Basic information
- CAS
129-46-4- Standard SMILES
Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1- InChIKey
FIAFUQMPZJWCLV-UHFFFAOYSA-N- Molecular formula
- C51H40N6O23S6
- Average molar mass
- 1,297.3 g/mol
- Monoisotopic mass
- 1,296.0469086
Overview
Suramin is a member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years. It has a role as an antinematodal drug, an antineoplastic agent, a trypanocidal drug, an EC 2.7.11.13 (protein kinase C) inhibitor, a GABA-gated chloride channel antagonist, an angiogenesis inhibitor, a GABA antagonist, a ryanodine receptor agonist, an apoptosis inhibitor and a purinergic receptor P2 antagonist. It is a member of phenylureas, a secondary carboxamide and a naphthalenesulfonic acid. It is functionally related to a naphthalene-1,3,5-trisulfonic acid. It is a conjugate acid of a suramin(6-).
Names & identifiers
- Preferred name
- Suramin
- IUPAC
- 8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid
- English name
- Suramin sodium
- Molecular formula
- C51H34N6Na6O23S6
- Molecular weight
- 1429.17
Names & synonyms
suraminSuramine145-63-1FourneauFarmaBelganylMetaretDTXSID1046344NSC-34936FARMA-9396032D45BEM1,3,5-naphthalenetrisulfonic acid, 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-
Show more names
SURAMIN SODIUM SALTSURAMIN HEXASODIUM SALTnf060reasodiumsaltsuraminesodiumnaphuridesodiumSuramin, Sodium Salt - CAS 129-46-4 - Calbiochem309fF-309
DTXCID9026344CHEBI:459061,3,5-Naphthalenetrisulfonic acid, 8,8'-(carbonylbis(imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino))bis-8-[[4-methyl-3-[[3-[[3-[[2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]benzoyl]amino]naphthalene-1,3,5-trisulfonic acid8,8'-(CARBONYLBIS(IMINO-3,1-PHENYLENECARBONYLIMINO(4-METHYL-3,1-PHENYLENE)CARBONYLIMINO))BIS-1,3,5-NAPHTHALENETRISULFONIC ACID8-[(4-methyl-3-{[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzene]amido}benzene)amido]naphthalene-1,3,5-trisulfonic acid8-((4-methyl-3-((3-(((3-((2-methyl-5-((4,6,8-trisulfonaphthalen-1-yl)carbamoyl)phenyl)carbamoyl)phenyl)carbamoyl)amino)benzene)amido)benzene)amido)naphthalene-1,3,5-trisulfonic acid8-((4-methyl-3-((3-((3-((2-methyl-5-((4,6,8-trisulfonaphthalen-1-yl)carbamoyl)phenyl)carbamoyl)phenyl)carbamoylamino)benzoyl)amino)benzoyl)amino)naphthalene-1,3,5-trisulfonic acid
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 534 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 23
- Rotatable bonds
- 16
- Heavy atoms
- 86
- Formal charge
- 0
- Complexity
- 3,020
Experimental & physicochemical properties
Solubility8.72e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 260 °C · >260°C (dec.)
- storage temp.
- 0 · 0-6°C
- solubility
- 2 O: · H2O: >10mg/mL
- form
- Crystalline Powder
- color
- White
- PH
- pH(10g/l, 25℃) : 5.0～8.0
- Water Solubility
- soluble
- BRN
- 3694087 · 3694087
- Stability
- Hygroscopic
- InChIKey
- VAPNKLKDKUDFHK-UHFFFAOYSA-H
- NCI Dictionary of Cancer Terms
- suramin
- FDA UNII
- 89521262 IH · 89521262IH
- NCI Drug Dictionary
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- QM7000000
- hs_code
- 29242998
- Toxicity
- LD50 in mice (mg/kg): ~620 i.v. (Hawking)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Chemistry & industry
Pharmacology
Protein BindingApproximately 99.7%
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.
Biological Half-LifeApproximately 36 to 60 days
Metabolism/MetabolitesLittle or no metabolism
MeSH Pharmacological Classification
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.
Absorption, Distribution and ExcretionPoorly absorbed from the gastrointestinal tract.
Cellular LocationsCytoplasm
Applications
DescriptionIntroduced into therapy for the treatment of early trypanosomiasis in the 1920s, suramin, a bis-hexasulfonatednaphthylurea, is still considered to be the drug of choice for treatment of non-CNS-associated African trypanosomiasis.
Usesantiviral
Suramin sodium is a compound with a dyelike structure. Suramin is most effective against T. b. rhodesiense, but has also been used against T. b. gambiense infection. The compound causes side effects such as nausea, photophobia, and peripheral neuropathy which disappear shortly after conclusion of administration. Because the drug is unable to pass the bloodbrain barrier, prompt treatment of patients is essential. Suramin in combination with tryparsamide is an alternative that has been investigated.
Related reactions
0 records
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Compound notes
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