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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=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)

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
Assessment of drugs against Cryptosporidium parvum using a simple in vitro screening method.
1999 Sep 15
Promotion of formation of amyloid fibrils by aluminium adenosine triphosphate (AlATP).
2001 Apr
Possible involvement of ERK 1/2 in UVA-induced melanogenesis in cultured normal human epidermal melanocytes.
2001 Apr
ATP and ADP hydrolysis in fish, chicken and rat synaptosomes.
2001 Apr
Adenosine triphosphate activates mitogen-activated protein kinase in human granulosa-luteal cells.
2001 Apr
Direct autocrine inhibition and cAMP-dependent potentiation of single L-type Ca2+ channels in bovine chromaffin cells.
2001 Apr 1
Dual mechanism of intercellular communication in HOBIT osteoblastic cells: a role for gap-junctional hemichannels.
2001 Aug
Intracellular re-routing of prion protein prevents propagation of PrP(Sc) and delays onset of prion disease.
2001 Aug 1
Purinergic-independent calcium signaling mediates recovery from hepatocellular swelling: implications for volume regulation.
2001 Aug 17
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
2001 Feb
Suramin prevents cerebellar granule cell-death induced by dequalinium.
2001 Feb
Neural mechanisms underlying migrating motor complex formation in mouse isolated colon.
2001 Jan
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
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
Apical P2Y4 purinergic receptor controls K+ secretion by vestibular dark cell epithelium.
2001 Jul
A Mg-dependent ecto-ATPase in Leishmania amazonensis and its possible role in adenosine acquisition and virulence.
2001 Jul 1
Cdc25A phosphatase suppresses apoptosis induced by serum deprivation.
2001 Jul 27
Aldosterone upregulates purinergic responses in larval amphibian skin epithelium.
2001 Jun
Inhibition of insulin-like growth factor I receptor increases the antitumor activity of doxorubicin and vincristine against Ewing's sarcoma cells.
2001 Jun
Genomic structure, developmental distribution and functional properties of the chicken P2X(5) receptor.
2001 Jun
Endothelium-dependent relaxation induced by cathepsin G in porcine pulmonary arteries.
2001 Jun
Extracellular nucleotides differentially regulate interleukin-1beta signaling in primary human astrocytes: implications for inflammatory gene expression.
2001 Jun 15
The P2Y11 receptor mediates the ATP-induced maturation of human monocyte-derived dendritic cells.
2001 Jun 15
Probing the interaction of dengue virus envelope protein with heparin: assessment of glycosaminoglycan-derived inhibitors.
2001 Jun 21
Nucleotide-evoked relaxation of rat vas deferens--a possible role for endogenous ATP released upon alpha(1)-adrenoceptor stimulation.
2001 Jun 22
Vascular smooth muscle cell proliferation is effectively suppressed by the non-specific growth factor inhibitor suramin.
2001 Mar
Pharmacological characterisation of pyrimidinoceptor responses in NG108-15 cells.
2001 Mar
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
Metabolic studies of glycosphingolipid accumulation in mucopolysaccharidosis IIID.
2001 Mar
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
Glucose deprivation and chemical hypoxia: neuroprotection by P2 receptor antagonists.
2001 Mar
Extracellular ATP or ADP induce chemotaxis of cultured microglia through Gi/o-coupled P2Y receptors.
2001 Mar 15
Mechanical response to electrical field stimulation of rat, guinea-pig, monkey and human detrusor muscle: a comparative study.
2001 May
Coronary vasomotor and cardiac electrophysiologic effects of diadenosine polyphosphates and nonhydrolyzable analogs in the guinea pig.
2001 May
Indomethacin and telomerase activity in tumor growth retardation.
2001 May
ATP induces intracellular calcium increases and actin cytoskeleton disaggregation via P2x receptors.
2001 May
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 Fri Dec 15 15:42:36 UTC 2023
Edited
by admin
on Fri Dec 15 15:42:36 UTC 2023
Record UNII
6032D45BEM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
FARMA
Brand 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 Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
FDA ORPHAN DRUG 797220
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
FDA ORPHAN DRUG 104897
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
Code System Code Type Description
NSC
34936
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
RXCUI
10256
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C853
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
FDA UNII
6032D45BEM
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
DRUG CENTRAL
2966
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
SMS_ID
100000084786
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
EVMPD
SUB04651MIG
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
DRUG BANK
DB04786
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
CAS
145-63-1
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
PUBCHEM
5361
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
CHEBI
45906
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
IUPHAR
1728
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
MESH
D013498
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
WIKIPEDIA
SURAMIN
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-658-4
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID1046344
Created by admin on Fri Dec 15 15:42:36 UTC 2023 , Edited by admin on Fri Dec 15 15:42:36 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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