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
SMILES
O=C(\C=C/C=C\C1=CC=C2OCOC2=C1)N3CCCCC3
InChI
InChIKey=MXXWOMGUGJBKIW-PORYWJCVSA-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-
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26560940 | https://www.ncbi.nlm.nih.gov/pubmed/26146123Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23625885
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3356 |
14.19 µM [IC50] | ||
Target ID: CHEMBL340 |
2.12 µM [IC50] | ||
Target ID: map04010 |
|||
Target ID: CHEMBL2321614 |
133.3 µM [IC50] | ||
Target ID: CHEMBL2321613 |
45.0 µM [IC50] | ||
Target ID: CHEMBL2331042 |
230.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Piperine blocks interleukin-2-driven cell cycle progression in CTLL-2 T lymphocytes by inhibiting multiple signal transduction pathways. | 2015-04-02 |
|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
|
| Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats. | 2014-09-25 |
|
| Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system. | 2013-12 |
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| Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. | 2013-10-01 |
|
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013-10 |
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| Anti-HBV active constituents from Piper longum. | 2013-04-01 |
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| Piperine inhibits PMA-induced cyclooxygenase-2 expression through downregulating NF-κB, C/EBP and AP-1 signaling pathways in murine macrophages. | 2012-07 |
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| 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. | 2011-05-30 |
|
| The plant alkaloid piperine as a potential inhibitor of ethidium bromide efflux in Mycobacterium smegmatis. | 2011-02 |
|
| Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
|
| Piperine as an inhibitor of Rv1258c, a putative multidrug efflux pump of Mycobacterium tuberculosis. | 2010-08 |
|
| Antioxidant effects of a Rhodobryum roseum extract and its active components in isoproterenol-induced myocardial injury in rats and cardiac myocytes against oxidative stress-triggered damage. | 2009-01 |
|
| Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation. | 2007-03 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Modulation of cadmium induced alterations in murine thymocytes by piperine: oxidative stress, apoptosis, phenotyping and blastogenesis. | 2006-08-14 |
|
| Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). | 2005-03 |
|
| Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression. | 2005 |
|
| 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. | 2004-12-20 |
|
| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004-04 |
|
| Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. | 2003-12 |
|
| Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells. | 2003 |
|
| Steroid hormone activity of flavonoids and related compounds. | 2000-07 |
|
| Action of intrathecal capsaicin and its structural analogues on the content and release of spinal substance P: selectivity of action and relationship to analgesia. | 1984-07-23 |
Sample Use Guides
A single dose of Piperine 20 mg was administered daily for 10 days
Route of Administration:
Oral
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
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| Record UNII |
95JV386FPD
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