Page last updated: 2024-11-10

acrivastine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

acrivastine: a second generation antihistamine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

acrivastine : A member of the class of pyridines that is (pyridin-2-yl)acrylic acid substituted at position 6 by a [(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl group. It is a non-sedating antihistamine used for treatment of hayfever, urticaria, and rhinitis. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5284514
CHEMBL ID1224
CHEBI ID83168
SCHEMBL ID4702
MeSH IDM0128312

Synonyms (72)

Synonym
BIDD:GT0209
AC-912
acrivastin
bw 825c
acrivastina [spanish]
2-propenoic acid, 3-(6-(1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl)-2-pyridinyl)-, (e,e)-
acrivastine [usan:inn:ban]
bw-825c
acrivastinum [latin]
semprex
(e)-6-((e)-3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylic acid
bw a825c
(e)-6-((e)-3-(1-pyrrolidinyl-1-p-tolylpropenyl)-2-pyridinacrylsaeure
(2e)-3-{6-[(1e)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-en-1-yl]pyridin-2-yl}prop-2-enoic acid
87848-99-5
D02760
acrivastine (usan/inn)
acrivastine
chebi:83168 ,
CHEMBL1224
AKOS005067182
NCGC00182053-02
(e)-3-[6-[(e)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridin-2-yl]prop-2-enoic acid
cas-87848-99-5
tox21_113015
dtxsid6022555 ,
dtxcid702555
acrivastina
acrivastinum
a20f9xai7w ,
unii-a20f9xai7w
S5718
acrivastine [vandf]
6-(3-(1-pyrrolidinyl)-1-p-tolylpropenyl)-2-pyridineacrylic acid
3-(6-(1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl)-2-pyridinyl)-
acrivastine [inn]
acrivastine [mi]
semprex-d component acrivastine
acrivastine [usan]
acrivastine [who-dd]
acrivastine [mart.]
acrivastine [orange book]
acrivastine component of semprex-d
smr004701250
MLS006010115
SCHEMBL4702
(2e)-3-{6-[(1e)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}acrylic acid
PWACSDKDOHSSQD-IUTFFREVSA-N
(e)-3-{6-[3-pyrrolidino-1-(4-tolyl)prop-1e-enyl]-2-pyridyl}acrylic acid
Q-200590
DB09488
HY-B1510
CS-6454
sr-01000942220
SR-01000942220-1
bdbm50487466
benadryl allgy relief plus decongest
acrivastine, >=98% (hplc)
(e)-3-(6-((e)-3-(pyrrolidin-1-yl)-1-(p-tolyl)prop-1-en-1-yl)pyridin-2-yl)acrylic acid
BCP06189
bw270c
Q342745
mfcd00869830
AS-14623
HMS3886E20
NCGC00182053-03
D70156
2-propenoic acid,3-[6-[(1e)-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propenyl]-2-pyridinyl]-,(2e)-
A916142
2-propenoic acid, 3-[6-[(1e)-1-(4-methylphenyl)-3-(1-pyrrolidinyl)-1-propen-1-yl]-2-pyridinyl]-, (2e)-
(2e)-3-{6-[(1e)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridin-2-yl}prop-2-enoic acid
EN300-7363287

Research Excerpts

Overview

Acrivastine is a second-generation H1-receptor antagonist, and its structure is sensitive to ultraviolet. It has been shown in vitro to reverse this form of resistance.

ExcerptReferenceRelevance
"Acrivastine is a second-generation H1-receptor antagonist, and its structure is sensitive to ultraviolet. "( Isolation, structure elucidation, and high-performance liquid chromatography quantification of photolytic degradation impurities in acrivastine.
He, DX; Li, Y; Lin, YM; Lv, JJ; Yu, J; Zeng, X; Zeng, XY, 2022
)
2.37
"Acrivastine is a hydrophylic antihistamine that has been shown in vitro to reverse this form of resistance."( A phase II study of vinblastine in combination with acrivastine in patients with advanced renal cell carcinoma.
Berlin, J; Clendeninn, NJ; Collier, M; Findlay, JW; King, AC; Kohler, P; Tutsch, K; Wilding, G, 1994
)
1.26
"Acrivastine is a second-generation H1-antagonist chemically related to triprolidine, but more polar and with less central nervous system penetration than triprolidine."( Efficacy of acrivastine plus pseudoephedrine for symptomatic relief of seasonal allergic rhinitis due to mountain cedar.
Frosolono, MF; Hull, H; McSorley, P; Sanders, RL; Williams, BO, 1996
)
2.12
"Acrivastine is a short acting histamine H1-receptor antagonist with a rapid onset of action. "( Acrivastine. A review of its pharmacological properties and therapeutic efficacy in allergic rhinitis, urticaria and related disorders.
Brogden, RN; McTavish, D, 1991
)
3.17
"Acrivastine is an antihistamine with reduced sedating potential. "( Acrivastine in allergic rhinitis: a review of clinical experience.
Bojkowski, CJ; Gibbs, TG; Hellstern, KH; Major, EW; Mullinger, B, 1989
)
3.16

Pharmacokinetics

ExcerptReferenceRelevance
"Six healthy male volunteers participated in this randomized, crossover open-label pharmacokinetic study consisting of two dosing segments separated by a washout period of at least 5 days."( Pharmacokinetics of acrivastine after oral and colonic administration.
Balasubramanian, R; Findlay, JW; Frosolono, MF; Klein, KB; Liao, SH; Pittman, AW, 1989
)
0.6
" Pharmacokinetic investigations have shown the drug to be highly bound to blood proteins, mainly serum albumin, and to have a low brain uptake, explaining its lack of sedative effects."( Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
Carrupt, PA; Jolliet, P; Morin, C; Morin, D; Pagliara, A; Rihoux, JP; Testa, B; Tillement, JP; Urien, S, 1998
)
0.3
" The method was successfully applied in a pharmacokinetic study of the acrivastine and pseudoephedrine hydrochloride compound capsule in humans."( Development and validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous determination of acrivastine and pseudoephedrine in human plasma and its application in pharmacokinetics.
Dong, LC; Feng, EF; He, JC; Li, HL; Liu, M; Tian, M; Xu, GL; Zhang, Q, 2012
)
0.82

Compound-Compound Interactions

Two studies were performed to measure the effects of acrivastine (BW825C), an antihistamine, in combination with alcohol on the central nervous system. After five patients were treated on a dose-finding study, seventeen patients with metastatic or unresectable renal cell carcinoma were entered into a phase II study.

ExcerptReferenceRelevance
"Two studies were performed to measure the effects of acrivastine (BW825C), an antihistamine, in combination with alcohol on the central nervous system."( The effects of acrivastine (BW825C), diphenhydramine and terfenadine in combination with alcohol on human CNS performance.
Cohen, AF; Hamilton, MJ; Peck, AW, 1987
)
0.88
" After five patients were treated on a dose-finding study, seventeen patients with metastatic or unresectable renal cell carcinoma were entered into a phase II study of vinblastine in combination with acrivastine."( A phase II study of vinblastine in combination with acrivastine in patients with advanced renal cell carcinoma.
Berlin, J; Clendeninn, NJ; Collier, M; Findlay, JW; King, AC; Kohler, P; Tutsch, K; Wilding, G, 1994
)
0.73

Bioavailability

ExcerptReferenceRelevance
"7 hr, and an oral bioavailability of 40%."( Disposition of acrivastine in the male beagle dog.
Chandrasurin, P; Deal, DL; Findlay, JW; McNulty, MJ; Nelson, FR; Shockcor, J; Weller, S,
)
0.48
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

Acrivastine administered 30, 45, 60 or 90 min before challenge produced a right-shift of the histamine dose-response curve of at least 8-fold. A clinically desired degree of H1-antagonism was present within 30 min of ingestion of the recommended therapeutic dose. The upper 95% confidence limit for time lag from dosing of acrivastne until reduction from placebo level commences was 6.4 micrograms histamine challenge 15 min after oral acrivstine dosing.

ExcerptRelevanceReference
"4 micrograms histamine challenge 15 min after oral acrivastine dosing when compared with placebo."( An evaluation of the antihistamine activity of acrivastine and its onset in human skin.
Gibson, JR; Manna, VK; Marks, P, 1992
)
0.79
" Acrivastine administered 30, 45, 60 or 90 min before challenge produced a right-shift of the histamine dose-response curve of at least 8-fold indicating that a clinically desired degree of H1-antagonism was present within 30 min of ingestion of the recommended therapeutic dose."( The onset of effect of the H1-antagonist acrivastine ("Semprex") assessed by histamine bronchial challenge in volunteers.
Adams, J; Phillips, S; Posner, J; Rolan, PE, 1990
)
1.46
" No accumulation of the drug following multiple dosing has been demonstrated."( Acrivastine: a review of its dermatopharmacology and clinical activity.
Gibson, JR; Manna, VK; Salisbury, J, 1989
)
1.72
"Six healthy male volunteers participated in this randomized, crossover open-label pharmacokinetic study consisting of two dosing segments separated by a washout period of at least 5 days."( Pharmacokinetics of acrivastine after oral and colonic administration.
Balasubramanian, R; Findlay, JW; Frosolono, MF; Klein, KB; Liao, SH; Pittman, AW, 1989
)
0.6
" The other study found the higher dosage regimen to be similar in efficacy to 1 mg clemastine given three times daily."( Acrivastine in seasonal allergic rhinitis: two randomized crossover studies to evaluate efficacy and safety.
Gibbs, TG; Irander, K; Salo, OP,
)
1.57
"For treatment of allergic rhinitis, acrivastine with pseudoephedrine in Semprex-D conventional capsules requires dosing every 6-8 hours."( Evaluation and comparison of five matrix excipients for the controlled release of acrivastine and pseudoephedrine.
Fediuk, DJ; Gu, X; Simons, FE; Simons, KJ, 2004
)
0.82
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
H1-receptor antagonistH1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
alpha,beta-unsaturated monocarboxylic acidA monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
N-alkylpyrrolidine
olefinic compoundAny organic molecular entity that contains at least one C=C bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Acrivastine H1-Antihistamine Action87

