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targets (7) enzymes (2)
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Identification
Name Suramin
Accession Number DB04786
Type small molecule
Groups approved
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 adult 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Bayer 205
Sodium suramin
Suramin sodium
Suramine
Suramine sodium
SVR
Salts Not Available
Brand names
Name Company
Antrypol
Belganyl
Farma
Fourneau
Germanin
Moranyl
Naganil
Naganin
Naganine
Naganol
Naphuride
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antineoplastic Agents
  • Trypanocidal Agents
  • Antinematodal Agents
CAS number 145-63-1
Weight Average: 1297.28
Monoisotopic: 1296.046905756
Chemical Formula C51H40N6O23S6
InChI Key InChIKey=FIAFUQMPZJWCLV-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
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
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Naphthalenes
  • Benzamides
Substructures
  • Hydroxy Compounds
  • Naphthalenes
  • Amino Ketones
  • Sulfonyls
  • Benzene and Derivatives
  • Ureas and Derivatives
  • Carboxylic Acids and Derivatives
  • Sulfonic Acids and Derivatives
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Benzoyl Derivatives
  • Benzamides
  • Anilines
Pharmacology
Indication For treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.
Pharmacodynamics Not Available
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.
Absorption Poorly absorbed from the gastrointestinal tract.
Volume of distribution Not Available
Protein binding Approximately 99.7%
Metabolism
Little or no metabolism
Route of elimination Not Available
Half life Approximately 36 to 60 days
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Yeast, Molds, Trypanosomes
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms
Form Route Strength
Injection, powder, for solution Intravenous
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 8.72e-03 g/l ALOGPS
logP -0.12 ALOGPS
logP 5.58 ChemAxon
logS -5.2 ALOGPS
pKa (strongest acidic) -3.5 ChemAxon
physiological charge -6 ChemAxon
hydrogen acceptor count 23 ChemAxon
hydrogen donor count 12 ChemAxon
polar surface area 483.75 ChemAxon
rotatable bond count 16 ChemAxon
refractivity 314.9 ChemAxon
polarizability 120.22 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07974 Link_out
PubChem Compound 5361 Link_out
PubChem Substance 46507013 Link_out
ChemSpider 5168 Link_out
ChEBI 45906 Link_out
ChEMBL 45906 Link_out
Therapeutic Targets Database DAP001031 Link_out
PharmGKB PA10292 Link_out
IUPHAR 1728 Link_out
Guide to Pharmacology 1728 Link_out
HET SVR Link_out
Wikipedia http://en.wikipedia.org/wiki/Suramin Link_out
ATC Codes
  • P01CX02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. P2Y purinoceptor 2

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P41231 Link_out
Gene: P2RY2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Trujillo CA, Nery AA, Martins AH, Majumder P, Gonzalez FA, Ulrich H: Inhibition mechanism of the recombinant rat P2X receptor in glial cells by suramin and TNP-ATP. Biochemistry. 2006 Jan 10;45(1):224-33. Pubmed
  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
  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

2. NAD-dependent deacetylase sirtuin-5

Pharmacological action: yes
Actions: inhibitor

Probable NAD-dependent deacetylase (By similarity)

Organism class: human
UniProt ID: Q9NXA8 Link_out
Gene: SIRT5
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

3. Follicle-stimulating hormone receptor

Pharmacological action: yes
Actions: antagonist

Receptor for follicle-stimulating hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase

Organism class: human
UniProt ID: P23945 Link_out
Gene: FSHR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Bose CK: Follicle stimulating hormone receptor (FSHR) antagonist and epithelial ovarian cancer (EOC). J Exp Ther Oncol. 2007;6(3):201-4. Pubmed

4. Ryanodine receptor 1

Pharmacological action: unknown
Actions: agonist

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

Organism class: human
UniProt ID: P21817 Link_out
Gene: RYR1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

5. Prothrombin

Pharmacological action: unknown
Actions: inhibitor

Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C

Organism class: human
UniProt ID: P00734 Link_out
Gene: F2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Monteiro RQ, Campana PT, Melo PA, Bianconi ML: Suramin interaction with human alpha-thrombin: inhibitory effects and binding studies. Int J Biochem Cell Biol. 2004 Oct;36(10):2077-85. Pubmed

6. Phospholipase A2, membrane associated

Pharmacological action: unknown
Actions: inhibitor

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

Organism class: human
UniProt ID: P14555 Link_out
Gene: PLA2G2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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

7. Complement control protein

Pharmacological action: unknown

Serves to protect the virus against complement attack by inhibiting both classical and alternative pathways of complement activation. Binds C3b and C4b

Organism class: viral
UniProt ID: P68638 Link_out
Gene: C3L
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ganesh VK, Muthuvel SK, Smith SA, Kotwal GJ, Murthy KH: Structural basis for antagonism by suramin of heparin binding to vaccinia complement protein. Biochemistry. 2005 Aug 16;44(32):10757-65. Pubmed
Enzymes

1. Arylsulfatase A

Actions: inhibitor

Hydrolyzes cerebroside sulfate

UniProt ID: P15289 Link_out
Gene: ARSA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Cytosolic phospholipase A2

Actions: inhibitor

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

UniProt ID: P47712 Link_out
Gene: PLA2G4A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Feb 3. Pubmed]
  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. Pubmed
Comments
Drug created on September 11, 2007 11:49 / Updated on February 08, 2013 16:23