Molecular Formula | C38H69NO13 |
Molar Mass | 747.95 |
Density | 1.1334 (rough estimate) |
Melting Point | 217-220°C |
Boling Point | 86℃ |
Specific Rotation(α) | D24 -90.4° (c = 1 in CHCl3) |
Flash Point | >110°(230°F) |
Water Solubility | 99.48mg/L(20 ºC) |
Solubility | 50 mg/mL in DMSO; Easily soluble in chloroform or acetone, slightly soluble in ethanol, ether or methanol, almost insoluble in water |
Vapor Presure | 5.06E-30mmHg at 25°C |
Appearance | White crystalline powder or colorless needle crystal |
Color | colorless to faint yellow |
Merck | 14,2339 |
pKa | pKa 8.99(H2O t=25.0 I=0.167) (Uncertain) |
Storage Condition | -20°C |
Stability | Store in Freezer |
Refractive Index | -92 ° (C=1, CHCl3) |
MDL | MFCD00865140 |
Physical and Chemical Properties | White crystalline powder or colorless needle Crystal, odorless, bitter taste. More soluble in chloroform or acetone, ethanol-soluble, ether or methanol, a few insoluble in water. From chloroform isopropyl ether (1:2) to give colorless needle-like crystals, melting point 217~220 °c (decomposition); Or from ethanol crystallization, melting point 222~225 °c. [Α]{D24-90.4 °(C = 1, chloroform). UV maximum absorption (chloroform):288nm (φ27.9). Acute toxicity LD50 male and female mice, male and female rats (mg/kg):2740,2700,3470,2700 oral; 1030.850,669,753 intraperitoneal injection. |
Use | Macrolide antibiotics for the treatment of upper and lower respiratory tract infections, subcutaneous soft tissue infections |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S60 - This material and its container must be disposed of as hazardous waste. |
WGK Germany | 3 |
RTECS | KF4997000 |
HS Code | 29419000 |
Toxicity | LD50 in male, female mice, male, female rats (mg/kg): 2740, 2700, 3470, 2700 orally, 1030, 850, 669, 753 i.p., >5000 all s.c. (Abe) |
Reference Show more | 1. Chen Shu-Xin, Wang Jing, He Shi-Chong, Liu Yan-Zheng, Feng Huajun, Mu Peng-Qian. Determination of 17 antibiotics in water by ultra performance liquid chromatography-tandem mass spectrometry [J]. China Environmental Monitoring, 2020,36(06):119-126. 2. Dong, Qian, et al. "In vitro and in vivo bacterial activity of Tinospora sagittata (Oliv.) gagnep. var. craveniana (SY Hu) Lo and its main effective component, palmatine, against porcine Helicobactor pylori." BMC complete and alternative medicine 1 3. Chunxi Zhao, Yang Jiao, He Gao, Yaling Yang, Hong Li, N, S co-doped carbon dots for temperature probe and the detection of tetracycline based on the inner filter effect, Journal of Photochemistry and Photobiology A: Chemistry, Volume 367, 2018, Pages 137- 4. [IF=3.659] Rong Qian et al."In vitro and in vivo bactericidal activity of Tinospora sagittata (Oliv.) Gagnep. var. craveniana (S.Y.Hu) Lo and its main effective component, palmatine, against porcine Helicobacter pylori."Bmc Complem Altern M. 2016 Dec;16(1):1-8 5. [IF=7.367] Zhengming Chen et al."Injectable and Self‐Healing Hydrogel with Anti‐Bacterial and Anti‐Inflammatory Properties for Acute Bacterial Rhinosinusitis with Micro Invasive Treatment."Adv Healthc Mater. 2020 Oct;9(20):2001032 6. [IF=3.631] Zhiya Yang et al."5-aminolevulinic acid-photodynamic therapy ameliorates cutaneous granuloma by killing drug-resistant Mycobacterium marinum."Photodiagn Photodyn. 2022 Mar;:102839 |
white crystalline powder or colorless needle Crystal, odorless, bitter taste. More soluble in chloroform or acetone, ethanol-soluble, ether or methanol, almost insoluble in water. Colorless needle-like crystals are obtained from chloroform-isopropyl ether (1:2), with a melting point of 217 to 220 ° C. (decomposition), or from ethanol, with a melting point of 222 to 225 ° C. UV maximum absorption (chloroform);288nm(& epsilon;27.9).
not less than 94.0% calculated as anhydrous} the pH value should be 7.5 to 10.0 [2mg of this product suspended in 1ml of a mixture of water and methanol (19:1)]; crystallinity should be in accordance with the provisions; Related substances should be in accordance with the provisions; Containing water shall not exceed 2. 0%; Ignition residue shall not exceed 0.3%; Heavy metal shall not exceed 0. 002%.
