Description In vitro Uses structure and hydrogen bonding Mechanism of action Pharmacokinetics Side Effects
ChemicalBook > CAS DataBase List > Azithromycin dihydrate

Azithromycin dihydrate

Description In vitro Uses structure and hydrogen bonding Mechanism of action Pharmacokinetics Side Effects
Product Name
Azithromycin dihydrate
CAS No.
117772-70-0
Chemical Name
Azithromycin dihydrate
Synonyms
1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-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)-β-D-xylo-hexopyranosyl]oxy]-, dihydrate, (2R,3S,4R,5R,8R,10R;CS-1348;CP-62993 DIHYDRAT;AZITHROMYCIN 2H2O;CP-62993 dihydrate;azithromycin hydrate;Azithromycin (100 mg);AZITHROMYCIN 2-HYDRATE;Azithromycin, CP 62993;Azithromycinedihydrate
CBNumber
CB8442886
Molecular Formula
C38H74N2O13
Formula Weight
767.01
MOL File
117772-70-0.mol
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Azithromycin dihydrate Property

Melting point:
126 C
Boiling point:
717℃
alpha 
D26 -41.4° (c = 1 in CHCl3)
RTECS 
RN6960000
refractive index 
-47 ° (C=2, EtOH)
Flash point:
>110°(230°F)
storage temp. 
room temp
solubility 
Soluble in DMSO at 20mg/ml. Also soluble in chloroform or ethylene chloride
form 
powder
color 
off-white
Sensitive 
Air Sensitive
Merck 
14,915
EPA Substance Registry System
1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-?-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)-?-D-xylo-hexopyranosyl]oxy]-, dihydrate, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)- (117772-70-0)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
24/25-36/37/39
WGK Germany 
3
HS Code 
29419000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1088
Product name
Azithromycin
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1g
Price
$114
Updated
2024/03/01
Sigma-Aldrich
Product number
1046056
Product name
Azithromycin
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$463
Updated
2024/03/01
TCI Chemical
Product number
A2076
Product name
Azithromycin Dihydrate
Purity
>98.0%(N)
Packaging
1g
Price
$80
Updated
2024/03/01
TCI Chemical
Product number
A2076
Product name
Azithromycin Dihydrate
Purity
>98.0%(N)
Packaging
5g
Price
$238
Updated
2024/03/01
Alfa Aesar
Product number
J66740
Product name
Azithromycin dihydrate
Packaging
5g
Price
$328
Updated
2024/03/01
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Azithromycin dihydrate Chemical Properties,Usage,Production

Description

Azithromycin is an azalide macrolide antibiotic derived from erythromycin. Azithromycin binds the bacterial 50S ribosomal subunit, inhibiting protein translation. Azithromycin displays antibacterial, anti-fibrotic, and anti-inflammatory activities. In epithelial cells, azithromycin inhibits the epithelial-to-mesenchymal transition (EMT) by inhibiting expression of Smad3. Additionally, azithromycin inhibits production of arachidonic acid, eicosanoids, IL-6, and IL-12 in LPS-stimulated macrophages.

In vitro

Azithromycin displays a similar spectrum of antimicrobial activity. Azithromycin is marginally less active than erythromycin in vitro against Gram-positive organisms, although this is of doubtful clinical significance as susceptibility concentration fall within the range of achievable tissue Azithromycin concentrations. The mean MIC90 of Azithromycin against erythromycin susceptible/βL-ve strains, Streptococcus strains and NS (not selected for antimicrobial sesitivity)/erythromycin susceptible strains is 0.63, 0.35, and <0.27 mg/L, respectively. In contrast, Azithromycin appears to be more active than erythromycin against many Gram-negative pathogens and several other pathogens, notably Haemophilus influenza (MIC90, 1.34 mg/L), H. parainfluenzae(MIC90, 1 mg/L), Moraxella catarrhalis (MIC90, <0.1 mg/L), Neisseria gonorrhoeae (MIC90, 0.25 mg/L), Ureaplasma urealyticum, Bordetella spp (MIC90, 0.03-0.24 mg/L) and Borrelia burgdorferi. Azithromycin is also activity against clinical isolates of anaerobic bacteria Gram-positive cocci and propionibacterium acnes with MIC90 of 2.3, 0.03 mg/L. Like erythromycin and other macromycin, the activity of Azithromycin is unaffected by the production of β-lactamase. However, erythromycin-resistant organisms are also resistant to Azithromycin.

