PINOCEMBRIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H12O4
Molecular Weight	256.2534
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC2=C(C(=O)C[C@H](O2)C3=CC=CC=C3)C(O)=C1

InChI

InChIKey=URFCJEUYXNAHFI-ZDUSSCGKSA-N

InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23984355 | https://www.ncbi.nlm.nih.gov/pubmed/25744566

Pinocembrin (5,7-dihydroxyflavanone) is one of the primary flavonoids isolated from the variety of plants, mainly from Pinus heartwood, Eucalyptus, Populus, Euphorbia, and Sparattosperma leucanthum. Pinocembrin is a major flavonoid molecule incorporated as multifunctional in the pharmaceutical industry. Its vast range of pharmacological activities has been well researched including antimicrobial, anti-inflammatory, antioxidant, and anticancer activities. In addition, pinocembrin can be used as neuroprotective against cerebral ischemic injury with a wide therapeutic time window, which may be attributed to its antiexcitotoxic effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25907027	Inhibitor 8504	44.9 µM [IC50]
Epoxide hydrolase 2 1 Target ID: CHEMBL5669 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23725831	Inhibitor 8504	2.58 µM [IC50]
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21802698	Inhibitor 8504	0.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144 Sources: http://adisinsight.springer.com/drugs/800042496 https://www.ncbi.nlm.nih.gov/pubmed/26380402	Primary		Phase II 1147	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22989295	Primary		Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
277 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24733513	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.82 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	60 mg 2 times / day multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.22 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.28 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
10338.1 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24733513	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
89.34 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
30.82 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	60 mg 2 times / day multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
44 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10.34 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
47.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24733513	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
54.5 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	150 mg single, intravenous dose: 150 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
50.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	60 mg 2 times / day multiple, intravenous dose: 60 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
55.7 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
47.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25814318	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PINOCEMBRIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00D96O	https://www.1pchem.com/search?query=1P00D96O
AK Scientific	V1518	https://aksci.com/item_detail.php?cat=V1518
Alfa Chemistry	ACM480397	http://www.alfa-chemistry.com/search.aspx?q=ACM480397
Angene	AGN-PC-0JL88F	http://www.angenechemical.com/productshow/AGN-PC-0JL88F.html
Angene	AGN-PC-0OASI9	http://www.angenechemical.com/productshow/AGN-PC-0OASI9.html
ApexBio Technology	N2094	https://www.apexbt.com/catalogsearch/result/?q=N2094
AstaTech	42725	http://astatechinc.com/CPSResult.php?CRNO=42725
Biopurify Phytochemicals	BP1107	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1107&searchhtmp=simplesearch&t=1
BLD Pharm	BD299899	http://www.bldpharm.com/search/Search.html?keyword=BD299899
BOC Sciences	480-39-7	http://www.bocsci.com/description.asp?cas=480-39-7
BOC Sciences	68745-38-0	http://www.bocsci.com/description.asp?cas=68745-38-0
Chem Scene	CS-0009111	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0009111
ChemShuttle	108472	https://www.chemshuttle.com/catalogsearch/result/?q=108472
Combi-Blocks	QV-1892	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-1892
Debye Scientific	DB-055185	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-055185
eMolecules	1935959	https://orderbb.emolecules.com/search/#?query=1935959
eMolecules	731556	https://orderbb.emolecules.com/search/#?query=731556
Frontier Scientific Services	501002243	http://orders.frontierssi.com/fssionline32/public/product.aspx?cat=501002243&type=hts
Indofine	21162	https://indofinechemical.com/details.aspx?Sku=021162
KeyOrganics	AS-56293	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56293
Lab Network	LN00364424	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00364424
Lab Network	LN01109265	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01109265
Matrix Scientific	146172	http://www.matrixscientific.com/146172.html
mcule	MCULE-6631561492	https://mcule.com/MCULE-6631561492/
mcule	MCULE-9302131889	https://mcule.com/MCULE-9302131889/
mcule	MCULE-9370973230	https://mcule.com/MCULE-9370973230/
MedChem Express	HY-N0575	https://www.medchemexpress.com/search.html?q=HY-N0575&ft=&fa=&fp=
Molnova	M18610	https://www.molnova.com/en/serch-list.html?keywords=M18610
MolPort	MolPort-000-165-378	https://www.molport.com/shop/molecule-link/MolPort-000-165-378
MolPort	MolPort-002-509-256	https://www.molport.com/shop/molecule-link/MolPort-002-509-256
MuseChem	R018916	https://www.musechem.com/product/R018916.html
PI Chemicals	PI-18828	http://www.pipharm.com/catalog_products/PI-18828.html
TargetMol	BBP00120	https://www.targetmol.com/search?keyword=BBP00120
TargetMol	T2992	https://www.targetmol.com/search?keyword=T2992
Tetrahedron	TS28909	http://www.thsci.com/search.do?q=TS28909
TimTec	SBB066101	http://www.echemstore.com/catalogsearch/result/?q=SBB066101
TimTec	ST024705	http://www.echemstore.com/catalogsearch/result/?q=ST024705
Toronto Research Chemicals	E921953	https://www.trc-canada.com/product-detail/?CatNum=E921953
Toronto Research Chemicals	P468500	https://www.trc-canada.com/product-detail/?CatNum=P468500

PubMed

Title	Date	PubMed
Phytochemical and antimicrobial investigations of stilbenoids and flavonoids isolated from three species of Combretaceae.	2012-07	22546149
NF-kappaB-activated tissue transglutaminase is involved in ethanol-induced hepatic injury and the possible role of propolis in preventing fibrogenesis.	2008-04-18	18295389
Combinatorial biosynthesis of flavones and flavonols in Escherichia coli.	2006-06	16133333
Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster.	2005-09	15770480
The inhibition of superoxide anion generation by neutrophils from Viscum articulactum.	2004-07	15256709
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.	2001-03	11181495
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000-08-23	10953322
Two antimicrobial flavanones from the leaves of Glycyrrhiza glabra.	1988-10	3245990
[On the antimicrobial activity of propolis and propolis constituents (author's transl)].	1979	108687
[Effect of propolis and pinocembrin on fungi].	1977-11	609603

Patents

Sample Use Guides

In Vivo Use Guide

A double-blind, placebo-controlled, randomized study was carried out in 58 healthy subjects. Single ascending doses of pinocembrin (20-150 mg) were evaluated in 5 cohorts. Multi-dose was studied at pinocembrin 60 mg. Pinocembrin displayed linear plasma pharmacokinetics over the dose range, 20-150 mg and was well tolerated up to 120 mg day(-1) when administered intravenously to healthy adults.

Route of Administration: Intravenous

In Vitro Use Guide

Pinocembrin (5 approximately 100 uM) induced relaxation in rat aortic rings pre-contracted with norepinephrine (NE, 1 uM) or KCl (60 mM), with pEC(50) value 4.37+/-0.02 and 4.52+/-0.04. Pretreatment with pinocembrin (30 or 50 uM) also inhibited contractile responses to NE and KCl.

Name

Type

Language

PINOCEMBRIN

Common Name

English

NSC-279005

Preferred Name

English

(+)-PINOCOEMBRIN

Common Name

English

5,7-DIHYDROXYFLAVANONE

Systematic Name

English

GALANGIN FLAVANONE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-PHENYL-, (2S)-

Systematic Name

English

DIHYDROCHRYSIN

Common Name

English

Classification Tree Code System Code

DSLD

1394 (Number of products:104)