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Suramin

July 24, 2017
Common Name

Suramin Description

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 adlit Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties. Suramin is manufactured by Bayer in Germany as Germanin®. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source 8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrislifonIC ACIDChEBI BelganylChEBI NaganolChEBI NaphurideChEBI 8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrislifonateGenerator 8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisliphonateGenerator 8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisliphonic acidGenerator Bayer 205HMDB Sodium suraminHMDB SuramineHMDB SVRHMDB Monosodium salt suraminMeSH MoranilMeSH Hexasodium salt suraminMeSH Suramin, hexasodium saltMeSH NaganinMeSH Salt suramin, hexasodiumMeSH Salt suramin, monosodiumMeSH Sodium, suraminMeSH Suramin sodiumMeSH Suramin, monosodium saltMeSH

Chemical Formlia

C51H40N6O23S6 Average Molecliar Weight

1297.28 Monoisotopic Molecliar Weight

1296.046905756 IUPAC Name

8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trislifonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trislifonic acid Traditional Name

suramin CAS Registry Number

145-63-1 SMILES

CC1=C(NC(=O)C2=CC(NC(=O)NC3=CC=CC(=C3)C(=O)NC3=C(C)C=CC(=C3)C(=O)NC3=C4C(C=C(C=C4S(O)(=O)=O)S(O)(=O)=O)=C(C=C3)S(O)(=O)=O)=CC=C2)C=C(C=C1)C(=O)NC1=C2C(C=C(C=C2S(O)(=O)=O)S(O)(=O)=O)=C(C=C1)S(O)(=O)=O

InChI Identifier

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)

InChI Key

FIAFUQMPZJWCLV-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R, where R,R= benzene. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Anilides Direct Parent

Benzanilides Alternative Parents

  • 1-naphthalene slifonates
  • 1-naphthalene slifonic acids and derivatives
  • 2-naphthalene slifonates
  • 2-naphthalene slifonic acids and derivatives
  • N-phenylureas
  • p-Toluamides
  • Benzamides
  • 1-slifo,2-unsubstituted aromatic compounds
  • Benzoyl derivatives
  • Slifonyls
  • Organoslifonic acids
  • Secondary carboxylic acid amides
  • Ureas
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Benzanilide
  • Naphthalene slifonate
  • 1-naphthalene slifonic acid or derivatives
  • 2-naphthalene slifonic acid or derivatives
  • Naphthalene slifonic acid or derivatives
  • 1-naphthalene slifonate
  • 2-naphthalene slifonate
  • N-phenylurea
  • Naphthalene
  • P-toluamide
  • Toluamide
  • Benzamide
  • Benzoic acid or derivatives
  • 1-slifo,2-unsubstituted aromatic compound
  • Arylslifonic acid or derivatives
  • Benzoyl
  • Toluene
  • Slifonyl
  • Organoslifonic acid
  • Organoslifonic acid or derivatives
  • Organic slifonic acid or derivatives
  • Carboxamide group
  • Urea
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organoslifur compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound

    • Molecliar Framework

    Aromatic homopolycyclic compounds External Descriptors

  • naphthaleneslifonic acid (CHEBI:45906 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antinematodal Agents
  • Antineoplastic Agents
  • Trypanocidal Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility8.72e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0087 mg/mLALOGPS logP-0.12ALOGPS logP5.58ChemAxon logS-5.2ALOGPS pKa (Strongest Acidic)-3.5ChemAxon Physiological Charge-6ChemAxon Hydrogen Acceptor Count23ChemAxon Hydrogen Donor Count12ChemAxon Polar Surface Area483.75 Å2ChemAxon Rotatable Bond Count16ChemAxon Refractivity314.9 m3·mol-1ChemAxon Polarizability120.22 Å3ChemAxon Number of Rings8ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04786

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04786

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04786 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5168 KEGG Compound ID

    C07974 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Suramin NuGOwiki Link

