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Piperine (1-Piperoylpiperidine; Bioperine; 1-Piperoyl piperidine), a natural alkaloid found in Piper nigrum L, is an alkaloid accounting for the pungency of black pepper and long pepper, which has been used in some forms of traditional medicine and as an insecticide. It inhibits P-glycoprotein and CYP3A4 activities with an IC50 value of 61.94±0.054 μg/mL in HeLa cell.
| ln Vitro |
It has been demonstrated in vitro and in silico investigations that piperine possesses cytotoxic action. The value of IC50 is 61.94 μg/mL. Based on computational analyses, it possesses the greatest number of hydrogen bonds, the lowest binding and docking energy, and is potentially an inhibitor of EGFR tyrosine kinase [1]. It has been discovered that piperine possesses anti-inflammatory, anti-cancer, antioxidant, anti-asthmatic, anti-ulcer, and anti-amoebic qualities [2]. By reducing CYP3A and P-glycoprotein activity, piperine can enhance the bioavailability of various medications, including paclitaxel, docetaxel, and rosuvastatin (DOX) [3].
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| ln Vivo |
Piperine has a 25.36% bioavailability at a dose of 3.5 mg/kg. Piperine has a disproportionate dose-dependent increase in its AUC0→t, suggesting the possibility of nonlinear pharmacokinetic properties. After combination use, it was discovered that the t1/2 of piperine and the AUC0→t and C0 of docetaxel were dramatically elevated. The data indicates that concomitant administration enhances both the bioavailability of docetaxel and piperine, potentially contributing to a greater overall improvement in pharmacological effects [3]. Piperine exhibits a dose-dependent inhibition of the phosphorylation of I-κB, p65, p38, ERK, and JNK, indicating its potential as an anti-inflammatory medication for endometritis and other Staphylococcus aureus-related illnesses [4].
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| Additional Infomation |
Piperine is a N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum. It has a role as a NF-kappaB inhibitor, a plant metabolite, a food component and a human blood serum metabolite. It is a member of benzodioxoles, a N-acylpiperidine, a piperidine alkaloid and a tertiary carboxamide. It is functionally related to an (E,E)-piperic acid.
Bioperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders. Piperine has been reported in Periconia, Piper khasianum, and other organisms with data available. See also: Black Pepper (part of) ... View More ... |
| Molecular Formula |
C17H19NO3
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| Molecular Weight |
285.3377
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| Exact Mass |
285.136
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| CAS # |
94-62-2
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| Related CAS # |
Isochavicine;30511-77-4
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| PubChem CID |
638024
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| Appearance |
White to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
498.5±40.0 °C at 760 mmHg
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| Melting Point |
131-135 °C(lit.)
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| Flash Point |
255.3±27.3 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.615
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| LogP |
2.66
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
21
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| Complexity |
412
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
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| InChi Key |
MXXWOMGUGJBKIW-YPCIICBESA-N
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| InChi Code |
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+
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| Chemical Name |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.76 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5046 mL | 17.5230 mL | 35.0459 mL | |
| 5 mM | 0.7009 mL | 3.5046 mL | 7.0092 mL | |
| 10 mM | 0.3505 mL | 1.7523 mL | 3.5046 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04731844 | Recruiting | Drug: Curcumin plus Piperine | Prostate Cancer Multiple Myeloma |
University of Rochester | December 14, 2021 | Phase 2 |
| NCT02598726 | Active, not recruiting | Drug: Curcumin Other: Laboratory Biomarker Analysis |
Bladder Spasm Malignant Neoplasm |
Mayo Clinic | March 1, 2016 | Phase 1 |
| NCT01383694 | Completed | Drug: Piperine | Deglutition Disorders | Hospital de Mataró | June 2011 | Phase 1 Phase 2 |
| NCT01893424 | Completed | Drug: Sativex buccal spray Drug: CBD-THC-Piperine-PNL capsule |
Pain | Hadassah Medical Organization | August 2013 | Phase 1 |
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