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Identification
NameSuramin
Accession NumberDB04786
TypeSmall Molecule
GroupsApproved
DescriptionA 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
Synonyms
8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic acid
Belganyl
Naganol
Naphuride
Suramin
Suramine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
309 FourneauNot Available
AntrypolNot Available
Bayer 205Not Available
BelganylNot Available
GermaninBayer
MoranylNot Available
NaganinNot Available
NaganineNot Available
NaganolNot Available
NaphurideNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Suramin sodium
129-46-4
Thumb
  • InChI Key: VAPNKLKDKUDFHK-UHFFFAOYSA-H
  • Monoisotopic Mass: 1427.938573614
  • Average Mass: 1429.171
DBSALT000540
Categories
UNII6032D45BEM
CAS number145-63-1
WeightAverage: 1297.28
Monoisotopic: 1296.046905756
Chemical FormulaC51H40N6O23S6
InChI KeyInChIKey=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)
IUPAC Name
8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2-naphthalene sulfonic acids and derivatives. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group (or a derivative thereof) at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthalene sulfonic acids and derivatives
Direct Parent2-naphthalene sulfonic acids and derivatives
Alternative Parents
Substituents
  • 2-naphthalene sulfonate
  • 1-naphthalene sulfonate
  • 2-naphthalene sulfonic acid or derivatives
  • 1-naphthalene sulfonic acid or derivatives
  • Naphthalene sulfonate
  • N-phenylbenzamide
  • N-arylamide
  • N-phenylurea
  • Aminobenzoic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • Benzoic acid or derivatives
  • Benzamide
  • Arylsulfonic acid or derivatives
  • Aminotoluene
  • Benzoyl
  • Toluene
  • Monocyclic benzene moiety
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Urea
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.
PharmacodynamicsNot Available
Mechanism of actionThe 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.
Related Articles
AbsorptionPoorly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingApproximately 99.7%
Metabolism

Little or no metabolism

Route of eliminationNot Available
Half lifeApproximately 36 to 60 days
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Yeast, Molds, Trypanosomes
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7333
Blood Brain Barrier+0.8186
Caco-2 permeable-0.5901
P-glycoprotein substrateNon-substrate0.7739
P-glycoprotein inhibitor INon-inhibitor0.8805
P-glycoprotein inhibitor IINon-inhibitor0.8545
Renal organic cation transporterNon-inhibitor0.9383
CYP450 2C9 substrateNon-substrate0.5122
CYP450 2D6 substrateNon-substrate0.8142
CYP450 3A4 substrateNon-substrate0.6631
CYP450 1A2 substrateNon-inhibitor0.7894
CYP450 2C9 inhibitorNon-inhibitor0.8854
CYP450 2D6 inhibitorNon-inhibitor0.9264
CYP450 2C19 inhibitorNon-inhibitor0.8912
CYP450 3A4 inhibitorNon-inhibitor0.9572
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.924
Ames testNon AMES toxic0.7113
CarcinogenicityCarcinogens 0.7574
BiodegradationNot ready biodegradable0.9699
Rat acute toxicity2.1516 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9836
hERG inhibition (predictor II)Non-inhibitor0.8448
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00872 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesP01CX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Suramin.
AmodiaquineThe serum concentration of Suramin can be decreased when it is combined with Amodiaquine.
BevacizumabBevacizumab may increase the cardiotoxic activities of Suramin.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Suramin.
ChloroquineThe serum concentration of Suramin can be decreased when it is combined with Chloroquine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Suramin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Suramin.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Suramin.
DigoxinDigoxin may decrease the cardiotoxic activities of Suramin.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Suramin.
HydroxychloroquineThe serum concentration of Suramin can be decreased when it is combined with Hydroxychloroquine.
OuabainOuabain may decrease the cardiotoxic activities of Suramin.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Suramin.
PrimaquineThe serum concentration of Suramin can be decreased when it is combined with Primaquine.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Suramin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Utp-activated nucleotide receptor activity
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:
42272.92 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
NAD-dependent lysine demalonylase, desuccinylase and deglutarylase that specifically removes malonyl, succinyl and glutaryl groups on target proteins (PubMed:21908771, PubMed:22076378, PubMed:24703693). Activates CPS1 and contributes to the regulation of blood ammonia levels during prolonged fasting: acts by mediating desuccinylation and deglutarylation of CPS1, thereby increasing CPS1 activity...
Gene Name:
SIRT5
Uniprot ID:
Q9NXA8
Molecular Weight:
33880.605 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled peptide receptor activity
Specific Function:
Receptor for follicle-stimulating hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Induces cAMP production through the activation of PI3K-AKT and SRC-ERK1/2 signaling pathways.
Gene Name:
FSHR
Uniprot ID:
P23945
Molecular Weight:
78264.07 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Voltage-gated calcium channel activity
Specific Function:
Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering muscle contraction following depolarization of T-tubules. Repeated very high-level exercise increases the open probability of the channel and leads to Ca(2+) leaking into the cytoplasm. Can also mediate the release of Ca(2+) from intracellular stores ...
Gene Name:
RYR1
Uniprot ID:
P21817
Molecular Weight:
565170.715 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Thrombospondin receptor activity
Specific Function:
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. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
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:15203120 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Phospholipid binding
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 Da
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 ]
Kind
Protein
Organism
VACV
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Serves to protect the virus against complement attack by inhibiting both classical and alternative pathways of complement activation. Binds C3b and C4b.
Gene Name:
Not Available
Uniprot ID:
P68638
Molecular Weight:
28629.03 Da
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:16086578 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sulfuric ester hydrolase activity
Specific Function:
Hydrolyzes cerebroside sulfate.
Gene Name:
ARSA
Uniprot ID:
P15289
Molecular Weight:
53587.6 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Phospholipase a2 activity
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:
85238.2 Da
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 ]
Comments
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24