    HMDB15582 Metagene Link

    HMDB15582 METLIN ID

    Not Available PubChem Compound

    5361 PDB ID

    SVR ChEBI ID

    45906

    Product: Ampicillin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in metabolic process
    Specific function:
    Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
    Gene Name:
    PLA2G4A
    Uniprot ID:
    P47712
    Molecular weight:
    85210.19
    References
    1. Vieira DS, Aragao EA, Lourenzoni MR, Ward RJ: Mapping of suramin binding sites on the group IIA human secreted phospholipase A2. Bioorg Chem. 2009 Apr;37(2):41-5. doi: 10.1016/j.bioorg.2009.01.002. Epub 2009 Feb 3. [PubMed:19251299 ]
    2. Aragao EA, Chioato L, Ferreira TL, de Medeiros AI, Secatto A, Faccioli LH, Ward RJ: Suramin inhibits macrophage activation by human group IIA phospholipase A2, but does not affect bactericidal activity of the enzyme. Inflamm Res. 2009 Apr;58(4):210-7. doi: 10.1007/s00011-008-8137-z. [PubMed:19169647 ]
    General function:
    Involved in phospholipase A2 activity
    Specific function:
    Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
    Gene Name:
    PLA2G2A
    Uniprot ID:
    P14555
    Molecular weight:
    16082.525
    References
    1. Murakami MT, Arruda EZ, Melo PA, Martinez AB, Calil-Elias S, Tomaz MA, Lomonte B, Gutierrez JM, Arni RK: Inhibition of myotoxic activity of Bothrops asper myotoxin II by the anti-trypanosomal drug suramin. J Mol Biol. 2005 Jul 15;350(3):416-26. [PubMed:15961104 ]
    2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
    General function:
    Involved in catalytic activity
    Specific function:
    Hydrolyzes cerebroside sulfate.
    Gene Name:
    ARSA
    Uniprot ID:
    P15289
    Molecular weight:
    53805.87
    References
    1. Constantopoulos G, Rees S, Cragg BG, Barranger JA, Brady RO: Effect of suramin on the activities of degradative enzymes of sphingolipids in rats. Res Commun Chem Pathol Pharmacol. 1981 Apr;32(1):87-97. [PubMed:7291729 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for ATP and UTP coupled to G-proteins that activate a phosphatidylinositol-calcium second messenger system. The affinity range is UTP = ATP > ATP-gamma-S >> 2-methylthio-ATP = ADP
    Gene Name:
    P2RY2
    Uniprot ID:
    P41231
    Molecular weight:
    42289.0
    References
    1. Charlton SJ, Brown CA, Weisman GA, Turner JT, Erb L, Boarder MR: PPADS and suramin as antagonists at cloned P2Y- and P2U-purinoceptors. Br J Pharmacol. 1996 Jun;118(3):704-10. [PubMed:8762097 ]
    2. Bogdanov YD, Wildman SS, Clements MP, King BF, Burnstock G: Molecular cloning and characterization of rat P2Y4 nucleotide receptor. Br J Pharmacol. 1998 Jun;124(3):428-30. [PubMed:9647463 ]
    3. Trujillo CA, Nery AA, Martins AH, Majumder P, Gonzalez FA, Ulrich H: Inhibition mechanism of the recombinant rat P2X(2) receptor in glial cells by suramin and TNP-ATP. Biochemistry. 2006 Jan 10;45(1):224-33. [PubMed:16388598 ]
    4. Churchill GC, Louis CF: Stimulation of P2U purinergic or alpha 1A adrenergic receptors mobilizes Ca2+ in lens cells. Invest Ophthalmol Vis Sci. 1997 Apr;38(5):855-65. [PubMed:9112981 ]
    5. Homma R, Kimoto T, Niimura Y, Krivosheev A, Hara T, Ohta Y, Kawato S: Real-time fluorescence analysis on molecular mechanisms for regulation of cytochrome P450scc activity upon steroidogenic stimulation in adrenocortical cells. J Inorg Biochem. 2000 Nov;82(1-4):171-80. [PubMed:11132624 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for follicle-stimulating hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase
    Gene Name:
    FSHR
    Uniprot ID:
    P23945
    Molecular weight:
    78294.1
    References
    1. McGeary RP, Bennett AJ, Tran QB, Cosgrove KL, Ross BP: Suramin: clinical uses and structure-activity relationships. Mini Rev Med Chem. 2008 Nov;8(13):1384-94. [PubMed:18991754 ]
    2. Bose CK: Follicle stimulating hormone receptor (FSHR) antagonist and epithelial ovarian cancer (EOC). J Exp Ther Oncol. 2007;6(3):201-4. [PubMed:17552360 ]
    General function:
    Involved in calcium channel activity
    Specific function:
    Communication between transverse-tubules and sarcoplasmic reticulum. Contraction of skeletal muscle is triggered by release of calcium ions from SR following depolarization of T-tubules
    Gene Name:
    RYR1
    Uniprot ID:
    P21817
    Molecular weight:
    565170.7
    References
    1. Wolner I, Kassack MU, Ullmann H, Karel A, Hohenegger M: Use-dependent inhibition of the skeletal muscle ryanodine receptor by the suramin analogue NF676. Br J Pharmacol. 2005 Oct;146(4):525-33. [PubMed:16056233 ]
    General function:
    Involved in zinc ion binding
    Specific function:
    NAD-dependent lysine demalonylase and desuccinylase that specifically removes malonyl and succinyl groups on target proteins. Activates CPS1 and contributes to the regulation of blood ammonia levels during prolonged fasting: acts by mediating desuccinylation of CPS1, thereby increasing CPS1 activity in response to elevated NAD levels during fasting. Has weak NAD-dependent protein deacetylase activity; however this activity may not be physiologically relevant in vivo. Can deacetylate cytochrome c (CYCS) and a number of other proteins in vitro.
    Gene Name:
    SIRT5
    Uniprot ID:
    Q9NXA8
    Molecular weight:
    31993.505
    References
    1. Schuetz A, Min J, Antoshenko T, Wang CL, Allali-Hassani A, Dong A, Loppnau P, Vedadi M, Bochkarev A, Sternglanz R, Plotnikov AN: Structural basis of inhibition of the human NAD+-dependent deacetylase SIRT5 by suramin. Structure. 2007 Mar;15(3):377-89. [PubMed:17355872 ]

    PMID: 25993107

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