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MedKoo Cat#: 598754 | Name: Lexithromycin
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Description:

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

Lexithromycin is a semi-synthetic antibiotic derived from erythromycin. Lexithromycin has improved absorption in vivo over erythromycin due to increased hydrophopicity and pH stability. As with other macrolides, lexithromycin prevents protein synthesis by binding the ribosome at the polypeptide exit tunnel. Formulations containing lexithromycin were tested in clinical trials as treatment for HIV but were discontinued.

Chemical Structure

Lexithromycin
CAS#53066-26-5

Theoretical Analysis

MedKoo Cat#: 598754

Name: Lexithromycin

CAS#: 53066-26-5

Chemical Formula: C38H70N2O13

Exact Mass: 762.4878

Molecular Weight: 762.98

Elemental Analysis: C, 59.82; H, 9.25; N, 3.67; O, 27.26

Price and Availability

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5mg USD 300.00 2 Weeks
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Related CAS #
No Data
Synonym
Lexithromycin; Wy-48314; Wy 48314; Wy48314;
IUPAC/Chemical Name
(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R,E)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-10-(methoxyimino)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one
InChi Key
HPZGUSZNXKOMCQ-SQYJNGITSA-N
InChi Code
InChI=1S/C38H70N2O13/c1-15-26-38(10,46)31(42)21(4)28(39-48-14)19(2)17-36(8,45)33(53-35-29(41)25(40(11)12)16-20(3)49-35)22(5)30(23(6)34(44)51-26)52-27-18-37(9,47-13)32(43)24(7)50-27/h19-27,29-33,35,41-43,45-46H,15-18H2,1-14H3/b39-28+/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
SMILES Code
CC[C@H]1OC([C@@H]([C@H]([C@@H]([C@H]([C@](O)(C[C@H](/C([C@@H]([C@H]([C@@]1(O)C)O)C)=N\OC)C)C)O[C@@H]2O[C@@H](C[C@H](N(C)C)[C@H]2O)C)C)O[C@H]3C[C@@](OC)([C@H]([C@@H](O3)C)O)C)C)=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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lexithromycin is an erythromycin A derivative, with antibacterial activity.
In vitro activity:
Infection experiments demonstrated that azithromycin, clarithromycin, and lexithromycin reduce the intracellular accumulation of viral RNA and virus spread as well as prevent virus-induced cell death, by inhibiting the SARS-CoV-2 entry into cells. Reference: J Chem Inf Model. 2021 Apr 26;61(4):2016-2025. https://pubmed.ncbi.nlm.nih.gov/33734704/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 50.0 65.53
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 762.98 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.

