Dirithromycin | LY-237216 | CAS#62013-04-1

MedKoo Cat#: 330169 | Name: Dirithromycin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dirithromycin is a macrolide glycopeptide antibiotic. Dirithromycin is a more lipid-soluble prodrug derivative of 9S-erythromycyclamine prepared by condensation of the latter with 2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes spontaneous hydrolysis to form erythromycyclamine.

Chemical Structure

Dirithromycin

CAS#62013-04-1

Theoretical Analysis

MedKoo Cat#: 330169

Name: Dirithromycin

CAS#: 62013-04-1

Chemical Formula: C42H78N2O14

Exact Mass: 834.5453

Molecular Weight: 835.09

Elemental Analysis: C, 60.41; H, 9.42; N, 3.35; O, 26.82

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 550.00	2 Weeks

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Synonym

Dirithromycin; Antibiotic AS-E 136; Dynabac; Dirithromycine; Diritromicina; NSC-758672; NSC758672; NSC 758672; LY-237216; LY 237216; LY237216;

IUPAC/Chemical Name

(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-ethyl-2,10-dihydroxy-7-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-15-((2-methoxyethoxy)methyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

InChi Key

WLOHNSSYAXHWNR-DWIOZXRMSA-N

InChi Code

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

SMILES Code

CC[C@@H]1[C@](O)(C)[C@@]2([H])[C@@H](C)[C@](N[C@@H](COCCOC)O2)([H])[C@H](C)C[C@@](C)(O)[C@@](O[C@]3([H])O[C@H](C)C[C@H](N(C)C)[C@H]3O)([H])[C@@H](C)[C@H](O[C@]4([H])O[C@@H](C)[C@H](O)[C@@](OC)(C)C4)[C@@H](C)C(O1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Erythromycyclamine is a semisynthetic derivative of erythromycin in which the 9-ketogroup of the erythronolide ring has been converted to an amino group. Erythromycyclamine retains the antibacterial properties of erythromycin oral administration. The prodrug, dirithromycin, is provided as enteric coated tablets to protect it from acid catalyzed hydrolysis in the stomach. Orally administered dirithromycin is absorbed rapidly into the plasma, largely from the small intestine. Spontaneous hydrolysis to erythromycyclamine occurs in the plasma. Oral bioavailability is estimated to be about 10%, but food does not affect absorption of the prodrug. Dirithromycin is no longer available in the United States. Since the production of dirithromycin is discontinued in the U.S, National Institutes of Health recommend that people taking dirithromycin should consult their physicians to discuss switching to another treatment. However, dirithromycin is still available in many European countries.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dirithromycin (LY237216) is a potent and orally active semi-synthetic macrolide antibiotic.

In vitro activity:

In this study, dirithromycin significantly induced SCE frequency at all concentrations in both 24 and 48 h treated cells (Table 1). The differences between the dirithromycin doses and control with regard to RI were not statistically significant (p > 0.05), as shown in Table 1. Reference: J Toxicol. 2015;2015:535490. https://pubmed.ncbi.nlm.nih.gov/26576152/

In vivo activity:

In vivo, dirithromycin is active against penicillin-susceptible Staphylococcus aureus, beta-hemolytic streptococci, and Streptococcus pneumoniae. Dirithromycin is as effective as penicillin VK against streptococcal pharyngitis and tonsilitis, and as effective as erythromycin against acute superimposed chronic bronchitis and skin and soft-tissue infections. Reference: Bioorg Med Chem. 1996 Apr;4(4):521-2. https://pubmed.ncbi.nlm.nih.gov/8735838/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	11.97
	DMSO	19.8	23.68
	Ethanol	56.7	67.86
	Ethanol:PBS (pH 7.2) (1:6)	0.1	0.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 835.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kayraldız A, Dönbak L, Yavuz Kocaman A, Köker E, Gökçe Ş. Evaluation of Possible Genotoxic Activity of Dirithromycin in Cultured Human Lymphocytes. J Toxicol. 2015;2015:535490. doi: 10.1155/2015/535490. Epub 2015 Oct 21. PMID: 26576152; PMCID: PMC4631994. 2. Moutard I, Gressier B, Bonte F, Dine T, Brunet C, Luyckx M, Ballester L, Cazin M, Cazin JC. In vitro effects of spiramycin and dirithromycin on IL1 beta production by human LPS-stimulated mononuclear cells. Therapie. 1999 Sep-Oct;54(5):607-12. PMID: 10667098. 3. Shinkai I, Ohta Y. New drugs--reports of new drugs recently approved by the FDA. Dirithromycin. Bioorg Med Chem. 1996 Apr;4(4):521-2. doi: 10.1016/0968-0896(96)00052-1. PMID: 8735838.

In vitro protocol:

In vivo protocol:

1. Shinkai I, Ohta Y. New drugs--reports of new drugs recently approved by the FDA. Dirithromycin. Bioorg Med Chem. 1996 Apr;4(4):521-2. doi: 10.1016/0968-0896(96)00052-1. PMID: 8735838.

