Piperine
Star3
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AAmine oxidase [flavin-containing] A inhibitorHumans AAmine oxidase [flavin-containing] B inhibitorHumans UNuclear receptor subfamily 1 group I member 2 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Piperine. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Piperine. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Piperine. Afatinib The serum concentration of Afatinib can be increased when it is combined with Piperine. Albendazole The metabolism of Albendazole can be decreased when combined with Piperine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Kaydia Patch Piperine (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) Patch Topical Strong Current Enterprises Limited 2020-05-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Kaydia Patch Piperine (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) Patch Topical Strong Current Enterprises Limited 2020-05-01 Not applicable US
Categories
- Drug Categories
- Alkenes
- Alkynes
- Amides
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dioxoles
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Hydrocarbons, Acyclic
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- P-glycoprotein inhibitors
- Piper nigrum
- 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
- External Links
- Human Metabolome Database
- HMDB0029377
- KEGG Compound
- C03882
- PubChem Compound
- 638024
- PubChem Substance
- 347828804
- ChemSpider
- 553590
- BindingDB
- 50148573
- 1311146
- ChEBI
- 28821
- ChEMBL
- CHEMBL43185
- ZINC
- ZINC000001529772
- PDBe Ligand
- AYR
- Wikipedia
- Piperine
- PDB Entries
- 6lzl / 7blw
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Multiple Myeloma (MM) 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Dysphagia / Oropharyngeal Dysphagia (OPD) / Stroke / Stroke, Acute 1 somestatus stop reason just information to hide 4 Unknown Status Prevention Impaired Glucose Tolerance 1 somestatus stop reason just information to hide 2 Completed Treatment Systemic Lupus Erythematosus 1 somestatus stop reason just information to hide 2 Recruiting Treatment Monoclonal Gammopathy of Undetermined Significance (MGUS) / Multiple Myeloma (MM) / Prostate Cancer / Smoldering Multiple Myeloma (SMM) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Patch Topical Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.149 mg/mL ALOGPS logP 3.38 ALOGPS logP 2.78 Chemaxon logS -3.3 ALOGPS pKa (Strongest Basic) -0.13 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 38.77 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 82.9 m3·mol-1 Chemaxon Polarizability 32.32 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.0276406 predictedDarkChem Lite v0.1.0 [M-H]- 192.0472406 predictedDarkChem Lite v0.1.0 [M-H]- 191.8248406 predictedDarkChem Lite v0.1.0 [M-H]- 192.2939406 predictedDarkChem Lite v0.1.0 [M-H]- 166.76486 predictedDeepCCS 1.0 (2019) [M+H]+ 193.0558406 predictedDarkChem Lite v0.1.0 [M+H]+ 179.4917034 predictedDarkChem Lite v0.1.0 [M+H]+ 192.7268406 predictedDarkChem Lite v0.1.0 [M+H]+ 192.8558406 predictedDarkChem Lite v0.1.0 [M+H]+ 169.12306 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.9856406 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.5834558 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.9178406 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.2702406 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.57353 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsAmine oxidase [flavin-containing] A
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsAmine oxidase [flavin-containing] B
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- 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
1. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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
1. DetailsATP-dependent translocase ABCB1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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 August 26, 2024 19:23