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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
Structure of SURAMIN

SMILES

CC1=C(NC(=O)C2=CC=CC(NC(=O)NC3=CC(=CC=C3)C(=O)NC4=C(C)C=CC(=C4)C(=O)NC5=CC=C(C6=CC(=CC(=C56)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)=C2)C=C(C=C1)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)

HIDE SMILES / InChI

Molecular Formula C51H40N6O23S6
Molecular Weight 1297.28
Charge 0
Count
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35625
Gene ID: 7078.0
Gene Symbol: TIMP3
Target Organism: Homo sapiens (Human)
1.9 nM [Kd]
Target ID: Q13616
Gene ID: 8454.0
Gene Symbol: CUL1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SURAMIN

Approved Use

Suramin 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.
Curative
SURAMIN

Approved Use

Suramin 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.
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Role of phosphoinositide 3OH-kinase in autocrine transformation by PDGF-BB.
2001-09
Dehydroepiandrosterone sulfate (DHEAS) suppresses P2X purinoceptor-coupled responses in PC12 cells.
2001-09
Purinergic-independent calcium signaling mediates recovery from hepatocellular swelling: implications for volume regulation.
2001-08-17
Protective action of the serine protease inhibitor N-tosyl-L-lysine chloromethyl ketone (TLCK) against acute soman poisoning.
2001-08-02
Intracellular re-routing of prion protein prevents propagation of PrP(Sc) and delays onset of prion disease.
2001-08-01
Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels.
2001-08
Methionine aminopeptidase-2 regulates human mesothelioma cell survival: role of Bcl-2 expression and telomerase activity.
2001-08
Cdc25A phosphatase suppresses apoptosis induced by serum deprivation.
2001-07-27
HGF/SF induces mesothelial cell migration and proliferation by autocrine and paracrine pathways.
2001-07-15
Toxicity, efficacy, and pharmacology of suramin in adults with recurrent high-grade gliomas.
2001-07-01
A Mg-dependent ecto-ATPase in Leishmania amazonensis and its possible role in adenosine acquisition and virulence.
2001-07-01
Prognostic significance of plasma vascular endothelial growth factor levels in patients with hormone-refractory prostate cancer treated on Cancer and Leukemia Group B 9480.
2001-07
Protein binding alters the activity of suramin, carboxyamidotriazole, and UCN-01 in an ex vivo rat aortic ring angiogenesis assay.
2001-07
Neural regulation of in vitro giant contractions in the rat colon.
2001-07
Apical P2Y4 purinergic receptor controls K+ secretion by vestibular dark cell epithelium.
2001-07
Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation.
2001-06-22
ATP modulates Na+ channel gating and induces a non-selective cation current in a neuronal hippocampal cell line.
2001-06-22
Probing the interaction of dengue virus envelope protein with heparin: assessment of glycosaminoglycan-derived inhibitors.
2001-06-21
Prognostic significance of reverse transcriptase polymerase chain reaction for prostate-specific antigen in men with hormone-refractory prostate cancer.
2001-06-15
Extracellular nucleotides differentially regulate interleukin-1beta signaling in primary human astrocytes: implications for inflammatory gene expression.
2001-06-15
The P2Y11 receptor mediates the ATP-induced maturation of human monocyte-derived dendritic cells.
2001-06-15
Synapse-glia interactions at the mammalian neuromuscular junction.
2001-06-01
Aldosterone upregulates purinergic responses in larval amphibian skin epithelium.
2001-06
Modulation of cyclooxygenase-2 and brain reactive astrogliosis by purinergic P2 receptors.
2001-06
Neural retina of chick embryo in organ culture: effects of blockade of growth factors by suramin.
2001-06
ATP but not adenosine inhibits nonquantal acetylcholine release at the mouse neuromuscular junction.
2001-06
Inhibition of insulin-like growth factor I receptor increases the antitumor activity of doxorubicin and vincristine against Ewing's sarcoma cells.
2001-06
Genomic structure, developmental distribution and functional properties of the chicken P2X(5) receptor.
2001-06
Endothelium-dependent relaxation induced by cathepsin G in porcine pulmonary arteries.
2001-06
EGR-1, a UV-inducible gene in p53(-/-) mouse cells.
2001-05-15
Transporters in African trypanosomes: role in drug action and resistance.
2001-05-01
Suramin and the suramin analogue NF307 discriminate among calmodulin-binding sites.
2001-05-01
Mechanical response to electrical field stimulation of rat, guinea-pig, monkey and human detrusor muscle: a comparative study.
2001-05
Coronary vasomotor and cardiac electrophysiologic effects of diadenosine polyphosphates and nonhydrolyzable analogs in the guinea pig.
2001-05
Indomethacin and telomerase activity in tumor growth retardation.
2001-05
ATP induces intracellular calcium increases and actin cytoskeleton disaggregation via P2x receptors.
2001-05
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.
2001-04-17
Effect on urinary bladder function and arterial blood pressure of the activation of putative purine receptors in brainstem areas.
2001-04-12
Effects of ATP on intracellular calcium dynamics of neurons and satellite cells in rat superior cervical ganglia.
2001-04
Promotion of formation of amyloid fibrils by aluminium adenosine triphosphate (AlATP).
2001-04
Treatment of patients with metastatic germ cell tumors relapsing after high-dose chemotherapy.
2001-04
Phase 1 drug interaction study of suramin and warfarin in patients with prostate cancer.
2001-04
Possible involvement of ERK 1/2 in UVA-induced melanogenesis in cultured normal human epidermal melanocytes.
2001-04
ATP and ADP hydrolysis in fish, chicken and rat synaptosomes.
2001-04
Molecular cloning and characterization of the mouse P2Y4 nucleotide receptor.
2001-03-30
Nicorandil--induced ATP release in endothelial cells of rat caudal artery is associated with increase in intracellular Ca(2+).
2001-03-30
Vascular endothelial growth factor and basic fibroblast growth factor urine levels as predictors of outcome in hormone-refractory prostate cancer patients: a cancer and leukemia group B study.
2001-03-15
Regulation of chicken gizzard ecto-ATPase activity by modulators that affect its oligomerization status.
2001-03-01
Vascular smooth muscle cell proliferation is effectively suppressed by the non-specific growth factor inhibitor suramin.
2001-03
Stimulation of mouse cultured sympathetic neurons by uracil but not adenine nucleotides.
2001
Patents