This product is 6-o-methylerythromycin. The content of clarithromycin (C38H69NO13) shall not be less than 94.0% calculated as anhydrous.
take this product, precision weighing, and chloroform dissolved and quantitative dilution of each lml solution containing about 10 mg, according to the law (General 0621), the specific rotation is from one to 89 ° to one to 95 °.
erythromycin is used as a raw material to hydrolyze and remove a methyl group from the amino group, and then react with benzyl chloroformate to protect the hydroxyl and amino groups on the 5-position side chain Tetrahydropyran ring. Then, methyl iodide is neutralized in dimethyl sulfoxide and tetrahydrofuran to methylate the hydroxyl group at the 6 position, and then the catalytic hydrogen is freed from the protecting group, and the formaldehyde is reacted to methylate the amino group, finally, it is reduced to a methyl group to obtain clarithromycin.
The company was developed in 1984 and launched in 1991. Macrolide antibiotics, derivatives of erythromycin. It has inhibitory effect on Gram-positive bacteria, such as Staphylococcus aureus, Streptococcus, Pneumonia cocci, etc. It has inhibitory effect on some Gram-negative bacteria, such as Haemophilus influenzae, Bordetella pertussis, Neisseria gonorrhoeae, legionella pneumophila and some anaerobic bacteria, such as Bacteroides fragilis, Streptococcus, Propionibacterium acnes, also have inhibitory effect, in addition to Mycoplasma also has inhibitory effect. It is effective for respiratory tract, urinary tract, skin, ENT and other infections.
take this product, water-methanol (19:1) mixed solution made of 2mg per lml of suspension, according to the law (General 0631) , pH value should be 7.5~10.0.
take this product, according to the law inspection (General 0981), should comply with the provisions.
take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make about 1 in each lml. 0 mg of the solution was used as a test solution; 5ml was accurately weighed, placed in a 100ml measuring flask, diluted to the scale with the mobile phase, and shaken to obtain a control solution. According to the chromatographic conditions under the content determination item, 20ul of each of the test solution and the control solution are accurately measured and injected into the liquid chromatograph respectively, and the chromatogram is recorded to 4 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (2.5%) of the area of the main peak of the control solution; the sum of each impurity peak area shall not be greater than 1.2 times (6.0%) of the main peak area of the control solution.
take this product, add 10% imidazole anhydrous methanol solution to dissolve, according to the moisture determination method (General 0832 first method 1), the water content shall not exceed 2.0%.
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.3%.
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
male and female mice, male and female rats by mouth (mg) kg LD50:2740, 2700, 3470, 2700. Male and female mice, male and female rats intraperitoneal injection (mg/kg)LDso:1030, 850, 669, 753.
measured by high performance liquid chromatography (General 0512).
silica gel bonded with octylsilane as filler; Phosphate buffer solution (take potassium dihydrogen phosphate 9.llg, dissolve with water and dilute to 1000ml, add triethylamine 2ml, adjust pH to 5.5 with phosphoric acid)-Acetonitrile (600:400) as mobile phase; Detection wavelength was 210nm; Column temperature was 45°C. The tailing factor of clarithromycin peak shall not exceed 2.0; The separation degree of clarithromycin peak from adjacent impurity peaks shall meet the requirements.
take an appropriate amount of this product, accurately weigh it, add the mobile phase to dissolve and quantitatively dilute it to make a solution containing about 0.35mg per 1 ml as the test solution, A 20ul injection liquid chromatograph was used to record the chromatogram. An appropriate amount of clarithromycin reference was taken and determined by the same method. According to the external standard method to calculate the peak area, that is.
macrolide antibiotics.
light shielding, sealed storage.
This product contains clarithromycin (C38H69N013) should be labeled the amount of 90.0% to 110.0%.
This product is white or white-like tablets or sugar-coated tablets or film-coated tablets, white or white after removing the coating.
In the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the control solution.
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about equivalent to clarithromycin 35mg), put it in a 100ml measuring flask, add the appropriate amount of mobile phase and shake sufficiently to dissolve and dilute to the scale, shake well, filter, take the filtrate, as a test solution, according to the method under the item of clarithromycin, then get.
