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

Identification

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Name
Piperine
Accession Number
DB12582
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
  • Bioperine
External IDs
FEMA NO. 2909
Categories
UNII
U71XL721QK
CAS number
94-62-2
Weight
Average: 285.3377
Monoisotopic: 285.136493479
Chemical Formula
C17H19NO3
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Piperine.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Piperine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Piperine.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Piperine.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Piperine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Piperine.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Piperine.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Piperine.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Piperine.
AcetyldigoxinPiperine may decrease the excretion rate of Acetyldigoxin which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0029377
KEGG Compound
C03882
PubChem Compound
638024
PubChem Substance
347828804
ChemSpider
553590
BindingDB
50148573
ChEBI
28821
ChEMBL
CHEMBL43185
Wikipedia
Piperine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic SciencePain1
1RecruitingSupportive CareBladder Spasms / Micturition urgency / Neoplasms, Malignant / Pain1
1, 2CompletedTreatmentDeglutition Disorders1
4RecruitingPreventionPre-Diabetic1
Not AvailableCompletedTreatmentMultiple Myeloma (MM)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

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
Benzodioxole / N-acyl-piperidine / Alkaloid or derivatives / Styrene / Piperidine / Benzenoid / Tertiary carboxylic acid amide / Carboxamide group / Acetal / Carboxylic acid derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-acylpiperidine, benzodioxoles, piperidine alkaloid, carboxamide (CHEBI:28821) / Piperidine alkaloids (C03882)

Targets

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. [PubMed:23707768]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
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. [PubMed:12130727]

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. [PubMed:12130727]

Drug created on October 20, 2016 17:01 / Updated on November 02, 2019 03:00