View source for It:Azithromycin

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! {{chembox header}}  colspan="3" |Azithromycin
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! {{chembox header}}  colspan="3" |Structure
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Azithromycin.png|200px|Azithromycin]] 
|-
! {{chembox header}}  colspan="3" |3D structure
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| align="center" colspan="3" bgcolor="#ffffff" | <jmol>
<jmolApplet>
<size>200</size>
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<inlineContents>REMARK   MSI WebLab Viewer PDB file
REMARK   Created:  Fri Oct 20 12:51:30 GMT Standard Time 2006
ATOM      1  C           0      -5.513  -2.324  -1.374  0.00  0.00
ATOM      2  C           0      -5.807  -0.900  -0.900  0.00  0.00
ATOM      3  C           0      -4.541  -0.293  -0.294  0.00  0.00
ATOM      4  O           0      -3.526  -0.151  -1.320  0.00  0.00
ATOM      5  C           0      -4.862   1.091   0.289  0.00  0.00
ATOM      6  C           0      -5.293   2.017  -0.848  0.00  0.00
ATOM      7  O           0      -5.920   0.965   1.238  0.00  0.00
ATOM      8  C           0      -3.609   1.642   0.967  0.00  0.00
ATOM      9  H           0      -2.830   1.775   0.212  0.00  0.00
ATOM     10  O           0      -3.151   0.695   1.938  0.00  0.00
ATOM     11  C           0      -3.897   2.967   1.651  0.00  0.00
ATOM     12  H           0      -4.943   3.256   1.514  0.00  0.00
ATOM     13  C           0      -3.596   2.894   3.143  0.00  0.00
ATOM     14  N           0      -3.056   4.039   1.023  0.00  0.00
ATOM     15  C           0      -3.215   5.141   2.036  0.00  0.00
ATOM     16  C           0      -1.660   3.589   1.321  0.00  0.00
ATOM     17  C           0      -0.799   3.883   0.085  0.00  0.00
ATOM     18  C           0       0.566   3.215   0.255  0.00  0.00
ATOM     19  H           0       0.461   2.329   0.883  0.00  0.00
ATOM     20  C           0       1.528   4.196   0.938  0.00  0.00
ATOM     21  C           0       1.140   2.816  -1.104  0.00  0.00
ATOM     22  O           0       0.378   3.413  -2.151  0.00  0.00
ATOM     23  C           0       2.586   3.330  -1.193  0.00  0.00
ATOM     24  C           0       1.151   1.293  -1.233  0.00  0.00
ATOM     25  H           0       0.920   0.857  -0.258  0.00  0.00
ATOM     26  O           0       2.466   0.869  -1.616  0.00  0.00
ATOM     27  C           0       3.250   0.827  -0.423  0.00  0.00
ATOM     28  O           0       3.007  -0.401   0.262  0.00  0.00
ATOM     29  C           0       3.662  -0.327   1.526  0.00  0.00
ATOM     30  C           0       3.272  -1.540   2.373  0.00  0.00
ATOM     31  C           0       5.179  -0.316   1.323  0.00  0.00
ATOM     32  C           0       5.564   0.921   0.503  0.00  0.00
ATOM     33  N           0       6.993   0.864   0.168  0.00  0.00
ATOM     34  C           0       7.318   2.128  -0.507  0.00  0.00
ATOM     35  C           0       7.726   0.865   1.441  0.00  0.00
ATOM     36  C           0       4.733   0.933  -0.785  0.00  0.00
ATOM     37  H           0       4.911   1.862  -1.325  0.00  0.00
ATOM     38  O           0       5.107  -0.176  -1.606  0.00  0.00
ATOM     39  C           0       0.147   0.808  -2.277  0.00  0.00
ATOM     40  C           0       0.801   0.841  -3.663  0.00  0.00
ATOM     41  C           0      -0.277  -0.628  -1.966  0.00  0.00
ATOM     42  O           0      -0.427  -0.807  -0.558  0.00  0.00
ATOM     43  C           0       0.042  -2.129  -0.255  0.00  0.00
ATOM     44  H           0       1.085  -2.194  -0.554  0.00  0.00
ATOM     45  O           0      -0.755  -3.071  -0.953  0.00  0.00
ATOM     46  C           0      -0.285  -4.388  -0.765  0.00  0.00
ATOM     47  C           0       1.020  -4.629  -1.523  0.00  0.00
ATOM     48  C           0      -0.169  -4.814   0.686  0.00  0.00
ATOM     49  H           0       0.469  -5.713   0.738  0.00  0.00
ATOM     50  O           0      -1.467  -5.191   1.173  0.00  0.00
ATOM     51  C           0       0.420  -3.755   1.609  0.00  0.00
ATOM     52  O           0       0.006  -4.049   2.959  0.00  0.00
ATOM     53  C           0       0.469  -2.973   3.777  0.00  0.00
ATOM     54  C           0       1.950  -3.787   1.573  0.00  0.00
ATOM     55  C           0      -0.088  -2.361   1.250  0.00  0.00
ATOM     56  C           0      -1.607  -0.943  -2.656  0.00  0.00
ATOM     57  C           0      -1.469  -2.228  -3.478  0.00  0.00
ATOM     58  C           0      -2.674  -1.146  -1.609  0.00  0.00
ATOM     59  O           0      -2.763  -2.206  -1.038  0.00  0.00
ATOM     60  H           0      -5.189  -2.930  -0.528  0.00  0.00
ATOM     61  H           0      -6.416  -2.757  -1.806  0.00  0.00
ATOM     62  H           0      -4.725  -2.302  -2.127  0.00  0.00
ATOM     63  H           0      -6.130  -0.294  -1.747  0.00  0.00
ATOM     64  H           0      -6.595  -0.923  -0.147  0.00  0.00
ATOM     65  H           0      -4.172  -0.940   0.502  0.00  0.00
ATOM     66  H           0      -6.178   1.607  -1.335  0.00  0.00
ATOM     67  H           0      -5.524   3.003  -0.445  0.00  0.00
ATOM     68  H           0      -4.485   2.101  -1.574  0.00  0.00
ATOM     69  H           0      -6.681   0.606   0.762  0.00  0.00
