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MedKoo Cat#: 540039 | Name: Azithromycin dihydrate
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Description:

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

Azithromycin dihydrate is a protein translation inhibitor used for it's antibacterial properties. It is also known to inhibit the epithelila-to-mesenchymal transition and suppresses LPS-stimulated production of pro-inflammatory cytokines in macrophages.

Chemical Structure

Azithromycin dihydrate
Azithromycin dihydrate
CAS#117772-70-0 (dihydrate)

Theoretical Analysis

MedKoo Cat#: 540039

Name: Azithromycin dihydrate

CAS#: 117772-70-0 (dihydrate)

Chemical Formula: C38H76N2O14

Exact Mass: 0.0000

Molecular Weight: 785.03

Elemental Analysis: C, 58.14; H, 9.76; N, 3.57; O, 28.53

Price and Availability

Size Price Availability Quantity
50mg USD 90.00 Ready to ship
100mg USD 150.00 Ready to ship
200mg USD 200.00 Ready to ship
500mg USD 350.00 Ready to ship
1g USD 550.00 2 Weeks
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Related CAS #
83905-01-5 (free) 90581-30-9 (HCl) 90581-31-0 (2HCl) 117772-70-0 (dihydrate) 121470-24-4 (monohydrate)
Synonym
Azitro; CP 62993; CP-62993; CP62993; Goxal; Odaz; Ribotrex; Toraseptol; Ultreon; XZ-450; XZ450; XZ 450; Zenstavion; Zithromax; Zmax
IUPAC/Chemical Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one dihydrate
InChi Key
SRMPHJKQVUDLQE-KUJJYQHYSA-N
InChi Code
InChI=1S/C38H72N2O12.2H2O/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28;;/h20-33,35,41-43,45-46H,15-19H2,1-14H3;2*1H2/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-;;/m1../s1
SMILES Code
CC[C@@H]1[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@@H](C)C(O1)=O.O.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
>2 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Azithromycin hydrate is a macrolide antibiotic useful for the treatment of a number of bacterial infections.
In vitro activity:
To determine whether Deg-AZM (deglycosylated azithromycin) affects TGF-β1-induced fibroblast proliferation and migration, NIH-3T3 cells were cultured with or without 5 ng/mL TGF-β1 and different doses of Deg-AZM for 24 h. The proliferation of NIH-3T3 cells was measured by MTT assays. This study found that Deg-AZM showed no obvious toxicity to normal cells, with an IC50 higher than 1 mM (Figure 4A,B). This study also used a wound healing assay to verify the effect of Deg-AZM on TGF-β1-induced fibroblast migration, and the results showed that Deg-AZM could inhibit fibroblast migration (Figure 4C). Reference: Molecules. 2021 May; 26(9): 2820. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8126120/
In vivo activity:
All of these changes were dramatically tempered in the AZM (azithromycin) group (Fig. 3A). Masson staining analysis revealed increased interstitial fibrosis and nearly complete glomerulosclerosis in the ALD-DNA group, which were significantly mitigated after AZM treatment (Fig. 3B). In addition, the capillary loops of the glomerulus were well defined and thin in the AZM group and normal control group, while the mesangial cells and matrix were hyperproliferative in the ALD-DNA group, as represented by periodic acid–Schiff (PAS) staining (Fig. 3C). Additionally, the ALD-DNA group had much more IgG deposition in the glomerulus than the AZM group (Fig. 3D). Reference: Cell Death Discov. 2021; 7: 82. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8050155/
Solvent mg/mL mM
Solubility
DMSO 100.0 127.38
Ethanol 100.0 127.38
Water 10.0 12.74
