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    Synopsis

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    Chemistry

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    Also known as: Zithromax, 83905-01-5, Sumamed, Hemomycin, Azasite, Zitromax
    Molecular Formula
    C38H72N2O12
    Molecular Weight
    749.0  g/mol
    InChI Key
    MQTOSJVFKKJCRP-BICOPXKESA-N
    FDA UNII
    J2KLZ20U1M
    Azithromycin
    A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.
    Azithromycin anhydrous is a Macrolide Antimicrobial.
    1 2D Structure

    Azithromycin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 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
    2.1.3 InChI Key
    MQTOSJVFKKJCRP-BICOPXKESA-N
    2.1.4 Canonical SMILES
    CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
    2.1.5 Isomeric SMILES
    CC[C@@H]1[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O
    2.2 Other Identifiers
    2.2.1 UNII
    J2KLZ20U1M
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Azadose

    2. Azithromycin Dihydrate

    3. Azithromycin Monohydrate

    4. Azitrocin

    5. Azythromycin

    6. Cp 62993

    7. Cp-62993

    8. Cp62993

    9. Dihydrate, Azithromycin

    10. Goxal

    11. Monohydrate, Azithromycin

    12. Sumamed

    13. Toraseptol

    14. Ultreon

    15. Vinzam

    16. Zentavion

    17. Zithromax

    18. Zitromax

    2.3.2 Depositor-Supplied Synonyms

    1. Zithromax

    2. 83905-01-5

    3. Sumamed

    4. Hemomycin

    5. Azasite

    6. Zitromax

    7. Zmax

    8. Azithromycine

    9. Azithromycinum

    10. Azenil

    11. Aziromycin

    12. Zithromac

    13. Azithromycine [french]

    14. Azithromycinum [latin]

    15. Azithromycin Dihydrate

    16. Cp 62993

    17. Cp-62993

    18. Azitromax

    19. Misultina

    20. Tromix

    21. Azithromycin Anhydrous

    22. Azithrocin

    23. Aruzilina

    24. Macrozit

    25. Trozocina

    26. Xithrone

    27. Zythromax

    28. Aziwin

    29. Durasite

    30. Xz-450

    31. Toraseptol

    32. Anhydrous Azithromycin

    33. 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A

    34. J2klz20u1m

    35. Chebi:2955

    36. (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

    37. Azitrocin

    38. Xz 405

    39. Xz 450

    40. Nsc-758625

    41. (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

    42. Ncgc00090753-01

    43. Aritromicina

    44. Mixoterin

    45. Zithrax

    46. Zitrotek

    47. Aziwok

    48. Aztrin

    49. Setron

    50. Zitrim

    51. Tobil

    52. Zifin

    53. Cp-62,993

    54. Zeto

    55. Zmas

    56. Zithromax Iv

    57. Dsstox_cid_10760

    58. Dsstox_rid_78858

    59. Dsstox_gsid_30760

    60. (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-beta-d-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-c-methyl-3-o-methyl-alpha-l-ribo-hexopyranoside

    61. Z-pak

    62. C38h72n2o12

    63. Aritromicina [spanish]

    64. Azitromicine

    65. Azithromycin (as Dihydrate)

    66. Trulimax

    67. Zentavion

    68. Drg-0104

    69. (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

    70. 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]-1-oxa-6-azacyclopentadecan-15-one

    71. Azm

    72. Smr000471864

    73. Zit

    74. Azithromycin (zithromax)

    75. Cas-83905-01-5

    76. Ccris 1961

    77. Azithromycin [inn]

    78. Hsdb 7205

    79. Z-pak (azithromycin)

    80. Azithromycin (anhydrous)

    81. Sr-05000002067

    82. Azithromycin, Antibiotic For Culture Media Use Only

    83. Unii-j2klz20u1m

    84. Brn 5387583

    85. Azithramycine

    86. Azitromicina

    87. Zithromycin

    88. Azifast

    89. Azigram

    90. Azimakrol

    91. Azitromin

    92. Azyter

    93. Azithromycin [usan:inn:ban]

    94. Nsc643732

    95. Azithromycin (aids Initiative)

    96. Azithromycin,(s)

    97. Zmax Sr

    98. (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

    99. (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-b-d-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-c-methyl-3-o-methyl-a-l-ribo-hexopyranoside

    100. Zitromax Avium 600

    101. Azitromicina [spanish]

    102. Spectrum_000307

    103. Azithromycin, Unspecified

    104. Dch3

    105. Spectrum2_001582

    106. Spectrum3_000653

    107. Spectrum4_000186

    108. Spectrum5_001867

    109. Azithromycin [mi]

    110. Chembl529

    111. Azithromycin [hsdb]

    112. Ec 617-500-5

    113. Schembl23481

    114. Bspbio_002285

    115. Kbiogr_000731

    116. Kbioss_000787

    117. (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

    118. 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-hexopyranosyl)oxy)-, (2r-(2r*,3s*,4r*,5r*,8r*,10r*,11r*,12s*,13s*,14r*))-

    119. Mls001055353

    120. Mls001066331

    121. Mls001201763

    122. Mls001304005

    123. Mls001332499

    124. Mls001332500

    125. Azithromycin [who-dd]

    126. Azithromycin, Unspecified Form

    127. Bidd:gt0792

    128. Divk1c_000233

    129. Spectrum1503679

    130. N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A

    131. Spbio_001544

    132. Gtpl6510

    133. Dtxsid8030760

    134. Azithromycin, Analytical Standard

    135. Hms500l15

    136. Kbio1_000233

    137. Kbio2_000787

    138. Kbio2_003355

    139. Kbio2_005923

    140. Kbio3_001505

    141. Ninds_000233

    142. Hms1922g12

    143. Hms2094m11

    144. Hms2232m10

    145. Hms3259d10

    146. Act03224

    147. Azithromycin [usp Monograph]

    148. Tox21_111008

    149. Tox21_201011

    150. Bdbm50373918

    151. Ccg-39360

    152. Mfcd00873574

    153. Zinc85537026

    154. Akos015895044

    155. Db00207

    156. Nc00712

    157. Nsc 758625

    158. Azithromycin 100 Microg/ml In Methanol

    159. Idi1_000233

    160. Ncgc00090753-02

    161. Ncgc00090753-03

    162. Ncgc00090753-04

    163. Ncgc00090753-06

    164. Ncgc00258564-01

    165. Ac-16014

    166. Cp62,993

    167. Hy-17506

    168. Sbi-0206706.p001

    169. Cp-62993-3

    170. A-9940

    171. A-9941

    172. N46072

    173. Ab00698251-10

    174. Ab00698251_11

    175. 905a015

    176. A905251

    177. Q165399

    178. Sr-05000002067-1

    179. Sr-05000002067-2

    180. Brd-k74501079-001-18-1

    181. Z1563146014

    182. Azithromycin, European Pharmacopoeia (ep) Reference Standard

    183. Azithromycin Identity, United States Pharmacopeia (usp) Reference Standard

    184. (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-((2s,3r,4s,6r)-

    185. Azithromycin For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    186. Azithromycin For System Suitability, European Pharmacopoeia (ep) Reference Standard

    187. (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-2-ethyl-3,4,10-trihydroxy-13-((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yloxy)-3,5,6,8,10,12,14-heptamethy...

    188. (2r,3s,4r,5r,8r,10r,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

    189. (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

    190. (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

    191. [2r-(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-

    192. 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

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 749.0 g/mol
    Molecular Formula C38H72N2O12
    XLogP34
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count7
    Exact Mass748.50852574 g/mol
    Monoisotopic Mass748.50852574 g/mol
    Topological Polar Surface Area180 Ų
    Heavy Atom Count52
    Formal Charge0
    Complexity1150
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameAzasite
    Drug LabelAzaSite (azithromycin ophthalmic solution) is a 1% sterile aqueous topical ophthalmic solution of azithromycin formulated in DuraSite (polycarbophil, edetate disodium, sodium chloride). AzaSite is an off-white, viscous liquid with an osmolality of...
    Active IngredientAzithromycin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyOak Pharms Akorn

    2 of 8  
    Drug NameAzithromycin
    PubMed HealthAzithromycin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelAzithromycin tablets and azithromycin for oral suspension contain the active ingredient azithromycin, an azalide, a subclass of macrolide antibiotics, for oral administration. Azithromycin has the chemical name (2R,3S,4R,5R,8R, 10R,11R,12S,13S,14R)-1...
    Active IngredientAzithromycin
    Dosage FormInjectable; Tablet; Solution; For suspension
    Routeophthalmic; Injection; Oral
    Strength1%; eq 600mg base; eq 500mg base; eq 500mg base/vial; eq 100mg base/5ml; eq 250mg base; eq 200mg base/5ml
    Market StatusTentative Approval; Prescription
    CompanyWockhardt; Sagent Strides; Teva Pharms; Fresenius Kabi Usa; Hospira; Gland Pharma; Teva; Apotex; Sun Pharm Inds; Pliva; Sandoz; Mylan