Suramin (CHEM018933)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:40:58 UTC
Update Date2016-11-09 01:15:53 UTC
Accession NumberCHEM018933
Identification
Common NameSuramin
ClassSmall Molecule
DescriptionA 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®.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonIC ACIDChEBI
BelganylChEBI
NaganolChEBI
NaphurideChEBI
8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonateGenerator
8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulphonateGenerator
8,8'-[CARBONYLBIS[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulphonic acidGenerator
Bayer 205HMDB
Sodium suraminHMDB
SuramineHMDB
SVRHMDB
Monosodium salt suraminHMDB
MoranilHMDB
Hexasodium salt suraminHMDB
Suramin, hexasodium saltHMDB
NaganinHMDB
Salt suramin, hexasodiumHMDB
Salt suramin, monosodiumHMDB
Sodium, suraminHMDB
Suramin sodiumHMDB
Suramin, monosodium saltHMDB
Chemical FormulaC51H40N6O23S6
Average Molecular Mass1297.280 g/mol
Monoisotopic Mass1296.047 g/mol
CAS Registry Number145-63-1
IUPAC Name8-{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
Traditional Namesuramin
SMILESCC1=C(NC(=O)C2=CC(NC(=O)NC3=CC=CC(=C3)C(=O)NC3=C(C)C=CC(=C3)C(=O)NC3=C4C(C=C(C=C4S(O)(=O)=O)S(O)(=O)=O)=C(C=C3)S(O)(=O)=O)=CC=C2)C=C(C=C1)C(=O)NC1=C2C(C=C(C=C2S(O)(=O)=O)S(O)(=O)=O)=C(C=C1)S(O)(=O)=O
InChI IdentifierInChI=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)
InChI KeyFIAFUQMPZJWCLV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentBenzanilides
Alternative Parents
Substituents
  • Benzanilide
  • Naphthalene sulfonate
  • 1-naphthalene sulfonic acid or derivatives
  • 2-naphthalene sulfonic acid or derivatives
  • Naphthalene sulfonic acid or derivatives
  • 1-naphthalene sulfonate
  • 2-naphthalene sulfonate
  • N-phenylurea
  • Naphthalene
  • P-toluamide
  • Toluamide
  • Benzamide
  • Benzoic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • Arylsulfonic acid or derivatives
  • Benzoyl
  • Toluene
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Carboxamide group
  • Urea
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0087 g/LALOGPS
logP-0.12ALOGPS
logP5.58ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)-3.5ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area483.75 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity314.9 m³·mol⁻¹ChemAxon
Polarizability120.22 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0032-0090013100-eb8fb42b491e752edbdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0290048610-b9492b764ed1509a1378Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-0373295240-a868fca31c5bc9d10337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0090016000-e9e628ec972887de519cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1070139000-847f410d8e31ba88b008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9163268000-de68781096a01c0b0b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0090004202-97ab3173a4c5a9871e59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ej-0093016204-c58f51b135c71226b6e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-0971432000-4dea5d878677b6175c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000019000-3f3b93d2f30dfc4e9b7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001m-6080029100-8d0809ddc0506453f85cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9230045000-dfd08ed7a2f58b885360Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04786
HMDB IDHMDB0015582
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSVR
Wikipedia LinkSuramin
Chemspider ID5168
ChEBI ID45906
PubChem Compound ID5361
Kegg Compound IDC07974
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11549724
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15733555
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15774519
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=28457855
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29414872
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=30172846
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=30393012
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=30449075
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=30528604
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=30543088
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=30771091
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=31346035
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=31409229
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=31667504
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31727005
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=31803569
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=31844000
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7947391
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=8769855
20.