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Details

Stereochemistry ACHIRAL
Molecular Formula C22H24N2O2
Molecular Weight 348.4382
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ACRIVASTINE

SMILES

CC1=CC=C(C=C1)C(=C/CN2CCCC2)\C3=CC=CC(\C=C\C(O)=O)=N3

InChI

InChIKey=PWACSDKDOHSSQD-IUTFFREVSA-N
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+

HIDE SMILES / InChI

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. It’s used for the relief of symptoms associated with seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion. Acrivastine, a structural analog of triprolidine hydrochloride, exhibits H1-antihistaminic activity in isolated tissues, animals, and humans, and has sedative effects in humans. The propionic acid derivative of acrivastine is a metabolite in several animal species (as well as in man) and also exhibits H1-antihistaminic activity.

CNS Activity

Approval Year

1994
149
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
SEMPREX-D

Approved Use

SEMPREX-D Capsules are indicated for relief of symptoms associated with seasonal allergic rhinitis such as sneezing, rhinorrhea, pruritus, lacrimation, and nasal congestion. SEMPREX-D Capsules should be administered when both the antihistaminic activity of acrivastine and the nasal decongestant activity of pseudoephedrine are desired (see CLINICAL PHARMACOLOGY). The efficacy of SEMPREX-D Capsules beyond 14 days of continuous treatment in patients with seasonal allergic rhinitis has not been adequately investigated in clinical trials. SEMPREX-D Capsules have not been adequately studied for effectiveness in relieving the symptoms of the common cold.

Launch Date

1994
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
227 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019806s013lbl.pdf
8 mg 4 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PSEUDOEPHEDRINE HYDROCHLORIDE
PSEUDOEPHEDRINE HYDROCHLORIDE
 ACRIVASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
220 μg/L
EXPERIMENT
http://en.cnki.com.cn/Article_en/CJFDTOTAL-XYYL200704004.htm
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACRIVASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
650 μg × h/L
EXPERIMENT
http://en.cnki.com.cn/Article_en/CJFDTOTAL-XYYL200704004.htm
16 mg single, oral
dose: 16 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACRIVASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019806s013lbl.pdf
8 mg 4 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PSEUDOEPHEDRINE HYDROCHLORIDE
PSEUDOEPHEDRINE HYDROCHLORIDE
 ACRIVASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019806s013lbl.pdf
8 mg 4 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: PSEUDOEPHEDRINE HYDROCHLORIDE
PSEUDOEPHEDRINE HYDROCHLORIDE
 ACRIVASTINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
24 mg 1 times / day single, oral
Highest studied dose
Dose: 24 mg, 1 times / day
Route: oral
Route: single
Dose: 24 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7867679/
healthy, 21-45 years
n = 18
Health Status: healthy
Age Group: 21-45 years
Sex: F
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/7867679/
Sources:
https://pubmed.ncbi.nlm.nih.gov/7867679/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
270

P-gp
1537
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
P-gp
1537
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:83168
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:83168
ChemicalBook
CB7494671
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7494671
MolPort
MolPort-005-942-272
https://www.molport.com/shop/molecule-link/MolPort-005-942-272
ZINC
ZINC000003776633
http://zinc15.docking.org/substances/ZINC000003776633
eMolecules
17497497
https://www.emolecules.com/cgi-bin/more?vid=17497497
PubMed

PubMed

TitleDatePubMed
An assessment of the novel antihistamine BW 825C in the treatment of chronic idiopathic urticaria. A placebo-controlled study.
1984
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria.
1989
A comparison of acrivastine versus clemastine and placebo in the treatment of patients with chronic idiopathic urticaria.
1989
A comparison of acrivastine versus hydroxyzine and placebo in the treatment of chronic idiopathic urticaria.
1989
A comparison of acrivastine versus terfenadine and placebo in the treatment of chronic idiopathic urticaria.
1989
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Patents

Patents

20010022964
11
20020012680
32

Sample Use Guides

In Vivo Use Guide
The recommended dosage for adults and adolescents 12 years and older is one capsule administered orally, every 4 to 6 hours four times a day.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ACRIVASTINE
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
2-PROPENOIC ACID, 3-(6-(1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1-PROPENYL)-2-PYRIDINYL)-, (E,E)-
Common Name English
ACRIVASTINE [MI]
Common Name English
ACRIVASTINE COMPONENT OF SEMPREX-D
Common Name English
BW 825C
Code English
ACRIVASTINE [USAN]
Common Name English
acrivastine [INN]
Common Name English
ACRIVASTINE [VANDF]
Common Name English
ACRIVASTINE [ORANGE BOOK]
Common Name English
(E)-6-((E)-3-(1-PYRROLIDINYL)-1-P-TOLYLPROPENYL)-2-PYRIDINEACRYLIC ACID
Common Name English
BW-825C
Code English
ACRIVASTINE [MART.]
Common Name English
6-(3-(1-PYRROLIDINYL)-1-P-TOLYLPROPENYL)-2-PYRIDINEACRYLIC ACID
Common Name English
Acrivastine [WHO-DD]
Common Name English
SEMPREX-D COMPONENT ACRIVASTINE
Common Name English
3-(6-(1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1-PROPENYL)-2-PYRIDINYL)-
Common Name English
Classification Tree Code System Code
NDF-RT N0000000190
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
NDF-RT N0000175587
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
WHO-VATC QR06AX18
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
LIVERTOX NBK548605
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
WHO-ATC R06AX18
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
Code System Code Type Description
PUBCHEM
5284514
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
NCI_THESAURUS
C47383
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
USAN
X-7
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL1224
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
DRUG CENTRAL
82
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
DRUG BANK
DB09488
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
LACTMED
Acrivastine
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
SMS_ID
100000087693
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022555
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
RXCUI
19959
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m1388
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY Merck Index
DAILYMED
A20F9XAI7W
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
MESH
C043648
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
EVMPD
SUB05252MIG
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
CHEBI
83168
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
WIKIPEDIA
ACRIVASTINE
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
INN
5548
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
CAS
87848-99-5
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
FDA UNII
A20F9XAI7W
Created by admin on Fri Dec 15 15:06:45 GMT 2023 , Edited by admin on Fri Dec 15 15:06:45 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of ACRIVASTINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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