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Basic Information

Molecular Structure:
CAS No.:	83905-01-5
Name:	Azithromycin
Article Data:	30

Formula:	C₃₈H₇₂N₂O₁₂
Molecular Weight:	748.996
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);
EINECS:	617-500-5
Density:	1.184 g/cm³
Melting Point:	113-115 °C
Boiling Point:	822.105 °C at 760 mmHg
Flash Point:	450.993 °C
Appearance:	white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	42/43
Safety:	22-36/37-45
PSA:	180.08000
LogP:	1.83860

Raw Materials

50-00-0

76801-85-9

64-18-6

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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): Irritant Xi
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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