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Igorgv68 (обговорення | внесок)
37 редагувань
Немає опису редагування
Igorgv68 (обговорення | внесок)
37 редагувань
Скасування редагування № 13414266 користувача Igorgv68 (обговорення)
Рядок 1:
{| class="infobox" style="width: 22em"
 
|+ {{{drug_name|{{{imagename|{{PAGENAME}} }}} }}}{{#ifeq:{{{type|}}}|mab|<sup>[[Nomenclature of monoclonal antibodies|?]]</sup>}}
{{Drugbox
|-
| verifiedrevid = 458267362
{{#if:{{{image|}}}{{{image2|}}}|
| IUPAC_name = (2''R'',3''S'',4''R'',5''R'',8''R'',10''R'',11''R'',12''S'',13''S'',14''R'')-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-<small>D</small>-''xylo''-]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3-''C''-methyl-3-''O''-methyl-α-<small>L</small>-''ribo''-hexopyranoside
{{#if:{{{image|}}}|{{!}}-
| image = Azithromycin structure.svg
{{!}} align="center" colspan="2" {{!}} [[Image:{{{image}}}{{!}}{{{width|220}}}px]] }}
| width = 200
{{#if:{{{image2|}}}|{{!}}-
| image2 = Azithromycin_3d_structure.png
{{!}} align="center" colspan="2" {{!}} [[Image:{{{image2}}}{{!}}{{{width|220}}}px]] }}|
 
{{#ifexist:Image:{{PAGENAME}}.png|{{!}}-
<!--Clinical data-->
{{!}} align="center" colspan="2" {{!}} [[Image:{{PAGENAME}}.png{{!}}{{{width|220}}}px{{!}}Chemical structure of {{PAGENAME}}]]|{{#ifeq: {{{type|}}} | mab | | {{#ifeq: {{{type|}}} | combo | | <includeonly>[[Category:Drug pages needing a structure drawing]]</includeonly>}}}} }} }}
| tradename = Zithromax, Azithrocin, Azin
|-
| Drugs.com = {{drugs.com|monograph|azithromycin}}
<!-- Top header for Combination, Monoclonal else defaut IUPAC header
| MedlinePlus = a697037
-->{{#switch: {{{type|}}}
| licence_US = Azithromycin
| combo = {{!}} align="center" colspan="2" bgcolor="#dddddd" {{!}} '''Combination of'''
| pregnancy_AU = B1
| mab = {{!}} align="center" colspan="2" bgcolor="#dddddd" {{!}} '''[[Monoclonal_antibody#Applications|Therapeutic monoclonal antibody]]'''
| pregnancy_US = B
| = {{!}} align="center" colspan="2" bgcolor="#dddddd" {{!}} '''Систематична назва ([[IUPAC]])''' }}
| legal_US = Rx-only
|-
| routes_of_administration = [[Wiktionary:oral|Oral]] (capsule or suspension), [[intravenous therapy|intravenous]], [[eye drop|ophthalmic]]
<!-- Naming 1) If not mab or combo show IUPAC value -->{{#ifeq: {{{type|}}} | mab | | {{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#eeeeee" style="text-align: center; vertical-align: top;" colspan="2" {{!}} {{#if:{{{IUPAC_name|}}} | <span style="font-size:11px">{{{IUPAC_name}}}</span> | ? }} {{#if:{{{систематична_назва|}}} |<br/><span style="font-size:11px">Переклад: {{{систематична_назва}}}</span>}} }} }}
 
|-
<!--Pharmacokinetic data-->
<!-- Naming 2) If type=mab then show monoclonal antibody details -->{{#ifeq: {{{type|}}} | mab | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[моноклональні антитіла|Джерело]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{source|}}} | {{{source}}} | ? }} }}
| bioavailability = 38% for 250 mg capsules
|-
| metabolism = [[Hepatic]]
{{#ifeq: {{{type|}}} | mab | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Antigen|Target]] {{!}}{{!}} Bgcolor="#eeeeee" {{!}} {{#if:{{{target|}}} | {{{target}}} | ? }} }}
| elimination_half-life = 11–14 h (single dose)
|-
68 h (multiple dosing)
<!-- Naming 3) if type=combo show its components (2 obligatory, 3 & 4 optional) -->{{#ifeq: {{{type|}}} | combo | {{!}} bgcolor="#ddeeff" {{!}} [[{{{component1|? Component}}}]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{{class1|? Class}}} }}
| excretion = [[Biliary]], [[renal]] (4.5%)
|-
 