Recalculate based on batch purity %
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. Galvez J, Zanni R, Galvez-Llompart M, Benlloch JM. Macrolides May Prevent Severe Acute Respiratory Syndrome Coronavirus 2 Entry into Cells: A Quantitative Structure Activity Relationship Study and Experimental Validation. J Chem Inf Model. 2021 Apr 26;61(4):2016-2025. doi: 10.1021/acs.jcim.0c01394. Epub 2021 Mar 18. PMID: 33734704; PMCID: PMC7986980.
In vitro protocol:
1. Galvez J, Zanni R, Galvez-Llompart M, Benlloch JM. Macrolides May Prevent Severe Acute Respiratory Syndrome Coronavirus 2 Entry into Cells: A Quantitative Structure Activity Relationship Study and Experimental Validation. J Chem Inf Model. 2021 Apr 26;61(4):2016-2025. doi: 10.1021/acs.jcim.0c01394. Epub 2021 Mar 18. PMID: 33734704; PMCID: PMC7986980.
In vivo protocol:
TBD
1: Shafuddin E, Mills GD, Holmes MD, Poole PJ, Mullins PR, Black PN. A double-blind, randomised, placebo-controlled study of roxithromycin and doxycycline combination, roxithromycin alone, or matching placebo for 12 weeks in adults with frequent exacerbations of chronic obstructive pulmonary disease. J Negat Results Biomed. 2015 Sep 7;14:15. doi: 10.1186/s12952-015-0034-8. PubMed PMID: 26346300; PubMed Central PMCID: PMC4562194. 2: Choi Y, Koh SJ, Lee HS, Kim JW, Gwan Kim B, Lee KL, Kim JS. Roxithromycin inhibits nuclear factor kappaB signaling and endoplasmic reticulum stress in intestinal epithelial cells and ameliorates experimental colitis in mice. Exp Biol Med (Maywood). 2015 Dec;240(12):1664-71. doi: 10.1177/1535370215591829. Epub 2015 Jun 18. PubMed PMID: 26088864; PubMed Central PMCID: PMC4935332. 3: Dai YR, Wu HY, Wu LQ, Xu H, Yin J, Yan SS, Zeng WX. Roxithromycin reduces the viability of cultured airway smooth muscle cells from a rat model of asthma. Eur Rev Med Pharmacol Sci. 2014;18(23):3564-72. PubMed PMID: 25535124. 4: Choe HS, Lee SJ, Han CH, Shim BS, Cho YH. Clinical efficacy of roxithromycin in men with chronic prostatitis/chronic pelvic pain syndrome in comparison with ciprofloxacin and aceclofenac: a prospective, randomized, multicenter pilot trial. J Infect Chemother. 2014 Jan;20(1):20-5. doi: 10.1016/j.jiac.2013.07.010. Epub 2013 Dec 11. PubMed PMID: 24462419. 5: Britzi M, Berkovitch M, Soback S, Leibovitz A, Segal R, Smagarinsky M, Lubart E. Roxithromycin Pharmacokinetics in Hospitalized Geriatric Patients: Oral Administration of Whole Versus Crushed Tablets. Ther Drug Monit. 2015 Aug;37(4):512-5. doi: 10.1097/FTD.0000000000000203. PubMed PMID: 26186658. 6: Agbokponto JE, Luo Z, Liu R, Liu Z, Liang M, Ding L. Study of pharmacokinetic interaction of paroxetine and roxithromycin on bencycloquidium bromide in healthy subjects. Eur J Pharm Sci. 2015 Mar 10;69:37-43. doi: 10.1016/j.ejps.2014.12.019. Epub 2015 Jan 2. PubMed PMID: 25559065. 7: Svanström H, Pasternak B, Hviid A. Use of clarithromycin and roxithromycin and risk of cardiac death: cohort study. BMJ. 2014 Aug 19;349:g4930. doi: 10.1136/bmj.g4930. PubMed PMID: 25139799; PubMed Central PMCID: PMC4138354. 8: Wosicka-Frąckowiak H, Cal K, Stefanowska J, Główka E, Nowacka M, Struck-Lewicka W, Govedarica B, Pasikowska M, Dębowska R, Jesionowski T, Srčič S, Markuszewski MJ. Roxithromycin-loaded lipid nanoparticles for follicular targeting. Int J Pharm. 2015 Nov 30;495(2):807-15. doi: 10.1016/j.ijpharm.2015.09.068. Epub 2015 Oct 9. PubMed PMID: 26456292. 