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    Chemistry

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    Also known as: 81103-11-9, Biaxin, 6-o-methylerythromycin, Klaricid, 6-o-methylerythromycin a, Abbott-56268
    Molecular Formula
    C38H69NO13
    Molecular Weight
    748.0  g/mol
    InChI Key
    AGOYDEPGAOXOCK-KCBOHYOISA-N
    FDA UNII
    H1250JIK0A
    Clarithromycin
    A semisynthetic macrolide antibiotic derived from ERYTHROMYCIN that is active against a variety of microorganisms. It can inhibit protein synthesis in bacteria by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation.
    Clarithromycin is a Macrolide Antimicrobial. The mechanism of action of clarithromycin is as a Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 3A Inhibitor, and P-Glycoprotein Inhibitor.
    1 2D Structure

    Clarithromycin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
    2.1.2 InChI
    InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
    2.1.3 InChI Key
    AGOYDEPGAOXOCK-KCBOHYOISA-N
    2.1.4 Canonical SMILES
    CCC1C(C(C(C(=O)C(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)OC)C)C)O)(C)O
    2.1.5 Isomeric SMILES
    CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[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)OC)C)C)O)(C)O
    2.2 Other Identifiers
    2.2.1 UNII
    H1250JIK0A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-o-methylerythromycin

    2. A 56268

    3. A-56268

    4. A56268

    5. Biaxin

    6. Te 031

    7. Te-031

    8. Te031

    2.3.2 Depositor-Supplied Synonyms

    1. 81103-11-9

    2. Biaxin

    3. 6-o-methylerythromycin

    4. Klaricid

    5. 6-o-methylerythromycin A

    6. Abbott-56268

    7. Clarithromycine

    8. Clathromycin

    9. Macladin

    10. Klacid

    11. Veclam

    12. Erythromycin, 6-o-methyl-

    13. Mavid

    14. Naxy

    15. A-56268

    16. Te-031

    17. Clarith

    18. Cyllind

    19. Kofron

    20. Zeclar

    21. Clarithromycinum

    22. Clarithromycin Identity

    23. Biaxin Xl

    24. Te031

    25. Nsc-758704

    26. Prevpac

    27. Chebi:3732

    28. H1250jik0a

    29. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-(((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