{{#ifeq: {{{type|}}} | combo | {{!}} bgcolor="#ddeeff" {{!}} [[{{{component2|? Component}}}]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{{class2|? Class}}} }}
<!--Identifiers-->
|-
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{{#ifeq: {{{type|}}} | combo | {{#if:{{{component3|}}} |
| CAS_number_Ref = {{cascite|correct|??}}
{{!}}-
| CAS_number = 83905-01-5
{{!}} bgcolor="#ddeeff" {{!}} [[{{{component3|?}}}]]
| ATC_prefix = J01
{{!}} bgcolor="#eeeeee" {{!}} {{{class3|? Class}}}
| ATC_suffix = FA10
}} }}
| ATC_supplemental = {{ATC|S01|AA26}}
|-
| PubChem = 55185
{{#ifeq: {{{type|}}} | combo | {{#if:{{{component4|}}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
{{!}}-
| DrugBank = DB00207
{{!}} bgcolor="#ddeeff" {{!}} [[{{{component4|?}}}]]
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
{{!}} bgcolor="#eeeeee" {{!}} {{{class4|? Class}}}
| ChemSpiderID = 10482163
}} }}
| UNII_Ref = {{fdacite|correct|FDA}}
|-
| UNII = J2KLZ20U1M
| colspan="2" bgcolor="#dddddd" | '''Ідентифікатори'''
| KEGG_Ref = {{keggcite|correct|kegg}}
|-
| KEGG = D07486
| bgcolor="#ddeeff" width="90" | [[Реєстраційний номер CAS|Номер CAS]]
| ChEBI_Ref = {{ebicite|correct|EBI}}
| bgcolor="#eeeeee" | {{#if:{{{CAS_number|}}} | <span class="reflink plainlinksneverexpand">[http://www.nlm.nih.gov/cgi/mesh/2006/MB_cgi?term={{{CAS_number}}}&rn=1 {{{CAS_number}}}]</span> | ? }} {{#if:{{{CAS_supplemental|}}} | <br>{{{CAS_supplemental|}}} }}
| ChEBI = 2955
|-
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| bgcolor="#ddeeff" | [[Анатомічна терапевтична хімічна класифікація|Код ATC]]
| ChEMBL = 529
| bgcolor="#eeeeee" | {{#if:{{{ATC_prefix|}}} | [[ATC_code_{{{ATC_prefix}}}|{{{ATC_prefix}}}]]{{#if:{{{ATC_suffix|}}} | <span class="reflink plainlinksneverexpand">[http://www.whocc.no/atc_ddd_index/?code={{{ATC_prefix}}}{{{ATC_suffix}}} {{{ATC_suffix}}}]</span> {{{ATC_supplemental|}}} }} | ? }}
| NIAID_ChemDB = 007311
|-
 
| bgcolor="#ddeeff" | [[PubChem]]
<!--Chemical data-->
| bgcolor="#eeeeee" | {{#if:{{{PubChem|}}} | <span class="reflink plainlinksneverexpand">[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid={{{PubChem}}} {{{PubChem}}}]</span> | ? }}
| C=38 | H=72 | N=2 | O=12
{{#if:{{{DrugBank|}}} |
| molecular_weight = 748.984 g·mol<sup>−1</sup>
{{!}}-
| smiles = CN(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]2(C)O)[C@@H]3O
{{!}} bgcolor="#ddeeff" {{!}} [[DrugBank]]
| InChI = 1/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
{{!}} bgcolor="#eeeeee" {{!}} <span class="reflink plainlinksneverexpand">[http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD={{{DrugBank}}} {{{DrugBank}}}]</span>
| InChIKey = MQTOSJVFKKJCRP-BICOPXKEBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MQTOSJVFKKJCRP-BICOPXKESA-N
| synonyms = <small>9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A</small>
}}
|-
 
<!-- If type=combo, then none of following physical data parameters to displayed
'''Azithromycin''' (Zithromax, Azithrocin, Zmax, Azin, Zedd,Azocam,Penalox, Azi-Once)<ref>{{cite web |url=http://www.nlm.nih.gov/medlineplus/druginfo/meds/a697037.html |title=Azithromycin |author=[[American Society of Health-System Pharmacists]] |work=[[MedlinePlus]] |publisher=[[United States National Library of Medicine]] |date=October 15, 2012 |accessdate=September 19, 2013}}</ref> is an [[azalide]], a subclass of [[macrolide]] [[antibiotics|antibiotics.]] It is derived from [[erythromycin]], with a [[methyl]]-substituted [[nitrogen]] [[atom]] incorporated into the [[lactone]] ring, thus making the lactone ring 15-membered.
-->{{#ifeq: {{{type|}}} | combo | | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Хімічні дані''' }}
 
|-
Azithromycin prevents [[bacterium|bacteria]] from growing by interfering with their [[protein synthesis]]. It binds to the 50S subunit of the bacterial [[ribosome]], and thus inhibits [[translation (biology)|translation]] of [[mRNA]].
{{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#ddeeff" {{!}} [[Хімічна формула|Формула]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{chemical_formula|}}} | {{{chemical_formula}}} | {{#if:{{{C|}}}{{{H|}}}{{{O|}}}{{{N|}}} | {{OrganicBox_{{#if:{{{C|}}} |atom }} | atom_name={{#if:{{{C|}}} |Вуглець}} | atom_color=rgb(000,000,000) | atom_abb=C | atom_number={{{C}}} |var1= }}<!--
 
