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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
Stimulation of mouse cultured sympathetic neurons by uracil but not adenine nucleotides.
2001
Promotion of formation of amyloid fibrils by aluminium adenosine triphosphate (AlATP).
2001 Apr
Treatment of patients with metastatic germ cell tumors relapsing after high-dose chemotherapy.
2001 Apr
Phase 1 drug interaction study of suramin and warfarin in patients with prostate cancer.
2001 Apr
Purinergic regulation of intracellular Ca2+ concentration of rat pituitary folliculo-stellate cells in primary culture.
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
Purinoceptor-mediated calcium mobilization and proliferation in HaCaT keratinocytes.
2001 Feb
Intercellular communication upon mechanical stimulation of CPAE- endothelial cells is mediated by nucleotides.
2001 Feb
Differential localization of P2 receptor subtypes in mesenteric arteries and veins of normotensive and hypertensive rats.
2001 Feb
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
2001 Feb
Analysis of purine- and pyrimidine-induced vascular responses in the isolated rat cerebral arteriole.
2001 Feb
Suramin prevents cerebellar granule cell-death induced by dequalinium.
2001 Feb
Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells.
2001 Jan
Multiple P2X receptors on guinea-pig pelvic ganglion neurons exhibit novel pharmacological properties.
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
Astrocyte-endothelial cell calcium signals conveyed by two signalling pathways.
2001 Jan
Uptake and mode of action of drugs used against sleeping sickness.
2001 Jan 1
Alteration of spontaneous firing rate of primary myelinated afferents by ATP in adjuvant-induced inflamed rats.
2001 Jan 15
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.
2001 Jan 5
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
Toxicity, efficacy, and pharmacology of suramin in adults with recurrent high-grade gliomas.
2001 Jul 1
Aldosterone upregulates purinergic responses in larval amphibian skin epithelium.
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
The P2Y11 receptor mediates the ATP-induced maturation of human monocyte-derived dendritic cells.
2001 Jun 15
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
Identification of P1 and P2 purinoceptors in the aorta of the lizard (Agama sp.).
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
Serum prostate-specific antigen decline as a marker of clinical outcome in hormone-refractory prostate cancer patients: association with progression-free survival, pain end points, and survival.
2001 Mar 1
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 Mar 15
Extracellular ATP or ADP induce chemotaxis of cultured microglia through Gi/o-coupled P2Y receptors.
2001 Mar 15
Nicorandil--induced ATP release in endothelial cells of rat caudal artery is associated with increase in intracellular Ca(2+).
2001 Mar 30
Coronary vasomotor and cardiac electrophysiologic effects of diadenosine polyphosphates and nonhydrolyzable analogs in the guinea pig.
2001 May
Transporters in African trypanosomes: role in drug action and resistance.
2001 May 1
Dehydroepiandrosterone sulfate (DHEAS) suppresses P2X purinoceptor-coupled responses in PC12 cells.
2001 Sep
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:42:36 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
FDA ORPHAN DRUG 797220
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
FDA ORPHAN DRUG 104897
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
Code System Code Type Description
NSC
34936
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
RXCUI
10256
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C853
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
FDA UNII
6032D45BEM
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
DRUG CENTRAL
2966
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
SMS_ID
100000084786
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
EVMPD
SUB04651MIG
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
DRUG BANK
DB04786
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
CAS
145-63-1
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
PUBCHEM
5361
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
CHEBI
45906
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
IUPHAR
1728
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
MESH
D013498
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
WIKIPEDIA
SURAMIN
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-658-4
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID1046344
Created by admin on Fri Dec 15 15:42:36 GMT 2023 , Edited by admin on Fri Dec 15 15:42:36 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY