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Identification
- Summary
Vilazodone is an antidepressant agent used for the treatment of major depressive disorder that targets the 5-HT transporter and 5-HT1A receptors.
- Brand Names
- Viibryd
- Generic Name
- Vilazodone
- DrugBank Accession Number
- DB06684
- Background
Vilazodone is a novel compound with combined high affinity and selectivity for the 5-hydroxytryptamine (5-HT) transporter and 5-HT(1A) receptorsLabel,2. Vilazodone may also be associated with less sexual dysfunction and weight gain3. Vilazodone was given FDA approval on January 21, 20115,2.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Vilazodone (DB06684)
- Weight
- Average: 441.5249
Monoisotopic: 441.216475133 - Chemical Formula
- C26H27N5O2
- Synonyms
- Vilazodona
- Vilazodone
- Vilazodonum
- External IDs
- EMD 515259
- EMD-515259
- EMD-68843
- SB 659746A
Pharmacology
- Indication
Vilazodone is approved for treatment of major depressive disorder.Label,1,2
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.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Major depressive disorder •••••••••••• •••••• - Contraindications & Blackbox Warnings
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Vilazodone increases serotonin levels in the brain by inhibiting the reuptake of serotonin while acting as a partial agonist on serotonin-1A receptorsLabel,1,3. Due to this activity vilazodone has sometimes been referred to as a selective partial agonist and reuptake inhibitor (SPARI)Label,3.
- Mechanism of action
Vilazodone selectively inhibits serotonin reuptake in the central nervous system as well as acting as a partial agonist of 5HT-1A receptorsLabel,1. The exact mechanism for how these effects translate to its antidepressant effects are not knownLabel, though there is an association between these effects and antidepressive activity3.
Target Actions Organism ASodium-dependent serotonin transporter inhibitorHumans U5-hydroxytryptamine receptor 1A agonistHumans - Absorption
Vilazodone's bioavailability is 72% when taken with foodLabel,1.
- Volume of distribution
Vilazodone's volume of distribution is unknown but largeLabel,1
- Protein binding
- Metabolism
Vilazodone is mainly metabolized by cytochrome P450(CYP)3A4 and also to a minor extent by CYP2C19 and CYP 2D6Label,1. Although the metabolic pathway for vilazodone has not been fully studied, a proposed mechanism for metabolism in rats was published in 20172.
- Route of elimination
1% of the dose is recovered unchanged in the urine and 2% of the dose is recovered unchanged in the fecesLabel,1,4.
- Half-life
25 hoursLabel,1. Other studies show a half life of 24±5.2h with a single 40mg dose and 28.9±3.2h with repeated doses4.
- Clearance
Clearance of vilazodone is 19.9-25.1L/h in patients with mild to moderate renal impairment compared to 26.4-26.9L/h in healthy controls4.
- Adverse Effects
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There is a lack of clinical studies of vilazodone in pregnancyLabel. Animal studies have shown the effects on offspring to be reduced fetal weight, increased mortality, delayed maturation, and decreased fertility in adulthood at doses well above the maximum recommended human doseLabel. Clinical cases of fetal and neonatal exposure to SSRIs and SNRIs have lead to a number of complications including respiratory distress, seizures, and temperature instabilityLabel. It is not know whether vilazodone is excreted in the breast milk of nursing mothers but animal studies show this is the case for ratsLabel. The risk and benefit of breast feeding while taking vilazodone for mother and child must be considered before a decision is madeLabel. Safety and effectiveness in pediatric patients has not been established in clinical trials though antidepressants are associated with an increased risk of suicidal thought and behaviour in patients under 24 yearsLabel. Clinical studies in geriatric patients showed to significant difference in response to vilazodone compared to younger patientsLabel. Geriatric patients should be started at a lower dose and titrated to an effective dose as they are more likely to have other comorbiditiesLabel. Dosage adjustments are not necessary for patients of different genders or with reduced hepatic and renal functionLabel.
- 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 software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Vilazodone is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Vilazodone can be increased when it is combined with Abametapir. Abatacept The metabolism of Vilazodone can be increased when combined with Abatacept. Abiraterone The metabolism of Vilazodone can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Vilazodone. - Food Interactions
- Avoid alcohol.
- Avoid St. John's Wort.
- Take with food.
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.- Product Ingredients
Ingredient UNII CAS InChI Key Vilazodone hydrochloride U8HTX2GK8J 163521-08-2 RPZBRGFNBNQSOP-UHFFFAOYSA-N - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Viibryd Tablet 20 mg/1 Oral Allergan, Inc. 2011-04-29 Not applicable US 
Viibryd Tablet 20 mg Oral Abbvie 2018-01-31 Not applicable Canada 
Viibryd Tablet 40 mg/1 Oral Cardinal Health 107, LLC 2011-04-29 2024-04-30 US 
Viibryd Tablet 40 mg/1 Oral Avera McKennan Hospital 2015-03-10 2017-05-24 US 
Viibryd Tablet, film coated 20 mg/1 Oral Trovis Pharmaceuticals LLC 2011-04-18 2011-04-18 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vilazodone Tablet 20 mg/1 Oral AvKARE 2024-06-05 Not applicable US Vilazodone Tablet 40 mg/1 Oral Golden State Medical Supply, Inc. 2021-01-21 2024-07-31 US Vilazodone Tablet 20 mg/1 Oral Apotex Corp 2022-06-04 Not applicable US Vilazodone Tablet 10 mg/1 Oral AvKARE 2024-06-05 Not applicable US Vilazodone Tablet 20 mg/1 Oral Golden State Medical Supply, Inc. 2021-01-21 2024-05-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1) Kit Oral Allergan, Inc. 2011-04-29 2016-08-31 US Viibryd Vilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) + Vilazodone hydrochloride (40 mg) Kit; Tablet Oral Forest Laboratories Not applicable Not applicable Canada Viibryd Vilazodone hydrochloride (10 mg) + Vilazodone hydrochloride (20 mg) Kit; Tablet Oral Abbvie 2018-07-06 2023-07-20 Canada Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) + Vilazodone hydrochloride (40 mg/1) Kit Oral Trovis Pharmaceuticals LLC 2011-04-18 2011-04-18 US Viibryd Vilazodone hydrochloride (10 mg/1) + Vilazodone hydrochloride (20 mg/1) Kit Oral Allergan, Inc. 2011-04-29 2023-10-31 US
Categories
- ATC Codes
- N06AX24 — Vilazodone
- Drug Categories
- Agents that produce hypertension
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Benzofurans
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Indoles
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Piperazines
- Psychoanaleptics
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin Agents
- Serotonin antagonist and reuptake inhibitors (SARIs)
- Serotonin Modulators
- Serotonin Receptor Agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- N-arylpiperazines
- Alternative Parents
- 3-alkylindoles / Benzofurans / 2-heteroaryl carboxamides / Furoic acid and derivatives / Dialkylarylamines / N-alkylpiperazines / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds show 10 more
- Substituents
- 2-heteroaryl carboxamide / 3-alkylindole / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzofuran / Carbonitrile show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- N-arylpiperazine, monocarboxylic acid amide, 1-benzofurans, indoles, nitrile, N-alkylpiperazine (CHEBI:70707)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S239O2OOV3
- CAS number
- 163521-12-8
- InChI Key
- SGEGOXDYSFKCPT-UHFFFAOYSA-N
- InChI
- InChI=1S/C26H27N5O2/c27-16-18-4-6-23-22(13-18)19(17-29-23)3-1-2-8-30-9-11-31(12-10-30)21-5-7-24-20(14-21)15-25(33-24)26(28)32/h4-7,13-15,17,29H,1-3,8-12H2,(H2,28,32)
- IUPAC Name
- 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxamide
- SMILES
- NC(=O)C1=CC2=CC(=CC=C2O1)N1CCN(CCCCC2=CNC3=C2C=C(C=C3)C#N)CC1
References
- General References
- Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [Article]
- Chavan BB, Kalariya PD, Tiwari S, Nimbalkar RD, Garg P, Srinivas R, Talluri MVNK: Identification and characterization of vilazodone metabolites in rats and microsomes by ultrahigh-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass Spectrom. 2017 Dec 15;31(23):1974-1984. doi: 10.1002/rcm.7982. [Article]
- Wang SM, Han C, Lee SJ, Patkar AA, Masand PS, Pae CU: A review of current evidence for vilazodone in major depressive disorder. Int J Psychiatry Clin Pract. 2013 Aug;17(3):160-9. doi: 10.3109/13651501.2013.794245. Epub 2013 May 29. [Article]
- Boinpally R, Alcorn H, Adams MH, Longstreth J, Edwards J: Pharmacokinetics of vilazodone in patients with mild or moderate renal impairment. Clin Drug Investig. 2013 Mar;33(3):199-206. doi: 10.1007/s40261-013-0061-5. [Article]
- FDA Drug Approval Package: Vilazodone [Link]
- External Links
- Human Metabolome Database
- HMDB0015637
- KEGG Drug
- D09698
- PubChem Compound
- 6918314
- PubChem Substance
- 175427083
- ChemSpider
- 5293518
- BindingDB
- 50151982
- 1086769
- ChEBI
- 70707
- ChEMBL
- CHEMBL439849
- ZINC
- ZINC000001542113
- PDBe Ligand
- YG7
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vilazodone
- PDB Entries
- 7lwd / 8fyl
- FDA label
- Download (385 KB)
- MSDS