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Azithromycin is used to treat or prevent certain [[bacterial infections]], most often those causing [[Otitis media|middle ear infections]], [[strep throat]], [[pneumonia]], [[typhoid]], [[bronchitis]] and [[sinusitis]]. In recent years, it has been used primarily to prevent bacterial infections in infants and those with weaker [[immune systems]]. It is also effective against certain sexually transmitted infections, such as [[nongonococcal urethritis]], [[chlamydia infection|chlamydia]], and [[cervicitis]]. Recent studies have indicated it also to be effective against late-onset [[asthma]], but these findings are controversial and not widely accepted.<ref>{{cite journal |pmid=7561707 |year=1995 |last1=Hahn |first1=DL |title=Treatment of Chlamydia pneumoniae infection in adult asthma: A before-after trial |volume=41 |issue=4 |pages=345–51 |journal=The Journal of family practice}}</ref><ref>{{cite journal |doi=10.1086/513818 |title=Enhanced Control of an Outbreak ofMycoplasma pneumoniaePneumonia with Azithromycin Prophylaxis |year=1998 |last1=Klausner |first1=Jeffrey D. |last2=Passaro |first2=Douglas |last3=Rosenberg |first3=Jon |last4=Thacker |first4=W. Lanier |last5=Talkington |first5=Deborah F. |last6=Werner |first6=S. Benson |last7=Vugia |first7=Duc J. |journal=The Journal of Infectious Diseases |volume=177 |pages=161–6 |pmid=9419183 |issue=1}}</ref>
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== Medical uses ==
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Azithromycin is used to treat many different infections, including [[acute otitis media]], nonstreptococcal bacterial [[pharyngitis]], gastrointestinal infections such as [[traveler's diarrhea]], respiratory tract infections such as [[pneumonia]], [[cellulitis]], [[babesiosis]], ''[[Bartonella]]'' infection, [[chancroid]] [[cholera]], [[donovanosis]], [[leptospirosis]], [[Lyme disease]], [[malaria]], [[mycobacterium avium complex|''Mycobacterium avium'' complex disease]], [[neisseria meningitis|''Neisseria'' meningitis]], [[pelvic inflammatory disease]], [[pertussis]], [[scrub typhus]], [[toxoplasmosis]], and [[salmonellosis]].<ref name=AHFS>{{drugs.com|monograph|azithromycin}}</ref> It is used to prevent [[bacterial endocarditis]] and some sexually transmitted infections including those from unprotected sex or sexual assault.<ref name=AHFS/> It is also effective against localized dental infections, uncomplicated skin and skin structure infections, urethritis and cervicitis and also genital ulcer disease. Azithromycin is used as a second line treatment for strep throat, for those allergic to penicillin. <ref name=Dajani et al>{{cite journal |pmid=7567345 |year=1995 |last1=Dajani |first1=Adnan |last2=Taubert |first2=Kathryn |last3=Ferrieri |first3=Patricia |last4=Peter |first4=Georges |last5=Shulman |first5=Stanford |title=Treatment of Acute Streptococcal Pharyngitis and Prevention of Rheumatic Fever: A Statement for Health Professionals |volume=96 |issue=4 |pages=758–64 |journal=Pediatrics |url=http://pediatrics.aappublications.org/content/96/4/758.short}}</ref> It has a similar antimicrobial spectrum as [[erythromycin]], but is more effective against certain [[Gram-negative]] bacteria, in particular, ''[[Haemophilus influenzae]]'' (although it would not be the first choice of treatment in this infection).<ref>{{cite web |first=Paul |last=Auwaerter |url=http://www.hopkinsguides.com/hopkins/ub/view/Johns_Hopkins_ABX_Guide/540253/all/Haemophilus_influenzae |work=Johns Hopkins ABX Guide |title=Haemophilus species |date=November 17, 2011 |accessdate=September 19, 2013}}</ref> Azithromycin resistance has been described<ref>{{cite journal |doi=10.1093/jac/dkp188 |title=Emergence of high-level azithromycin resistance in Neisseria gonorrhoeae in England and Wales |year=2009 |last1=Chisholm |first1=S. A. |last2=Neal |first2=T. J. |last3=Alawattegama |first3=A. B. |last4=Birley |first4=H. D. L. |last5=Howe |first5=R. A. |last6=Ison |first6=C. A. |journal=Journal of Antimicrobial Chemotherapy |volume=64 |issue=2 |pages=353–8 |pmid=19468025}}</ref> and is [[endemic (epidemiology)|endemic]] in many areas. Long-term use in treating ''[[Staphylococcus aureus]]'' infections with azithromycin may increase bacterial resistance to this and other macrolide antibiotics.<ref>{{cite journal |doi=10.1016/j.jcf.2008.09.001 |title=Long-term, low-dose azithromycin treatment reduces the incidence but increases macrolide resistance in Staphylococcus aureus in Danish CF patients |year=2009 |last1=Hansen |first1=C.R. |last2=Pressler |first2=T. |last3=Hoiby |first3=N. |last4=Johansen |first4=H.K. |journal=Journal of Cystic Fibrosis |volume=8 |pages=58–62 |pmid=18849202 |issue=1}}</ref>
