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=CC(O)=C2C(=O)C[C@H](OC2=C1)C3=CC=CC=C3

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 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25907027	Inhibitor 8297	44.9 µM [IC50]
Epoxide hydrolase 2 1 Target ID: CHEMBL5669 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23725831	Inhibitor 8297	2.58 µM [IC50]
Cytochrome P450 19A1 39 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21802698	Inhibitor 8297	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 1132	Unknown Approved Use Unknown
Alzheimer’s disease 272 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
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
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
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

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
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
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
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

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
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
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
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

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
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
Biopurify Phytochemicals	BP1107	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP1107&searchhtmp=simplesearch&t=1
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
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
MedChem Express	HY-N0575	https://www.medchemexpress.com/search.html?q=HY-N0575&ft=&fa=&fp=
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
Molnova	M18610	https://www.molnova.com/en/serch-list.html?keywords=M18610
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
eMolecules	1935959	https://orderbb.emolecules.com/search/#?query=1935959
eMolecules	731556	https://orderbb.emolecules.com/search/#?query=731556
mcule	MCULE-6631561492	https://mcule.com/MCULE-6631561492/
mcule	MCULE-9302131889	https://mcule.com/MCULE-9302131889/
mcule	MCULE-9370973230	https://mcule.com/MCULE-9370973230/

PubMed

Title	Date	PubMed
[Effect of propolis and pinocembrin on fungi].	1977 Nov	609603
Two antimicrobial flavanones from the leaves of Glycyrrhiza glabra.	1988 Oct	3245990
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
NF-kappaB-activated tissue transglutaminase is involved in ethanol-induced hepatic injury and the possible role of propolis in preventing fibrogenesis.	2008 Apr 18	18295389
Phytochemical and antimicrobial investigations of stilbenoids and flavonoids isolated from three species of Combretaceae.	2012 Jul	22546149

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

(+)-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

NSC-279005

Code

English

DIHYDROCHRYSIN

Common Name

English

Classification Tree Code System Code

DSLD

1394 (Number of products:104)