ATOM     70  H           0      -2.360   1.074   2.346  0.00  0.00
ATOM     71  H           0      -2.523   2.767   3.291  0.00  0.00
ATOM     72  H           0      -3.922   3.816   3.625  0.00  0.00
ATOM     73  H           0      -4.126   2.048   3.580  0.00  0.00
ATOM     74  H           0      -2.669   4.882   2.943  0.00  0.00
ATOM     75  H           0      -2.819   6.071   1.627  0.00  0.00
ATOM     76  H           0      -4.271   5.269   2.271  0.00  0.00
ATOM     77  H           0      -1.290   4.159   2.165  0.00  0.00
ATOM     78  H           0      -1.639   2.525   1.516  0.00  0.00
ATOM     79  H           0      -1.307   3.477  -0.793  0.00  0.00
ATOM     80  H           0      -0.672   4.957  -0.024  0.00  0.00
ATOM     81  H           0       1.132   4.472   1.915  0.00  0.00
ATOM     82  H           0       2.502   3.723   1.061  0.00  0.00
ATOM     83  H           0       1.633   5.089   0.323  0.00  0.00
ATOM     84  H           0       0.435   4.370  -2.028  0.00  0.00
ATOM     85  H           0       3.120   3.071  -0.279  0.00  0.00
ATOM     86  H           0       3.083   2.870  -2.047  0.00  0.00
ATOM     87  H           0       2.579   4.413  -1.316  0.00  0.00
ATOM     88  H           0       2.975   1.662   0.221  0.00  0.00
ATOM     89  H           0       3.359   0.585   2.039  0.00  0.00
ATOM     90  H           0       3.663  -2.447   1.911  0.00  0.00
ATOM     91  H           0       3.688  -1.434   3.374  0.00  0.00
ATOM     92  H           0       2.185  -1.605   2.436  0.00  0.00
ATOM     93  H           0       5.676  -0.280   2.293  0.00  0.00
ATOM     94  H           0       5.483  -1.217   0.790  0.00  0.00
ATOM     95  H           0       5.360   1.821   1.082  0.00  0.00
ATOM     96  H           0       7.110   2.962   0.163  0.00  0.00
ATOM     97  H           0       8.374   2.134  -0.778  0.00  0.00
ATOM     98  H           0       6.712   2.225  -1.408  0.00  0.00
ATOM     99  H           0       8.796   0.933   1.244  0.00  0.00
ATOM    100  H           0       7.411   1.719   2.041  0.00  0.00
ATOM    101  H           0       7.515  -0.057   1.982  0.00  0.00
ATOM    102  H           0       4.562  -0.130  -2.403  0.00  0.00
ATOM    103  H           0      -0.735   1.448  -2.274  0.00  0.00
ATOM    104  H           0       1.675   0.190  -3.667  0.00  0.00
ATOM    105  H           0       0.087   0.495  -4.410  0.00  0.00
ATOM    106  H           0       1.106   1.861  -3.896  0.00  0.00
ATOM    107  H           0       0.486  -1.316  -2.339  0.00  0.00
ATOM    108  H           0      -1.042  -5.061  -1.235  0.00  0.00
ATOM    109  H           0       1.805  -4.000  -1.104  0.00  0.00
ATOM    110  H           0       1.306  -5.677  -1.431  0.00  0.00
ATOM    111  H           0       0.880  -4.382  -2.576  0.00  0.00
ATOM    112  H           0      -1.770  -5.925   0.622  0.00  0.00
ATOM    113  H           0       0.056  -3.076   4.780  0.00  0.00
ATOM    114  H           0       1.557  -2.996   3.827  0.00  0.00
ATOM    115  H           0       0.145  -2.025   3.347  0.00  0.00
ATOM    116  H           0       2.303  -3.265   0.683  0.00  0.00
ATOM    117  H           0       2.345  -3.295   2.462  0.00  0.00
ATOM    118  H           0       2.292  -4.821   1.547  0.00  0.00
ATOM    119  H           0       0.497  -1.608   1.784  0.00  0.00
ATOM    120  H           0      -1.137  -2.265   1.542  0.00  0.00
ATOM    121  H           0      -1.897  -0.120  -3.307  0.00  0.00
ATOM    122  H           0      -1.199  -3.053  -2.819  0.00  0.00
ATOM    123  H           0      -2.417  -2.449  -3.967  0.00  0.00
ATOM    124  H           0      -0.693  -2.095  -4.231  0.00  0.00          
TER
</inlineContents>
</jmolApplet>
</jmol>
|-
| align="center" colspan="3" bgcolor="#ffffff" |
|- 
! {{chembox header}} colspan="3" | General
|- 
| colspan="1" |[http://en.wikipedia.org/wiki/IUPAC_nomenclature Systematic name]
| colspan="2"|9-deoxy-9a-aza-9a-methyl-9a- <br />homoerythromycin A
|-
| colspan="1" |Synonyms
| colspan="2" |Zithromax<br />Zmax<br />Sumamed<br />Aztrin
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| colspan="2" |C<sub>38</sub>H<sub>72</sub>N<sub>2</sub>O<sub>12</sub>
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| colspan="2" |CCC(O1)[C@@](C)(O)[C@H](O)[C@@H]<br />(C)N(C)CC[C@H](C)[C@@](O)(C)[C@H]<br />(OC3OC(C)CC(N(C)C)[C@H]3O)C(C)C<br />(O[C@@H]2OC(C)[C@H](O)[C@@](OC)<br />(C)C2)C(C)C1=O
|-
| colspan="1" |[http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| colspan="2" | 748.88 g/mol
|-
| colspan="1" |Appearance
| colspan="2" |Mottled pink tablets
|-
| colspan="1" |[http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| colspan="2" |83905-01-5
|-
| colspan="1" |[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| colspan="2" |J01 FA10
|-
! {{chembox header}} colspan="3"| Pharmacokinetic data
|-
| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| colspan="2" |38% for 250mg capsules
|-
| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| colspan="2" |[http://en.wikipedia.org/wiki/hepatic hepatic]
|-
| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| colspan="2" | 68 hours
|- 
| [http://en.wikipedia.org/wiki/Excretion Excretion]
| colspan="2" | [http://en.wikipedia.org/wiki/biliary Biliary], [http://en.wikipedia.org/wiki/renal Renal]