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Azithromycin has been shown to be effective against [[malaria]] when used in combination with [[artesunate]] or [[quinine]]; the optimal dose for this is not yet known.<ref>{{cite journal |doi=10.1086/508175 |title=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 |year=2006 |last1=Noedl |first1=H. |last2=Krudsood |first2=S. |last3=Chalermratana |first3=K. |last4=Silachamroon |first4=U. |last5=Leowattana |first5=W. |last6=Tangpukdee |first6=N. |last7=Looareesuwan |first7=S. |last8=Miller |first8=R. S. |last9=Fukuda |first9=M. |last10=Jongsakul |first10=K. |last11=Sriwichai |first11=S. |last12=Rowan |first12=J. |last13=Bhattacharyya |first13=H. |last14=Ohrt |first14=C. |last15=Knirsch |first15=C. |journal=Clinical Infectious Diseases |volume=43 |issue=10 |pages=1264–71 |pmid=17051490}}</ref>
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== Adverse effects ==
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Most common side-effects are gastrointestinal: diarrhea (5%), nausea (3%), abdominal pain (3%), and vomiting. Fewer than 1% of patients stop taking the drug due to side-effects. Nervousness, dermatologic reactions, and [[anaphylaxis]] have been reported. As with all antimicrobial agents, [[pseudomembranous colitis]] can occur during and up to several weeks after Azithromycin therapy. In the past, physicians cautioned women that antibiotics can reduce the effectiveness of oral contraceptives. However, new research shows that antibiotics, with the exception of rifampin and rifabutin, do not affect the effectiveness of hormonal contraceptives, such as the pill, patch or vaginal ring.<ref>{{cite journal |doi=10.1016/j.contraception.2010.08.020 |title=Antibiotics and oral contraceptive failure — a case-crossover study |year=2011 |last1=Toh |first1=Sengwee |last2=Mitchell |first2=Allen A. |last3=Anderka |first3=Marlene |last4=de Jong-Van den Berg |first4=Lolkje T.W. |last5=Hernández-Díaz |first5=Sonia |journal=Contraception |volume=83 |issue=5 |pages=418–25 |pmid=21477683 |author6=National Birth Defects Prevention Study |pmc=3326585}}</ref> This change in advice comes because to date there is no evidence that conclusively demonstrates that antibiotics (other than rifampicin or rifabutin) affect these contraceptives.
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Azithromycin suspension has an objectionable taste, so it can be difficult to administer to young children, i.e., 2–5 years, who may spit it out.<ref>{{cite web |url=http://www.ehow.co.uk/how_7369920_give-child-azithromycin.html |title=How to Give a Child Azithromycin |first=China |last=Zmuida |date= |accessdate=2013-01-06}}{{MEDRS|date=September 2013}}{{self-published inline|date=September 2013}}</ref>
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Occasionally, patients have developed cholestatic [[hepatitis]] or [[delirium]]. Accidental intravenous overdosage in an infant caused severe heart block, resulting in residual encephalopathy.<ref>{{cite journal |doi=10.1592/phco.2006.26.1.147 |title=Life-Threatening Bradyarrhythmia After Massive Azithromycin Overdose |year=2006 |last1=Tilelli |first1=John A. |last2=Smith |first2=Kathleen M. |last3=Pettignano |first3=Robert |journal=Pharmacotherapy |volume=26 |pages=147–50 |pmid=16506357 |issue=1}}</ref><ref>{{ cite book | author = Baselt, R. | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | year = 2008 | pages = 132–133 }}</ref>
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In 2013, the FDA issued a warning saying that azithromycin "can cause abnormal changes in the electrical activity of the heart that may lead to a potentially fatal irregular heart rhythm." The FDA noted in the warning a 2012 study released by the ''New England Journal of Medicine'' that found the drug may increase the risk of death, especially in those with heart problems, compared with those on other antibiotics such as amoxicillin or no antibiotic. The warning indicated that people with preexistent conditions are at particular risk, such as those with QT interval prolongation, low blood levels of potassium or magnesium, a slower than normal heart rate, or those who use of certain drugs used to treat abnormal heart rhythms, or arrhythmias.