(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Base Information

• Chemical Name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
• CAS No.: 83905-01-5
• Molecular Formula: C₃₈H₇₂N₂O₁₂
• Molecular Weight: 748.996
• Hs Code.: 29419090
• European Community (EC) Number: 617-500-5
• Wikipedia: Azithromycin
• Mol file: 83905-01-5.mol

Synonyms:CP 63956;CP-63,956

Chemical Property of (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.51E-31mmHg at 25°C
• Melting Point: 113-115 °C
• Refractive Index: 1.536
• Boiling Point: 822.105 °C at 760 mmHg
• PKA: pKa 8.74 (H2O t=25 I=0.167) (Uncertain);9.45(H2O t=25 I=0.167) (Uncertain)
• Flash Point: 450.993 °C
• PSA: 180.08000
• Density: 1.184 g/cm³
• LogP: 1.83860
• Storage Temp.: Store at -20°C
• Solubility.: Practically insoluble in water, freely soluble in anhydrous ethanol and in methylene chloride.
• XLogP3: 4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 748.50852574
• Heavy Atom Count: 52
• Complexity: 1150

Purity/Quality:

83.1%,83.3%, ^*data from raw suppliers

Azithromycin-13CD3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
• Isomeric SMILES: 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)OC2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)OC3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
• Recent EU Clinical Trials: An open label randomized controlled trial comparing the effect of ceftriaxone plus azithromycin versus ceftriaxone for the treatment of Neisseria gonorrhoeae on the resistome
• Uses: Azithromycin is used to treat certain bacterial infections, such as bronchitis; pneumonia; sexually transmitted diseases (STD); and infections of the ears, lungs, sinuses, skin, throat, and reproductive organs.As for Gram-negative bacteria such as Haemophilus influenzae, Salmonella, E. coli, Shigella bacteria, it have strong antibacterial activity. And it is acid stable and well tolerated. It has a very good therapeutic effect on respiratory tract infections, skin and soft tissue infections, sexually transmitted diseases which are caused by sensitive bacteria.
• Description: Azithromycin was the first of the azalides and was designed to improve the stability and biological half-life of erythromycin A, as well as improve activity against Gram negative bacteria. Azithromycin is a long-acting macrolide antibiotic structurally related to erythromycin A (EA), having a methyl-substituted nitrogen at position 9a in the aglycone ring.
• Indications: Azithromycin in a 500-mg dose three times a week has been shown to yield a 60% reduction in inflammatory papules in 83% of patients enrolled in a 12- week study. There is no associated pseudotumor cerebri and, therefore, it can be used for an acne flare during early Accutane therapy.
• Therapeutic Function: Antibiotic
• Clinical Use: This product is suitable for the treatment of the following symptoms of infection caused by susceptible bacteria:1. For acute pharyngitis and acute tonsillitis caused by Streptococcus pyogenes and for nasosinusitis, acute otitis media, acute bronchitis, and acute exacerbation of chronic bronchitis caused by sensitive bacteria.2. For pneumonia caused by Mycoplasma pneumonia, Streptococcus pneumonia and Haemophilus influenza.3. For urethritis, cervicitis and pelvic inflammatory disease caused by chlamydia and non-multiple drug resistance Neisseria gonorrhoeae, and for simple genital infection caused by non-multiple drug resistance Neisseria gonorrhoeae (exclude co-infection of Misu spirochetes).4. For skin and soft tissue infections caused by sensitive bacteria.
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: increased toxicity with disopyramide; increased risk of ventricular arrhythmias with dronedarone - avoid. Antibacterials: possibly increased rifabutin concentration (increased risk of uveitis and neutropenia) - reduce dose of rifabutin. Anticoagulants: effect of coumarins may be enhanced. Antidepressants: the manufacturer of reboxetine advises to avoid concomitant use. Antihistamines: may inhibit the metabolism of mizolastine (risk of hazardous arrhythmias) - avoid. Antimalarials: avoid with artemether/lumefantrine; increased risk of ventricular arrhythmias with piperaquine with artenimol - avoid. Antipsychotics: increased risk of ventricular arrhythmias with droperidol - avoid. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: may inhibit the metabolism of ciclosporin (increased ciclosporin levels). Colchicine: treatment with both agents has been shown in a study to increase the risk of fatal colchicine toxicity, especially in patients with renal impairment - avoid. Ergot alkaloids: increased risk of ergotism - avoid. Statins: possible increased risk of myopathy with atorvastatin and simvastatin.

Technology Process of (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

There total 43 articles about (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C5H12O*C38H72N2O12*H2O → Zithromax(R) (83905-01-5,92470-27-4)

Guidance literature:

at 80 ℃; under 15.0015 Torr;

Reference yield: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 9-Deoxo-9a-aza-9a-homoerythromycin A (76801-85-9) → Zithromax(R) (83905-01-5,92470-27-4)

Guidance literature:

With formic acid; In acetone; at 30 - 55 ℃; for 4h;

Reference yield: 89.0%

C50H100N2O12Si2 (1148112-33-7) → Zithromax(R) (83905-01-5,92470-27-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.200805334

upstream raw materials:

formaldehyd

formic acid

C₃₇H₆₆N₂O₁₂

9-Deoxo-9a-aza-9a-homoerythromycin A

Downstream raw materials:

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐2‐ethyl‐3,4,10‐trihydroxy‐13‐{(2R,4R,5S,6S)‐5‐hydroxy‐4‐methoxy‐4,6‐dimethyl-tetrahydropyran‐2‐yloxy}‐11‐{(2S,3R,4S,6R)‐3‐hydroxy‐6‐methyl‐4‐methylamino-tetrahydropyran‐2‐yloxy}‐3,5,6,8,10,12,14‐heptamethyl‐1‐oxa‐6‐azacyclopentadecan‐15‐one

3'-N,N-didemethyl-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A

3,O³-dimethyl-α-L-ribo-2,6-dideoxy-hexopyranose

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)‐11-((2S,3R,4S,6R)‐4-dimethylamino-3-hydroxy-6-methyl-tetrahydropyran-2-yloxy)-2-ethyl-3,4,10,13-tetrahydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopetadecan-15-one

Refernces

• 1、 Kiely-Collins,Sechi,Brennan,McLaughlin. "Mild, calcium catalysed Beckmann rearrangements". supporting information. p. 654 - 657. Retrieved 2018/02/06.
• 2、 -. "Preparation method of norazithromycin". Paragraph 0101; 0102; 0103. . Retrieved 2017/10/26.