Same as clarithromycin.
(l)50mg (2)0.125g (3)0.25g
shade, seal, and store in a cool and dry place.
This product contains clarithromycin (C38H69N013) should be labeled the amount of 90.0% to 110.0%.
The content of this product is white or white particles or crystalline powder.
In the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the control solution.
take the contents under the difference of loading amount, mix well, weigh an appropriate amount (about 35mg equivalent to clarithromycin), and put it in a 100ml measuring flask, add the appropriate amount of mobile phase and shake sufficiently to dissolve and dilute to the scale, shake well, filter, take the filtrate, as a test solution, according to the method under the item of clarithromycin, then get.
Same as clarithromycin.
(1)0.125g (2)0.25g
shade, seal, and store in a cool and dry place.
This product contains clarithromycin (C38H69N013) should be labeled the amount of 90.0% to 110.0%.
This product is suspended particles or suspended coated particles.
In the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the control solution.
take the contents under the difference of loading amount, grind them finely, weigh them accurately, shake them thoroughly with mobile phase, dissolve them and quantitatively dilute them to make a solution containing about 0.35mg of clarithromycin per 1 ml, the filtrate was collected by filtration and obtained as a test solution by measurement according to the method described for clarithromycin.
Same as clarithromycin.
(1)0.05g (2)0.lg (3)0.125g (4)0.25g
shade, seal, and store in a cool and dry place.
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
macrolide antibiotic | clarithromycin, also known as clarithromycin, is a derivative of erythromycin and a macrolide antibiotic, mainly used for diseases caused by bacterial infections, including for lower respiratory tract infections, such as bronchitis and Pneumonia; For Upper Respiratory Infections, such as pharyngitis and sinusitis; Can also be used for skin and soft tissue infections, such as folliculitis, cellulitis, erysipelas, etc. It can also be used for local infection, diffuse infection and mixed infection. Clarithromycin can be combined with other drugs to eradicate Helicobacter pylori infection. It can also be used for odontogenic infections, so clarithromycin is a broad spectrum antibiotic. The most common adverse reactions of clarithromycin were Abdominal Pain, Diarrhea, Nausea, Vomit and taste abnormalities, and these adverse reactions were usually mild. There is also a risk of severe torsades de pointes. |
pharmacological action | clarithromycin is a 14-membered ring macrolide broad-spectrum antibiotic. Its mechanism of action is the same as that of erythromycin, and it mainly binds to the 50S ribosomal subunit of bacteria, and inhibits the synthesis of bacterial proteins by blocking the transpeptide action and mRNA translocation, thereby playing an antibacterial role. Compared with erythromycin, clarithromycin has the characteristics of good oral absorption, fast peak time, high blood concentration, long half-life and small individual difference. Clarithromycin has a slightly stronger antibacterial effect on methicillin-sensitive staphylococci and streptococci than erythromycin. The antibacterial activity against influenza bacilli is 2-4 times stronger than erythromycin (its metabolites 14-hydroxy clarithromycin and clarithromycin have synergistic antibacterial effect on influenza bacilli). The effect on Legionella pneumophila, Chlamydia trachomatis and Ureaplasma urealyticum was stronger than erythromycin. Clarithromycin has bacteriostatic effect on Staphylococcus aureus and Streptococcus, bactericidal effect on Pneumonia cocci and influenza bacilli. Clarithromycin has strong antibacterial activity against Staphylococcus aureus, Streptococcus, Haemophilus influenzae, Legionella, Neisseria gonorrhoeae, catarrhalis and Helicobacter pylori,? Mycobacterium, leprosy bacilli also have antibacterial effect; In addition, Pneumonia of Mycoplasma, Chlamydia trachomatis, Ureaplasma urealyticum is also effective. The role of erythromycin sensitive bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Pneumonia Diplococcus was significantly better than erythromycin, Streptococcus faecalis and Haemophilus influenzae antibacterial effect and erythromycin the same, cross resistance with erythromycin. Drug-resistant bacteria produce an enzyme that methylates RNA, which methylates the binding site of the ribosome, so that the drug cannot bind to the ribosome. In vivo antibacterial test, clarithromycin on Staphylococcus aureus, Streptococcus pyogenes, Pneumonia Diplococcus, Haemophilus influenzae antibacterial effect than erythromycin strong 2~10 times. |
indication | 1. It can be used to treat pharyngitis and tonsillitis caused by Streptococcus pyogenes. 2. Can be used for the treatment of sensitive bacteria caused by acute otitis media, sinusitis, acute bronchitis, acute exacerbation of chronic bronchitis and Pneumonia. 3. It can be used to treat skin and soft tissue infection caused by sensitive bacteria. 4. Can be used for the treatment of Pneumonia Mycoplasma Pneumonias Pneumonia, Chlamydia trachomatis urethritis and nonspecific urethritis (cervicitis). 5. Can be used to treat Legionnaires' disease (Legionella infection). 6. Clarithromycin can also be used in combination with other drugs to treat Mycobacterium avium infection and Helicobacter pylori infection. |
Application | clarithromycin is a semi-synthetic macrolide antibiotic, which can inhibit bacterial protein synthesis and achieve antibacterial effect, the Gram-positive bacteria, gram-negative bacteria can play a strong antibacterial effect, can significantly improve the clinical symptoms of patients. Clinical application is extensive, including soft tissue infection, skin infection, respiratory system, urinary system infection and eradication of Helicobacter pylori treatment. |
clinical findings | 1. Clarithromycin and other macrolides are prohibited for patients with heart disease; 2, to Monitor liver function and electrolyte levels during oral clarithromycin; 3, the use of hypoglycemic drugs in patients with diabetes and lipid-lowering therapy in patients with hyperlipidemia: clarithromycin with caution, timely monitoring of blood glucose and rhabdomyolysis-related biochemical indicators, including renal function, CK, serum potassium, myoglobinuria, etc. 4. Patients using digoxin should closely observe the relevant drug concentrations. |
risk of drug combination | Cytochrome P450 proteins (CYP450) is a terminal oxygenase, it mainly exists in the endoplasmic reticulum and mitochondrial inner membrane, and is the main drug metabolizing enzyme in human body. Many serious and even fatal drug interactions are related to it. Clarithromycin is a strong inhibitor of CYP3A4 (one of the CYP450 subfamily), which increases the risk of adverse reactions when combined with drugs metabolized by the CYP system. (1) calcium channel blocker combined with clarithromycin: dihydropyridine calcium channel blocker (CCB) combined with clarithromycin has the highest risk, and Nifedipine is the most serious. Nifedipine is metabolized by CYP3A4 system, and clarithromycin can inhibit CYP3A4, thereby inhibiting the metabolism of nifedipine, increasing its blood concentration, leading to hypotension and renal damage. (2) combination of statins and clarithromycin: rhabdomyolysis rarely occurs when taking normal doses of statins alone, and when lovastatin, simvastatin and clarithromycin are metabolized by CYP3A4, there is an increased likelihood of such an adverse event (although there are also investigations that rosuvastatin, pravastatin, fluvastatin, etc., although not metabolized by CYP3A4, concomitant use of clarithromycin is also associated with the risk of kidney injury and hyperkalemia). (3) sulfonylureas and clarithromycin combination: such as glipizide, glibenclamide metabolism by CYP450, combined with clarithromycin will increase the blood concentration of sulfonylurea drugs, leading to hypoglycemia. For the same reason, clarithromycin significantly interacts with colchicine, and several deaths have been reported. |
Use | A macrolide antibiotic, A derivative of erythromycin, which changes the OH group at position 6 of erythromycin A to och3, that is, clarithromycin. It is effective against gram-positive and negative bacteria, chlamydia and mycobacteria, and can effectively inhibit almost all respiratory pathogens. The stability of gastric acid, oral absorption, high blood concentration, long blood half-life. Its use and erythromycin similar to the respiratory tract, urinary tract, skin, otolaryngology and other infections effective. macrolide antibiotics, used for the treatment of upper and lower respiratory tract infections, subcutaneous soft tissue infections, etc. other raw materials |
production method | with Erythromycin as the raw material, a methyl group on the amino group was hydrolyzed and removed, and then reacted with benzyl chloroformate, the hydroxyl group and amino group on the 5-position side chain Tetrahydropyran ring are protected, and then methyl iodide is neutralized in dimethyl sulfoxide and tetrahydrofuran to methylate the hydroxyl group on the 6-position, re-catalyzed hydrogen to remove the protective group, and formaldehyde reaction of amino hydroxymethylation, and finally reduced to methyl, that is, clarithromycin. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |