Identification

Name
Acrivastine
Accession Number
DB09488
Type
Small Molecule
Groups
Approved
Description

Acrivastine is a triprolidine analog antihistamine indicated for the treatment of allergies and hay fever. 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 currently available in combination with pseudoephedrine as the FDA-approved product Semprex-D.

Structure
Thumb
Synonyms
  • (2E)-3-{6-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}acrylic acid
External IDs
BW 825C / BW A825C / BW-825C / BW-A825C / BW825C / BWA825C
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Semprex DAcrivastine (8 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)CapsuleOralEndo Pharmaceuticals2012-01-26Not applicableUs
Categories
UNII
A20F9XAI7W
CAS number
87848-99-5
Weight
Average: 348.4382
Monoisotopic: 348.183778022
Chemical Formula
C22H24N2O2
InChI Key
PWACSDKDOHSSQD-IUTFFREVSA-N
InChI
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+
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
SMILES
[H]\C(CN1CCCC1)=C(\C1=CC=C(C)C=C1)C1=CC=CC(=N1)C(\[H])=C(/[H])C(O)=O

Pharmacology

Indication

For the relief of symptoms associated with seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption

Acrivastine was absorbed rapidly from the combination capsule following oral administration and was as bioavailable as a solution of acrivastine. After administration of SEMPREX-D Capsules, maximum plasma acrivastine concentrations were achieved at 1.14 ± 0.23 hour.

Volume of distribution

0.46 ± 0.05 L/kg

Protein binding

Acrivastine binding to human plasma proteins was 50 ± 2.0%.

Metabolism
Not Available
Route of elimination

A mass balance study in 7 healthy volunteers showed that acrivastine is primarily eliminated by the kidneys. Over a 72-hour collection period, about 84% of the administered total radioactivity was recovered in urine and about 13% in feces, for a combined recovery of about 97%.

Half life

The mean terminal half-life for acrivastine was 1.9 ± 0.3 hours following single oral doses and increased to 3.5 ± 1.9 hours at steady state. The terminal half-life for the propionic acid metabolite was 3.8 ± 1.4 hours.

Clearance

2.9 ± 0.7 mL/min/kg

Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Acrivastine H1-Antihistamine ActionDrug action
Acrivastine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Acrivastine.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Acrivastine.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Acrivastine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Acrivastine.Experimental, Illicit
AmiodaroneThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Amiodarone.Approved, Investigational
AmphetamineAmphetamine may decrease the sedative activities of Acrivastine.Approved, Illicit, Investigational
BenzatropineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Benzatropine.Approved
BenzphetamineBenzphetamine may decrease the sedative and stimulatory activities of Acrivastine.Approved, Illicit
Benzylpenicilloyl PolylysineAcrivastine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BepridilThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Bepridil.Approved, Withdrawn
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Acrivastine.Approved, Investigational
BrompheniramineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Brompheniramine.Approved
CetirizineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Cetirizine.Approved
ChlorphenamineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Chlorphenamine.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Acrivastine.Illicit, Withdrawn
CinnarizineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Cinnarizine.Approved, Investigational
CiprofloxacinThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Ciprofloxacin.Approved, Investigational
ClemastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Clemastine.Approved, Investigational
DexbrompheniramineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dexbrompheniramine.Approved
DextroamphetamineDextroamphetamine may decrease the sedative activities of Acrivastine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative and stimulatory activities of Acrivastine.Approved, Illicit
DimenhydrinateThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dimenhydrinate.Approved
DiphenhydramineThe risk or severity of QTc prolongation can be increased when Diphenhydramine is combined with Acrivastine.Approved, Investigational
DoxylamineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Doxylamine.Approved, Vet Approved
FamotidineThe risk or severity of QTc prolongation can be increased when Famotidine is combined with Acrivastine.Approved
FluoxetineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Fluoxetine.Approved, Vet Approved
GepefrineGepefrine may decrease the sedative activities of Acrivastine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Acrivastine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Acrivastine.Approved
HydroxyzineThe risk or severity of QTc prolongation can be increased when Hydroxyzine is combined with Acrivastine.Approved
IbandronateThe risk or severity of QTc prolongation can be increased when Ibandronate is combined with Acrivastine.Approved, Investigational
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Acrivastine.Approved
IsradipineThe risk or severity of QTc prolongation can be increased when Isradipine is combined with Acrivastine.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Acrivastine.Approved, Investigational
LoratadineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Loratadine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Acrivastine.Investigational
MephentermineMephentermine may decrease the sedative activities of Acrivastine.Approved
MepyramineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Mepyramine.Approved, Vet Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Acrivastine.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Acrivastine.Experimental
MetoclopramideThe risk or severity of QTc prolongation can be increased when Metoclopramide is combined with Acrivastine.Approved, Investigational
MidomafetamineMidomafetamine may decrease the sedative activities of Acrivastine.Experimental, Illicit, Investigational
MMDAMMDA may decrease the sedative activities of Acrivastine.Experimental, Illicit
MoxifloxacinThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Moxifloxacin.Approved, Investigational
NicardipineThe risk or severity of QTc prolongation can be increased when Nicardipine is combined with Acrivastine.Approved, Investigational
OndansetronThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Ondansetron.Approved
ParoxetineThe risk or severity of QTc prolongation can be increased when Paroxetine is combined with Acrivastine.Approved, Investigational
PheniramineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Pheniramine.Approved
PhenterminePhentermine may decrease the sedative activities of Acrivastine.Approved, Illicit
PromethazineThe risk or severity of QTc prolongation can be increased when Promethazine is combined with Acrivastine.Approved, Investigational
PropafenoneThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Propafenone.Approved
PseudoephedrinePseudoephedrine may decrease the sedative and stimulatory activities of Acrivastine.Approved
QuetiapineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Quetiapine.Approved
RitobegronRitobegron may decrease the sedative activities of Acrivastine.Investigational
SalbutamolThe risk or severity of QTc prolongation can be increased when Salbutamol is combined with Acrivastine.Approved, Vet Approved
SalmeterolThe risk or severity of QTc prolongation can be increased when Salmeterol is combined with Acrivastine.Approved
TerodilineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Terodiline.Experimental
Valproic AcidThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Valproic Acid.Approved, Investigational
VenlafaxineThe risk or severity of QTc prolongation can be increased when Venlafaxine is combined with Acrivastine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0240231
KEGG Drug
D02760
PubChem Compound
5284514
PubChem Substance
310265225
ChemSpider
4447574
ChEBI
83168
ChEMBL
CHEMBL1224
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Acrivastine
ATC Codes
R06AX18 — Acrivastine
FDA label
Download (2.43 MB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00994 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity115.08 m3·mol-1ChemAxon
Polarizability39.09 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Styrenes
Direct Parent
Styrenes
Alternative Parents
Toluenes / Pyridines and derivatives / N-alkylpyrrolidines / Heteroaromatic compounds / Trialkylamines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Styrene / Toluene / Pyridine / N-alkylpyrrolidine / Pyrrolidine / Heteroaromatic compound / Amino acid or derivatives / Tertiary amine / Tertiary aliphatic amine / Amino acid
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridines, alpha,beta-unsaturated monocarboxylic acid, olefinic compound, N-alkylpyrrolidine (CHEBI:83168)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da

Drug created on November 30, 2015 12:10 / Updated on August 02, 2018 06:18