<ref>{{cite news |work=[[The New York Times]] |title=Popular Antibiotic May Raise Risk of Sudden Death |author=Denise Grady |date=May 16, 2012|accessdate=May 18, 2012 | url = http://www.nytimes.com/2012/05/17/health/research/popular-antibiotic-may-raise-risk-of-sudden-death.html }}</ref><ref name="pmid22591294">{{cite journal |doi=10.1056/NEJMoa1003833 |title=Azithromycin and the Risk of Cardiovascular Death |year=2012 |last1=Ray |first1=Wayne A. |last2=Murray |first2=Katherine T. |last3=Hall |first3=Kathi |last4=Arbogast |first4=Patrick G. |last5=Stein |first5=C. Michael |journal=New England Journal of Medicine |volume=366 |issue=20 |pages=1881–90 |pmid=22591294 |pmc=3374857}}</ref><ref>[http://www.fda.gov/Drugs/DrugSafety/ucm304372.htm FDA Statement regarding azithromycin (Zithromax, '''Azithrocin''') and the risk of cardiovascular death]</ref><ref>[http://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm304503.htm Zithromax (azithromycin): FDA Statement on risk of cardiovascular death]</ref><ref>[http://www.fda.gov/drugs/drugsafety/ucm341822.htm FDA Drug Safety Communication: Azithromycin (Zithromax or Zmax) and the risk of potentially fatal heart rhythms]</ref>
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== Mechanism of action ==
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Azithromycin prevents [[bacterium|bacteria]] from growing by interfering with their [[protein synthesis]]. It binds to the 50S subunit of the bacterial [[ribosome]], and thus inhibits [[translation (biology)|translation]] of [[mRNA]]. Nucleic acid synthesis is not affected.<ref>{{cite web|url=http://www.medicinenet.com/azithromycin/article.htm |title=azithromycin (Zithromax, Zmax, Z-Pak) - Side Effects, Drug Interactions |publisher=MedicineNet |date= |accessdate=2013-01-06}}</ref>
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== Spectrum of bacterial susceptibility and resistance ==
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''[[Chlamydia pneumoniae]], [[Chlamydia trachomatis]], [[Eikenella corrodens]], [[Escherichia coli]], [[Haemophilus influenzae]], [[Moraxella catarrhalis]], Mycobacterium chelonae, Mycoplasma fermentans, [[Neisseria gonorrhoeae]]'' and ''[[Ureaplasma urealyticum]]'' are generally susceptible to azithromycin dihydrate, while ''[[Pseudomonas aeruginosa]], and [[Staphylococcus aureus]] ''are resistant to azithromycin dihydrate. In general, Streptococcus pyogenes is susceptible.<ref>{{cite journal |doi=10.1099/00222615-43-5-386 |title=Susceptibility of Streptococcus pyogenes to azithromycin, clarithromycin, erythromycin and roxithromycin in vitro |year=1995 |last1=Van Asselt |first1=G. J. |last2=Sloos |first2=J. H. |last3=Mouton |first3=R. P. |last4=Van Boven |first4=C. P. A. |last5=Van De Klundert |first5=J. A. M. |journal=Journal of Medical Microbiology |volume=43 |issue=5 |pages=386–91 |pmid=7563004}}</ref> Some ''[[Brevibacterium]]'' spp., ''Corynebacterium amycolatum, [[Haemophilus influenzae]]'' and ''[[Mycobacterium abscessus]]'' have developed resistance to azithromycin dihydrate to varying degrees.<ref>{{cite web |title=Azithromycin Dihydrate – Product Data Sheet |url=http://www.toku-e.com/Upload/Products/PDS/20120517005791.pdf |date=December 1, 2010 |publisher=[[TOKU-E]]}}</ref>
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== Pharmacokinetics ==
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{{unreferenced section|date=May 2012}}
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Unlike erythromycin, azithromycin is acid-stable, so it can be taken orally with no need of protection from gastric acids. It is readily absorbed, but its absorption is greater on an empty stomach. Time to peak concentration in adults is 2.1 to 3.2 hours for oral dosage forms and one to two hours after a dose. 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,{{fact|date=November 2011}} due to [[ion trapping]] and its high lipid solubility (volume of distribution is too high).
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{{!}} bgcolor="#ddeeff" {{!}} [[SMILES]]
Azithromycin's half-life allows a large single dose to be administered and yet maintain bacteriostatic levels in the infected tissue for several days.
{{!}} bgcolor="#eeeeee" {{!}} <!-- exluded until it is clear how we can use a nowiki-tag for template replacements <small><small><small><small>{{{smiles}}}</small></small></small></small><br> --><span class="reflink plainlinksneverexpand">[http://www.emolecules.com/cgi-bin/search?t=ex&q={{urlencode:{{{smiles}}}}} eMolecules]</span> & <span class="reflink plainlinksneverexpand">[http://pubchem.ncbi.nlm.nih.gov/search/?smarts={{urlencode:{{{smiles}}}}} PubChem]</span>
 
