APIGENIN

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10O5
Molecular Weight	270.2369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2=CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=KZNIFHPLKGYRTM-UHFFFAOYSA-N

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Potency
Central benzodiazepine receptor (bovine) 1 Target ID: Central benzodiazepine receptor (bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7617761	Binding Agent 1064	3.0 µM [Ki]
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17685652	Antagonist 2778

PubMed

Title	Date	PubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).	2001	11708609
[Investigation on method speliality in identifying Fructus Crataegi with vitexin rhamnoside].	2001 Dec	11917841
Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.	2001 Dec	11773526
Antioxidant capacity of a 3-deoxyanthocyanidin from soybean.	2001 Dec	11730874
Protein kinase CK2: signaling and tumorigenesis in the mammary gland.	2001 Nov	11827167
Flavonoids differentially inhibit guinea pig epidermal cytosolic phospholipase A2.	2001 Nov-Dec	11993721
In vivo hepatoprotective activity of active fraction from ethanolic extract of Eclipta alba leaves.	2001 Oct	11883149
Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation.	2001 Oct	11814152
Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L.	2001 Sep-Oct	11876448
HET-CAM bioassay as in vitro alternative to the croton oil test for investigating steroidal and non-steroidal compounds.	2002	12098009
Dietary flavonoids: bioavailability, metabolic effects, and safety.	2002	12055336
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.	2002 Apr	12046870
Prevention of cellular ROS damage by isovitexin and related flavonoids.	2002 Apr	11988866
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.	2002 Apr	11901089
Botanical antioxidants for chemoprevention of photocarcinogenesis.	2002 Apr 1	11897547
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).	2002 Aug	12127590
Dimerization and phosphorylation of thyrotropin-releasing hormone receptors are modulated by agonist stimulation.	2002 Aug 2	12023974
Regulation of histone deacetylase 2 by protein kinase CK2.	2002 Aug 30	12082111
Functional interaction of protein kinase CK2 and c-Myc in lymphomagenesis.	2002 Aug 8	12149649
Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.).	2002 Feb	11942684
The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds.	2002 Feb	11849977
Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms.	2002 Feb	11842175
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.	2002 Feb	11750278
Regulatory effects of stem cell factor and interleukin-4 on adhesion of human mast cells to extracellular matrix proteins.	2002 Feb 1	11807000
Effect of flavonoids on cell cycle progression in prostate cancer cells.	2002 Feb 8	11790449
Estrogenic and cholinergic properties of the methanol extract of Ruellia praetermissa Sceinf. ex. Lindau (Acanthaceae) in female rats.	2002 Jan	11924764
A p21(waf1)-independent pathway for inhibitory phosphorylation of cyclin-dependent kinase p34(cdc2) and concomitant G(2)/M arrest by the chemopreventive flavonoid apigenin.	2002 Jan	11807956
Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.	2002 Jan	11752233
Intracellular flavonoids as electron donors for extracellular ferricyanide reduction in human erythrocytes.	2002 Jan 1	11755318
Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease.	2002 Jan 15	11841797
Apigenin and LY294002 prolong EGF-stimulated ERK1/2 activation in PC12 cells but are unable to induce full differentiation.	2002 Jan 16	11801244
Effects of apigenin on the serum- and platelet derived growth factor-BB-induced proliferation of rat aortic vascular smooth muscle cells.	2002 Jul	12142993
Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship.	2002 Jul	12132661
In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.	2002 Jul	12126705
Oxidation of quercetin by salivary components. Quercetin-dependent reduction of salivary nitrite under acidic conditions producing nitric oxide.	2002 Jul 17	12105964
Phytochemical constituents from the herba of Artemisia apiacea.	2002 Jun	12135098
Interactions of different phenolic acids and flavonoids with soy proteins.	2002 Jun 18	12063116
Flavonoids differentially regulate IFN gamma-induced ICAM-1 expression in human keratinocytes: molecular mechanisms of action.	2002 Jun 5	12044887
Effects of flavonoid phytochemicals on cortisol production and on activities of steroidogenic enzymes in human adrenocortical H295R cells.	2002 Mar	11948020
Relationships of urinary phyto-oestrogen excretion to BMD in postmenopausal women.	2002 Mar	11940043
Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter.	2002 Mar 1	11864778
In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids.	2002 May	11955666
Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements.	2002 May	11950788
Rapid quantification of constituents in St. John's wort extracts by NIR spectroscopy.	2002 May 15	12008122
Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells.	2002 May 23	12032841
Molecular modeling of flavonoids that inhibits xanthine oxidase.	2002 May 31	12054758
Flavonoids from Ficaria verna Huds.	2002 May-Jun	12132681
Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-alpha and IL-4 production from RBL-2H3 cells.	2002 Oct	12150856
High-affinity activators of cystic fibrosis transmembrane conductance regulator (CFTR) chloride conductance identified by high-throughput screening.	2002 Oct 4	12161441

Patents

Name

Type

Language

APIGENIN

Official Name

English

APIGENINE

Common Name

English

APIGENOL

Common Name

English

CI NATURAL YELLOW 1

Common Name

English

APIGENIN [USP-RS]

Common Name

English

APIGENIN [HSDB]

Common Name

English

4',5,7-TRIHYDROXYFLAVONE

Systematic Name

English

UCCF-031

Code

English

APEGENIN

Common Name

English

VERSULIN

Common Name

English

LY-080400

Code

English

FLAVONE, 4',5,7-TRIHYDROXY-

Systematic Name

English

APIGENIN [MI]

Common Name

English

Apigenin [WHO-DD]

Common Name

English

5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

APIGENIN [INCI]

Common Name

English

NSC-83244

Code

English

APIGENIN (CONSTITUENT OF CHAMOMILE) [DSC]

Common Name

English

PELARGIDENON-1449

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-

Systematic Name

English

2-(P-HYDROXYPHENYL)-5,7-DIHYDROXYCHROMONE

Common Name

English

Classification Tree Code System Code

DSLD

222 (Number of products:60)