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=CC2=C(OCO2)C=C1)N3CCCCC3
InChI
InChIKey=MXXWOMGUGJBKIW-MFDSWNTHSA-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+
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 |
|---|---|---|
| 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 Jul 23 |
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| Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
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| Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells. | 2003 |
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| 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 Dec |
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| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
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| 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 |
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| Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression. | 2005 |
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| Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). | 2005 Mar |
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| Modulation of cadmium induced alterations in murine thymocytes by piperine: oxidative stress, apoptosis, phenotyping and blastogenesis. | 2006 Aug 14 |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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| Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation. | 2007 Mar |
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| 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 Jan |
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| Piperine as an inhibitor of Rv1258c, a putative multidrug efflux pump of Mycobacterium tuberculosis. | 2010 Aug |
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| Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. | 2011 |
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| The plant alkaloid piperine as a potential inhibitor of ethidium bromide efflux in Mycobacterium smegmatis. | 2011 Feb |
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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 May 30 |
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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 Jul |
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| Anti-HBV active constituents from Piper longum. | 2013 Apr 1 |
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| Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system. | 2013 Dec |
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| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | 2013 Oct |
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| Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. | 2013 Oct 1 |
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| Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats. | 2014 Sep 25 |
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| Piperine blocks interleukin-2-driven cell cycle progression in CTLL-2 T lymphocytes by inhibiting multiple signal transduction pathways. | 2015 Apr 2 |
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| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015 Jan 5 |
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.
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SUBSTANCE RECORD
