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    Azithromycin Monohydrate
    Also known as: 117772-70-0, Vinzam, Toraseptol, Azithromycin (hydrate), Azitro, 5fd1131i7s
    Molecular Formula
    C38H76N2O14
    Molecular Weight
    785.0  g/mol
    InChI Key
    SRMPHJKQVUDLQE-KUJJYQHYSA-N
    FDA UNII
    5FD1131I7S
    A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis.
    1 2D Structure

    Azithromycin Monohydrate

    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;dihydrate
    2.1.2 InChI
    InChI=1S/C38H72N2O12.2H2O/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;2*1H2/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
    SRMPHJKQVUDLQE-KUJJYQHYSA-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.O.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.O.O
    2.2 Other Identifiers
    2.2.1 UNII
    5FD1131I7S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Azadose

    2. Azithromycin

    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. 117772-70-0

    2. Vinzam

    3. Toraseptol

    4. Azithromycin (hydrate)

    5. Azitro

    6. 5fd1131i7s

    7. 117772-70-0 (dihydrate)

    8. Azithromycin Hydrate

    9. Azitromax

    10. Misultina

    11. Tromix

    12. Azadose

    13. Ribotrex

    14. Ultreon

    15. Zenstavion

    16. Azatek

    17. Goxal

    18. (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 Dihydrate

    19. Azithromycin (as Dihydrate)

    20. Odaz

    21. (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 Dihydrate

    22. Aciphar

    23. Acitrocin

    24. Azidromic

    25. Azitral

    26. Azitrix

    27. Azitrom

    28. Azitrox

    29. Azitroxil

    30. Azimix

    31. Unii-5fd1131i7s

    32. Azitrona Klonal

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

    34. Azithromycin [mart.]

    35. Schembl134723

    36. Chebi:34546

    37. Dtxsid80922539

    38. Azithromycin Dihydrate 100 Microg/ml In Acetonitrile

    39. Azithromycin Hydrate [jan]

    40. Azithromycin Dihydrate [mi]

    41. Ac-093

    42. Hy-17506a

    43. Azithromycin Dihydrate [vandf]

    44. Akos015896370

    45. Azithromycin Dihydrate [who-dd]

    46. Azithromycin Dihydrate, >=98% (hplc)

    47. (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 Dihydrate

    48. 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)-, Dihydrate, (2r-(2r*,3s*,4r*,5r*,8r*,10r*,11r*,12s*,13s*,14r*))-

    49. Azithromycin Dihydrate [orange Book]

    50. Azithromycin Dihydrate [ep Monograph]

    51. Azithromycin Dihydrate [usp Monograph]

    52. 772a700

    53. N-methyl-11-aza-10-deoxo-10-dihydro Erythromycin A

    54. Q27116139

    55. Azithromycin, United States Pharmacopeia (usp) Reference Standard

    56. N-methyl-11-aza-10-deoxo-10-dihydroerythromycin A Dihydrate

    57. Azithromycin, Pharmaceutical Secondary Standard; Certified Reference Material

    58. (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-onedihydrate

    59. (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-o

    60. (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;dihydrate

    61. 1-oxa-6-azacyclopentadecan-15-one, 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]-, Dihydrate, (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 785.0 g/mol
    Molecular Formula C38H76N2O14
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count7
    Exact Mass784.52965510 g/mol
    Monoisotopic Mass784.52965510 g/mol
    Topological Polar Surface Area182 Ų
    Heavy Atom Count54
    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 Count3
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Macrolides [CS]; Macrolide Antimicrobial [EPC]
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