Uses

Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration 3. It was initially approved by the FDA in 1991. It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead of other macrolides for some sexually transmitted and enteric infections. It is structurally related to erythromycin.

structure and hydrogen bonding

Azithromycin [9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin] is a part of the azalide subclass of macrolides, and contains a 15-membered ring, with a methyl-substituted nitrogen instead of a carbonyl group at the 9a position on the aglycone ring, which allows for the prevention of its metabolism. This differentiates azithromycin from other types of macrolides .

Mechanism of action

Azithromycin prevents bacteria from growing by interfering with their protein synthesis. It binds to the 50S subunit of the bacterial ribosome, thus inhibiting translation of mRNA. Nucleic acid synthesis is not affected.

Pharmacokinetics

Azithromycin is an acid-stable antibiotic, so it can be taken orally with no need of protection from gastric acids. It is readily absorbed, but absorption is greater on an empty stomach. Time to peak concentration (Tmax) in adults is 2.1 to 3.2 hours for oral dosage forms. Due to its high concentration in phagocytes, azithromycin is actively transported to the site of infection. During active phagocytosis, large concentrations are released. The concentration of azithromycin in the tissues can be over 50 times higher than in plasma due to ion trapping and its high lipid solubility.[citation needed] Azithromycin's half-life allows a large single dose to be administered and yet maintain bacteriostatic levels in the infected tissue for several days. Following a single dose of 500 mg, the apparent terminal elimination half-life of azithromycin is 68 hours. Biliary excretion of azithromycin, predominantly unchanged, is a major route of elimination. Over the course of a week, about 6% of the administered dose appears as unchanged drug in urine.

Side Effects

Stomach upset, diarrhea/loose stools, nausea, vomiting, or abdominal pain may occur. This medication may rarely cause a severe intestinal condition (Clostridium difficile-associated diarrhea) due to a resistant bacteria. This condition may occur during treatment or weeks to months after treatment has stopped. Use of this medication for prolonged or repeated periods may result in oral thrush or a new yeast infection. A very serious allergic reaction to this drug is rare. However, get medical help right away if you notice any symptoms of a serious allergic reaction, including: fever that doesn't go away, new or worsening lymph node swelling, rash, itching/swelling (especially of the face/tongue/throat), severe dizziness, trouble breathing.

Chemical Properties

White Solid

Uses

H1 antihistamine, nonsedating

Uses

Azithromycin dihydrate has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis. It shows an azalide antimicrobial agent active in vitro against various pathogens.

Uses

Semi-synthetic macrolide antibiotic; related to Erythromycin A. Antibacterial.

Definition

ChEBI: Azithromycin dihydrate is a hydrate. It contains an azithromycin.

brand name

Zithromax (Pfizer); Zmax (Pfizer).

Biochem/physiol Actions

Azithromycin dihydrate is a macrolide antibiotic, azalide subclass. It binds to the 50S subunit of the 70S bacterial ribosomes and inhibits RNA-dependent protein synthesis in bacterial cells. Azithromycin also has anti-immunomodulatory/anti-inflammatory properties, which make it useful in treating cystic fibrosis.

Azithromycin dihydrate Preparation Products And Raw materials

Raw materials

Preparation Products

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Azithromycin dihydrate Suppliers

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View Lastest Price from Azithromycin dihydrate manufacturers

Hebei Dangtong Import and export Co LTD
Product
Azithromycin dihydrate 117772-70-0
Price
US $232.00-225.00/kg
Min. Order
10kg
Purity
99.99%
Supply Ability
100Tons
Release date
2023-03-17
Henan Suikang Pharmaceutical Co.,Ltd.
Product
Azithromycin dihydrate 117772-70-0
Price
US $0.00/kg
Min. Order
25kg
Purity
99.0%
Supply Ability
10tons
Release date
2024-05-08
Sinoway Industrial co., ltd.
Product
Azithromycin Dihydrate 117772-70-0
Price
US $135.00-65.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2023-12-15