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 785.03 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. Ruan H, Gao S, Li S, Luan J, Jiang Q, Li X, Yin H, Zhou H, Yang C. Deglycosylated Azithromycin Attenuates Bleomycin-Induced Pulmonary Fibrosis via the TGF-β1 Signaling Pathway. Molecules. 2021 May 10;26(9):2820. doi: 10.3390/molecules26092820. PMID: 34068694; PMCID: PMC8126120. 2. Du X, Zuo X, Meng F, Han C, Ouyang W, Han Y, Gu Y, Zhao X, Xu F, Qin FX. Direct inhibitory effect on viral entry of influenza A and SARS-CoV-2 viruses by azithromycin. Cell Prolif. 2021 Jan;54(1):e12953. doi: 10.1111/cpr.12953. Epub 2020 Nov 19. PMID: 33211371; PMCID: PMC7744835. 3. Wang J, Chen Q, Zhang Z, Wang S, Wang Y, Xiang M, Liang J, Xu J. Azithromycin alleviates systemic lupus erythematosus via the promotion of M2 polarisation in lupus mice. Cell Death Discov. 2021 Apr 16;7(1):82. doi: 10.1038/s41420-021-00466-4. PMID: 33863874; PMCID: PMC8050155. 4. Thomsen K, Christophersen L, Lerche CJ, Holmgaard DB, Calum H, Høiby N, Moser C. Azithromycin potentiates avian IgY effect against Pseudomonas aeruginosa in a murine pulmonary infection model. Int J Antimicrob Agents. 2021 Jan;57(1):106213. doi: 10.1016/j.ijantimicag.2020.106213. Epub 2020 Oct 23. PMID: 33256950.
In vitro protocol:
1. Ruan H, Gao S, Li S, Luan J, Jiang Q, Li X, Yin H, Zhou H, Yang C. Deglycosylated Azithromycin Attenuates Bleomycin-Induced Pulmonary Fibrosis via the TGF-β1 Signaling Pathway. Molecules. 2021 May 10;26(9):2820. doi: 10.3390/molecules26092820. PMID: 34068694; PMCID: PMC8126120. 2. Du X, Zuo X, Meng F, Han C, Ouyang W, Han Y, Gu Y, Zhao X, Xu F, Qin FX. Direct inhibitory effect on viral entry of influenza A and SARS-CoV-2 viruses by azithromycin. Cell Prolif. 2021 Jan;54(1):e12953. doi: 10.1111/cpr.12953. Epub 2020 Nov 19. PMID: 33211371; PMCID: PMC7744835.
In vivo protocol:
1. Wang J, Chen Q, Zhang Z, Wang S, Wang Y, Xiang M, Liang J, Xu J. Azithromycin alleviates systemic lupus erythematosus via the promotion of M2 polarisation in lupus mice. Cell Death Discov. 2021 Apr 16;7(1):82. doi: 10.1038/s41420-021-00466-4. PMID: 33863874; PMCID: PMC8050155. 2. Thomsen K, Christophersen L, Lerche CJ, Holmgaard DB, Calum H, Høiby N, Moser C. Azithromycin potentiates avian IgY effect against Pseudomonas aeruginosa in a murine pulmonary infection model. Int J Antimicrob Agents. 2021 Jan;57(1):106213. doi: 10.1016/j.ijantimicag.2020.106213. Epub 2020 Oct 23. PMID: 33256950.
1: Bakheit AH, Al-Hadiya BM, Abd-Elgalil AA. Azithromycin. Profiles Drug Subst Excip Relat Methodol. 2014;39:1-40. doi: 10.1016/B978-0-12-800173-8.00001-5. Review. PubMed PMID: 24794904. 2: Smith C, Egunsola O, Choonara I, Kotecha S, Jacqz-Aigrain E, Sammons H. Use and safety of azithromycin in neonates: a systematic review. BMJ Open. 2015 Dec 9;5(12):e008194. doi: 10.1136/bmjopen-2015-008194. Review. PubMed PMID: 26656010; PubMed Central PMCID: PMC4679913. 3: Bin Abdulhak AA, Khan AR, Garbati MA, Qazi AH, Erwin P, Kisra S, Aly A, Farid T, El-Chami M, Wimmer AP. Azithromycin and Risk of Cardiovascular Death: A Meta-Analytic Review of Observational Studies. Am J Ther. 2015 Sep-Oct;22(5):e122-9. doi: 10.1097/MJT.0000000000000138. Review. PubMed PMID: 25748818. 4: Taylor SP, Sellers E, Taylor BT. Azithromycin for the Prevention of COPD Exacerbations: The Good, Bad, and Ugly. Am J Med. 2015 Dec;128(12):1362.e1-6. doi: 10.1016/j.amjmed.2015.07.032. Epub 2015 Aug 17. Review. PubMed PMID: 26291905. 5: Aucamp M, Odendaal R, Liebenberg W, Hamman J. Amorphous azithromycin with improved aqueous solubility and intestinal membrane permeability. Drug Dev Ind Pharm. 2015;41(7):1100-8. doi: 10.3109/03639045.2014.931967. Epub 2014 Jul 1. PubMed PMID: 24980913. 6: Wong C, Jayaram L, Karalus N, Eaton T, Tong C, Hockey H, Milne D, Fergusson W, Tuffery C, Sexton P, Storey L, Ashton T. Azithromycin for prevention of exacerbations in non-cystic fibrosis bronchiectasis (EMBRACE): a randomised, double-blind, placebo-controlled trial. Lancet. 2012 Aug 18;380(9842):660-7. doi: 10.1016/S0140-6736(12)60953-2. PubMed PMID: 22901887. 7: Goldstein LH, Gabin A, Fawaz A, Freedberg NA, Schwartz N, Elias M, Saliba W. Azithromycin is not associated with QT prolongation in hospitalized patients with community-acquired pneumonia. Pharmacoepidemiol Drug Saf. 2015 Oct;24(10):1042-8. doi: 10.1002/pds.3842. Epub 2015 Aug 2. PubMed PMID: 26238864. 8: Solleti VS, Alhariri M, Halwani M, Omri A. Antimicrobial properties of liposomal azithromycin for Pseudomonas infections in cystic fibrosis patients. J Antimicrob Chemother. 