}} }}
== Metabolism ==
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{{#ifeq: {{{type|}}} | combo | | {{#if:{{{synonyms|}}} |
According to Davis' Drug Guide for Nurses, following a single dose of 500&nbsp;mg, the half-life of azithromycin is 11–14 h. The longer half-life of 68 h is achieved only when multiple doses are consumed. [[bilirubin|Biliary]] excretion of azithromycin, predominantly unchanged, is a major route of elimination. Over the course of a week, approximately 6% of the administered dose appears as unchanged drug in [[urine]].
{{!}} bgcolor="#ddeeff" {{!}} [[Синонім]]и
 
{{!}} bgcolor="#eeeeee" {{!}} {{{synonyms}}}
== Etymology ==
}} }}
{{unreferenced section|date=May 2012}}
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The name Azithromycin is derived from the '''az'''ane-substituent and [[erythromycin]].
{{#ifeq: {{{type|}}} | combo | | {{#if:{{{density|}}} | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Фізичні дані''' |
 
{{#if:{{{melting_point|}}} | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Фізичні дані''' |
== History ==
{{#if:{{{boiling_point|}}} | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Фізичні дані''' |
A team of researchers at the [[Croatia]]n pharmaceutical company [[Pliva]] — Gabrijela Kobrehel, Gorjana Radobolja-Lazarevski, and Zrinka Tamburašev, led by Dr. Slobodan Đokić — discovered azithromycin in 1980. It was patented in 1981. 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. Pliva put its azithromycin on the market in Central and Eastern Europe under the brand name of Sumamed in 1988. Pfizer launched azithromycin under Pliva's license in other markets under the brand name Zithromax in 1991.<ref>{{cite journal|last=Banić Tomišić|first=Z.|title=The Story of Azithromycin|journal=Kemija u industriji|year=2011|volume=60|issue=12|pages=603–617|issn=00229830|url=http://pierre.fkit.hr/hdki/kui/en/vol60/abstracts/617.html}}</ref> Pfizer's exclusive rights have since lapsed and Pliva-manufactured azithromycin is also marketed in the United States by generic drug maker [[Teva Pharmaceuticals]] (which now owns Pliva).
{{#if:{{{solubility|}}} | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Фізичні дані''' |
 
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After several years, the [[Food and Drug Administration|U.S. Food and Drug Administration]] (FDA) approved AzaSite, an ophthalmic formulation of azithromycin, for the treatment of eye infections. AzaSite is marketed in the U.S. and Canada by Inspire Pharmaceuticals, a wholly owned subsidiary of [[Merck & Co.|Merck]].<ref>{{ cite press release | url = http://www.merck.com/newsroom/news-release-archive/corporate/2011_0516.html | title = Merck Completes Acquisition of Inspire Pharmaceuticals, Inc. | publisher = Merck }}</ref>
}} }} }} }} }} }} }}
 
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In 2010 azithromycin was the most prescribed antibiotic in outppatients in the US<ref>{{ cite nejm | url = http://www.nejm.org/doi/full/10.1056/NEJMc1212055 | title = U.S. Outpatient Antibiotic Prescribing, 2010 | publisher = nejm}}</ref>, whereas in Sweden where outpatient antibiotic usage is a third macrolides are only on 4% of presriptions. <ref>{{ cite nejm | url = http://www.nejm.org/doi/full/10.1056/NEJMc1306863 | title = More on U.S. Outpatient Antibiotic Prescribing, 2010 | publisher = nejm}}</ref>
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{{!}} bgcolor="#ddeeff" {{!}} [[Густина]]
== Available forms ==
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[[File:Azithromycin 250mg.jpg|thumb|Azithromycin 250 mg capsules ("Z-Pak") from Serbia]]
}} }}
[[File:Sumamed tablete 091208.jpg|thumb|Sumamed - azithromycin tablets from Croatia]]
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Azithromycin is commonly administered in tablet or oral [[suspension (chemistry)|suspension]] (a one-dose version was made available in 2005). It is also available for [[intravenous therapy|intravenous]] [[injection (medicine)|injection]] and in a 1% ophthalmic solution. Tablets come in doses of 250&nbsp;mg and 500&nbsp;mg. Oral suspension comes in strengths of 100&nbsp;mg/5 ml and 200&nbsp;mg/5 ml. The 250-mg tablets are often dispensed in packages of six and commonly referred to as a "Z-Pak," whereas the 500-mg tablets are commonly available commercially in a pack of three tablets, or "Tri-Pak," intended as a three-day treatment. A common dose of oral azithromycin therapy consists of a "double dose" of medication on the first day of treatment and subsequent treatment for four or five additional days. With the "Z-Pak", this means two 250-mg tablets (a total of 500&nbsp;mg) on the first day and one 250-mg tablet once daily for the next four days.
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{{!}} bgcolor="#ddeeff" {{!}} [[Температура плавлення|Т плавлення]]
Pfizer brand name, i.e. Zithromax, azithromycin tablets are mottled pink, unscored, film-coated, modified oval-shaped tablets containing azithromycin monohydrate and the following inactive ingredients: [[butylated hydroxytoluene]], [[calcium phosphate]], [[carmine]], [[colloidal]] [[silicon dioxide]], [[FD&C]] [[Allura Red AC|red # 40]] [[Food coloring#Dyes and lakes|lake]], [[FD&C]] [[Sunset Yellow FCF|yellow # 6]] [[Food coloring#Dyes and lakes|lake]], [[hypromellose]] (2910, 15cP), [[lactose|lactose monohydrate]], [[magnesium stearate]], [[Starch|pregelatinized starch]], [[sodium lauryl sulfate]], [[talc]], [[titanium dioxide]], and [[triacetin]]. In Colombia (South America), it is marketed under the name Zaret from Laboratorios Bussié. In Bangladesh, it is marketed under the name Azithin from Chemist Laboratories Ltd. and Penalox from Rephco Pharmaceuticals Limited.
{{!}} bgcolor="#eeeeee" {{!}} {{{melting_point}}}{{#if:{{{melting_high|}}}| –{{{melting_high}}}}}&nbsp;°C ({{#expr: ( {{{melting_point}}} * 9 / 5 ) + 32 round 0 }}{{#if:{{{melting_high|}}}| –{{#expr: ( {{{melting_high}}} * 9 / 5 ) + 32 round 0 }} }}&nbsp;°F) {{{melting_notes|}}}
In Canada azithromycin is marketed by [[Sandoz]].
}} }}
 