1: Zhang HL, Tan M, Qiu AM, Tao Z, Wang CH. Antibiotics for treatment of acute exacerbation of chronic obstructive pulmonary disease: a network meta-analysis. BMC Pulm Med. 2017 Dec 12;17(1):196. doi: 10.1186/s12890-017-0541-0. PubMed PMID: 29233130; PubMed Central PMCID: PMC5727987. 2: Ünal D, Demir S, Gelincik A, Olgaç M, Coşkun R, Çolakoğlu B, Büyüköztürk S. Diagnostic Value of Oral Challenge Testing in the Diagnosis of Macrolide Hypersensitivity. J Allergy Clin Immunol Pract. 2018 Mar - Apr;6(2):521-527. doi: 10.1016/j.jaip.2017.06.036. Epub 2017 Sep 8. PubMed PMID: 28923488. 3: Simmons KB, Haddad LB, Nanda K, Curtis KM. Drug interactions between non-rifamycin antibiotics and hormonal contraception: a systematic review. Am J Obstet Gynecol. 2018 Jan;218(1):88-97.e14. doi: 10.1016/j.ajog.2017.07.003. Epub 2017 Jul 8. Review. PubMed PMID: 28694152. 4: Liang Z, Wang Y, Wang W, Han X, Chen JF, Xue C, Zhao H. Structural Correspondence of the Oriented Attachment Growth Mechanism of Crystals of the Pharmaceutical Dirithromycin. Langmuir. 2015 Dec 29;31(51):13802-12. doi: 10.1021/acs.langmuir.5b02901. Epub 2015 Dec 15. PubMed PMID: 26632998. 5: Kayraldız A, Dönbak L, Yavuz Kocaman A, Köker E, Gökçe Ş. Evaluation of Possible Genotoxic Activity of Dirithromycin in Cultured Human Lymphocytes. J Toxicol. 2015;2015:535490. doi: 10.1155/2015/535490. Epub 2015 Oct 21. PubMed PMID: 26576152; PubMed Central PMCID: PMC4631994. 6: Cai HL, Wang F, Li HD, Peng WX, Zhu RH, Deng Y, Jiang P, Yan M, Hu SM, Lei SY, Chen C. Quantitative analysis of erythromycylamine in human plasma by liquid chromatography-tandem mass spectrometry and its application in a bioequivalence study of dirithromycin enteric-coated tablets with a special focus on the fragmentation pattern and carryover effect. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 1;947-948:156-63. doi: 10.1016/j.jchromb.2013.12.019. Epub 2013 Dec 27. PubMed PMID: 24424301. 7: Kurinčič M, Klančnik A, Smole Možina S. Epigallocatechin gallate as a modulator of Campylobacter resistance to macrolide antibiotics. Int J Antimicrob Agents. 2012 Nov;40(5):467-71. doi: 10.1016/j.ijantimicag.2012.07.015. Epub 2012 Sep 20. PubMed PMID: 22999765. 8: Berrada H, Moltó JC, Mañes J, Font G. Determination of aminoglycoside and macrolide antibiotics in meat by pressurized liquid extraction and LC-ESI-MS. J Sep Sci. 2010 Mar;33(4-5):522-9. doi: 10.1002/jssc.200900682. PubMed PMID: 20155746. 9: Alexander RE, Grogan DM. Long-acting erythromycins: assessing their role in treating outpatient odontogenic infections. Tex Dent J. 2009 Apr;126(4):326-33. Review. Erratum in: Tex Dent J. 2009 May;126(5):383. PubMed PMID: 19472551. 10: Araújo L, Demoly P. Macrolides allergy. Curr Pharm Des. 2008;14(27):2840-62. Review. PubMed PMID: 18991703. 11: Diana J, Manyanga V, Hoogmartens J, Adams E. Development and validation of an improved liquid chromatographic method for the analysis of dirithromycin. Talanta. 2006 Dec 15;70(5):1064-72. doi: 10.1016/j.talanta.2006.02.035. Epub 2006 Apr 3. PubMed PMID: 18970882. 12: Liu YQ, Chen QY, Chen BM, Liu SG, Deng FL, Zhou P. Quantitative determination of erythromycylamine in human plasma by liquid chromatography-mass spectrometry and its application in a bioequivalence study of dirithromycin. 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. PubMed PMID: 18296129. 13: Diana J, Govaerts C, Hoogmartens J, Van Schepdael A, Adams E. Characterization of impurities in dirithromycin by liquid chromatography/ion trap mass spectrometry. J Chromatogr A. 2006 Aug 25;1125(1):52-66. Epub 2006 Jun 19. PubMed PMID: 16782117. 14: Yamazhan T, Aydemir S, Tünger A, Serter D, Gökengin D. In vitro activities of various antimicrobials against Brucella melitensis strains in the Aegean region in Turkey. Med Princ Pract. 2005 Nov-Dec;14(6):413-6. PubMed PMID: 16220015. 15: Ranque S, Molet B, Christmann D, Candolfi E. In vitro activity of azithromycin and dirithromycin against axenic Entamoeba histolytica. Eur J Clin Microbiol Infect Dis. 2004 Dec;23(12):932-3. PubMed PMID: 15599659. 16: Jain R, Danziger LH. The macrolide antibiotics: a pharmacokinetic and pharmacodynamic overview. Curr Pharm Des. 2004;10(25):3045-53. Review. PubMed PMID: 15544496. 17: Arda B, Tunçel M, Yaimazhan T, Gökengin D, Gürel O. Efficacy of oral levofloxacin and dirithromycin alone and in combination with rifampicin in the treatment of experimental murine Brucella abortus infection. Int J Antimicrob Agents. 2004 Feb;23(2):204-7. PubMed PMID: 15013048. 18: Duran D, Aviyente V, Baysal C. A computational approach to the synthesis of dirithromycin. J Mol Model. 2004 Apr;10(2):94-101. Epub 2004 Jan 13. PubMed PMID: 14722740. 19: Barry A, Bryskier A, Traczewski M, Brown S. Preparation of stock solutions of macrolide and ketolide compounds for antimicrobial susceptibility tests. Clin Microbiol Infect. 2004 Jan;10(1):78-83. PubMed PMID: 14706092. 20: Parsad D, Pandhi R, Dogra S. A guide to selection and appropriate use of macrolides in skin infections. Am J Clin Dermatol. 2003;4(6):389-97. Review. PubMed PMID: 12762831.