- Download (22.3 KB)
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 Hot Flashes 1 somestatus stop reason just information to hide Not Available Terminated Not Available Bipolar Disorder (BD) 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Social Anxiety Disorder (SAD) 1 somestatus stop reason just information to hide 4 Completed Other Healthy (Controls) / Major Depressive Disorder (MDD) 1 somestatus stop reason just information to hide 4 Completed Treatment Depression / Post Traumatic Stress Disorder (PTSD) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral Kit; tablet Oral Tablet Oral 10 mg Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet Oral 20 mg Tablet Oral 40 mg/1 Tablet Oral 40 mg Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 10 mg Tablet, film coated Oral 20 mg Tablet, film coated Oral 40 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7834020 Yes 2010-11-16 2022-12-05 US US8193195 Yes 2012-06-05 2022-12-05 US US8236804 Yes 2012-08-07 2022-12-05 US US8673921 Yes 2014-03-18 2022-12-05 US US5532241 No 1996-07-02 2019-09-29 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.123 mg/mL ALOGPS logP 4.21 ALOGPS logP 3.72 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 14.19 Chemaxon pKa (Strongest Basic) 8.6 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 102.29 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 129.71 m3·mol-1 Chemaxon Polarizability 50.03 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9959 Blood Brain Barrier + 0.9694 Caco-2 permeable - 0.6764 P-glycoprotein substrate Substrate 0.6362 P-glycoprotein inhibitor I Inhibitor 0.581 P-glycoprotein inhibitor II Inhibitor 0.9022 Renal organic cation transporter Non-inhibitor 0.527 CYP450 2C9 substrate Non-substrate 0.9138 CYP450 2D6 substrate Non-substrate 0.5431 CYP450 3A4 substrate Substrate 0.5983 CYP450 1A2 substrate Non-inhibitor 0.5637 CYP450 2C9 inhibitor Inhibitor 0.5397 CYP450 2D6 inhibitor Non-inhibitor 0.7021 CYP450 2C19 inhibitor Inhibitor 0.6998 CYP450 3A4 inhibitor Non-inhibitor 0.6258 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8731 Ames test Non AMES toxic 0.6088 Carcinogenicity Non-carcinogens 0.9181 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6208 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8967 hERG inhibition (predictor II) Inhibitor 0.87
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0pb9-1892200000-e80db0623de8c5d5253b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0000900000-b7296c52e92303c27b43 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dm-0003900000-eb92ab589376718266c6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0097-0201900000-a8eee8f3f272a9b91497 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-5009700000-4eef03aa94a42392c657 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6x-0981200000-127d97e11992d536148b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-1495400000-111188bd6b56494c80b6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 238.0315313 predictedDarkChem Lite v0.1.0 [M-H]- 202.66661 predictedDeepCCS 1.0 (2019) [M+H]+ 238.2635313 predictedDarkChem Lite v0.1.0 [M+H]+ 205.02461 predictedDeepCCS 1.0 (2019) [M+Na]+ 238.2641313 predictedDarkChem Lite v0.1.0 [M+Na]+ 211.11775 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
- Specific Function
- Actin filament binding
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [Article]
- Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [Article]
- Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I: Behavioral and neurochemical effects of 5-(4-[4-(5-Cyano-3-indolyl)-butyl)-butyl]-1-piperazinyl)-benzofuran-2-carboxamide (EMD 68843): a combined selective inhibitor of serotonin reuptake and 5-hydroxytryptamine(1A) receptor partial agonist. J Pharmacol Exp Ther. 2002 Sep;302(3):1220-7. [Article]
- Adamec R, Bartoszyk GD, Burton P: Effects of systemic injections of vilazodone, a selective serotonin reuptake inhibitor and serotonin 1A receptor agonist, on anxiety induced by predator stress in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):65-77. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, 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) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). 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) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Cruz MP: Vilazodone HCl (Viibryd): A Serotonin Partial Agonist and Reuptake Inhibitor For the Treatment of Major Depressive Disorder. P T. 2012 Jan;37(1):28-31. [Article]
Drug created at March 19, 2008 16:49 / Updated at August 02, 2024 07:30