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    Paromomycin

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    2D Structure
    Also known as: Aminosidin, Catenulin, Neomycin e, Hydroxymycin, Aminosidine, Monomycin a
    Molecular Formula
    C23H45N5O14
    Molecular Weight
    615.6  g/mol
    InChI Key
    UOZODPSAJZTQNH-LSWIJEOBSA-N
    FDA UNII
    61JJC8N5ZK
    An aminoglycoside antibacterial and antiprotozoal agent produced by species of STREPTOMYCES.
    Paromomycin is an Antiprotozoal.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
    2.1.2 InChI
    InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
    2.1.3 InChI Key
    UOZODPSAJZTQNH-LSWIJEOBSA-N
    2.1.4 Canonical SMILES
    C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N
    2.1.5 Isomeric SMILES
    C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    61JJC8N5ZK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aminosidine

    2. Beta-d-glucopyranosyl-isomer Paromomycin

    3. Catenulin

    4. Estomycin

    5. Gabbromycin

    6. Humatin

    7. Hydroxymycin

    8. Neomycin E

    9. Paramomycin

    10. Paromomycin I

    11. Paromomycin Phosphate

    12. Paromomycin Sulfate

    13. Paromomycin Sulfate (1:1)

    14. Paromomycin Sulfate (2:5)

    15. Paromomycin, Beta D Glucopyranosyl Isomer

    16. Paromomycin, Beta-d-glucopyranosyl-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. Aminosidin

    2. Catenulin

    3. Neomycin E

    4. Hydroxymycin

    5. Aminosidine

    6. Monomycin A

    7. Crestomycin

    8. Estomycin

    9. Paucimycin

    10. 7542-37-2

    11. Paromomycin I

    12. Zygomycin A1

    13. Paromomycine

    14. Gabromycin

    15. Humatin

    16. Quintomycin C

    17. Paramomycin Sulfate

    18. Paromomicina

    19. Paromomycinum

    20. Paucimycinum

    21. Antibiotic 503-3

    22. Gabbromycin

    23. Paromomycin [inn]

    24. Antibiotic Sf 767b

    25. Gabbromicina

    26. Paromomycin (inn)

    27. R 400

    28. (1r,2r,3s,4r,6s)-4,6-diamino-2-{[3-o-(2,6-diamino-2,6-dideoxy-beta-l-idopyranosyl)-beta-d-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-d-glucopyranoside

    29. 61jjc8n5zk

    30. Antibiotic Sf-767b

    31. Amminosidin

    32. Humycin

    33. Aminosidine I

    34. Chebi:7934

    35. (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol

    36. R-400

    37. Antibiotic 2230d

    38. Paramomycin Sulphate

    39. Hydroxymycin Sulfate

    40. 134235-09-9

    41. Paramomycin

    42. Monomycin

    43. Paromomycin (tn)

    44. Paromomycin Sulfate Rx346208

    45. (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-(((2r,3s,4r,5s)-5-(((1r,2r,3s,5r,6s)-3,5-diamino-2-(((2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-6-hydroxycyclohexyl)oxy)-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)tetrahydro-2h-pyran-3,4-diol

    46. Aminosidine, Sulfate

    47. Hatt & Paromomycin

    48. Paromomycin [inn:ban]

    49. Unii-61jjc8n5zk

    50. Paromomycine [inn-french]

    51. Paromomycinum [inn-latin]

    52. Paromomicina [inn-spanish]

    53. (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl]oxy-tetrahydropyran-3,4-diol

    54. Einecs 231-423-0

    55. Brn 0072285

    56. Human .alpha.-1-antitrypsin & Paromomyin

    57. Paromomycin [mi]

    58. Paromomycin [vandf]

    59. Schembl4072

    60. Paromomycin [who-dd]

    61. 4-18-00-07534 (beilstein Handbook Reference)

    62. Chembl370143

    63. Dtxsid8023424

    64. Gtpl12160

    65. Zinc60183170

    66. Akos030489917

    67. Db01421

    68. Ncgc00166210-02

    69. D-streptamine, O-2-amino-2-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(o-2,6-diamino-2,6-dideoxy-beta-l-idopyranosyl-(1-3)-beta-d-ribofuranosyl-(1-5))-2-deoxy-

    70. O-2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-[o-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-.beta.d-ribofuranosyl(1->5)]-2-deoxy-d-streptamine

    71. C00832

    72. D07467

    73. Ab00639998_04

    74. Neomycin Sulfate Impurity E [ep Impurity]

    75. Q415625

    76. Paromomycin I; Amminosidin; Catenulin; Crestomycin; Monomycin A; Neomycin E

    77. (2r,3s,4r,5r,6s)-5-amino-6-{[(1r,2r,3s,4r,6s)-4,6-diamino-2-{[(2s,3r,4s,5r)-4-{[(2r,3r,4r,5s,6s)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

    78. D-streptamine, O-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-o-.beta.-d-ribofuranosyl-(1->5)-o-(2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1-.4))-2-deoxy-

    79. D-streptamine, O-2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(o-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-.beta.-d-ribofuranosyl-(1->5))-2-deoxy-

    80. Diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-o-.beta.-d-ribofuranosyl-(1->5)-o-(2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1->4))-2-deoxystreptamine

    81. O-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-o-.beta.-d-ribofuranosyl-(1->5)-o-(2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1->4))-2-deoxystreptamine

    82. O-2-amino-2-deoxy-.alpha.-d-glucopyranosyl-(1->4)-o-(o-2,6-diamino-2,6-dideoxy-.beta.-l-idopyranosyl-(1->3)-.beta.-d-ribofuranosyl-(1->5))-2-deoxy-d-streptamine

    83. Streptamine, O-2,6-diamino-2,6-dideoxy-beta-l-idopyranosyl-(1-3)-o-beta-d-ribofuranosyl-(1-5)-o-(2-amino-2-deoxy-alpha-d-glucopyranosyl-(1-4))-2-deoxy-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 615.6 g/mol
    Molecular Formula C23H45N5O14
    XLogP3-8.7
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count19
    Rotatable Bond Count9
    Exact Mass615.29630113 g/mol
    Monoisotopic Mass615.29630113 g/mol
    Topological Polar Surface Area347 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity870
    Isotope Atom Count0
    Defined Atom Stereocenter Count19
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Paromomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. The in vitro and in vivo antibacterial action of paromomycin closely parallels that of neomycin.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    Antiprotozoal Agents

    Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PAROMOMYCIN
    5.3.2 FDA UNII
    61JJC8N5ZK
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Antiprotozoal
    5.4 ATC Code

    A07AA06

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    A - Alimentary tract and metabolism

    A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

    A07A - Intestinal antiinfectives

    A07AA - Antibiotics

    A07AA06 - Paromomycin

    5.5 Absorption, Distribution and Excretion

    Absorption

    Poorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool.

    5.6 Mechanism of Action

    Paromomycin inhibits protein synthesis by binding to 16S ribosomal RNA. Bacterial proteins are synthesized by ribosomal RNA complexes which are composed of 2 subunits, a large subunit (50s) and small (30s) subunit, which forms a 70s ribosomal subunit. tRNA binds to the top of this ribosomal structure. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death.