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Azi-Once™ (6 x 250mg capsules) is manufactured by Jamjoom Pharmaceuticals in Jeddah, Kingdom of Saudi Arabia
{{#ifeq: {{{type|}}} | combo | | {{#if:{{{boiling_point|}}} |
 
{{!}} bgcolor="#ddeeff" {{!}} [[Температура кипіння|Т кипіння]]
{{clear}}
{{!}} bgcolor="#eeeeee" {{!}} {{{boiling_point}}}&nbsp;°C ({{#expr: ( {{{boiling_point}}} * 9 / 5 ) + 32 round 0 }}&nbsp;°F) {{{boiling_notes|}}}
 
}} }}
== References ==
|-
{{reflist|30em}}
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{{!}} bgcolor="#ddeeff" {{!}} [[Розчинність]] у [[Вода|воді]]
== External links ==
{{!}} bgcolor="#eeeeee" {{!}} {{{solubility}}}&nbsp;мг/мл (20&nbsp;°C)
* {{Medicinenet|azithromycin}}
}} }}
* {{cite web | url = http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Azithromycin | title = Azithromycin | work = Drug Information Portal | publisher = [[United States National Library of Medicine]] (NLM) }}
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* [http://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0001009/ Azithromycin] PubMed Health
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* [http://www.drugs.com/dosage/azithromycin.html Azithromycin Dosage] on Drugs.com
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[[Category:Antimalarial agents]]
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[[Category:Macrolide antibiotics]]
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[[Category:Pfizer]]
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[[Category:World Health Organization essential medicines]]
}} }}
[[Category:Croatian inventions]]
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{{#ifeq: {{{type|}}} | combo | | {{!}} colspan="2" bgcolor="#dddddd" {{!}} '''Фармакокінетичні дані''' }}
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{{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Біодоступність]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{bioavailability|}}} | {{{bioavailability}}} | ? }} }}
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{{!}}-
{{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Зв'язування з білками плазми|Зв'язування]]
{{!}} bgcolor="#eeeeee" {{!}} {{{protein_bound}}}
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{{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Метаболізм лікувального препарату|Метаболізм]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{metabolism|}}} | {{{metabolism}}} | ? }} }}
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{{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Період напіврозпаду|Період&nbsp;напіврозпаду]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{elimination_half-life|}}} | {{{elimination_half-life}}} | ? }} }}
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{{#ifeq: {{{type|}}} | combo | | {{!}} bgcolor="#ddeeff" style="vertical-align: top;" {{!}} [[Виділення]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} {{#if:{{{excretion|}}} | {{{excretion}}} | ? }} }}
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| colspan="2" bgcolor="#dddddd" | '''Терапевтичні застереження'''
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{{#if:{{{licence_EU|}}} | {{!}} bgcolor="#ddeeff" {{!}} [[Regulation of therapeutic goods|Licence data]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} |
{{#if:{{{licence_US|}}} | {{!}} bgcolor="#ddeeff" {{!}} [[Regulation of therapeutic goods|Licence data]] {{!}}{{!}} bgcolor="#eeeeee" {{!}} |
}} }}
{{#if:{{{licence_EU|}}} | <span class="reflink plainlinksneverexpand">[http://www.emea.europa.eu/humandocs/Humans/EPAR/{{{licence_EU}}}/{{{licence_EU}}}.htm EU]</span>{{#if:{{{licence_US|}}} | ,&nbsp; }}
}}{{#if:{{{licence_US|}}} | <span class="reflink plainlinksneverexpand">[http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.SearchAction&SearchTerm={{{licence_US}}}&SearchType=BasicSearch US]</span>
}}
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| bgcolor="#ddeeff" style="vertical-align: top;" | [[Категорія вагітності|Кат. вагітності]]
| bgcolor="#eeeeee" |
{{#if:{{{pregnancy_AU|}}} |
{{#switch: {{{pregnancy_AU|}}}
| a | A = A
| b1 | B1 = B1
| b2 | B2 = B2
| b3 | B3 = B3
| b | B = B?
| c | C = C
| d | D = D
| x | X = X
| ?
}}<small>([[Австралійський Союз|AU]]) </small>
}}{{#if:{{{pregnancy_US|}}} |
{{#switch: {{{pregnancy_US|}}}
