ACRIVASTINE

US Previously Marketed

First approved in 1994

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 Search

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

Molecular Formula	C22H24N2O2
Molecular Weight	348.4382
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=51500008-2034-452c-8e9b-bb112d1b9039

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

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=51500008-2034-452c-8e9b-bb112d1b9039	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Seasonal allergic rhinitis 64 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=51500008-2034-452c-8e9b-bb112d1b9039	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270 P-gp 1537

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/1715267/	no
P-gp 1537	substrate 3367 Sources: http://orca.cf.ac.uk/84217/1/2015pricedfphd.pdf#page=9	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/10444235/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
An assessment of the novel antihistamine BW 825C in the treatment of chronic idiopathic urticaria. A placebo-controlled study.	1984	6149965
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942

Patents

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:44 GMT 2023`
Record UNII	A20F9XAI7W
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ACRIVASTINE

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