Roxithromycin

Base Information

• Chemical Name: Roxithromycin
• CAS No.: 80214-83-1
• Molecular Formula: C41H76N2O15
• Molecular Weight: 837.059
• Hs Code.: 3004.20
• European Community (EC) Number: 617-007-5
• DSSTox Substance ID: DTXSID8041117
• Wikipedia: Roxithromycin
• NCI Thesaurus Code: C818
• ChEMBL ID: CHEMBL1476500
• Mol file: 80214-83-1.mol

Synonyms:Biaxsig;Claramid;Infectoroxit;Macrosil;MTW-Roxithromycin;Rotesan;Rotramin;Roxi 1A Pharma;Roxi Basics;Roxi TAD;roxi von ct;Roxi-paed 1A Pharma;Roxi-Puren;Roxi-Q;Roxi-saar;Roxi-Wolff;Roxibeta;roxidura;Roxigamma;Roxigrün;Roxihexal;Roxithro-Lich;Roxithromycin;RU 28965;RU 965;RU-28965;RU-965;RU28965;RU965;Rulid;Rulide

Chemical Property of Roxithromycin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.17E-35mmHg at 25°C
• Melting Point: 111-118 °C
• Refractive Index: 1.535
• Boiling Point: 864.7 °C at 760 mmHg
• PKA: pKa 9.27±0.01(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain)
• Flash Point: 476.7 °C
• PSA: 216.89000
• Density: 1.25 g/cm³
• LogP: 2.20960
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble10mg/mL
• Water Solubility.: Soluble in water to 18µg/ml
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 13
• Exact Mass: 836.52456972
• Heavy Atom Count: 58
• Complexity: 1310

Purity/Quality:

