8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonic acid

• ChemBase ID: 4332
• Molecular Formular: C51H40N6O23S6
• Molecular Mass: 1297.2797
• Monoisotopic Mass: 1296.04690757
• SMILES: S(=O)(=O)(O)c1c2c(c(S(=O)(=O)O)ccc2NC(=O)c2cc(NC(=O)c3cc(NC(=O)Nc4cc(C(=O)Nc5cc(C(=O)Nc6c7c(c(S(=O)(=O)O)cc6)cc(S(=O)(=O)O)cc7S(=O)(=O)O)ccc5C)ccc4)ccc3)c(cc2)C)cc(S(=O)(=O)O)c1
• Canonical SMILES: O=C(Nc1cccc(c1)C(=O)Nc1cc(ccc1C)C(=O)Nc1ccc(c2c1c(cc(c2)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)Nc1cccc(c1)C(=O)Nc1cc(ccc1C)C(=O)Nc1ccc(c2c1c(cc(c2)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O
• InChI: 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)
• InChIKey: FIAFUQMPZJWCLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonic acid
• IUPAC Traditional name: 8-{4-methyl-3-[3-({[3-({2-methyl-5-[(4,6,8-trisulfonaphthalen-1-yl)carbamoyl]phenyl}carbamoyl)phenyl]carbamoyl}amino)benzamido]benzamido}naphthalene-1,3,5-trisulfonic acid
• Brand Name: Germanin; Antrypol; Fourneau; Farma; Belganyl; Moranyl; Naganil; Naganin; Naganine; Naganol; Naphuride
• Synonyms: Bayer 205; SVR; Sodium suramin; Suramin sodium; Suramine; Suramine sodium; Suramin

Database IDs

• CAS Number: 145-63-1
• PubChem SID: 160967764; 46507013
• PubChem CID: 5361

CALCULATED PROPERTIES

JChem

• Acid pKa: -3.4551167
• H Acceptors: 23
• H Donor: 12
• LogD (pH = 5.5): -8.680967
• LogD (pH = 7.4): -8.681957
• Log P: 5.577431
• Molar Refractivity: 314.9046 cm^3
• Polarizability: 121.06225 Å^3
• Polar Surface Area: 483.75 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.12
• LOG S: -5.17
• Solubility (Water): 8.72e-03 g/l

DETAILS

DrugBank - DB04786

• Drug Groups: approved
• Description: 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?.
• Indication: For treatment of human sleeping sickness, onchocerciasis and other diseases caused by trypanosomes and worms.
• Affected Organisms: Yeast, Molds, Trypanosomes
• Biotransformation: Little or no metabolism
• Absorption: Poorly absorbed from the gastrointestinal tract.
• Half Life: Approximately 36 to 60 days
• Protein Binding: Approximately 99.7%
• External Links: Wikipedia