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    Ivermectin Merck Brand

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    2D Structure
    Also known as: Ivermectin, Dihydroavermectin b1a, 70288-86-7, 22,23-dihydroavermectin b1a, 70161-11-4, Ivermectin component b1a
    Molecular Formula
    C48H74O14
    Molecular Weight
    875.1  g/mol
    InChI Key
    AZSNMRSAGSSBNP-XPNPUAGNSA-N
    FDA UNII
    91Y2202OUW
    A mixture of mostly avermectin H2B1a (RN 71827-03-7) with some avermectin H2B1b (RN 70209-81-3), which are macrolides from STREPTOMYCES avermitilis. It binds glutamate-gated chloride channel to cause increased permeability and hyperpolarization of nerve and muscle cells. It also interacts with other CHLORIDE CHANNELS. It is a broad spectrum antiparasitic that is active against microfilariae of ONCHOCERCA VOLVULUS but not the adult form.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
    2.1.2 InChI
    InChI=1S/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1
    2.1.3 InChI Key
    AZSNMRSAGSSBNP-XPNPUAGNSA-N
    2.1.4 Canonical SMILES
    CCC(C)C1C(CCC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)C
    2.2 Other Identifiers
    2.2.1 UNII
    91Y2202OUW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Eqvalan

    2. Ivermectin

    3. Ivomec

    4. Mectizan

    5. Mk 933

    6. Mk-933

    7. Mk933

    8. Stromectol

    2.3.2 Depositor-Supplied Synonyms

    1. Ivermectin

    2. Dihydroavermectin B1a

    3. 70288-86-7

    4. 22,23-dihydroavermectin B1a

    5. 70161-11-4

    6. Ivermectin Component B1a

    7. 71827-03-7

    8. Avermectin H2b1a

    9. 5-o-demethyl-22,23-dihydroavermectin A1a

    10. Chebi:63941

    11. 91y2202ouw

    12. (2ae,4e,5's,6s,6'r,7s,8e,11r,13r,15s,17ar,20r,20ar,20bs)-6'-[(2s)-butan-2-yl]-20,20b-dihydroxy-5',6,8,19-tetramethyl-17-oxo-3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-tetradecahydro-2h,7h-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-4-o-(2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)-3-o-methyl-alpha-l-arabino-hexopyranoside

    13. Mk-933

    14. (1r,4s,5's,6r,6'r,8r,10e,12s,13s,14e,16e,20r,21r,24s)-6'-[(2s)-butan-2-yl]-21,24-dihydroxy-12-[(2r,4s,5s,6s)-5-[(2s,4s,5s,6s)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

    15. Ivermectin B1a-d2

    16. C48h74o14

    17. Unii-91y2202ouw

    18. 22,23-dihydroavermectin B(1)a

    19. Ncgc00163233-01

    20. Ivermectin (ivm)

    21. Ivm

    22. Einecs 276-046-2

    23. Dihydro Avermectin Bla

    24. Brn 4643153

    25. 22,23-dihydro-5-o-demethylavermectin A1a

    26. H2b1a

    27. Prestwick3_000156

    28. Dsstox_cid_3181

    29. Ivermectin (mk-0933)

    30. Dsstox_rid_76909

    31. Dsstox_gsid_23181

    32. Bspbio_000292

    33. Schembl312795

    34. Bpbio1_000322

    35. Chembl263291

    36. Dtxsid8023181

    37. Chebi:94551

    38. Hms2089m09

    39. Hms2095o14

    40. Hms3712o14

    41. Wca82703

    42. Tox21_112034

    43. Bdbm50409816

    44. Mfcd30496678

    45. S1351

    46. Akos027470116

    47. Ivermectin Component B1a [mi]

    48. Zinc238808778

    49. Zinc252286706

    50. Ac-6014

    51. Ccg-220156

    52. Ncgc00186639-01

    53. Ncgc00186639-03

    54. As-14167

    55. Bi166167

    56. Cas-71827-03-7

    57. Hy-126937

    58. Ab00513813

    59. Cs-0108408

    60. 22,23-dihydroavermectin B1a; Ivermectin

    61. Ab00513813-02

    62. Ab00513813-03

    63. Ab00513813_04

    64. Avermectin A1a, 22,23-dihydro-5-o-demethyl-

    65. 288i867

    66. Ivermectin, Antibiotic For Culture Media Use Only

    67. Q-201262

    68. Brd-k24652731-001-02-7

    69. Brd-k85554912-001-08-9

    70. Q27132923

    71. Ivermectin, British Pharmacopoeia (bp) Reference Standard

    72. Ivermectin, European Pharmacopoeia (ep) Reference Standard

    73. Ivermectin, United States Pharmacopeia (usp) Reference Standard

    74. Ivermectin, Pharmaceutical Secondary Standard; Certified Reference Material

    75. (2ae,4e,5's,6s,6'r,7s,8e,11r,13r,15s,17ar,20r,20ar,20bs)-6'-[(2s)-butan-2-yl]-20,20b-dihydroxy-5',6,8,19-tetramethyl-17

    76. Clooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-4-o-(2,6-dideoxy-3-o-methyl-alpha-l-arabino-hexopyranosyl)-3-o-methyl-alpha-l-arabino-hexopyranoside

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 875.1 g/mol
    Molecular Formula C48H74O14
    XLogP34.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count8
    Exact Mass874.50785703 g/mol
    Monoisotopic Mass874.50785703 g/mol
    Topological Polar Surface Area170 Ų
    Heavy Atom Count62
    Formal Charge0
    Complexity1680
    Isotope Atom Count0
    Defined Atom Stereocenter Count20
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count3
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of rosacea

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antiparasitic Agents

    Drugs used to treat or prevent parasitic infections. (See all compounds classified as Antiparasitic Agents.)

    Insecticides

    Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Pediculicide [EPC]; Antiparasitic [EPC]
    5.3 ATC Code

    D - Dermatologicals

    D11 - Other dermatological preparations

    D11A - Other dermatological preparations

    D11AX - Other dermatologicals

    D11AX22 - Ivermectin

    P - Antiparasitic products, insecticides and repellents

    P02 - Anthelmintics

    P02C - Antinematodal agents

    P02CF - Avermectines

    P02CF01 - Ivermectin