Piperine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Piperine
DrugBank Accession Number
DB12582
Background

Bioperine has been used in trials studying the treatment of Multiple Myeloma and Deglutition Disorders.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 285.3377
Monoisotopic: 285.136493479
Chemical Formula
C17H19NO3
Synonyms
  • Bioperine
External IDs
  • FEMA NO. 2909

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Piperine.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Piperine.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Piperine.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Piperine.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Piperine.
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Kaydia PatchPiperine (0.2 g/100g) + Arnica montana flower (0.5 g/100g) + Curcumin (1 g/100g) + Ginger (0.5 g/100g) + Magnesium chloride hexahydrate (2 g/100g) + Pyridoxine (1 g/100g) + Thiamine chloride (1 g/100g)PatchTopicalStrong Current Enterprises Limited2020-05-01Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Kaydia PatchPiperine (0.2 g/100g) + Arnica montana flower (0.5 g/100g) + Curcumin (1 g/100g) + Ginger (0.5 g/100g) + Magnesium chloride hexahydrate (2 g/100g) + Pyridoxine (1 g/100g) + Thiamine chloride (1 g/100g)PatchTopicalStrong Current Enterprises Limited2020-05-01Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Not Available
Sub Class
Not Available
Direct Parent
Alkaloids and derivatives
Alternative Parents
N-acylpiperidines / Benzodioxoles / Styrenes / Tertiary carboxylic acid amides / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Acetal / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-acylpiperidine, benzodioxoles, piperidine alkaloid, carboxamide (CHEBI:28821) / Piperidine alkaloids (C03882)
Affected organisms
Not Available

Chemical Identifiers

UNII
U71XL721QK
CAS number
94-62-2
InChI Key
MXXWOMGUGJBKIW-YPCIICBESA-N
InChI
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+
IUPAC Name
(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
SMILES
O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N1CCCCC1

References

General References
Not Available
Human Metabolome Database
HMDB0029377
KEGG Compound
C03882
PubChem Compound
638024
PubChem Substance
347828804
ChemSpider
553590
BindingDB
50148573
RxNav
1311146
ChEBI
28821
ChEMBL
CHEMBL43185
ZINC
ZINC000001529772
PDBe Ligand
AYR
Wikipedia
Piperine
PDB Entries
6lzl / 7blw

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusPreventionImpaired Glucose Tolerance1
2CompletedTreatmentSystemic Lupus Erythematosus1
2RecruitingTreatmentMonoclonal Gammopathy of Undetermined Significance (MGUS) / Multiple Myeloma (MM) / Prostate Cancer / Smoldering Multiple Myeloma (SMM)1
1Active Not RecruitingSupportive CareBladder Spasms / Malignant Neoplasm / Pain / Urinary Urgency1
1CompletedBasic SciencePain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PatchTopical
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.149 mg/mLALOGPS
logP3.38ALOGPS
logP2.78Chemaxon
logS-3.3ALOGPS
pKa (Strongest Basic)-0.13Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area38.77 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity82.9 m3·mol-1Chemaxon
Polarizability32.32 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0ru3-5490000000-47caa063ebe950468c83
GC-MS Spectrum - EI-BGC-MSsplash10-0fe0-0590000000-49115b64f9d288ede20b
GC-MS Spectrum - EI-BGC-MSsplash10-0uki-1980000000-0d80d5bd56077694f4ab
Mass Spectrum (Electron Ionization)MSsplash10-0v4r-4970000000-d7ea6f47f4b46495acb4
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0udi-0910000000-28987f355a39728ed8e4
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0udi-0090000000-6221df9a927cf5dae43f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0090000000-f586ee65972a8599fb3e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0190000000-9f77f056ac9f2e385656
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0090000000-d91bf95f43f53499a538
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0190000000-1f5b570135a2c33d60cb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0190000000-c67e35d994bd1857d3b3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0190000000-38727bddc27cc1f12b21
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004r-0032950000-09b8545ba31f6fbf5243
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01ti-0044970000-8efb835b518a1f9d631e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004r-0033960000-0ebcac3b31c8914732a9
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0009700000-45fc15cfc95d4cb7619c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0009500000-356adf7cecbec3f587a1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004r-0022950000-438f2d66c26e4fad4df9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-0930000000-08188c35582e879e867f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0090000000-c04e6e33b8d5a311e0dd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-4ec2248067b1d3bb72ce
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ul0-0590000000-4283fe974a492b10eadc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-059f-0490000000-3affbbe1a09f91d97915
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-0790000000-d7499c4e88e85c9b34f9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-2940000000-537999941a72d7b7e456
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.0276406
predicted
DarkChem Lite v0.1.0
[M-H]-192.0472406
predicted
DarkChem Lite v0.1.0
[M-H]-191.8248406
predicted
DarkChem Lite v0.1.0
[M-H]-192.2939406
predicted
DarkChem Lite v0.1.0
[M-H]-166.76486
predicted
DeepCCS 1.0 (2019)
[M+H]+193.0558406
predicted
DarkChem Lite v0.1.0
[M+H]+179.4917034
predicted
DarkChem Lite v0.1.0
[M+H]+192.7268406
predicted
DarkChem Lite v0.1.0
[M+H]+192.8558406
predicted
DarkChem Lite v0.1.0
[M+H]+169.12306
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.9856406
predicted
DarkChem Lite v0.1.0
[M+Na]+189.5834558
predicted
DarkChem Lite v0.1.0
[M+Na]+192.9178406
predicted
DarkChem Lite v0.1.0
[M+Na]+192.2702406
predicted
DarkChem Lite v0.1.0
[M+Na]+175.57353
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Wang YM, Lin W, Chai SC, Wu J, Ong SS, Schuetz EG, Chen T: Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):96-107. doi: 10.1016/j.taap.2013.05.014. Epub 2013 May 22. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF: Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther. 2002 Aug;302(2):645-50. doi: 10.1124/jpet.102.034728. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF: Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther. 2002 Aug;302(2):645-50. doi: 10.1124/jpet.102.034728. [Article]

Drug created at October 20, 2016 23:01 / Updated at June 12, 2020 16:53