details of the OA growth mechanism of other compounds and to design nanomaterials with a desirable morphology and physical and chemical properties.
4.Epigallocatechin gallate as a modulator of Campylobacter resistance to macrolide antibiotics.
Kurinčič M1, Klančnik A, Smole Možina S. Int J Antimicrob Agents. 2012 Nov;40(5):467-71. doi: 10.1016/j.ijantimicag.2012.07.015. Epub 2012 Sep 20.
Comprehensive therapeutic use of macrolides in humans and animals is important in the selection of macrolide-resistant Campylobacter isolates. This study shows high co-resistance to erythromycin, azithromycin, clarithromycin, dirithromycin and tylosin, with contributions from the 23S rRNA gene and drug efflux systems. The CmeABC efflux pump plays an important role in reduced macrolide susceptibility, accompanied by contributions from the CmeDEF efflux pump and potentially a third efflux pump. To improve clinical performance of licensed antibiotics and chemotherapeutic agents, it is important to understand the factors in Campylobacter that affect susceptibility to macrolide antibiotics. Using mutants that lack the functional genes coding for the CmeB and CmeF efflux pump proteins and the CmeR transcriptional repressor, we show that these efflux pumps are potential targets for the development of therapeutic strategies that use a combination of a macrolide with an efflux pump inhibitor (EPI) to restore macrolide efficacy.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
