levodropropizine (CHEM043395)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:52:29 UTC
Update Date2016-11-09 01:22:55 UTC
Accession NumberCHEM043395
Identification
Common Namelevodropropizine
ClassSmall Molecule
DescriptionA member of the class of N-arylpiperazines that is N-phenylpiperazine in which the amino hydrogen is replaced by a 2,3-dihydroxypropyl group (the S-enantiomer). A peripherally acting antitussive drug that is used as an alternative to opioids.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-(S)-3-(4-Phenyl-1-piperazinyl)-1,2-propanediolChEBI
(-)-DropropizineChEBI
LevdropropizineChEBI
LevodropropizinaChEBI
LevodropropizinumChEBI
S-(-)-3-(4-Phenylpiperazin-1-yl)propane-1,2-diolChEBI
LevoprontKegg
DipropizineMeSH
TautossMeSH
LevotussMeSH
ZyploMeSH
Dipropizine, (S)-isomerMeSH
DropropizineMeSH
DitustatMeSH
Chemical FormulaC13H20N2O2
Average Molecular Mass236.315 g/mol
Monoisotopic Mass236.152 g/mol
CAS Registry Number99291-25-5
IUPAC Name(2S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol
Traditional Namelevodropropizine
SMILES[H][C@@](O)(CO)CN1CCN(CC1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1
InChI KeyPTVWPYVOOKLBCG-ZDUSSCGKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • Phenylpiperazine
  • N-arylpiperazine
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Aniline or substituted anilines
  • N-alkylpiperazine
  • Benzenoid
  • Monocyclic benzene moiety
  • 1,3-aminoalcohol
  • 1,2-diol
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility97.1 g/LALOGPS
logP0.63ALOGPS
logP0.61ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)14ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.94 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.79 m³·mol⁻¹ChemAxon
Polarizability26.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02di-6940000000-2c6f504ceae818e3ed7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-662191795582867362e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p0-1890000000-d3c64a5db7e2fc44e014Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aba-6910000000-691a7998fe7f4c6d84b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-80b45998796f9889cd16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-029i-1590000000-df0d73266ebc5cacfdcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-9500000000-2b1af987bb0b92c3f8c4Spectrum
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 IDDB12472
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevodropropizine
Chemspider IDNot Available
ChEBI ID82722
PubChem Compound ID65859
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14505734
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1611233
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1820875
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1827388
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19796190
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21806417
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22771902
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23225830
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23351597
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23509871
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23641334
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24085318
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2631057
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2798991
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=3196407
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=3196408
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3196411
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=8147948