Suramin
Identification
- Generic Name
- Suramin
- DrugBank Accession Number
- DB04786
- Background
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®.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 1297.28
Monoisotopic: 1296.046905756 - Chemical Formula
- C51H40N6O23S6
- Synonyms
- Suramin
- Suramine
Pharmacology
- Indication
For treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.
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- 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.
Target Actions Organism AP2Y purinoceptor 2 antagonistHumans ANAD-dependent protein deacylase sirtuin-5, mitochondrial inhibitorHumans AFollicle-stimulating hormone receptor antagonistHumans URyanodine receptor 1 agonistHumans UProthrombin inhibitorHumans UPhospholipase A2, membrane associated inhibitorHumans UComplement control protein C3 Not Available VACV - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Suramin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Suramin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Suramin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Suramin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Suramin is combined with Bupivacaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Suramin sodium 89521262IH 129-46-4 VAPNKLKDKUDFHK-UHFFFAOYSA-H - International/Other Brands
- 309 Fourneau / Antrypol / Bayer 205 / Belganyl / Germanin (Bayer) / Moranyl / Naganin / Naganine / Naganol / Naphuride
Categories
- ATC Codes
- P01CX02 — Suramin sodium
- Drug Categories
- Agents Against Leishmaniasis and Trypanosomiasis
- Anti-Infective Agents
- Antinematodal Agents
- Antineoplastic Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Arylsulfonates
- Arylsulfonic Acids
- Naphthalenes
- Naphthalenesulfonates
- Sulfonic Acids
- Sulfur Acids
- Sulfur Compounds
- Trypanocidal Agents
- Chemical TaxonomyProvided by Classyfire
- 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 sulfonates / 1-naphthalene sulfonic acids and derivatives / 2-naphthalene sulfonates / 2-naphthalene sulfonic acids and derivatives / N-phenylureas / p-Toluamides / Benzamides / 1-sulfo,2-unsubstituted aromatic compounds / Benzoyl derivatives / Sulfonyls show 8 more
- Substituents
- 1-naphthalene sulfonate / 1-naphthalene sulfonic acid or derivatives / 1-sulfo,2-unsubstituted aromatic compound / 2-naphthalene sulfonate / 2-naphthalene sulfonic acid or derivatives / Aromatic homopolycyclic compound / Arylsulfonic acid or derivatives / Benzamide / Benzanilide / Benzoic acid or derivatives show 26 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- naphthalenesulfonic acid (CHEBI:45906)
- Affected organisms
- Yeast, Molds, Trypanosomes
Chemical Identifiers
- UNII
- 6032D45BEM
- CAS number
- 145-63-1
- InChI Key
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015582
- KEGG Compound
- C07974
- PubChem Compound
- 5361
- PubChem Substance
- 46507013
- ChemSpider
- 5168
- BindingDB
- 50336799
- 10256
- ChEBI
- 45906
- ChEMBL
- CHEMBL265502
- Therapeutic Targets Database
- DAP001031
- PharmGKB
- PA10292
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- SVR
- Wikipedia
- Suramin
- PDB Entries
- 1y4l / 2h9t / 2nyr / 3bf6 / 3bjw / 3gan / 3ur0 / 4j4v / 4x3u / 4yv5 … show 4 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Prostate Cancer 2 2 Active Not Recruiting Prevention Acute Kidney Injury (AKI) 1 2 Completed Treatment Autism Disorder / Coronavirus Disease 2019 (COVID‑19) 1 2 Completed Treatment Brain and Central Nervous System Tumors 2 2 Completed Treatment Multiple Myeloma and Plasma Cell Neoplasm 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00872 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 314.9 m3·mol-1 Chemaxon Polarizability 120.22 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7333 Blood Brain Barrier + 0.8186 Caco-2 permeable - 0.5901 P-glycoprotein substrate Non-substrate 0.7739 P-glycoprotein inhibitor I Non-inhibitor 0.8805 P-glycoprotein inhibitor II Non-inhibitor 0.8545 Renal organic cation transporter Non-inhibitor 0.9383 CYP450 2C9 substrate Non-substrate 0.5122 CYP450 2D6 substrate Non-substrate 0.8142 CYP450 3A4 substrate Non-substrate 0.6631 CYP450 1A2 substrate Non-inhibitor 0.7894 CYP450 2C9 inhibitor Non-inhibitor 0.8854 CYP450 2D6 inhibitor Non-inhibitor 0.9264 CYP450 2C19 inhibitor Non-inhibitor 0.8912 CYP450 3A4 inhibitor Non-inhibitor 0.9572 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.924 Ames test Non AMES toxic 0.7113 Carcinogenicity Carcinogens 0.7574 Biodegradation Not ready biodegradable 0.9699 Rat acute toxicity 2.1516 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9836 hERG inhibition (predictor II) Non-inhibitor 0.8448
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 336.24915 predictedDeepCCS 1.0 (2019) [M+H]+ 337.97287 predictedDeepCCS 1.0 (2019) [M+Na]+ 344.30185 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- P2Y purinoceptor 2
- Molecular Weight
- 42272.92 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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:24703...
- Gene Name
- SIRT5
- Uniprot ID
- Q9NXA8
- Uniprot Name
- NAD-dependent protein deacylase sirtuin-5, mitochondrial
- Molecular Weight
- 33880.605 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 S...
- Gene Name
- FSHR
- Uniprot ID
- P23945
- Uniprot Name
- Follicle-stimulating hormone receptor
- Molecular Weight
- 78264.07 Da
References
- 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. [Article]
- Bose CK: Follicle stimulating hormone receptor (FSHR) antagonist and epithelial ovarian cancer (EOC). J Exp Ther Oncol. 2007;6(3):201-4. [Article]
- Kind
- Protein
- Organism
- Humans
- 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-tu...
- Gene Name
- RYR1
- Uniprot ID
- P21817
- Uniprot Name
- Ryanodine receptor 1
- Molecular Weight
- 565170.715 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 homeostas...
- Gene Name
- F2
- Uniprot ID
- P00734
- Uniprot Name
- Prothrombin
- Molecular Weight
- 70036.295 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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-ph...
- Gene Name
- PLA2G2A
- Uniprot ID
- P14555
- Uniprot Name
- Phospholipase A2, membrane associated
- Molecular Weight
- 16082.525 Da
References
- 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. [Article]
- 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. [Article]
- 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
- Uniprot Name
- Complement control protein C3
- Molecular Weight
- 28629.03 Da
References
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sulfuric ester hydrolase activity
- Specific Function
- Hydrolyzes cerebroside sulfate.
- Gene Name
- ARSA
- Uniprot ID
- P15289
- Uniprot Name
- Arylsulfatase A
- Molecular Weight
- 53587.6 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- PLA2G4A
- Uniprot ID
- P47712
- Uniprot Name
- Cytosolic phospholipase A2
- Molecular Weight
- 85238.2 Da
References
- 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. [Article]
- 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. [Article]
Drug created at September 11, 2007 17:49 / Updated at November 03, 2023 23:48