Details
Stereochemistry | ACHIRAL |
Molecular Formula | C51H40N6O23S6 |
Molecular Weight | 1297.28 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1NC(=O)C2=CC(NC(=O)NC3=CC=CC(=C3)C(=O)NC4=CC(=CC=C4C)C(=O)NC5=CC=C(C6=C5C(=CC(=C6)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)=CC=C2)C(=O)NC7=CC=C(C8=C7C(=CC(=C8)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O
InChI
InChIKey=FIAFUQMPZJWCLV-UHFFFAOYSA-N
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)
Molecular Formula | C51H40N6O23S6 |
Molecular Weight | 1297.28 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Suramin is an antiprotozoal and anthelmintic compound. It is indicated for the treatment of African trypanosomiasis (African sleeping sickness; trypanosome fever) and Onchocerciasis (river blindness). Additionally, suramin exhibits antineoplastic action. It was discovered that suramin produced dramatic, but transient, improvement of core symptoms of autism spectrum disorder.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800004055 | https://www.ncbi.nlm.nih.gov/pubmed/21563369
Curator's Comment: # Bayer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1825 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1325955 |
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Target ID: P35625 Gene ID: 7078.0 Gene Symbol: TIMP3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28798097 |
1.9 nM [Kd] | ||
Target ID: Q13616 Gene ID: 8454.0 Gene Symbol: CUL1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27001857 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | SURAMIN Approved UseSuramin is used as a primary agent in the treatment of African trypanosomiasis (African sleeping sickness; trypanosome fever) caused by Trypanosoma brucei gambiense or T. b. rhodesiense in patients with early or hemolymphatic disease without central nervous system (CNS) involvement. In patients with late stage or chronic trypanosomiasis caused by T. b. gambiense or T. b. rhodesiense involving the CNS, the primary agent is the toxic arsenical compound melarsoprol. Suramin may be administered as a preliminary agent prior to starting melarsoprol therapy in order to reduce the number of trypanosomes in the blood, thereby minimizing the adverse effects of melarsoprol. For patients who cannot tolerate melarsoprol, an alternative treatment is a combination of suramin and tryparsamide. These 2 medications are synergistic in action, and good therapeutic results have been obtained with combined administration. Eflornithine is another agent that has been found to be effective for T. b. gambiense infections. However, eflornithine has variable efficacy against T. b. rhodesiense infections.
Suramin is used as a secondary agent in the treatment of onchocerciasis (river blindness) caused by Onchocerca volvulus . This agent is effective in killing the adult worm (macrofilaricidal) and also has partial microfilaricidal action. However, because of its intrinsic toxicity, suramin is now rarely used for this indication. Currently, its use is restricted to radical cure of selected individuals in areas without transmission of onchocerciasis, for expatriates leaving the endemic area, and for severe hyperreactive onchodermatitis in patients whose symptoms are not adequately controlled by repeated treatment with ivermectin. Ivermectin is considered the primary agent in the treatment of onchocerciasis as a microfilaricide; it has been shown to have little or no macrofilaricidal effect. or heavily infected patients, ivermectin may be given prior to suramin therapy to reduce the microfilarial load. |
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Curative | SURAMIN Approved UseSuramin is used as a primary agent in the treatment of African trypanosomiasis (African sleeping sickness; trypanosome fever) caused by Trypanosoma brucei gambiense or T. b. rhodesiense in patients with early or hemolymphatic disease without central nervous system (CNS) involvement. In patients with late stage or chronic trypanosomiasis caused by T. b. gambiense or T. b. rhodesiense involving the CNS, the primary agent is the toxic arsenical compound melarsoprol. Suramin may be administered as a preliminary agent prior to starting melarsoprol therapy in order to reduce the number of trypanosomes in the blood, thereby minimizing the adverse effects of melarsoprol. For patients who cannot tolerate melarsoprol, an alternative treatment is a combination of suramin and tryparsamide. These 2 medications are synergistic in action, and good therapeutic results have been obtained with combined administration. Eflornithine is another agent that has been found to be effective for T. b. gambiense infections. However, eflornithine has variable efficacy against T. b. rhodesiense infections.
