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Basic information

  • Name:

  • Azithromycin

  • CAS No.:

  • 83905-01-5

  • Formula:
  • C38H72N2O12
  • 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);

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Chemistry

Structure of Azithromycin (CAS NO.83905-01-5):

Empirical Formula: C38H72N2O12
Molecular Weight: 748.9845 
Index of Refraction: 1.536
Molar Refractivity: 197.56 cm3
Molar Volume: 632.6 cm3
Polarizability: 78.32×10-24cm3
Surface Tension: 50.5 dyne/cm
Density: 1.18 g/cm3
Flash Point: 451 °C
Enthalpy of Vaporization: 135.99 kJ/mol 
Melting Point: 113-115°C
Boiling Point: 822.1 °C at 760 mmHg
Vapour Pressure: 2.51E-31 mmHg at 25°C 
Physical Appearance: White Crystalline Powder
Product Categories: Antibiotics;Antibiotic;Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;API's;NeatsMore...Close...;1694 Pharmaceuticals&Personal Care Products;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;AntiviralAntibiotics;Chemical Structure Class;Interferes with Protein SynthesisAntibiotics;MacrolidesEPA;Mechanism of Action;Spectrum of Activity;veterinary medicine,soluble powder,preparation;Peptide Synthesis/Antibiotics

History

Name of Azithromycin (CAS NO.83905-01-5) is derived from the azane-substituent and erythromycin. Its formal chemical name is (2R,3S,4R,5R,8R,10R,11R,12S,13S,14S)-11-((2S,3R,4S,6R)- 4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)- 2-ethyl-3,4,10-trihydroxy-13-((2S,4R,5S)-5-hydroxy- 4-methoxy-4-methyltetrahydro-2H-pyran-2-yloxy)- 3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one.
 In 1980,Gabrijela Kobrehel, Gorjana Radobolja-Lazarevski and Zrinka Tambura?ev,Researchers at the Croatian pharmaceutical company Pliva, discovered azithromycin.the team led by Dr. Slobodan ?oki?.
 In 1981,It was patented , and was later found by Pfizer's scientists while going through patent documents. 
 In 1986,Pliva and Pfizer signed a licensing agreement which gave Pfizer exclusive rights for the sale of azithromycin in Western Europe and the United States.
 In 1988,Pliva brought their azithromycin on the market in Central and Eastern Europe under the brand name of Sumamed , Pfizer Zithromax in 1991, and Zentiva Azitrox. After several years, the US FDA approved AzaSite, an ophthalmic formulation of azithromycin, for the treatment of eye infections.
     Currently,AzaSite is  marketed in the US by Inspire Pharmaceuticals.

Uses

 Azithromycin (CAS NO.83905-01-5) can be used  following :
1.Semi-synthetic macrolide antibiotic;
2.related to Erythromycin A;
3.Antibacterial

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 21mg/kg/3D-I (21mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"		 American Journal of Medicine. Vol. 102, Pg. 217, 1997.
man TDLo oral 32mg/kg/9D-I (32mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI

KIDNEY, URETER, AND BLADDER: HEMATURIA		 Annals of Internal Medicine. Vol. 119, Pg. 636, 1993.
mouse LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
mouse LDLo intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
rat LD50 oral > 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.
rat LDLo intraperitoneal 900mg/kg (900mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 51, Pg. 53, 1996.

Safety Profile

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.

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 .
 

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