| a | A = A
| b | B = B
| c | C = C
| d | D = D
| x | X = X
| ?
}}<small>([[США]]) </small>
}}{{#if:{{{pregnancy_category|}}} | {{{pregnancy_category}}} | {{#if:{{{pregnancy_AU|}}} | | {{#if:{{{pregnancy_US|}}} | | ? }} }} }}
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| bgcolor="#ddeeff" style="vertical-align: top;" | [[Регулювання терапевтичних препаратів|Лег. статус]]
| bgcolor="#eeeeee" | <!--
All but first country block must start the '{{#ifeq' on same line as preceeding block's closing '}}'.
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{{#if:{{{legal_AU|}}} |
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| unscheduled | Unscheduled = U<small>nscheduled</small> |
| s2 | S2 | Schedule 2 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 2 Pharmacy Medicine|Pharmacy Only (S2)]]
| s3 | S3 | Schedule 3 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 3 Pharmacist Only Medicine|Pharmacist Only (S3)]]
| s4 | S4 | Schedule 4 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 4 Prescription Only Medicine|Prescription Only (S4)]]
| s5 | S5 | Schedule 5 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 5 Caution|Caution (S5)]]
| s6 | S6 | Schedule 6 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 6 Poison|Poison (S6)]]
| s7 | S7 | Schedule 7 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 7 Dangerous Poison|Dangerous Poison (S7)]]
| s8 | S8 | Schedule 8 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 8 Controlled Drug|Controlled (S8)]]
| s9 | S9 | Schedule 9 = [[Standard for the Uniform Scheduling of Drugs and Poisons#Schedule 9 Prohibited Substance|Prohibited (S9)]]
| ?
}}<small>([[Австралійський Союз|AU]]) </small>
}}{{#if:{{{legal_CA|}}} |
{{#switch: {{{legal_CA|}}}
| Schedule I = [[Controlled_Drugs_and_Substances_Act#Schedule_I|Schedule I]]
| Schedule II = [[Controlled_Drugs_and_Substances_Act#Schedule_II|Schedule II]]
| Schedule III = [[Controlled_Drugs_and_Substances_Act#Schedule_II|Schedule III]]
| Schedule IV = [[Controlled_Drugs_and_Substances_Act#Schedule_IV|Schedule IV]]
| Schedule V = [[Controlled_Drugs_and_Substances_Act#Schedule_V|Schedule V]]
| Schedule VI = [[Controlled_Drugs_and_Substances_Act#Schedule_VI_(Precursors)|Schedule VI]]
| Schedule VII = [[Controlled_Drugs_and_Substances_Act#Schedule_VII|Schedule VII]]
| Schedule VIII= [[Controlled_Drugs_and_Substances_Act#Schedule_VIII|Schedule VIII]]
| ?
}}<small>([[Канада|CA]]) </small>
}}{{#if:{{{legal_UK|}}} |
{{#switch: {{{legal_UK|}}}
| gsl | GSL = GSL
| p | P =P
| pom | POM = [[Prescription drug|POM]]
| cd | CD =CD
| Class A = [[Misuse_of_Drugs_Act_1971#Class_A_drugs|Class A]]
| Class B = [[Misuse_of_Drugs_Act_1971#Class_B_drugs|Class B]]
| Class C = [[Misuse_of_Drugs_Act_1971#Class_C_drugs|Class C]]
| ?
}}<small>([[Велика Британія|UK]]) </small>
}}{{#if:{{{legal_US|}}} |
{{#switch: {{{legal_US|}}}
| otc | OTC = [[Over-the-counter drug|OTC]]
| {{Unicode|℞}}-only | {{Unicode|℞}} | rx | Rx | rx-only | Rx-only = [[Prescription drug|{{Unicode|℞}}<small>-only</small>]]
| Schedule I = [[Controlled_Substances_Act#Schedule_I_drugs|Schedule I]]
| Schedule II = [[Controlled_Substances_Act#Schedule_II_drugs|Schedule II]]
| Schedule III = [[Controlled_Substances_Act#Schedule_III_drugs|Schedule III]]
| Schedule IV = [[Controlled_Substances_Act#Schedule_IV_drugs|Schedule IV]]
| Schedule V = [[Controlled_Substances_Act#Schedule_V_drugs|Schedule V]]
| ?
}}<small>([[США|US]]) </small>
}}{{#if:{{{legal_status|}}} |
{{#switch: {{{legal_status|}}}
| rx | RX | Rx | rx-only | Rx-only = {{Unicode|℞}} P<small>rescription only</small>
| {{{legal_status}}}
}}
}}
|-
{{#if:{{{dependency_liability|}}} |
{{!}}-
{{!}} bgcolor="#ddeeff" style="vertical-align: top; white-space: nowrap;" {{!}} [[Наркоманія|Залежність]]
{{!}} bgcolor="#eeeeee" style="vertical-align: top;" {{!}} {{{dependency_liability}}}
}}
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| bgcolor="#ddeeff" style="vertical-align: top;" | [[Засіб використання|Використання]]
| bgcolor="#eeeeee" | {{#if:{{{routes_of_administration|}}} | {{{routes_of_administration}}} | ? }}
{{#if: {{{chemical_formula|}}} | [[Category:Drug pages needing formula fontification]] |}}
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|}<noinclude>
{{documentation}}
</noinclude>
Отримано з https://uk.wikipedia.org/wiki/Шаблон:Drugbox