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency26.83250.000221.22318,912.5098AID743035
estrogen nuclear receptor alphaHomo sapiens (human)Potency23.91450.000229.305416,493.5996AID743075
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency39.81070.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID26291Partition coefficient (logD9.4)1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26562compound was evaluated for rate constant of transfer (log K1) at pH 6.81998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID78181Histamine induced in lethality in guinea pigs at 8 h after oral dose of 0.16 mg/kg1995Journal of medicinal chemistry, Feb-03, Volume: 38, Issue:3
Amphoteric drugs. 3. Synthesis and antiallergic activity of 3-[(5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11- ylidene)piperidino]propionic acid derivatives and related compounds.
AID26542compound was evaluated for reverse occurs for the rate constant(log K-1) at pH 1.51998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26550compound was evaluated for reverse occurs for the rate constant(log K-1) at pH 9.41998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26565compound was evaluated for rate constant of transfer (log K1) at pH 9.41998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26289Partition coefficient (logD6.8)1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26286Partition coefficient (logD3.0)1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID476929Human intestinal absorption in po dosed human2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Neural computational prediction of oral drug absorption based on CODES 2D descriptors.
AID234738Selectivity as the ratio of ID50 value to that of ED50 value in mice.1995Journal of medicinal chemistry, Feb-03, Volume: 38, Issue:3
Amphoteric drugs. 3. Synthesis and antiallergic activity of 3-[(5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11- ylidene)piperidino]propionic acid derivatives and related compounds.
AID26547compound was evaluated for reverse occurs for the rate constant(log K-1) at pH 6.81998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26287Partition coefficient (logD3.0)1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID113865Inhibitory effect on histamine-induced increase in vascular permeability in mice upon oral administration1995Journal of medicinal chemistry, Feb-03, Volume: 38, Issue:3
Amphoteric drugs. 3. Synthesis and antiallergic activity of 3-[(5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11- ylidene)piperidino]propionic acid derivatives and related compounds.
AID91481Binding constant against human serum albumin (HSA)2001Journal of medicinal chemistry, Dec-06, Volume: 44, Issue:25
Cheminformatic models to predict binding affinities to human serum albumin.
AID26559compound was evaluated for rate constant of transfer (log K1) at pH 31998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID592681Apparent permeability across human Caco2 cell membrane after 2 hrs by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
QSAR-based permeability model for drug-like compounds.
AID178104Antiallergic activity was evaluated by inhibitory effect on compound 48/80-induced lethality in rats at a dose 10 (mg/kg, po)1995Journal of medicinal chemistry, Feb-03, Volume: 38, Issue:3
Amphoteric drugs. 3. Synthesis and antiallergic activity of 3-[(5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11- ylidene)piperidino]propionic acid derivatives and related compounds.
AID26544compound was evaluated for reverse occurs for the rate constant(log K-1) at pH 31998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26543compound was evaluated for reverse occurs for the rate constant(log K-1) at pH 121998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26285Partition coefficient (logD1.5)1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26557compound was evaluated for rate constant of transfer (log K1) at pH 1.51998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID26558compound was evaluated for rate constant of transfer (log K1) at pH 121998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Molecular properties and pharmacokinetic behavior of cetirizine, a zwitterionic H1-receptor antagonist.
AID87373Ex vivo inhibition of [3H]mepyramine binding to mouse brain membrane H1 receptor after oral administration1995Journal of medicinal chemistry, Feb-03, Volume: 38, Issue:3
Amphoteric drugs. 3. Synthesis and antiallergic activity of 3-[(5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11- ylidene)piperidino]propionic acid derivatives and related compounds.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (76)

TimeframeStudies, This Drug (%)All Drugs %
pre-199023 (30.26)18.7374
1990's30 (39.47)18.2507
2000's12 (15.79)29.6817
2010's7 (9.21)24.3611
2020's4 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 54.88

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index54.88 (24.57)
Research Supply Index4.81 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index102.31 (26.88)
Search Engine Supply Index2.29 (0.95)

This Compound (54.88)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials42 (52.50%)5.53%
Reviews7 (8.75%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other31 (38.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]