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Prestwick3_000804

Prestwick3_000804

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Also known as: 1695-77-8, Actinospectacin, Espectinomicina, Trobicin, Antibiotic 2233wp, Spectam

Molecular Formula

C₁₄H₂₄N₂O₇

Molecular Weight

332.35 g/mol

InChI Key

UNFWWIHTNXNPBV-WXKVUWSESA-N

FDA UNII

93AKI1U6QF

An antibiotic produced by Streptomyces spectabilis. It is active against gram-negative bacteria and used for the treatment of gonorrhea.

1 2D Structure

Prestwick3_000804

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3S,5R,8R,10R,11S,12S,13R,14S)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

2.1.2 InChI

InChI=1S/C14H24N2O7/c1-5-4-6(17)14(20)13(21-5)22-12-10(19)7(15-2)9(18)8(16-3)11(12)23-14/h5,7-13,15-16,18-20H,4H2,1-3H3/t5-,7-,8+,9+,10+,11-,12-,13+,14+/m1/s1

2.1.3 InChI Key

UNFWWIHTNXNPBV-WXKVUWSESA-N

2.1.4 Canonical SMILES

CC1CC(=O)C2(C(O1)OC3C(C(C(C(C3O2)NC)O)NC)O)O

2.1.5 Isomeric SMILES

C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3[C@H]([C@@H]([C@@H]([C@@H]([C@H]3O2)NC)O)NC)O)O

2.2 Other Identifiers

2.2.1 UNII

93AKI1U6QF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Actinospectacin

2. Adspec

3. Ferkel Spectam

4. Kempi

5. Prospec

6. Salmosan T

7. Salmosan-t

8. Spectam

9. Spectam, Ferkel

10. Spectinomycin Dihydrochloride, Anhydrous

11. Spectinomycin Dihydrochloride, Pentahydrate

12. Spectinomycin Hydrochloride

13. Stanilo

14. Trobicin

2.3.2 Depositor-Supplied Synonyms

1. 1695-77-8

2. Actinospectacin

3. Espectinomicina

4. Trobicin

5. Antibiotic 2233wp

6. Spectam

7. Togamycin

8. Spectinomycine

9. Spectinomycinum

10. Spectinomicina [italian]

11. Actinospectacina [italian]

12. Prospec

13. Adspec

14. Spectinomycin Hydrochloride

15. Spectinomycine [inn-french]

16. Spectinomycinum [inn-latin]

17. Espectinomicina [inn-spanish]

18. M-141

19. Spectinomycin Dihydrochloride

20. 93aki1u6qf

21. Chebi:9215

22. Scm

23. Chx-3101

24. Spectinomycin (inn)

25. Actinospectacina

26. Spectinomycin [inn]

27. 22189-32-8

28. (1r,3s,5r,8r,10r,11s,12s,13r,14s)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.03,8]tetradecan-7-one

29. (2r,4ar,5ar,6s,7s,8r,9s,9ar,10as)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)decahydro-4h-pyrano[2,3-b][1,4]benzodioxin-4-one

30. 4h-pyrano(2,3-b)(1,4)benzodioxin-4-one, Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-

31. 4h-pyrano[2,3-b][1,4]benzodioxin-4-one, Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2r,4ar,5ar,6s,7s,8r,9s,9ar,10as)-

32. M 141

33. U 18409

34. Spectinomycin [inn:ban]

35. 4h-pyrano(2,3-b)(1,4)benzodioxin-4-one, Decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-, (2r,4ar,5ar,6s,7s,8r,9s,9ar,10as)-

36. U 18409 E

37. Xk 43-1

38. U-18409e

39. Einecs 216-911-3

40. Unii-93aki1u6qf

41. Spectinomycin Hcl/ Sulphate

42. Brn 2171701

43. Specitinomycin

44. Sr-05000001868

45. (2r,4ar,5ar,6s,7s,8r,9s,9ar,10as)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-3,5a,6,7,8,9,9a,10a-octahydro-2h-benzo[[?]]pyrano[[?]][1,4]dioxin-4-one

