Identification
- Name
- Enzalutamide
- Accession Number
- DB08899
- Description
Enzalutamide is an androgen receptor inhibitor for the treatment of castration-resistant prostate cancer. FDA approved on August 31, 2012.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Enzalutamide (DB08899)
- Weight
- Average: 464.436
Monoisotopic: 464.093009286 - Chemical Formula
- C21H16F4N4O2S
- Synonyms
- Enzalutamida
- Enzalutamide
- External IDs
- MDV 3100
- MDV-3100
- MDV3100
Pharmacology
- Indication
Enzalutamide is indicated for the treatment of patients with metastatic castration-resistant prostate cancer who have previously received docetaxel.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Resitance to enzalutamide therapy has been observed. This may occurred due to an upregulation of NF-κB2/p52.
- Mechanism of action
Enzalutamide is a competitive androgen receptor inhibitor that effects multiple stages of the signalling pathway. It is able to inhibit androgen binding to its receptor, androgen receptor nuclear translocation, and subsequent interaction with DNA. As a result, proliferation of prostate cancer cells decreases which ultimately leads to apoptosis and decreased tumour volume.
Target Actions Organism AAndrogen receptor inhibitorHumans - Absorption
The pharmacokinetic profile of enzalutamide and N-desmethyl enzalutamide (its major active metabolite) is described by a linear two-compartment model with first-order absorption. Enzalutamide also accumulates. Food does not affect its absorption. Tmax, prostate cancer patients = 1 hour (range of 0.5-3 hours); Cmax, steady state, enzalutamide = 16.6 μg/mL; Cmax, steady state, N-desmethyl enzalutamide = 12.7 μg/mL; Time to steady state, daily dosing = 28 days;
- Volume of distribution
Apparent volume of distribution (Vd/F), single oral dose = 110 L
- Protein binding
Enzalutamide is 97% to 98% bound to plasma proteins, primarily albumin. N-desmethyl enzalutamide is 95% bound to plasma proteins.
- Metabolism
Enzalutamide is hepatically metabolized, primarily by CYP2C8 and CYP3A4. The enzyme that converts enzalutamide to its active metabolite, N-desmethyl enzalutamide, is CYP2C8. The activity of N-desmethyl-enzalutamide is similar to that of the parent compound.
- Route of elimination
Enzalutamide is primarily eliminated by hepatic metabolism. 71% of the dose is recovered in urine (including only trace amounts of enzalutamide and N-desmethyl enzalutamide), and 14% is recovered in feces (0.4% of dose as unchanged enzalutamide and 1% as N-desmethyl enzalutamide).
- Half-life
The mean terminal half-life (t1/2) for enzalutamide in patients after a single oral dose is 5.8 days (range 2.8 to 10.2 days). Following a single 160 mg oral dose of enzalutamide in healthy volunteers, the mean terminal t1/2 for N-desmethyl enzalutamide is approximately 7.8 to 8.6 days.
- Clearance
Apparent clearance (CL/F), single oral dose = 0.56 L/h (range of 0.33 - 1.02 L/h)
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The most common adverse reactions (≥ 5%) are asthenia/fatigue, back pain, diarrhea, arthralgia, hot flush, peripheral edema, musculoskeletal pain, headache, upper respiratory infection, muscular weakness, dizziness, insomnia, lower respiratory infection, spinal cord compression and cauda equina syndrome, hematuria, paresthesia, anxiety, and hypertension.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Enzalutamide which could result in a higher serum level. Abametapir The serum concentration of Enzalutamide can be increased when it is combined with Abametapir. Abatacept The metabolism of Enzalutamide can be increased when combined with Abatacept. Abiraterone The metabolism of Abiraterone can be increased when combined with Enzalutamide. Acalabrutinib The metabolism of Enzalutamide can be increased when combined with Acalabrutinib. Acarbose Acarbose may decrease the excretion rate of Enzalutamide which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Enzalutamide which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Enzalutamide which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Enzalutamide. Acetaminophen Acetaminophen may decrease the excretion rate of Enzalutamide which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid St. John's Wort. This herb induces the CYP3A4 metabolism of enzalutamide and may reduce its serum concentration.
- Take with or without food.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataXtandi Capsule 40 mg/1 Oral Astellas Pharma US, Inc. 2012-08-31 Not applicable US 
Xtandi Tablet 80 mg/1 Oral Astellas Pharma US, Inc. 2020-08-04 Not applicable US Xtandi Capsule 40 mg Oral Astellas Pharma Europe Bv 2013-06-21 Not applicable EU 
Xtandi Tablet 40 mg/1 Oral Astellas Pharma US, Inc. 2020-08-04 Not applicable US Xtandi Capsule 40 mg Oral Astellas Pharma Inc 2013-06-07 Not applicable Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L02BB04 — Enzalutamide
- Drug Categories
- Androgen Receptor Antagonists
- Androgen Receptor Inhibitor
- Antiandrogens
- Antiandrogens, non-steroidal
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (moderate)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Inducers
- Cytochrome P-450 CYP2C9 Inducers (moderate)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inducers (strong)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strong)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strong)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Endocrine Therapy
- Hormone Antagonists and Related Agents
- Hydantoins
- Imidazoles
- Imidazolidines
- P-glycoprotein inhibitors
- Thyroxine-binding globulin substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylimidazolidines. These are polycyclic compounds containing an imidazoline substituted by a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azolidines
- Sub Class
- Imidazolidines
- Direct Parent
- Phenylimidazolidines
- Alternative Parents
- Trifluoromethylbenzenes / 2-halobenzoic acids and derivatives / Alpha amino acids and derivatives / N-phenylthioureas / Benzamides / Benzoyl derivatives / Benzonitriles / Fluorobenzenes / Aryl fluorides / Imidazolidinones show 11 more
- Substituents
- 2-halobenzoic acid or derivatives / Alkyl fluoride / Alkyl halide / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzamide / Benzenoid show 29 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- benzamides, nitrile, imidazolidinone, monofluorobenzenes, (trifluoromethyl)benzenes, thiocarbonyl compound (CHEBI:68534)
Chemical Identifiers
- UNII
- 93T0T9GKNU
- CAS number
- 915087-33-1
- InChI Key
- WXCXUHSOUPDCQV-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
- IUPAC Name
- 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-methylbenzamide
- SMILES
- CNC(=O)C1=C(F)C=C(C=C1)N1C(=S)N(C(=O)C1(C)C)C1=CC=C(C#N)C(=C1)C(F)(F)F
References
- General References
- Nadiminty N, Tummala R, Liu C, Yang J, Lou W, Evans CP, Gao AC: NF-kappaB2/p52 induces resistance to enzalutamide in prostate cancer: role of androgen receptor and its variants. Mol Cancer Ther. 2013 Aug;12(8):1629-37. doi: 10.1158/1535-7163.MCT-13-0027. Epub 2013 May 22. [PubMed:23699654]
- External Links
- KEGG Drug
- D10218
- PubChem Compound
- 15951529
- PubChem Substance
- 175427141
- ChemSpider
- 13093347
- BindingDB
- 50425732
- 1307298
- ChEBI
- 68534
- ChEMBL
- CHEMBL1082407
- ZINC
- ZINC000034806477
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Enzalutamide
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- FDA label
- Download (393 KB)
- MSDS
- Download (89.