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Chemical Product CAS:83905-01-5Azithromycin

CAS:83905-01-5
Azithromycin

  • CAS No:

    83905-01-5
  • Name:

    Azithromycin
  • Molecular Formula:

    C38H72N2O12
  • Molecular Weight:

    748.99
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Azithromycin ( CASNO:83905-01-5 )

Identification and Related Records
Name:
Azithromycin
CAS Registry number:
83905-01-5
Iupac name:
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,
6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,
10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,
6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,
14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
Synonyms:
Azithromycin [USAN:BAN:INN]
Misultina
1-Oxa-6-azacyclopentadecan-15-one,13-[(2,- 6-dideoxy-3-C-methyl-3-O-methyl-R-Lribo- hexopyranosyl)oxy]-2-ethyl-3,4,10- trihydroxy-3,5,6,8,10,12,14-heptamethyl-11- [[3,4,6-trideoxy-3-(dimethylamino)-a-D-xylohexopyranosyl] oxy]-,(2R,3S,4R,5R,8R,10R,11R,- 12S,13S,14R)-
Azithromycin (AIDS Initiative)
Hemomycin
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one
9-Deoxo-9a-aza-9a-methyl-9a-homoerythromycin A
Zithromax
Tobil
Zitrotek
Aritromicina [Spanish]
(2R,3R,4R,5R,8R,10R,11R,13S,14R)-11-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
Azitromax
Azithromycinum [Latin]
CP-62993
Setron
Sumamed
Azithromycine [French]
Zeto
Zitromax
Aztrin
Zithrax
1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methylhexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
Zifin
[2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-
Azithromycin? /Azithromycin Dihydrate
Azithromycin Dihydrate
Azithromycin(water soluble)
Molecular Formula:
C38H72N2O12
Molecular Weight:
748.99
Inchi:
InChI=1/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
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
Isomers 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)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
Chemical and Physical Properties
Appearance:
white crystalline powder
Density:
1.18 g/cm3
Melting Point:
113-115℃
Boiling Point:
822.1 °C at 760 mmHg
Refractive Index:
1.536
Flash Point:
451 °C
Solubilities:
Insoluble
Color/Form:
Crystals
Stability:
Stable. Incompatible with strong oxidizing agents.
Storage temp:
Store at -20°C
Computed Properties:
Molecular Weight:748.98448 [g/mol]
Molecular Formula:C38H72N2O12
XLogP3:4
H-Bond Donor:5
H-Bond Acceptor:14
Rotatable Bond Count:7
Tautomer Count:2
Exact Mass:748.508526
MonoIsotopic Mass:748.508526
Topological Polar Surface Area:180
Heavy Atom Count:52
Formal Charge:0
Complexity:1150
Isotope Atom Count:0
Defined Atom Stereocenter Count:18
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Safety and Handling
Hazard Codes:
Xi: Irritant;
Safety:
Hazard Codes of Azithromycin (CAS NO.83905-01-5):?IrritantXi
RTECS: RN6960000
The Most common side effects are gastrointestinal; diarrhea , nausea , abdominal pain and vomiting.Serious allergic reactions, nervousness, dermatologic reactions, and fatalities have been reported? extremely rare.As with all antimicrobial agents, pseudomembranous colitis can occur during and up to several weeks after azithromycin therapy. Azithromycin may interfere with the effectiveness of birth control pills; other forms of contraception may be required during the treatment period.
Formulations/Preparations:
Oral: For suspension: 100 mg (of anhydrous azithromycin) per 5 mL, Zithromax (Pfizer); 200 mg (of anhydrous azithromycin) per 5 mL, Zithromax (Pfizer); 1 g (of anhydrous azithromycin) per packet, Zithromax Single Dose Packets (Pfizer); Tablets, film coated: 250 mg (of anhydrous azithromycin), Zithromax (scored, (Pfizer), Zithromax Z-Pak (scored; available as a 5 day mnemonic pack of 6 tablets), (Pfizer); 500 mg (of anhydrous azithromycin), Zithromax (scored), (Pfizer), Zithromax Tri-Paks, (scored; available as a 3 day mnemonic pack of 3 tablets), (Pfizer); 600 mg (of anhydrous azithromycin), Zithromax, (scored), (Pfizer).
Parenteral: For injection, for IV infusion only: 500 mg (of anhydrous azithromycin), (Zithromax), (Pfizer).
Exposure Standards and Regulations:
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl azithromycin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Specification:
? Azithromycin ,?its cas register number is 83905-01-5. It also can be called?(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one ; 9-Deoxo-9a-aza-9a-methyl-9a-homoerythromycin A ; Aritromicina ; Azasite ; Azenil ; Azitrocin ; Azitromax ; Aztrin ;
?Hemomycin ; Misultina ; Mixoterin ; Setron ; Sumamed ; Tobil ; Tromix ; Trulimax ; Zithrax ; Zithromax .
?
Octanol/Water Partition Coefficient:
log Kow = 4.02 [McFarland JW et al; J Med Chem 40: 1340-6 (1997)] PubMed Abstract
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
Usage:
Semi-synthetic macrolide antibiotic; related to Erythromycin A. Antibacterial
Biomedical Effects and Toxicity
Biological Activity:
Macrolide antibiotic. Inhibits 50S ribosomal subunit formation and elongation at transpeptidation step in gram-positive and gram-negative organisms. Orally active with improved pharmacokinetics over erythromycin in mouse models.
Pharmacological Action:
- Substances that reduce the growth or reproduction of BACTERIA.
