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Paromomycin

Synopsis, Chemistry

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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

Paromomycin

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 Formula	C₂₃H₄₅N₅O₁₄
Molecular Weight	615.6 g/mol
XLogP3	-8.7
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	9
Exact Mass	615.29630113 g/mol
Monoisotopic Mass	615.29630113 g/mol
Topological Polar Surface Area	347 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	870
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.