46. Prospec (tn)

47. Adspec (tn)

48. Spcm

49. Nsc132679

50. Spectrum_000954

51. 21736-83-4

52. Prestwick0_000804

53. Prestwick1_000804

54. Prestwick2_000804

55. Prestwick3_000804

56. Spectrum2_001315

57. Spectrum3_000898

58. Spectrum4_000993

59. Spectrum5_001407

60. Spectinomycin [mi]

61. Schembl3533

62. Chembl1167

63. Bspbio_000667

64. Kbiogr_001425

65. Kbioss_001434

66. Spectinomycin [vandf]

67. Divk1c_000137

68. Spectinomycin [mart.]

69. Spbio_001409

70. Spbio_002588

71. Spectinomycin [who-dd]

72. Bpbio1_000735

73. Dtxsid9023592

74. Gtpl11127

75. Kbio1_000137

76. Kbio2_001434

77. Kbio2_004002

78. Kbio2_006570

79. Kbio3_001816

80. Ninds_000137

81. Hms2089c03

82. Spectinomycin [green Book]

83. Hy-b1828

84. Zinc53006806

85. Akos015961272

86. Ccg-208273

87. Db00919

88. Idi1_000137

89. Smp1_000276

90. Ncgc00017354-02

91. Ncgc00017354-03

92. Ncgc00017354-04

93. Ncgc00142531-01

94. Ncgc00142531-02

95. Ac-13570

96. Nci60_000023

97. Sbi-0051514.p003

98. Cs-0013897

99. C02078

100. D08526

101. U18409

102. Ab00642548-10

103. Ab00642548-11

104. Ab00642548_12

105. Ab00642548_13

106. A878657

107. Q416154

108. U-18409

109. Actinospectacin; Espectinomicina; Chx-3101

110. Sr-05000001868-4

111. Ethyl2-anilino-4-chloro-5-formyl-3-thiophenecarboxylate

112. (1r,3s,5r,8r,10r,11s,12s,13r,14s)-8,12,14-trihydroxy-5-methyl-11,13-bis(methylamino)-2,4,9-trioxatricyclo[8.4.0.0^{3,8}]tetradecan-7-one

113. (2r,4ar,5ar,6s,7s,8r,9s,9ar,10as)-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)octahydro-2h-benzo[b]pyrano[2,3-e][1,4]dioxin-4(3h)-one

114. (2r-(2.alpha.,4a.beta.,5a.beta.,6.beta.,7.beta.,8.beta.,9.alpha.,9a.alpha.,10a.beta.))-decahydro-4a,7,9-trihydroxy-2-methyl-6,8-bis(methylamino)-4h-pyrano(2,3-b)(1,4)benzodioxin-4-one

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₂₄N₂O₇
Molecular Weight	332.35 g/mol
XLogP3	-3.1
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	332.15835111 g/mol
Monoisotopic Mass	332.15835111 g/mol
Topological Polar Surface Area	130 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	478
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
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 use in the treatment of acute gonorrheal urethritis and proctitis in the male and acute gonorrheal cervicitis and proctitis in the female when due to susceptible strains of Neisseria gonorrhoeae.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Spectinomycin is an aminocyclitol antibiotic produced by a species of soil microorganism designated as Streptomyces spectabilis. In vitro studies have shown spectinomycin to be active against most strains of Neisseria gonorrhoeae (minimum inhibitory concentration <7.5 to 20 mcg/mL). Footprint studies indicate that spectinomycin exerts regional effects on ribosomal structure.

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.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XX - Other antibacterials

J01XX04 - Spectinomycin

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly and almost completely absorbed after intramuscular injection.

5.5 Biological Half-Life

1 to 3 hours in patients with normal renal function and 10 to 30 hours in patients with impaired renal function with a creatinine clearance < 20 mL per minute.

5.6 Mechanism of Action

Spectinomycin is an inhibitor of protein synthesis in the bacterial cell; the site of action is the 30S ribosomal subunit. It is bactericidal in its action.