Acrivastine

Identification

Summary

Acrivastine is an antihistamine agent used for the symptomatic relief of seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion.

Brand Names
Semprex-D
Generic Name
Acrivastine
DrugBank Accession Number
DB09488
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 348.4382
Monoisotopic: 348.183778022
Chemical Formula
C22H24N2O2
Synonyms
  • (2E)-3-{6-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}acrylic acid
  • acrivastina
  • Acrivastine
External IDs
  • BW 825C
  • BW A825C
  • BW-825C
  • BW-A825C
  • BW825C
  • BWA825C

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Adefovir dipivoxilAdefovir dipivoxil may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AdenosineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Adenosine.
Interactions
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Food Interactions
No interactions found.

Products

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Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DUACT 8 MG/60 MG KAPSÜL, 30 ADETAcrivastine (8 mg) + Pseudoephedrine hydrochloride (60 mg)CapsuleOralGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Semprex DAcrivastine (8 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)CapsuleOralEndo Pharmaceuticals Inc.2012-01-262020-12-31US flag
Semprex-DAcrivastine (8 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)CapsuleOralUcb Inc2008-05-27Not applicableUS flag53014 040420210224 7642 1mdocc8

Categories

ATC Codes
R06AX18 — Acrivastine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Amino acid / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridines, alpha,beta-unsaturated monocarboxylic acid, olefinic compound, N-alkylpyrrolidine (CHEBI:83168)
Affected organisms
Not Available

Chemical Identifiers

UNII
A20F9XAI7W
CAS number
87848-99-5
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

References

General References
Not Available
Human Metabolome Database
HMDB0240231
KEGG Drug
D02760
PubChem Compound
5284514
PubChem Substance
310265225
ChemSpider
4447574
RxNav
19959
ChEBI
83168
ChEMBL
CHEMBL1224
ZINC
ZINC000003776633
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Acrivastine
FDA label
Download (2.43 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Syrup
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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 19:10 / Updated on February 21, 2021 18:52