Sample Use Guides

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
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 Mon Mar 31 18:06:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:17 GMT 2025
Record UNII
6032D45BEM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FARMA
Preferred Name English
SURAMIN
WHO-DD  
Common Name English
NAGANOL
Brand Name English
8,8'-(CARBONYLBIS(IMINO-3,1-PHENYLENECARBONYLIMINO(4-METHYL-3,1-PHENYLENE)CARBONYLIMINO))BIS-1,3,5-NAPHTHALENETRISULFONIC ACID
Common Name English
1,3,5-NAPHTHALENETRISULFONIC ACID, 8,8'-(CARBONYLBIS(IMINO-3,1-PHENYLENECARBONYLIMINO(4-METHYL-3,1-PHENYLENE)CARBONYLIMINO))BIS-
Systematic Name English
FARMA-939
Code English
Suramin [WHO-DD]
Common Name English
SURAMINE
Common Name English
8,8'-(UREYLENEBIS(M-PHENYLENECARBONYLIMINO(4-METHYL-M-PHENYLENE)CARBONYLIMINO))DI-1,3,5-NAPHTHALENETRISULFONIC ACID
Common Name English
FOURNEAU
Brand Name English
NSC-34936
Code English
METARET
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1971
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
FDA ORPHAN DRUG 797220
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
FDA ORPHAN DRUG 104897
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
Code System Code Type Description
NSC
34936
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
RXCUI
10256
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C853
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
FDA UNII
6032D45BEM
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
DRUG CENTRAL
2966
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
SMS_ID
100000084786
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
EVMPD
SUB04651MIG
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
DRUG BANK
DB04786
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
CAS
145-63-1
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
PUBCHEM
5361
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
CHEBI
45906
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
IUPHAR
1728
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
MESH
D013498
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
WIKIPEDIA
SURAMIN
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-658-4
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID1046344
Created by admin on Mon Mar 31 18:06:17 GMT 2025 , Edited by admin on Mon Mar 31 18:06:17 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY