PIPERINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19NO3
Molecular Weight	285.3377
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N3CCCCC3

InChI

InChIKey=MXXWOMGUGJBKIW-YPCIICBESA-N

InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

HIDE SMILES / InChI

Molecular Formula	C17H19NO3
Molecular Weight	285.3377
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26560940 | https://www.ncbi.nlm.nih.gov/pubmed/26146123
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23625885

Piperine is a simple and pungent alkaloid found in the seeds of black pepper (Piper nigrum). Following its isolation and full characterization, the biological properties of piperine have been extensively studied, and piperine-like derivatives have shown an interesting range of pharmacological activities. Piperine is currently paving its way to become a privileged scaffold for the development of bioactive compounds with therapeutic application in multiple human diseases. In particular, piperine derivatives were shown to modulate the activity of several targets related to neurological disorders, including epilepsy, Parkinson's disease, depression and pain related disorders. Moreover, the efflux pump inhibitory ability of piperine and its analogues tackles important drug resistance mechanisms and may improve the clinical efficacy of antibiotic and anticancer drugs. Piperine has been found to have immunomodulatory, anti-oxidant, anti-asthmatic, anti-carcinogenic, anti-inflammatory, anti-ulcer, and anti-amoebic properties.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27821437	Inhibitor 8297	14.19 µM [IC50]
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27821437 \| https://www.ncbi.nlm.nih.gov/pubmed/12130727	Inhibitor 8297	2.12 µM [IC50]
MAPK signaling pathway 26 Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25471891	Inhibitor 8297
Potassium channel subfamily K member 9 6 Target ID: CHEMBL2321614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912	Inhibitor 8297	133.3 µM [IC50]
Potassium channel subfamily K member 3 10 Target ID: CHEMBL2321613 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912	Inhibitor 8297	45.0 µM [IC50]
Potassium channel subfamily K member 18 4 Target ID: CHEMBL2331042 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24302912	Inhibitor 8297	230.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Deglutition disorders 3 Sources: https://clinicaltrials.gov/ct2/show/NCT01383694	Primary		Phase II 1132	Unknown Approved Use Unknown
Ureteral stent-induced symptoms in patients with cancer 3 Sources: https://clinicaltrials.gov/ct2/show/NCT02598726	Palliative		Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.	2004 Apr	15120460
Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells.	2004 Dec 20	15531295
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
The plant alkaloid piperine as a potential inhibitor of ethidium bromide efflux in Mycobacterium smegmatis.	2011 Feb	21051548
Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKCα/ERK1/2-dependent matrix metalloproteinase-9 expression.	2011 May 30	21354279
Anti-HBV active constituents from Piper longum.	2013 Apr 1	23434420
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.	2013 Oct	23942037

Patents

Sample Use Guides

In Vivo Use Guide

A single dose of Piperine 20 mg was administered daily for 10 days

Route of Administration: Oral

In Vitro Use Guide

Piperine inhibited the proliferation of SW480 and HT-29 cells in a dose-dependent manner, it had low cytotoxicity on these cell lines with 50 % inhibiting concentration (IC50) values greater than 100 uM. Pretreatment of the cells with 40 uM piperine for 1 h significantly inhibited the mRNA production of CXCL8 in response to LPS stimulation in SW480 and HT-29 cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:56 GMT 2023` Edited by `admin` on `Fri Dec 15 15:58:56 GMT 2023`
Record UNII	U71XL721QK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIPERINE

Official Name

English

PIPERINE [FHFI]

Common Name

English

NSC-21727

Code

English

PIPERINE [INCI]

Common Name

English

PIPERINE [USP-RS]

Common Name

English

BIOPERINE

Common Name

English

PIPERINE (CONSTITUENT OF BLACK PEPPER) [DSC]

Common Name

English

(E,E)-1-(5-(1,3-BENZODIOXOL-5-YL)-2,4-PENTADIENOYL)PIPERIDINE

Systematic Name

English

PIPERINE [MI]

Common Name

English

(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one

Systematic Name

English

FEMA NO. 2909

Code

English

PIPERIDINE, 1-(5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-, (E,E)-

Common Name

English

Piperine [WHO-DD]

Common Name

English

Classification Tree Code System Code

DSLD

2372 (Number of products:123)