    30. Claritromicina

    31. Abbotic

    32. Astromen

    33. Bicrolid

    34. Clacine

    35. Clambiotic

    36. Claribid

    37. Claricide

    38. Claridar

    39. Claripen

    40. Fromilid

    41. Heliclar

    42. Klaciped

    43. Mabicrol

    44. Clacee

    45. Clacid

    46. Clarem

    47. Crixan

    48. Cyllid

    49. Klabax

    50. Klarid

    51. Klarin

    52. Maclar

    53. Helas

    54. Adel

    55. Biaxin Filmtab

    56. Klax

    57. Biaxin Hp

    58. Biaxin Xl Filmtab

    59. Klaricid Pediatric

    60. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

    61. Cla

    62. Clarithromycin Extended Release

    63. Drg-0099

    64. Klaricid H.p.

    65. Cty

    66. Smr000466382

    67. Clarithromycine [inn-french]

    68. Clarithromycinum [inn-latin]

    69. Claritromicina [inn-spanish]

    70. Sr-05000001992

    71. Clarithromycin (biaxin, Klacid)

    72. Clarithromycina

    73. Unii-h1250jik0a

    74. Clarosip

    75. Ccris 8833

    76. Klaricid Xl

    77. Hsdb 8055

    78. (14r)-14-hydroxyclarithromycin

    79. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

    80. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy

    81. Clarithromycin,(s)

    82. Biaxin (tn)

    83. Spectrum_000089

    84. Cpd000466382

    85. Clarithromycin [usan:usp:inn:ban:jan]

    86. Specplus_000559

    87. 6-o-methyl Erythromycin

    88. O(6)-methylerythromycin

    89. Spectrum2_001668

    90. Spectrum3_001667

    91. Spectrum4_000629

    92. Spectrum5_001729

    93. 6-0-methylerythromycin A

    94. A56268

    95. Clarithromycin [mi]

    96. Chembl1741

    97. Clarithromycin [inn]

    98. Clarithromycin [jan]

    99. Schembl38125

    100. Bspbio_003453

    101. Kbiogr_001218

    102. Kbioss_000509

    103. Mls000759516

    104. Mls001201751

    105. Mls001424066

    106. Bidd:gt0200

    107. Clarithromycin [vandf]

    108. Divk1c_006655

    109. Spectrum1504231

    110. Spbio_001855

    111. Clarithromycin [mart.]

    112. Lactoferrin B & Clarithromycin

    113. Lactoferrin H & Clarithromycin

    114. Clarithromycin [usp-rs]

    115. Clarithromycin [who-dd]

    116. Dtxsid3022829

    117. Clarithromycin & Interleukin-12

    118. Clm & Il-12

    119. Gtpl10903

    120. Kbio1_001599

    121. Kbio2_000509

    122. Kbio2_003077

    123. Kbio2_005645

    124. Kbio3_002673

    125. Anx-015

    126. Sdp-015

    127. Clarithromycin (jp17/usp/inn)

    128. Clarithromycin, >=95% (hplc)

    129. Clarithromycin, >=98% (hplc)

    130. Hms1922h09

    131. Hms2051g18

    132. Hms2090o11

    133. Hms2094m05

    134. Hms2231a08

    135. Hms3715j17

    136. Pharmakon1600-01504231

    137. Clarithromycin [orange Book]

    138. Bdbm50404044

    139. Ccg-39086

    140. Clarithromycin [ep Monograph]

    141. Clarithromycin [usp Impurity]

    142. Lmpk04000014

    143. Nsc758704

    144. S2555

    145. Zinc85534098

    146. Clarithromycin [usp Monograph]

    147. Akos015894242

    148. Prevpac Component Clarithromycin

    149. Cs-2576

    150. Db01211

    151. Nc00140

    152. Nsc 758704

    153. Clarithromycin Identity [usp-rs]

    154. Ncgc00178054-01

    155. Ncgc00178054-06

    156. Clarithromycin 100 Microg/ml In Methanol

    157. Clarithromycin Component Of Prevpac

    158. Hy-17508

    159. Sbi-0206716.p001

    160. Clarithromycin 100 Microg/ml In Acetonitrile

    161. C06912

    162. D00276

    163. F14975

    164. Ab00053394-10

    165. Ab00053394-12

    166. Ab00053394-13

    167. Ab00053394_14

    168. Ab00053394_15

    169. 103c119

    170. A840042

    171. Q118551

    172. Q-200870

    173. Sr-05000001992-1

    174. Sr-05000001992-2

    175. Brd-k49668410-001-07-1

    176. Brd-k49668410-001-18-8

    177. Clarithromycin, European Pharmacopoeia (ep) Reference Standard

    178. Clarithromycin, United States Pharmacopeia (usp) Reference Standard

    179. Clarithromycin Identity, United States Pharmacopeia (usp) Reference Standard

    180. Clarithromycin, Ready Made Solution, 50 Mg/ml In Dmso, 0.2 Mum Filtered

    181. Clarithromycin For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    182. Clarithromycin, Pharmaceutical Secondary Standard; Certified Reference Material

    183. (3r,4s,5r,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4r,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacy

    184. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-((2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-14-ethyl-12,13-dihydroxy-4-((2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yloxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

    185. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dion

    186. (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred Name)

    187. (3r,4s,5s,6r,7r,9r,11s, 12r,13s,14s)-6-{[(2s,3r,4s,6r)- 4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy- 4-{[(2r,4s,5s,6s)-5-hydroxy-4-methoxy-4,6- Dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1- Oxacyclotetradecane-2,10-dione

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 748.0 g/mol
    Molecular Formula C38H69NO13
    XLogP33.2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count8
    Exact Mass747.47689126 g/mol
    Monoisotopic Mass747.47689126 g/mol
    Topological Polar Surface Area183 Ų
    Heavy Atom Count52
    Formal Charge0
    Complexity1