Suramin is used as a secondary agent in the treatment of onchocerciasis (river blindness) caused by Onchocerca volvulus . This agent is effective in killing the adult worm (macrofilaricidal) and also has partial microfilaricidal action. However, because of its intrinsic toxicity, suramin is now rarely used for this indication. Currently, its use is restricted to radical cure of selected individuals in areas without transmission of onchocerciasis, for expatriates leaving the endemic area, and for severe hyperreactive onchodermatitis in patients whose symptoms are not adequately controlled by repeated treatment with ivermectin. Ivermectin is considered the primary agent in the treatment of onchocerciasis as a microfilaricide; it has been shown to have little or no macrofilaricidal effect. or heavily infected patients, ivermectin may be given prior to suramin therapy to reduce the microfilarial load. |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Assessment of drugs against Cryptosporidium parvum using a simple in vitro screening method. | 1999 Sep 15 |
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Promotion of formation of amyloid fibrils by aluminium adenosine triphosphate (AlATP). | 2001 Apr |
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Possible involvement of ERK 1/2 in UVA-induced melanogenesis in cultured normal human epidermal melanocytes. | 2001 Apr |
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ATP and ADP hydrolysis in fish, chicken and rat synaptosomes. | 2001 Apr |
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Adenosine triphosphate activates mitogen-activated protein kinase in human granulosa-luteal cells. | 2001 Apr |
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Direct autocrine inhibition and cAMP-dependent potentiation of single L-type Ca2+ channels in bovine chromaffin cells. | 2001 Apr 1 |
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Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels. | 2001 Aug |
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Intracellular re-routing of prion protein prevents propagation of PrP(Sc) and delays onset of prion disease. | 2001 Aug 1 |
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Purinergic-independent calcium signaling mediates recovery from hepatocellular swelling: implications for volume regulation. | 2001 Aug 17 |
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The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus. | 2001 Feb |
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Suramin prevents cerebellar granule cell-death induced by dequalinium. | 2001 Feb |
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Neural mechanisms underlying migrating motor complex formation in mouse isolated colon. | 2001 Jan |
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Potentiation of cytokine induction of group IIA phospholipase A(2) in rat mesangial cells by ATP and adenosine via the A2A adenosine receptor. | 2001 Jan |
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Early elicitor-induced events in chickpea cells: functional links between oxidative burst, sequential occurrence of extracellular alkalinisation and acidification, K+/H+ exchange and defence-related gene activation. | 2001 Jan-Feb |
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Apical P2Y4 purinergic receptor controls K+ secretion by vestibular dark cell epithelium. | 2001 Jul |
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A Mg-dependent ecto-ATPase in Leishmania amazonensis and its possible role in adenosine acquisition and virulence. | 2001 Jul 1 |
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Cdc25A phosphatase suppresses apoptosis induced by serum deprivation. | 2001 Jul 27 |
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Aldosterone upregulates purinergic responses in larval amphibian skin epithelium. | 2001 Jun |
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Inhibition of insulin-like growth factor I receptor increases the antitumor activity of doxorubicin and vincristine against Ewing's sarcoma cells. | 2001 Jun |
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Genomic structure, developmental distribution and functional properties of the chicken P2X(5) receptor. | 2001 Jun |
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Endothelium-dependent relaxation induced by cathepsin G in porcine pulmonary arteries. | 2001 Jun |
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Extracellular nucleotides differentially regulate interleukin-1beta signaling in primary human astrocytes: implications for inflammatory gene expression. | 2001 Jun 15 |
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The P2Y11 receptor mediates the ATP-induced maturation of human monocyte-derived dendritic cells. | 2001 Jun 15 |
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Probing the interaction of dengue virus envelope protein with heparin: assessment of glycosaminoglycan-derived inhibitors. | 2001 Jun 21 |
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Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation. | 2001 Jun 22 |
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Vascular smooth muscle cell proliferation is effectively suppressed by the non-specific growth factor inhibitor suramin. | 2001 Mar |
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Pharmacological characterisation of pyrimidinoceptor responses in NG108-15 cells. | 2001 Mar |
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Nerve evoked P2X receptor contractions of rat mesenteric arteries; dependence on vessel size and lack of role of L-type calcium channels and calcium induced calcium release. | 2001 Mar |
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Metabolic studies of glycosphingolipid accumulation in mucopolysaccharidosis IIID. | 2001 Mar |
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Coexpression of P2X(3) and P2X(2) receptor subunits in varying amounts generates heterogeneous populations of P2X receptors that evoke a spectrum of agonist responses comparable to that seen in sensory neurons. | 2001 Mar |
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Glucose deprivation and chemical hypoxia: neuroprotection by P2 receptor antagonists. | 2001 Mar |
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Extracellular ATP or ADP induce chemotaxis of cultured microglia through Gi/o-coupled P2Y receptors. | 2001 Mar 15 |
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Mechanical response to electrical field stimulation of rat, guinea-pig, monkey and human detrusor muscle: a comparative study. | 2001 May |
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Coronary vasomotor and cardiac electrophysiologic effects of diadenosine polyphosphates and nonhydrolyzable analogs in the guinea pig. | 2001 May |
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Indomethacin and telomerase activity in tumor growth retardation. | 2001 May |
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ATP induces intracellular calcium increases and actin cytoskeleton disaggregation via P2x receptors. | 2001 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/mmx/suramin-sodium.html
Usual adult dose
[Trypanosomiasis, African (treatment)]
Early stage: Intravenous, 100 to 200 mg (0.1 to 0.2 gram) administered slowly as a test dose for hypersensitivity. This is followed after twenty-four hours by a dose of 20 mg per kg of body weight per day to a maximum of 1 gram on days one, three, seven, fourteen, and twenty-one, or weekly, until a total dose of 5 grams is achieved. {56} Patients in poor general condition should receive approximately one-quarter of the normal dose.
Late stage: Intravenous, 100 to 200 mg (0.1 to 0.2 gram) administered slowly as a test dose for hypersensitivity. This is followed after twenty-four hours by a dose of 10 mg per kilogram (kg) of body weight per day every five days for a total of twelve injections. This is given in combination with tryparsamide at a dose of 30 mg per kg of body weight (maximum of 2 grams) per day, also administered intravenously every five days, for a total of twelve injections. One month after completion of therapy, a second course of this combined treatment may be repeated, if necessary.
[Onchocerciasis (treatment)]
Intravenous, 100 to 200 mg (0.1 to 0.2 gram) administered slowly as a test dose for hypersensitivity. Treatment with the full dose may then be started after one week. A total of 66.7 mg per kg of body weight should be administered in six incremental weekly doses apportioned as follows: 3.3 mg/kg week one, 6.7 mg/kg week two, 10 mg/kg week three, 13.3 mg/kg week four, 16.7 mg/kg week five, and 16.7 mg/kg week six.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26112648
Suramin inhibits Chikungunya virus (CHIKV) RNA synthesis (IC50 of ∼5μM). The compound inhibited replication of various CHIKV isolates in cell culture with an EC50 of ∼80μM (CC50>5mM) and was also active against Sindbis virus and Semliki Forest virus.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:42:36 UTC 2023
by
admin
on
Fri Dec 15 15:42:36 UTC 2023
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Record UNII |
6032D45BEM
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1971
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FDA ORPHAN DRUG |
797220
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FDA ORPHAN DRUG |
104897
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C853
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