You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:38:54 UTC
Update Date2019-07-23 14:38:53 UTC
HMDB IDHMDB0240231
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcrivastine
DescriptionAcrivastine, also known as BW 825C or semprex, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Acrivastine is a drug which is used for the relief of symptoms associated with seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion. Acrivastine is a triprolidine analog antihistamine indicated for the treatment of allergies and hay fever. Acrivastine is a very strong basic compound (based on its pKa). In humans, acrivastine is involved in acrivastine h1-antihistamine action. As an H1 receptor antagonist, it functions by blocking the action of histamine at this receptor thereby preventing the symptoms associated with histamine release such as pruritis, vasodilation, hypotension, edema, bronchoconstriction, and tachycardia. Acrivastine is a potentially toxic compound. Acrivastine is currently available in combination with pseudoephedrine as the FDA-approved product Semprex-D.
Structure
Data?1563892733
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 Weight348.4382
Monoisotopic Molecular Weight348.183778022
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
CAS Registry Number87848-99-5
SMILES
[H]\C(CN1CCCC1)=C(\C1=CC=C(C)C=C1)C1=CC=CC(=N1)C(\[H])=C(/[H])C(O)=O
InChI Identifier
InChI=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
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09488
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcrivastine
METLIN IDNot Available
PubChem Compound5284514
PDB IDNot Available
ChEBI ID83168
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:2570003 ]