2015 Mar;70(3):784-96. doi: 10.1093/jac/dku452. Epub 2014 Nov 21. PubMed PMID: 25416744. 9: Merchan LM, Hassan HE, Terrin ML, Waites KB, Kaufman DA, Ambalavanan N, Donohue P, Dulkerian SJ, Schelonka R, Magder LS, Shukla S, Eddington ND, Viscardi RM. Pharmacokinetics, microbial response, and pulmonary outcomes of multidose intravenous azithromycin in preterm infants at risk for Ureaplasma respiratory colonization. Antimicrob Agents Chemother. 2015 Jan;59(1):570-8. doi: 10.1128/AAC.03951-14. Epub 2014 Nov 10. PubMed PMID: 25385115; PubMed Central PMCID: PMC4291400. 10: Arnež M, Ružić-Sabljić E. Azithromycin Is Equally Effective as Amoxicillin in Children with Solitary Erythema Migrans. Pediatr Infect Dis J. 2015 Oct;34(10):1045-8. doi: 10.1097/INF.0000000000000804. PubMed PMID: 26186104. 11: Sundaramurthi P, Suryanarayanan R. Azithromycin hydrates-implications of processing-induced phase transformations. J Pharm Sci. 2014 Oct;103(10):3095-106. doi: 10.1002/jps.24084. Epub 2014 Aug 19. PubMed PMID: 25139082. 12: Li H, Liu DH, Chen LL, Zhao Q, Yu YZ, Ding JJ, Miao LY, Xiao YL, Cai HR, Zhang DP, Guo YB, Xie CM. Meta-analysis of the adverse effects of long-term azithromycin use in patients with chronic lung diseases. Antimicrob Agents Chemother. 2014;58(1):511-7. doi: 10.1128/AAC.02067-13. Epub 2013 Nov 4. PubMed PMID: 24189261; PubMed Central PMCID: PMC3910718. 13: Matzneller P, Krasniqi S, Kinzig M, Sörgel F, Hüttner S, Lackner E, Müller M, Zeitlinger M. Blood, tissue, and intracellular concentrations of azithromycin during and after end of therapy. Antimicrob Agents Chemother. 2013 Apr;57(4):1736-42. doi: 10.1128/AAC.02011-12. Epub 2013 Jan 28. PubMed PMID: 23357769; PubMed Central PMCID: PMC3623349. 14: Venkatesh MP, Kumar TM, Avinash BS, Kumar GS. Development, in vitro and in vivo evaluation of novel injectable smart gels of azithromycin for chronic periodontitis. Curr Drug Deliv. 2013 Apr;10(2):188-97. PubMed PMID: 23003342. 15: Hart JD, Edwards T, Burr SE, Harding-Esch EM, Takaoka K, Holland MJ, Sillah A, Mabey DC, Bailey RL. Effect of azithromycin mass drug administration for trachoma on spleen rates in Gambian children. Trop Med Int Health. 2014 Feb;19(2):207-11. doi: 10.1111/tmi.12234. Epub 2014 Jan 17. PubMed PMID: 24433194. 16: Renna M, Schaffner C, Brown K, Shang S, Tamayo MH, Hegyi K, Grimsey NJ, Cusens D, Coulter S, Cooper J, Bowden AR, Newton SM, Kampmann B, Helm J, Jones A, Haworth CS, Basaraba RJ, DeGroote MA, Ordway DJ, Rubinsztein DC, Floto RA. Azithromycin blocks autophagy and may predispose cystic fibrosis patients to mycobacterial infection. J Clin Invest. 2011 Sep;121(9):3554-63. doi: 10.1172/JCI46095. Epub 2011 Aug 1. PubMed PMID: 21804191; PubMed Central PMCID: PMC3163956. 17: Khoshnood A, Hakimi P, Salman-Roghani H, Reza Mirjalili M. Replacement of clarithromycin with azithromycin in triple therapy regimens for the eradication of Helicobacter pylori: A randomized clinical trial. J Med Life. 2014 Jun 15;7(2):254-9. Epub 2014 Jun 25. PubMed PMID: 25408735; PubMed Central PMCID: PMC4197489. 18: Hao K, Qi Q, Hao H, Wang G, Chen Y, Liang Y, Xie L. The pharmacokinetic-pharmacodynamic model of azithromycin for lipopolysaccharide-induced depressive-like behavior in mice. PLoS One. 2013;8(1):e54981. doi: 10.1371/journal.pone.0054981. Epub 2013 Jan 24. PubMed PMID: 23358536; PubMed Central PMCID: PMC3554664. 19: Yan M, Ma X, Dong R, Li X, Zhao C, Guo Z, Shen Y, Liu F, Ma R, Ma S. Synthesis and antibacterial activity of 4″-O-(trans-β-arylacrylamido)carbamoyl azithromycin analogs. Eur J Med Chem. 2015 Oct 20;103:506-15. doi: 10.1016/j.ejmech.2015.09.020. Epub 2015 Sep 15. PubMed PMID: 26402728. 20: Leclere M, Magdesian KG, Cole CA, Szabo NJ, Ruby RE, Rhodes DM, Edman J, Vale A, Wilson WD, Tell LA. Pharmacokinetics and preliminary safety evaluation of azithromycin in adult horses. J Vet Pharmacol Ther. 2012 Dec;35(6):541-9. doi: 10.1111/j.1365-2885.2011.01351.x. Epub 2011 Dec 5. PubMed PMID: 22136612.