Tìm theo
Azithromycin
Các tên gọi khác (12 ) :
  • (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
  • Azenil
  • Azifast
  • Azigram
  • Azimakrol
  • Azithromycine
  • Azithromycinum
  • Azitromicina
  • Azitromin
  • Hemomycin
  • Zithromax
  • Zmax
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 83905-01-5
ATC: J01FA10, S01AA26
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C38H72N2O12
PTK: 748.9845
Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C38H72N2O12
Phân tử khối
748.9845
Monoisotopic mass
748.508525778
InChI
InChI=1S/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
InChI Key
InChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N
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
Traditional IUPAC Name
azithromycin
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
Độ tan chảy
114 °C
Độ hòa tan
slight
logP
4.02
logS
-3.2
pKa (strongest acidic)
12.43
pKa (Strongest Basic)
9.57
PSA
180.08 Å2
Refractivity
194.11 m3·mol-1
Polarizability
83.11 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
13
H Bond Donor Count
5
Physiological Charge
2
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
pKa
8.74 (at 25 °C)
Dược Lực Học : Azithromycin, a semisynthetic antibiotic belonging to the macrolide subgroup of azalides, is used to treat STDs due to chlamydia and gonorrhea, community-acquired pneumonia, pelvic inflammatory disease, pediatric otitis media and pharyngitis, and Mycobacterium avium complex (MAC) in patients with advanced HIV disease. Similar in structure to erythromycin. azithromycin reaches higher intracellular concentrations than erythromycin, increasing its efficacy and duration of action.
Cơ Chế Tác Dụng : Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides. Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells.
Dược Động Học :
▧ Absorption :
Bioavailability is 37% following oral administration. Absorption is not affected by food. Azithromycin is extensively distributed in tissues with tissue concentrations reaching up to 50 times greater than plasma concentrations. Drug becomes concentrated within macrophages and polymorphonucleocytes giving it good activity against Chlamydia trachomatis.
▧ Volume of Distribution :
* 31.1 L/kg
▧ Protein binding :
Serum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at 0.02 µg/mL to 7% at 2 µg/mL.
▧ Metabolism :
Hepatic. In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed.
▧ Route of Elimination :
Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.
▧ Half Life :
68 hours
▧ Clearance :
* apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
Độc Tính : Potentially serious side effects of angioedema and cholestatic jaundice were reported
Chỉ Định : For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions: H. influenzae, M. catarrhalis, S. pneumoniae, C. pneumoniae, M. pneumoniae, S. pyogenes, S. aureus, S. agal
Tương Tác Thuốc :
  • Acenocoumarol Azithromycin may increase the anticoagulant effect of acenocoumarol by increasing its serum concentration.
  • Anisindione Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Cyclosporine The macrolide, azithromycin, may increase the effect of cyclosporine.
  • Dicoumarol Azithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration.
  • Disopyramide The macrolide, azithromycin, may increase the effect of disopyramide.
  • Lovastatin The macrolide antibiotic, azithromycin, may increase the serum concentration of lovastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of lovastatin if azithromycin is initiated, discontinued or dose changed.
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Vismodegib P-glycoprotein inhibitors may increase the chance of adverse drug reactions.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Warfarin Azithromycin may increase the anticoagulant effect of warfarin by increasing its serum concentration.
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Powder, for solution - Intravenous
Powder, for solution - Oral
Powder, for suspension - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : AzaSite
  • Công ty :
    Sản phẩm biệt dược : Azenil
  • Công ty :
    Sản phẩm biệt dược : Azibiot
  • Công ty :
    Sản phẩm biệt dược : Azin
  • Công ty :
    Sản phẩm biệt dược : Azithrocin
  • Công ty :
    Sản phẩm biệt dược : Azitromax
  • Công ty :
    Sản phẩm biệt dược : Aztrin
  • Công ty :
    Sản phẩm biệt dược : Hemomycin
  • Công ty :
    Sản phẩm biệt dược : Misultina
  • Công ty :
    Sản phẩm biệt dược : Penalox
  • Công ty :
    Sản phẩm biệt dược : Sumamed
  • Công ty :
    Sản phẩm biệt dược : Vinzam
  • Công ty :
    Sản phẩm biệt dược : Zifin
  • Công ty :
    Sản phẩm biệt dược : Zithromax
  • Công ty :
    Sản phẩm biệt dược : Zitrocin
  • Công ty :
    Sản phẩm biệt dược : Zitrotek
  • Công ty :
    Sản phẩm biệt dược : Zmax
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00207
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06838
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50197040
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0069-3060-30
PharmGKB
http://www.pharmgkb.org/drug/PA448519
Wikipedia
http://en.wikipedia.org/wiki/Azithromycin
RxList
http://www.rxlist.com/cgi/generic/zithromax.htm
Drugs.com
http://www.drugs.com/cdi/azithromycin-drops.html
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