98%min ^*data from raw suppliers

Roxithromycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=NOCOCCOC)C(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)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=NOCOCCOC)[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)O)(C)O
• Recent ClinicalTrials: Effects of Roxithromycin on Quality of Life and Physiological Outcomes in Bronchiectasis
• Recent EU Clinical Trials: Shortened Antibiotic Treatment in Community-Acquired Pneumonia: A Nationwide Danish Randomized Controlled Trial
• Recent NIPH Clinical Trials: Examination of combination and maintenance therapy with Adapalene Gel 0.1% for acne vulgaris
• Indications: This product is applicable to the purulent Streptococcus caused pharyngitis and tonsillitis, susceptible bacteria-caused sinusitis, otitis media, acute bronchitis, acute exacerbation of chronic bronchitis, Mycoplasma pneumoniae or Chlamydia pneumoniae caused pneumonia; Chlamydia trachomatis caused urinary reproductive system infections (urethritis and cervicitis); sensitive bacteria caused infection of skin soft tissue and other parts of the body; it can also used for non-specific and gonococcal genital infection, Legionella caused infection and Pediatric Infections. Roxithromycin is characterized by acid resistance and excellent oral absorption with T1/2 being 12 to 14 hours which is 6 times higher than erythromycin. It has wide distribution in the body and is able to reach high concentration in both the upper and lower respiratory tract, reproductive tract and skin and maintain for a long time. Most of the metabolism occurs in vivo. Roxithromycin clinical evaluation: the curing rate of chlamydia urethritis, cervicitis clinical and bacteriological was 93% to 97%; the efficacy against genital infection is similar to doxycycline; the cure rate for skin infection is 90% or more; the effectiveness for the treatment of respiratory infections is 83% and 50% while the effectiveness for the treatment of pneumonia and dental infections are 79% and 85%.
• Uses: 1.? It belongs to macrolide antibiotics, being a kind of erythromycin derivative with the antibacterial spectrum being similar as erythromycin but having a 6 times stronger effect on erythromycin with high bioavailability. It is used for the treatment of respiratory tract infection, such as pneumonia, acute bronchitis, acute infection of chronic bronchitis, atypical pneumonia, and genitourinary system infection, skin and soft tissue infections, having good therapeutic effect and tolerance with smaller adverse reactions than erythromycin. 2.? As the new generation of macrolide antibiotics; 3.? The product belongs to a new generation of macrolide antibiotics, mainly used for Gram-positive bacteria, anaerobes, chlamydia and mycoplasma. Its antibacterial activity in vitro is similar as erythromycin with its in vivo effect being 1-4 times stronger than erythromycin. Pharmacological effects and indications 1, it has strong bactericidal effect on Gram-negative bacteria and some Gram-negative bacteria (meningococcus, Neisseria gonorrhoeae, influenza bacilli, pertussis, Brucella) and spirochetes, Mycoplasma pneumoniae and Rickettsia. Legionella is sensitive to it; its effect against mycoplasma and chlamydia is further enhanced. 4.? 2, antibacterial mechanism: it can bind to the bacterial ribosome 50S subunit, through blocking the peptidyl transfer and MRNA displacement, further inhibiting the protein synthesis. 3, this product has excellent oral absorption and quick efficacy with stronger bioavailability and plasma concentrations than erythromycin. According to reports, oral administration of 150 mg can lead to a peak plasma concentration of up to 6.6~7.9 ug/ml while the value for erythromycin under the same conditions is only 0.2~0.4ug/ml; roxithromycin is mainly distributed in body fluids and tissues, with high and durable tissue concentration and cell concentration. Moreover, it has a half-life of up to 12 h while the value for erythromycin is only 1.5~2.0h. 4, in clinical medicine, it is the first-choice drug for the treatment of drug-resistance Staphylococcus aureus and hemolytic streptococcus. In veterinary clinical practice, it is used for the treatment of penicillin-resistant staphylococcus aureus caused severe infection, pneumonia, uterine inflammation and poultry chronic respiratory disease. 5, the goods are mainly used for the treatment of livestock and poultry chronic respiratory disease with good efficacy in the treatment of livestock and poultry staphylococcus and streptococcal disease, chlamydia, spirocheal disease (swine dysentery), infectious pleurisy and rhinitis. 6, indications: avian neck swelling, local heat, pain, difficulty breathing, mouth and nose flow white foam, mucous membranes and skin cyanosis and other symptoms. Roxithromycin was one of the new generation erythromycins introduced in the 1980s. Improved acid stability was achieved by converting the 9-keto group to the more stable oxime and alkylation of the oxime to provide the methoxyethoxymethyl ether oxime. In vivo, roxithromycin exhibits higher tissue levels and a longer half-life while being slightly less potent than erythromycin in vitro. Semisynthetic erythromycin derivative. Antibacterial
• Production method: Take erythromycin as raw materials for reaction with hydroxylamine hydrochloride in triethylamine and methanol, generating oxime, followed by reaction with methoxy ethoxymethyl chloride in acetone to derive roxithromycin.
• Description: Roxithromycin, an oxime ether derivative of erythromycin, is a new macrolide antibiotic of high potency and long duration. Its in v i m activity spectrum is similar to that of erythromycin, but is superior to the latter against Legionella, Mycoplasma and Chlamydia.

Technology Process of Roxithromycin

There total 2 articles about Roxithromycin 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:

2-Methoxyethoxymethyl chloride (3970-21-6) + (9-E)-deoxo-9-hydroximinoerythromycin A (13127-18-9) → roxithromycin (80214-83-1)

Guidance literature:

With sodium ethanolate; In acetone; at 0 - 5 ℃; for 0.416667h;

Reference yield:

→ roxithromycin (80214-83-1)

Guidance literature:

Reference yield: 98.0%

roxithromycin (80214-83-1) → Decladinoseroxithromycin (214902-82-6)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 12h;

upstream raw materials:

2-Methoxyethoxymethyl chloride

(9-E)-deoxo-9-hydroximinoerythromycin A

Downstream raw materials:

(E)-N-Demethylroxithromycin

Decladinoseroxithromycin

Refernces

• 1、 -. "Process for preparing erythromycin derivative, such as roxithromycin, from the corresponding oxime". . . Retrieved 2008/06/13.