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    Suramin

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    2D Structure
    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

    2D Structure

    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 Weight 1297.3 g/mol
    Molecular Formula C51H40N6O23S6
    XLogP31.5
    Hydrogen Bond Donor Count12
    Hydrogen Bond Acceptor Count23
    Rotatable Bond Count16
    Exact Mass1296.0469086 g/mol
    Monoisotopic Mass1296.0469086 g/mol
    Topological Polar Surface Area534 Ų
    Heavy Atom Count86
    Formal Charge0
    Complexity3020
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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 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.