Azithromycin
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MedKoo CAT#: 341047

CAS#: 83905-01-5

Description: Azithromycin is a macrolide antibiotic.

Chemical Structure

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Azithromycin
CAS# 83905-01-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 341047
Name: Azithromycin
CAS#: 83905-01-5
Chemical Formula: C38H72N2O12
Exact Mass: 748.51
Molecular Weight: 748.996
Elemental Analysis: C, 60.94; H, 9.69; N, 3.74; O, 25.63

Price and Availability

Size Price Availability Quantity
1g USD 350 2 Weeks
2g USD 550 2 Weeks
5g USD 1250 2 Weeks
10g USD 1950 2 Weeks
25g USD 2950 2 Weeks
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Synonym: Azithromycin; CP 62,993; Z-Pak

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

InChi Key: MQTOSJVFKKJCRP-BICOPXKESA-N

InChi Code: InChI=1S/C38H72N2O12/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/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@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(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: >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 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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 16.0 21.36
Ethanol 63.6 84.95
Ethanol:PBS (pH 7.2) (1:1) 0.5 0.67

Preparing Stock Solutions

The following data is based on the product molecular weight 749.00 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.

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1: Damião Gouveia AC, Unemo M, Jensen JS. In vitro activity of zoliflodacin (ETX0914) against macrolide-resistant, fluoroquinolone-resistant and antimicrobial-susceptible Mycoplasma genitalium strains. J Antimicrob Chemother. 2018 Feb 12. doi: 10.1093/jac/dky022. [Epub ahead of print] PubMed PMID: 29444242.

2: Cai X, Zhou H, Xie Y, Yu D, Wang Z, Ren H. Anti-N-methyl-D-aspartate receptor encephalitis associated with acute Toxoplasma gondii infection: A case report. Medicine (Baltimore). 2018 Feb;97(7):e9924. doi: 10.1097/MD.0000000000009924. PubMed PMID: 29443773.

3: Stieger N, Joubert A, Liebenberg W. Solution-mediated crystallization of amorphous azithromycin. Pharmazie. 2017 Aug 1;72(8):447-448. doi: 10.1691/ph.2017.7035. PubMed PMID: 29441902.

4: Feng X, Liu J. A combination of irsogladine maleate and azithromycin exhibits addictive protective effects in LPS-induced human gingival epithelial cells. Pharmazie. 2017 Feb 1;72(2):91-94. doi: 10.1691/ph.2017.6697. PubMed PMID: 29441859.

5: O'Brien S, Wilson S, Gill FJ, Cotterell E, Borland ML, Oakley E, Dalziel SR; Paediatric Research in Emergency Departments International Collaborative (PREDICT) network, Australasia. The management of children with bronchiolitis in the Australasian hospital setting: development of a clinical practice guideline. BMC Med Res Methodol. 2018 Feb 12;18(1):22. doi: 10.1186/s12874-018-0478-x. PubMed PMID: 29433429.

6: Khatun H, Islam SB, Naila NN, Islam SA, Nahar B, Alam MNH, Ahmed T. Clinical profile, antibiotic susceptibility pattern of bacterial isolates and factors associated with complications in culture-proven typhoid patients admitted to an urban hospital in Bangladesh. Trop Med Int Health. 2018 Feb 12. doi: 10.1111/tmi.13037. [Epub ahead of print] PubMed PMID: 29432657.

7: Traoré L, Dembele B, Keita M, Reid S, Dembéle M, Mariko B, Coulibaly F, Goldman W, Traoré D, Coulibaly D, Guindo B, Amon J, Knieriemen M, Zhang Y. Prevalence of trachoma in the Kayes region of Mali eight years after stopping mass drug administration. PLoS Negl Trop Dis. 2018 Feb 12;12(2):e0006289. doi: 10.1371/journal.pntd.0006289. [Epub ahead of print] PubMed PMID: 29432434.

8: Chandra NL, Broad C, Folkard K, Town K, Harding-Esch EM, Woodhall SC, Saunders JM, Sadiq ST, Dunbar JK. Detection of Chlamydia trachomatis in rectal specimens in women and its association with anal intercourse: a systematic review and meta-analysis. Sex Transm Infect. 2018 Feb 3. pii: sextrans-2017-053161. doi: 10.1136/sextrans-2017-053161. [Epub ahead of print] Review. PubMed PMID: 29431148.

9: Chen QF, Zhang YW. [Clinical effect of Saccharomyces boulardii powder combined with azithromycin sequential therapy in treatment of children with diarrhea secondary to Mycoplasma pneumoniae pneumonia]. Zhongguo Dang Dai Er Ke Za Zhi. 2018 Feb;20(2):116-120. Chinese. PubMed PMID: 29429459.