9: Suke SG, Chahande AD, Kasliwal RH, Asnani AJ. Roxithromycin potency quantification in pharmaceutical preparation by applying a validated bioassay method and comparison with HPLC analysis. Ann Pharm Fr. 2015 Sep;73(5):340-50. doi: 10.1016/j.pharma.2015.04.007. Epub 2015 May 26. PubMed PMID: 26021576. 10: Morimura S, Sugaya M, Kai H, Miyagaki T, Asano Y, Tada Y, Kadono T, Murakami T, Sato S. Depsipeptide and roxithromycin induce apoptosis of lymphoma cells by blocking extracellular signal-regulated kinase activation. J Dermatol. 2014 Jan;41(1):57-62. doi: 10.1111/1346-8138.12351. PubMed PMID: 24438145. 11: Wu LQ, Wang RL, Dai YR, Li FQ, Wu HY, Yan SS, Wang LR, Jin LD, Xia XD. Roxithromycin suppresses airway remodeling and modulates the expression of caveolin-1 and phospho-p42/p44MAPK in asthmatic rats. Int Immunopharmacol. 2015 Feb;24(2):247-255. doi: 10.1016/j.intimp.2014.11.015. Epub 2014 Nov 25. PubMed PMID: 25479721. 12: Lee JH, Park YJ, Oh JH, Lee YJ. Decrease in gastrointestinal absorption of roxithromycin in bile duct cannulated rats due to depletion of bile salts. Biopharm Drug Dispos. 2013 Sep;34(6):360-4. doi: 10.1002/bdd.1845. Epub 2013 May 23. PubMed PMID: 23703541. 13: Takakusagi K, Takakusagi Y, Suzuki T, Toizaki A, Suzuki A, Kawakatsu Y, Watanabe M, Saito Y, Fukuda R, Nakazaki A, Kobayashi S, Sakaguchi K, Sugawara F. Multimodal biopanning of T7 phage-displayed peptides reveals angiomotin as a potential receptor of the anti-angiogenic macrolide Roxithromycin. Eur J Med Chem. 2015 Jan 27;90:809-21. doi: 10.1016/j.ejmech.2014.12.015. Epub 2014 Dec 12. PubMed PMID: 25528335. 14: Skovbølling SL, Lindelof M. [Myopathy and rhabdomyolysis after treatment with simvastatin, amlodipine, and roxithromycin]. Ugeskr Laeger. 2014 Oct 6;176(41). pii: V04140212. Danish. PubMed PMID: 25331664. 15: Rocas P, Hoyos-Nogués M, Rocas J, Manero JM, Gil J, Albericio F, Mas-Moruno C. Installing multifunctionality on titanium with RGD-decorated polyurethane-polyurea roxithromycin loaded nanoparticles: toward new osseointegrative therapies. Adv Healthc Mater. 2015 Sep 16;4(13):1956-60. doi: 10.1002/adhm.201500245. Epub 2015 Aug 14. PubMed PMID: 26274361. 16: Liu J, Lu G, Wang Y, Yan Z, Yang X, Ding J, Jiang Z. Bioconcentration, metabolism, and biomarker responses in freshwater fish Carassius auratus exposed to roxithromycin. Chemosphere. 2014 Mar;99:102-8. doi: 10.1016/j.chemosphere.2013.10.036. Epub 2013 Nov 8. PubMed PMID: 24210552. 17: Wahba ME. Liquid chromatographic determination of roxithromycin: application to stability studies. J Chromatogr Sci. 2013 Jan;51(1):44-52. doi: 10.1093/chromsci/bms104. Epub 2012 Jun 19. PubMed PMID: 22718747. 18: Das S, Mondal S, Dey JK. Roxithromycin-induced toxic epidermal necrolysis. Ther Drug Monit. 2012 Aug;34(4):359-62. doi: 10.1097/FTD.0b013e318260b087. PubMed PMID: 22777150. 19: Aucamp M, Stieger N, Barnard N, Liebenberg W. Solution-mediated phase transformation of different roxithromycin solid-state forms: Implications on dissolution and solubility. Int J Pharm. 2013 Jun 5;449(1-2):18-27. doi: 10.1016/j.ijpharm.2013.03.048. Epub 2013 Apr 8. PubMed PMID: 23578825. 20: Ding J, Zhang F, Zhang X, Wang L, Wang C, Zhao Q, Xu Y, Ding L, Ren N. Determination of roxithromycin from human plasma samples based on magnetic surface molecularly imprinted polymers followed by liquid chromatography-tandem mass spectromer. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 15;1021:221-228. doi: 10.1016/j.jchromb.2015.08.001. Epub 2015 Aug 4. PubMed PMID: 26300321.

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