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药品详细

Azithromycin (阿奇霉素 )

化学结构式图
中文名
阿奇霉素
英文名
Azithromycin
分子式
Not Available
化学名
(2R,3S,4R,5R,8R,10R,11R,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
分子量
Average: 748.9845
Monoisotopic: 748.508525778
CAS号
83905-01-5
ATC分类
J01F 未知
药物类型
small molecule
阶段
商品名
Azenil;Azibiot;Azifine;Azitromax;Aziwok;Aztrin;Hemomycin;Misultina;Mixoterin;Setron;Sumamed;Tobil;Tromix;Vinzam;Zeto;Zifin;Zithrax;Zithromax;Zitrim;Zitrocin;Zitromax;Zitrotek;Zmax;
同义名
Aritromicina [Spanish];Azithramycine;Azithromycin Dihydrate;Azithromycine [French];Azithromycinum [Latin];
基本介绍

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.

生产厂家
  • App pharmaceuticals llc
  • Gland pharma ltd
  • Hospira inc
  • Inspire pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Pfizer central research
  • Pfizer chemicals div pfizer inc
  • Pfizer global research development
  • Pfizer inc
  • Pliva hrvatska doo
  • Pliva inc
  • Sagent strides llc
  • Sandoz inc
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. Pubmed
剂型
Form Route Strength
Powder, for solution Intravenous
Powder, for solution Oral
Powder, for suspension Oral
Tablet Oral
规格
Unit description Cost Unit
Zithromax 3 1 gm Packets Box 118.26 USD box
Azithromycin 2.5 gm bulk vial 75.6 USD each
Zmax adult-ped 2 g/60 ml susp 70.39 USD each
Zithromax Tri-Pak 3 500 mg tablet Disp Pack 69.67 USD disp
Zithromax Z-Pak 6 250 mg tablet Disp Pack 68.62 USD disp
Zmax 2 g/60 ml susp sr 67.04 USD each
Zmax pediatric 2 g/60 ml susp 67.04 USD each
Zithromax 200 mg/5ml Suspension 30ml Bottle 52.0 USD bottle
Zithromax 100 mg/5ml Suspension 15ml Bottle 51.6 USD bottle
Zithromax 200 mg/5ml Suspension 15ml Bottle 50.46 USD bottle
Zithromax 200 mg/5ml Suspension 22.5ml Bottle 50.46 USD bottle
Azithromycin 3 500 mg tablet Disp Pack 48.52 USD disp
Azithromycin 6 250 mg tablet Disp Pack 48.52 USD disp
Azasite 1% eye drops 42.85 USD ml
Zithromax i.v. 500 mg vial 34.39 USD vial
Azithromycin 200 mg/5ml Suspension 15ml Bottle 34.25 USD bottle
Zithromax 600 mg tablet 27.22 USD tablet
Zithromax 500 mg tablet 22.68 USD tablet
Zithromax tri-pak 500 mg tablet 22.24 USD tablet
Azithromycin 600 mg tablet 19.04 USD tablet
Azithromycin 500 mg tablet 15.87 USD tablet
Trimox 125 mg/5ml Suspension 100ml Bottle 11.99 USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle 11.99 USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle 11.99 USD bottle
Zithromax 250 mg z-pak tablet 11.12 USD tablet
Azithromycin i.v. 500 mg vial 11.09 USD each
Azithromycin powder 10.89 USD g
Zithromax 250 mg tablet 9.41 USD tablet
Azithromycin 250 mg tablet 6.33 USD tablet
Apo-Azithromycin 250 mg Tablet 3.11 USD tablet
Co Azithromycin 250 mg Tablet 3.11 USD tablet
Mylan-Azithromycin 250 mg Tablet 3.11 USD tablet
Novo-Azithromycin 250 mg Tablet 3.11 USD tablet
Phl-Azithromycin 250 mg Tablet 3.11 USD tablet
Pms-Azithromycin 250 mg Tablet 3.11 USD tablet
Ratio-Azithromycin 250 mg Tablet 3.11 USD tablet
Sandoz Azithromycin 250 mg Tablet 3.11 USD tablet
Zithromax 40 mg/ml Suspension 1.7 USD ml
Zithromax 20 mg/ml Suspension 1.2 USD ml
Novo-Azithromycin 40 mg/ml Suspension 0.95 USD ml
Pms-Azithromycin 40 mg/ml Suspension 0.95 USD ml
Sandoz Azithromycin 40 mg/ml Suspension 0.95 USD ml
Novo-Azithromycin 20 mg/ml Suspension 0.67 USD ml
Pms-Azithromycin 20 mg/ml Suspension 0.67 USD ml
Sandoz Azithromycin 20 mg/ml Suspension 0.67 USD ml
化合物类型
Type small molecule
Classes
  • Macrolides
Substructures
  • Carboxylic Acids and Derivatives
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetates
  • Acetals and Derivatives
  • Lactones
  • Ethers
  • Aliphatic and Aryl Amines
  • Macrolides
  • Alcohols and Polyols
  • Heterocyclic compounds
适应症
antibacterials 抗细菌;
药理
Indication 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
Pharmacodynamics 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.
Mechanism of action Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells.
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]
Toxicity Potentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Pathway Name SMPDB ID
Smp00247 Azithromycin Pathway SMP00247
理化性质
Properties
State solid
Melting point 113-115 oC
Experimental Properties
Property Value Source
water solubility slight PhysProp
logP 4.02 [MCFARLAND,JW ET AL. (1997)] PhysProp
pKa 8.74 Various sources
Predicted Properties
Property Value Source
water solubility 5.14e-01 g/l ALOGPS
logP 3.03 ALOGPS
logP 2.44 ChemAxon Molconvert
logS -3.16 ALOGPS
pKa 12.90 ChemAxon Molconvert
hydrogen acceptor count 13 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 180.08 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 194.11 ChemAxon Molconvert
polarizability 82.40 ChemAxon Molconvert
药物相互作用
Drug Interaction
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.
Dicumarol 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.
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).
食物相互作用
  • Do not take Aluminum or magnesium antacids or supplements while on this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

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