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Metastatic Castration Resistant Prostate Cancer 1 4 Active Not Recruiting Treatment Metastatic Hormone Refractory Prostate Cancer 1 4 Active Not Recruiting Treatment Prostate Cancer 1 4 Completed Treatment Metastatic Castration Resistant Prostate Cancer 1 4 Completed Treatment Metastatic Castration-Resistant Prostate Cancer (mCRPC) 1 4 Completed Treatment Prostate Cancer 1 4 Recruiting Supportive Care Castration-Resistant Prostatic Cancer / Hormone-Refractory Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer 1 4 Recruiting Treatment Prostatic Neoplasms, Castration-Resistant 1 4 Terminated Treatment Metastatic Castration Resistant Prostate Cancer 1 3 Active Not Recruiting Treatment Adenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Capsule Oral 40 mg/1 Capsule Oral 40 mg Tablet Oral 40 mg/1 Tablet Oral 80 mg/1 Tablet, film coated Oral 40 MG Tablet, film coated Oral 80 MG Capsule, liquid filled Oral 40 mg Capsule 40 mg Capsule Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS8183274 No 2012-05-22 2026-05-15 US US9126941 No 2015-09-08 2026-05-15 US US7709517 No 2010-05-04 2027-08-13 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Insoluble FDA label - Predicted Properties
Property Value Source Water Solubility 0.00136 mg/mL ALOGPS logP 3.75 ALOGPS logP 4.16 ChemAxon logS -5.5 ALOGPS pKa (Strongest Acidic) 13.05 ChemAxon pKa (Strongest Basic) -1.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 76.44 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 113.48 m3·mol-1 ChemAxon Polarizability 42.71 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9356 Blood Brain Barrier + 0.8514 Caco-2 permeable + 0.5219 P-glycoprotein substrate Non-substrate 0.7609 P-glycoprotein inhibitor I Inhibitor 0.6464 P-glycoprotein inhibitor II Inhibitor 0.5693 Renal organic cation transporter Non-inhibitor 0.899 CYP450 2C9 substrate Non-substrate 0.7447 CYP450 2D6 substrate Non-substrate 0.8061 CYP450 3A4 substrate Substrate 0.5589 CYP450 1A2 substrate Non-inhibitor 0.5613 CYP450 2C9 inhibitor Inhibitor 0.7126 CYP450 2D6 inhibitor Non-inhibitor 0.9148 CYP450 2C19 inhibitor Inhibitor 0.6882 CYP450 3A4 inhibitor Inhibitor 0.6184 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6711 Ames test Non AMES toxic 0.683 Carcinogenicity Non-carcinogens 0.7232 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4319 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9911 hERG inhibition (predictor II) Inhibitor 0.7079
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-014i-0321900000-b1c610c4a717fdea030e
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- Gibbons JA, de Vries M, Krauwinkel W, Ohtsu Y, Noukens J, van der Walt JS, Mol R, Mordenti J, Ouatas T: Pharmacokinetic Drug Interaction Studies with Enzalutamide. Clin Pharmacokinet. 2015 Oct;54(10):1057-69. doi: 10.1007/s40262-015-0283-1. [PubMed:25929560]
- FDA table of interactions [Link]
- Enzalutamide FDA label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
References
- Golshayan AR, Antonarakis ES: Enzalutamide: an evidence-based review of its use in the treatment of prostate cancer. Core Evid. 2013;8:27-35. doi: 10.2147/CE.S34747. Epub 2013 Apr 4. [PubMed:23589709]
- Enzalutamide FDA label [File]
- Xtandi Monograph [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Gibbons JA, de Vries M, Krauwinkel W, Ohtsu Y, Noukens J, van der Walt JS, Mol R, Mordenti J, Ouatas T: Pharmacokinetic Drug Interaction Studies with Enzalutamide. Clin Pharmacokinet. 2015 Oct;54(10):1057-69. doi: 10.1007/s40262-015-0283-1. [PubMed:25929560]
- Ezalutamide FDA label [File]
- 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
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Enzalutamide FDA Review [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Oxygen binding
- 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
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Major thyroid hormone transport protein in serum.
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- CYTOMEL (liothyronine) FDA label [File]
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
Drug created on June 04, 2013 23:12 / Updated on October 21, 2020 01:55
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