117772-70-0, Azithromycin dihydrateRelated Search:

AzithroMycin N-Oxide N'-DesMethyl AzithroMycin AzithroMycin N-Oxide N',N'-Di(desmethyl) Azithromycin AZITHROMYCIN IMPURITY B 3’-N-Desmethyl-3’-N-formyl Azithromycin 3'-N,N-Di(desMethyl)-3'-N-forMyl AzithroMycin Azathramycin DesosaMinylazithroMycin Metronidazole AZITHROMYCIN DIHYDRATE(COMPACTED),Azithromycin(Dihydrate)Usp27,Azithromycin /Azithromycin Dihydrate AZITHROMYCIN-D3 FOROXYMITHINE Azithromycin dihydrate 11-(4-DIMETHYLAMINO-3-HYDROXY-6-METHYL-OXAN-2-YL)OXY-2-ETHYL-3,4,10-TRIHYDROXY-13-(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

  • AZITHROMYCIN 2-HYDRATE
  • 1-Oxa-6-azacyclopentadecan-15-one, 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-hexopyranosyloxy-, dihydrate, (2R,3S,4R,5R,8
  • AZITHROMYCINDIHYDRATE(PATENTED-NOSUPPLY)
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-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)-β-D-xylo-hexopyranosyl]oxy]-, dihydrate, (2R,3S,4R,5R,8R,10R
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-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)-β-D-xylo-hexopyranosyl]oxy]-, dihydrate, [2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-
  • azithromycin hydrate
  • Azithromycin, CP 62993
  • CS-1348
  • (2R,3S,4R,5R,8R,11R,12S,13S,14R)-11-[[(3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-2-oxanyl]oxy]-2-ethyl-3,4,10-trihydroxy-13-[[(2R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-2-oxanyl]oxy]-3,5,6,8,10,
  • Azithromycin dihydrate Manufacturer
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-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)-β-D-xylo-hexopyranosyl]oxy]-, dihydra
  • Azithromycin - CP 62993 | Zithromax
  • CP-62993 DIHYDRAT
  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-Methyl-3-O-Methyl-α-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)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one Dihydrate
  • N-METHYL-11,AZA-10,DEOXO-10, DIHYDROERYTHROMYcIN A DIHYDRATE
  • Azithromycin (100 mg)
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-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)-β-D-xylo-hexopyranosyl]oxy]-, dihydrate, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
  • Azithromycin dihydrate, 945-1030 ug/mg
  • Azithromycinedihydrate
  • azithromycin dihydrate Skype : honestcooperation
  • AZITHROMYCIN 2H2O
  • AZITHROMYCIN DIHYDRATE
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  • Azithromycin Dihydrate&gt
  • CP-62993 dihydrate
  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one dihydrate
  • Azithromycin aspartate USP/EP/BP
  • Azithromycin dihydrate USP/EP/BP
  • Factory Supply Pharmaceutical Azithromycin Dihydrate CAS?117772-70-0
  • Azithromycin (Y0000306)
  • Azithromycin dihydrateQ: What is Azithromycin dihydrate Q: What is the CAS Number of Azithromycin dihydrate Q: What is the storage condition of Azithromycin dihydrate Q: What are the applications of Azithromycin dihydrate
  • Azithromycin Dihydrate (AZA), 96%
  • Azithromycin (1046056)
  • 1-Oxa-6-azacyclopentadecan-15-one,13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-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)-b-D-xy
  • Azithromycin dihydrate 99% CAS NO.117772-70-0
  • AZITHROMYCIN DIHYDRATE/TRIHYDRATE
  • Azithromycin Dihydrate, ≥ 98.0%
  • (2R,3S,4R,5R,8R,10S,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
  • 117772-70-0
  • 8390-1-5
  • 8390-01-5
  • 17772-70-0
  • C38H76N2O14
  • C38H72N2O122H2O
  • Inhibitors
  • Carbohydrates & Derivatives
  • Chiral Reagents
  • Intermediates & Fine Chemicals
  • Pfizer compounds
  • Pharmaceuticals
  • SELDANE
  • Macrolides (Antibiotics for Research and Experimental Use)
  • Antibiotics for Research and Experimental Use
  • Biochemistry
  • 117772-70-0