10: Mitjà O, Godornes C, Houinei W, Kapa A, Paru R, Abel H, González-Beiras C, Bieb SV, Wangi J, Barry AE, Sanz S, Bassat Q, Lukehart SA. Re-emergence of yaws after single mass azithromycin treatment followed by targeted treatment: a longitudinal study. Lancet. 2018 Feb 7. pii: S0140-6736(18)30204-6. doi: 10.1016/S0140-6736(18)30204-6. [Epub ahead of print] PubMed PMID: 29428183.

11: Pomares X, Montón C, Bullich M, Cuevas O, Oliva JC, Gallego M, Monsó E. Clinical and safety outcomes of long-term azithromycin therapy in severe COPD beyond the first year of treatment. Chest. 2018 Feb 7. pii: S0012-3692(18)30245-9. doi: 10.1016/j.chest.2018.01.044. [Epub ahead of print] PubMed PMID: 29427576.

12: Kafaei R, Papari F, Seyedabadi M, Sahebi S, Tahmasebi R, Ahmadi M, Sorial GA, Asgari G, Ramavandi B. Occurrence, distribution, and potential sources of antibiotics pollution in the water-sediment of the northern coastline of the Persian Gulf, Iran. Sci Total Environ. 2018 Jan 31;627:703-712. doi: 10.1016/j.scitotenv.2018.01.305. [Epub ahead of print] PubMed PMID: 29426195.

13: Hara H, Hirano D. Azithromycin suppressed relapses of idiopathic nephrotic syndrome in a child. Clin Kidney J. 2018 Feb;11(1):54-55. doi: 10.1093/ckj/sfx099. Epub 2017 Sep 1. PubMed PMID: 29423202; PubMed Central PMCID: PMC5798145.

14: Levine A, Kori M, Kierkus J, Sigall Boneh R, Sladek M, Escher JC, Wine E, Yerushalmi B, Amil Dias J, Shaoul R, Veereman Wauters G, Boaz M, Abitbol G, Bousvaros A, Turner D. Azithromycin and metronidazole versus metronidazole-based therapy for the induction of remission in mild to moderate paediatric Crohn's disease : a randomised controlled trial. Gut. 2018 Feb 2. pii: gutjnl-2017-315199. doi: 10.1136/gutjnl-2017-315199. [Epub ahead of print] PubMed PMID: 29420227.

15: Terzic S, Udikovic-Kolic N, Jurina T, Krizman-Matasic I, Senta I, Mihaljevic I, Loncar J, Smital T, Ahel M. Biotransformation of macrolide antibiotics using enriched activated sludge culture: Kinetics, transformation routes and ecotoxicological evaluation. J Hazard Mater. 2018 Jan 31;349:143-152. doi: 10.1016/j.jhazmat.2018.01.055. [Epub ahead of print] PubMed PMID: 29414746.

16: Butcher RMR, Sokana O, Jack K, Kalae E, Sui L, Russell C, Houghton J, Palmer C, Holland MJ, Le Mesurier RT, Solomon AW, Mabey DCW, Roberts CH. Active Trachoma Cases in the Solomon Islands Have Varied Polymicrobial Community Structures but Do Not Associate with Individual Non-Chlamydial Pathogens of the Eye. Front Med (Lausanne). 2018 Jan 23;4:251. doi: 10.3389/fmed.2017.00251. eCollection 2017. PubMed PMID: 29410954; PubMed Central PMCID: PMC5787070.

17: Brereton CJ, Lennon D, Browning S, Dunn E, Ferguson JK, Davis JS. Is gentamicin safe and effective for severe community acquired pneumonia? an 8 year retrospective cohort study. Int J Antimicrob Agents. 2018 Feb 2. pii: S0924-8579(18)30021-9. doi: 10.1016/j.ijantimicag.2018.01.018. [Epub ahead of print] PubMed PMID: 29410326.

18: Qin JZ, Diniz CP, Coleman JS. Pharmacy-level Barriers to Implementing Expedited Partner Therapy in Baltimore, Maryland. Am J Obstet Gynecol. 2018 Jan 31. pii: S0002-9378(18)30085-1. doi: 10.1016/j.ajog.2018.01.036. [Epub ahead of print] PubMed PMID: 29410060.

19: Yin YP, Han Y, Dai XQ, Zheng HP, Chen SC, Zhu BY, Yong G, Zhong N, Hu LH, Cao WL, Zheng ZJ, Wang F, Zhi Q, Zhu XY, Chen XS. Susceptibility of Neisseria gonorrhoeae to azithromycin and ceftriaxone in China: A retrospective study of national surveillance data from 2013 to 2016. PLoS Med. 2018 Feb 6;15(2):e1002499. doi: 10.1371/journal.pmed.1002499. eCollection 2018 Feb. PubMed PMID: 29408881.

20: Wang Q, Mi G, Hickey D, Li Y, Tu J, Webster TJ, Shen Y. Azithromycin-loaded respirable microparticles for targeted pulmonary delivery for the treatment of pneumonia. Biomaterials. 2018 Feb 1;160:107-123. doi: 10.1016/j.biomaterials.2018.01.022. [Epub ahead of print] PubMed PMID: 29407340.