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Suramin

Suramin

Synopsis, Chemistry

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Also known as: Naganol, Suramine, Fourneau, Farma, 145-63-1, Germanin

Molecular Formula

C₅₁H₄₀N₆O₂₃S₆

Molecular Weight

1297.3 g/mol

InChI Key

FIAFUQMPZJWCLV-UHFFFAOYSA-N

FDA UNII

6032D45BEM

A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.

1 2D Structure

Suramin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid

2.1.2 InChI

InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80)

2.1.3 InChI Key

FIAFUQMPZJWCLV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=C(C=C1)C(=O)NC2=C3C(=CC(=CC3=C(C=C2)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)NC(=O)C4=CC(=CC=C4)NC(=O)NC5=CC=CC(=C5)C(=O)NC6=C(C=CC(=C6)C(=O)NC7=C8C(=CC(=CC8=C(C=C7)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

6032D45BEM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Germanin

2. Hexasodium Salt Suramin

3. Monosodium Salt Suramin

4. Moranil

5. Naganin

6. Naganol

7. Naphuride

8. Salt Suramin, Hexasodium

9. Salt Suramin, Monosodium

10. Sodium, Suramin

11. Suramin Sodium

12. Suramin, Hexasodium Salt

13. Suramin, Monosodium Salt

2.3.2 Depositor-Supplied Synonyms

1. Naganol

2. Suramine

3. Fourneau

4. Farma

5. 145-63-1

6. Germanin

7. Belganyl

8. Naphuride

9. Sodium Suramin

10. Naganin

11. Farma 939

12. Antrypol

13. Moranyl

14. Metaret

15. Naganine

16. Suramine Sodium

17. Bayer 205

18. Nsc-34936

19. Farma-939

20. M,m'-ureylen-bis-(8-(m-(benzamido)-p-toluamido)naphthalin-1,3,5-trisulfonsaeure)

21. Chembl265502

22. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic Acid

23. Harnstoff, Symmetischer Der 3-aminobenzoyl-3-amino-4-methylbenzoyl-1-naphthylamin-4,6,8-trisulfonsaeure

24. Svr

25. Chebi:45906

26. Nsc 34936

27. 6032d45bem

28. Nsc34936

29. Carbanilide, 3,3'-bis((5-((4,6,8-trisulfo-1-naphthyl)carbamoyl)-o-tolyl)carbamoyl)-

30. Naphuride Sodium

31. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bis-

32. Ncgc00163318-01

33. Naganil

34. Dsstox_cid_26344

35. Dsstox_rid_81548

36. Dsstox_gsid_46344

37. 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bisnaphthalene-1,3,5-trisulphonic Acid

38. Bay 205

39. Naganol 6 Na

40. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-

41. 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-1,3,5-naphthalenetrisulfonic Acid

42. 8-[(4-methyl-3-{[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzene]amido}benzene)amido]naphthalene-1,3,5-trisulfonic Acid

43. Cas-145-63-1

44. Sk 24728

45. Einecs 205-658-4

46. 309 F

47. Brn 3230873

48. Sgcto-001

49. Unii-6032d45bem

50. 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bis-1,3,5-naphthalenetrisulfonic Acid

51. 8,8'-(ureylenebis(m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino))di-1,3,5-naphthalenetrisulfonic Acid

52. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfon Ic Acid

53. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic Acid

54. Spectrum_001877

55. 5,5'',5''''-[1,3,6-naphthalenetriyltris(sulfonylimino)]tris[1,3-benzenesulfonate Analogue

56. Specplus_000662

57. Spectrum3_000724

58. Spectrum4_001247

59. Suramin [who-dd]

60. Schembl3161

61. Lopac0_001182

62. Us8835659, Suramin

63. Bspbio_002248

64. Kbiogr_001774

65. Kbioss_002402

66. 3-14-00-02267 (beilstein Handbook Reference)

67. 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic Acid

68. Divk1c_006758

69. Gtpl1728

70. Dtxsid1046344

71. Kbio1_001702

72. Kbio2_002397

73. Kbio2_004965

74. Kbio2_007533

75. Kbio3_001468

76. Hy-b0879

77. Tox21_112045

78. Bdbm50336799

79. Ccg-36173

80. Mmv637953

81. Tox21_112045_1

82. Cs-4444

83. Db04786

84. Sym-bis(m-aminobenzoyl-m-amino-p-methylbenzoyl-1-napthylamino-4,6,8-trisulfonate) Carbamide

85. Ncgc00025177-08

86. Ncgc00163318-02

87. Ncgc00163318-03

88. 1,3,5-naphthylenetrisulfonic Acid, 8,8'-(ureylenebis(m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino))di-

89. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-naphthalenetrisulfonic Acid

90. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-napthalenetrisulfonic Acid

91. 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic Acid

92. C07974

93. L000585

94. Q425946

95. Brd-k70327167-348-01-9

96. Brd-k70327167-348-09-2

97. Sr-01000075238-10

98. 1-(3-benzamido-4-methylbenzamido)naphthalene-4,8-trisulfonic Acid Sym-3''-urea Sodium Salt

99. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis- (9ci)

100. 1,3,5-naphthalenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di- (8ci)

101. 1,5-naphthalenetrisulfonic Acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-, Hexasodium Salt

102. 1,5-naphthalenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-, Hexasodium Salt

103. 1,5-naphthylenetrisulfonic Acid, 8,8'-[ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di-, Hexasodium Salt

104. 8,8''-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bisnaphthalene-1,3,5-trisulphonic Acid

105. 8,8''-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-naphthalenetrisulfonic Acid(suramin)

106. 8,8''-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic Acid

107. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfon

108. 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulphonic Acid

109. 8,8-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic Acid

110. 8-[(4-methyl-3-{[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzoyl]amino}benzoyl)amino]naphthalene-1,3,5-trisulfonic Acid

111. Wln: L66j Bswq Dswq Gswq Jmvr D1 Cmvr Cmvmr Cvmr B1 Evm-jl66j Bswq Dswq Gswq &-na-6

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₅₁H₄₀N₆O₂₃S₆
Molecular Weight	1297.3 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	23
Rotatable Bond Count	16
Exact Mass	1296.0469086 g/mol
Monoisotopic Mass	1296.0469086 g/mol
Topological Polar Surface Area	534 Å²
Heavy Atom Count	86
Formal Charge	0
Complexity	3020
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Trypanocidal Agents

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

5.2 Absorption, Distribution and Excretion

Absorption

Poorly absorbed from the gastrointestinal tract.

5.3 Metabolism/Metabolites

Little or no metabolism

5.4 Biological Half-Life

Approximately 36 to 60 days

5.5 Mechanism of Action

The mechanism is unknown, but the trypanocidal activity may be due to the inhibition of enzymes involved with the oxidation of reduced nicotinamide-adenine dinucleotide (NADH), which functions as a co-enzyme in many cellular reactions, such as respiration and glycolysis, in the trypanosome parasite. Suramin's action in the treatment of onchocerciasis is macrofilaricidal and partially microfilaricidal. It may also act as an antagonist of P2 receptors and as an agonist of Ryanodine receptors. It also can inhibit follicle-stimulating hormone receptors.