Acrivastine (CHEM003603)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-08 02:39:57 UTC
Update Date2026-05-14 19:06:13 UTC
Accession NumberCHEM003603
Identification
Common NameAcrivastine
ClassSmall Molecule
DescriptionAcrivastine is a medication used for the treatment of allergies and hay fever. It is a second-generation H1-receptor antagonist antihistamine (like its base molecule triprolidine) and works by blocking Histamine H1 receptors. Anticholinergic (primarily antimuscarinic) effects develop in overdose due to antagonism of central H1 receptors. Large overdoses of H1 blockers, particularly diphenhydramine, may cause sodium channel antagonism. Decongestants can lead to sympathomimetic (e.g., hypertension, tachycardia, hyperventilation, intercranial hemorrhage) symptoms. (1)
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Drug
  • Ester
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-6-((e)-3-(1-Pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylic acidChEBI
AcrivastinaChEBI
AcrivastinumChEBI
BW 825CChEBI
BW a825cChEBI
(e)-6-((e)-3-(1-Pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylateGenerator
Glaxo wellcome brand OF acrivastineHMDB
GlaxoSmithKline brand OF acrivastineHMDB
BW-825CHMDB
SemprexHMDB
BW 0270CHMDB
AcrivastineHMDB
Chemical FormulaC22H24N2O2
Average Molecular Mass348.438 g/mol
Monoisotopic Mass348.184 g/mol
CAS Registry Number87848-99-5
IUPAC Name(2E)-3-{6-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}prop-2-enoic acid
Traditional Nameacrivastine
SMILES[H]\C(CN1CCCC1)=C(\C1=CC=C(C)C=C1)C1=CC=CC(=N1)C(\[H])=C(/[H])C(O)=O
InChI IdentifierInChI=1S/C22H24N2O2/c1-17-7-9-18(10-8-17)20(13-16-24-14-2-3-15-24)21-6-4-5-19(23-21)11-12-22(25)26/h4-13H,2-3,14-16H2,1H3,(H,25,26)/b12-11+,20-13+
InChI KeyPWACSDKDOHSSQD-IUTFFREVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • Toluene
  • Pyridine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Histamine H1 Receptor AntagonistsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0099 g/LALOGPS
logP4.29ALOGPS
logP1.71ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)8.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity115.08 m³·mol⁻¹ChemAxon
Polarizability39.09 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0019000000-493921d575d914f7b11eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3098000000-5715f5f3fecad2878fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-6190000000-309f537ccb55c7d2fca6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-dcd0d0405c8fbed5a6c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdk-6129000000-2b4ad715a102c1e262faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9010000000-114f1744e79f1cffa123Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0089000000-a0e5de9cf0148aa87b23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0095000000-5c51d64287d69c6ebceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-1090000000-d03769fc06fa854ee9f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-8e999f7ede2a1b9b3e15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uea-1289000000-b6b87278e71e3f51bcc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-0a754c6dfb4be95035daSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAcrivastine is a medication used for the treatment of allergies and hay fever.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09488
HMDB IDHMDB0240231
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcrivastine
Chemspider ID4447574
ChEBI ID83168
PubChem Compound ID5284514
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=1355745
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1715267
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18968530
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1970907
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22936420
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23047471
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24813276
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2569998
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=2569999
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2570000
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2570001
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2570003
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2574054
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2859204
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=2901993
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2906886
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6149965
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7860231
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=8630717
20. Bojkowski CJ, Gibbs TG, Hellstern KH, Major EW, Mullinger B: Acrivastine in allergic rhinitis: a review of clinical experience. J Int Med Res. 1989;17 Suppl 2:54B-68B.