Delavirdine (CHEM016656)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:39:35 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016656
Identification
Common NameDelavirdine
ClassSmall Molecule
DescriptionThe amide resulting from the formal condensation of 5--1H-indole-2-carboxylic acid and 4-amino group of 1-piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(N-[2-[4-[3-(1-Methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide)ChEBI
1-(3-((1-Methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazineChEBI
2-(4-(5-Methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamineChEBI
N-(2-(1-(3-(Isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamideChEBI
N-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamideChEBI
(N-[2-[4-[3-(1-Methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulphonamide)Generator
1-(3-((1-Methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulphonyl)amino)-1H-indol-2-yl)carbonyl)piperazineGenerator
2-(4-(5-Methanesulphonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamineGenerator
N-(2-(1-(3-(Isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulphonamideGenerator
N-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulphonamideGenerator
Mesylate, delavirdineHMDB
Pfizer brand OF delavirdine mesilateHMDB
Delavirdine mesylateHMDB
RescriptorHMDB
Chemical FormulaC22H28N6O3S
Average Molecular Mass456.561 g/mol
Monoisotopic Mass456.194 g/mol
CAS Registry Number136817-59-9
IUPAC NameN-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1H-indol-5-yl]methanesulfonamide
Traditional Namedelavirdine
SMILESCC(C)NC1=C(N=CC=C1)N1CCN(CC1)C(=O)C1=CC2=C(N1)C=CC(NS(C)(=O)=O)=C2
InChI IdentifierInChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3
InChI KeyWHBIGIKBNXZKFE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Aromatic monoterpenoid
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.086 g/LALOGPS
logP2.77ALOGPS
logP1.02ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)6.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.64 m³·mol⁻¹ChemAxon
Polarizability50.01 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-004i-1869800000-919b00dc1b3b74381f73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-1149800000-a0f76f90872cbd99d53cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1219000000-cb09ea0c014410a3499eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-2920000000-12fdf4d7579108e38ed2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-7011900000-47425ff75ae0b4e2aab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9121100000-a64588514bc1394a9cf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-116fecaf8ef4fa6935bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-75f8f7bd14bf867bf702Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0010900000-5d8c991ffb8be5810226Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1933300000-5ce651b88994073e97edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0010900000-6d8ef33136c03f3466f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r2-0008900000-4a049c134472e688dda8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9652200000-831ce982d916abfa0628Spectrum
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 IDDB00705
HMDB IDHMDB0014843
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSPP
Wikipedia LinkDelavirdine
Chemspider ID5423
ChEBI ID119573
PubChem Compound ID5625
Kegg Compound IDC06941
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11124228
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11225565
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11327199
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11363651
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11363709
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11364022
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11364099
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=11364363
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=11364481
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=11590527
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16449090
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21080015
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21683601
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21865017