|-
| {{chembox header}} colspan="3"| <small>Except where noted otherwise, data are given for<br> materials in their [http://en.wikipedia.org/wiki/Standard_state standard state (at 25 &deg;C, 100 kPa)]<br/>[http://en.wikipedia.org/wiki/Wikipedia:Chemical_infobox Infobox disclaimer and references]]</small>
|-
|}

'''Azithromycin''' is one of the world's biggest selling antibiotics, commonly used in the treatment of tonsillitis, bronchitis, pneumonia and many ear and throat infections. It is also an effective treatment for [http://en.wikipedia.org/wiki/chlamydia chlamydia]. Coming in the form of a capsule that can be taken orally in many cases it is prefered to other treatments due to the ease of administration.

==History==
A team of researchers at the Croation laboratory [http://en.wikipedia.org/wiki/Pliva Pliva]led by Dr Slobodan Dokic, discovered azithromycin in 1980. It was patented in 1981, and was later discovered by scientists at [http://en.wikipedia.org/wiki/Pfizer Pfizer] while going through patent documents. In 1986 Pliva and Pfizer signed an agreement which gave Pfizer rights for the sale of azithromycin in Western Europe and the USA. Azithromycin was brought on to the market in Central and Eastern Europe under the brand names of '''Sumamed''' by Pliva in 1988, and  '''Zithromax''' by Pfizer in 1991.

==Structure==
Azithromycin is derived from [http://en.wikipedia.org/wiki/erythromycin erythromycin] but differs from erythromycin by the inclusion of a methyl substituted nitrogen in a 15-membered lactone ring.

==Mode of action==
Azithromycin works by binding to the active site of bacterial ribosomes, this prevents the translation (the "decoding" of a of mRNA to produce a polypeptide chain) and hence the synthesis of proteins, however the synthesis of the bacteria's DNA is not affected.

==Pharmacokinetics==
Unlike its parent compound, erythromycin, azithromycin is stable to acids and can therefore be taken in the form of an oral capsule with no fear of stomach acid breaking it down. It is absorbed easily into most tissues, due to its high solubility in lipids, and is  carried in particularly high concentrations in phagocytes (cells of the [http://en.wikipedia.org/wiki/immune_system immune system] that ingests foreign matter). As the phagocytes collect in large numbers at the site of an infection this means that the antibiotic is present exactly where in the body it is needed.

==Treatment of chlamydia==
Azithromycin is the antibiotic of choice for the treatment of chlamydia due to its unusual pharmokinetic properties. its long half-life means that it remains in cells and tissues at an anti-chlamydial levels for far longer than other simmilarly working antibiotics, meaning a single dose of azithromycin can have the same effect as repeated doses of other drugs. This is particularly useful when a patient may be unlikely to complete a longer couse of antibiotics.