8,8'-[Carbonylbis[imino-3,1-phenylencarbonylimino(4-methyl-3,1-phenylen)carbonylimino]]bisnaphthalin-1,3,5-trisulfonsure
5-(Hydroxy-oxo-oxoniumylidene-lambda6-sulfanyl)-4-[[3-[[3-[[3-[[5-[[8-(hydroxy-oxo-oxoniumylidene-lambda6-sulfanyl)-6-sulfo-4-sulfonatonaphthalen-1-yl]carbamoyl]-2-methylphenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]-4-methylbenzoyl]amino]-7-sulfonaphthalene-1-sulfonate
Grundinformationen
- CAS
145-63-1- Standard-SMILES
Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)[O-])c3cc(S(=O)([O-])=[OH+])cc(S(=O)(O)=[OH+])c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)[O-])c5cc(S(=O)([O-])=[OH+])cc(S(=O)(O)=[OH+])c45)ccc3C)c2)c1- InChIKey
FIAFUQMPZJWCLV-UHFFFAOYSA-N- Summenformel
- C51H40N6O23S6
- Durchschnittliche Molmasse
- 1.297,3 g/mol
- Monoisotopische Masse
- 1.296,0469086
Überblick
A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties. Suramin is manufactured by Bayer in Germany as Germanin®.
Namen und Bezeichner
- Bevorzugter Name
- 5-(Hydroxy-oxo-oxoniumylidene-lambda6-sulfanyl)-4-[[3-[[3-[[3-[[5-[[8-(hydroxy-oxo-oxoniumylidene-lambda6-sulfanyl)-6-sulfo-4-sulfonatonaphthalen-1-yl]carbamoyl]-2-methylphenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]-4-methylbenzoyl]amino]-7-sulfonaphthalene-1-sulfonate
- IUPAC
- 5-(hydroxy-oxo-oxoniumylidene-λ6-sulfanyl)-4-[[3-[[3-[[3-[[5-[[8-(hydroxy-oxo-oxoniumylidene-λ6-sulfanyl)-6-sulfo-4-sulfonatonaphthalen-1-yl]carbamoyl]-2-methylphenyl]carbamoyl]phenyl]carbamoylamino]benzoyl]amino]-4-methylbenzoyl]amino]-7-sulfonaphthalene-1-sulfonate
- Lokaler Name
- 8,8'-[Carbonylbis[imino-3,1-phenylencarbonylimino(4-methyl-3,1-phenylen)carbonylimino]]bisnaphthalin-1,3,5-trisulfonsure
- Englischer Name
- 8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic acid
- Summenformel
- C51H40N6O23S6
- Molmasse
- 1297.28
Namen und Synonyme
SuramineNaganilFourneauNaphurideFarma 939Aids000067Aids-0000678,8-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic acid8,8'-[Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonyl-imino]]bis-1,3,5-naphthalenetrisulfonic acid8,8'-[carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bisnaphthalene-1,3,5-trisulphonic acid
Datenbank-Bezeichner
- CAS
145-63-1- PubChem CID
- 4261196
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,9
- Polarare Oberfläche (TPSA)
- 481 Ų
- H-Brücken-Donoren
- 12
- H-Brücken-Akzeptoren
- 19
- Frei drehbare Bindungen
- 14
- Schwere Atome
- 86
- Formalladung
- 0
- Komplexität
- 3.010
Experimentelle und physikochemische Eigenschaften
Solubility8.72e-03 g/L
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 128 °C · 128 °C(Solv: ethyl ether (60-29-7))
- Dichte
- 1.2629 · 1.2629 (rough estimate)
- Brechungsindex
- 1.777 · 1.7770 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- Soluble in DMSO
- pka
- -1.35 · -1.35±0.40(Predicted)
- Farbe
- Pinkish-white, hygroscopic powder
- EPA chemische Informationen
- Suramin (145-63-1)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Toxizität
- LD50 intravenous in mouse: 620mg/kg
Chemie und Industrie
Pharmakologische Informationen
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
Absorption, Distribution and ExcretionPoorly absorbed from the gastrointestinal tract.
Cellular LocationsCytoplasm
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