Therapeutic Uses:
Azithromycin is indicated in the treatment of cervicitis or urethritis due to Chlamydia trachomatis or Neisseria gonorrhea. /Included in US product labeling/
Azithromycin is indicated in the treatment of bacterial exacerbations of chronic bronchitis or acute otitis media due to Hemophilus influenza, Moraxella catarrhalis, or Streptococcus pneumonia. However, azithromycin is not recommended as the first line of therapy for otitis media. /Included in US product labeling/
Azithromycin is indicated in the treatment of genital ulcer disease in men due to Hemophilus ducreyi. /Included in US product labeling/
Azithromycin is indicated in the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced human immunodeficiency virus (HIV) infection. /Included in US product labeling/
Azithromycin is indicated in the treatment of pelvic inflammatory disease due to Chlamydia trachomatis, Mycoplasma hominis, or Neisseria gonorrhea. /Included in US product labeling/
Azithromycin is indicated in the treatment of pharyngitis or tonsillitis due to Streptococcus pyogenes. /Included in US product labeling/
Azithromycin is indicated in the treatment of community-acquired pneumonia due to Chlamydia pneumonia, Hemophilus influenza, Legionella pneumophila, Moraxella catarrhalis, Mycoplasma pneumonia, Staphylococcus aureus, or Streptococcus pneumonia. /Included in US product labeling/
Azithromycin is indicated in the treatment of uncomplicated skin and soft tissue infections due to Staphylococcus aureus, Streptococcus agalactia, or Streptococcus pyogenes. /Included in US product labeling/
Azithromycin is indicated in the treatment of trachoma due to Chlamydia trachomatis. /NOT included in US product labeling/
Acne vulgaris is a common skin disease seen primarily in adolescent and young adults. As the treatment involves long term therapy with antibiotics, an agent with a long half life can be very useful in increasing the compliance. To evaluate the role of a monthly dose of azithromycin and compare it with daily doxycycline, we conducted this randomized comparative study. Sixty patients with moderate to severe acne were randomly assigned to two treatment groups, A & B. Patients in group A received 100 mg doxycycline daily in addition to topical 0.05% tretinoin cream, whereas patients in group B were given 500 mg azithromycin once a day for four days per month along with 0.05% topical tretinoin for a total of 12 weeks. Of the 60 patients, 22 in group A and 28 in group B were evaluated. The monthly dose of azithromycin was found to be as effective as daily doxycycline on a pure protocol basis and statistically significantly better than doxycycline by intention to treat analysis. [Parsad D et al; J Dermatol 28 (1): 1-4 (2001)]
Biomedical Effects and Toxicity:
Biliary excretion of azithromycin, predominantly as unchanged drug is a major route of elimination following oral administration.
Azithromycin is rapidly absorbed from the GI tract after oral administration; absorption of the drug is incomplete but exceeds that of erythromycin. The absolute oral bioavailability of azithromycin is reported to be approximately 34-52% with single doses of 500 mg to 1.2 g administered as various oral dosage forms. Limited evidence indicates that the low bioavailability of zithromycin results from incomplete GI absorption rather acid degradation of the drug or extensive first-pss metabolism.
Azithromycin appears to be distributed into most body tissues and fluids after oral or IV administration. The extensive tissue uptake of azithromycin has been attributed to cellular uptake of this basic antibiotic into relatively acidic lysosomes as a result of iron trapping and to an energy-dependent pathway associated with the nucleoside transport system.
Because of rapid distribution into tissues and high intracellular concentrations of azithromycin, tissue concentrations of the drug generally exceed plasma concentrations by 10- to 100-fold following single dose administration; with multiple dosing, the tissue-to-plasma ratio increases.
Administration of a single 500 mg oral dose of azithromycin generally produces drug concentrations of 1-9 ug/g in various tissues, including lung, gastric, prostatic, and gynecologic tissue.
Azithromycin has been detected in human milk.
In an open-label study, the concentrations of azithromycin in middle ear effusions and plasma were determined in 29 children between 1 and 8 years of age with a diagnosis of either secretory otitis media of at least 1 month's duration or acute otitis media. Azithromycin (10 mg/kg) was administered as a single dose 12, 24 or 48 hr before the insertion of tympanostomy tubes to 17 children with secretory otitis media and once daily for 5 days (10 mg/kg on day 1, 5 mg/kg on days 2-5) to 12 children with acute otitis media. In the 16 evaluable patients with secretory otitis media, azithromycin penetrated middle ear effusions, with group mean concentrations approximately two orders of magnitude greater than the concurrent plasma concentrations 12, 24 and 48 hr after administration. Similar plasma:effusion ratios were found 24 and 48 hr after starting once-daily therapy in 10 evaluable patients with acute otitis media.
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