Enzalutamide
Identification
- Summary
Enzalutamide is a second-generation androgen receptor inhibitor used to treat castration-resistant prostate cancer and metastatic castration-sensitive prostate cancer.
- Brand Names
- Xtandi
- Generic Name
- Enzalutamide
- DrugBank Accession Number
- DB08899
- Background
Enzalutamide is an androgen receptor (AR) inhibitor for the treatment of castration-resistant prostate cancer (CRPC), both metastatic and non-metastatic.8 It is a second-generation antiandrogen agent that the FDA approved on August 31, 2012.8,7 Although androgen deprivation therapy (ADT) is the first-line treatment of prostate cancer and remission can be achieved, arising resistance is inevitable, becoming castration-resistant prostate cancer.7 Until recently, docetaxel is the only treatment available for metastatic CRPC; however, AR inhibitors have been developed for more targeted therapy, although first-generation AR inhibitors like bicalutamide did not substantially increase the survival rate.7 Second-generation such as enzalutamide is more efficacious due to a higher affinity to AR and no partial agonist activity compared to bicalutamide.7,1
Due to a favorable pharmacological profile, a phase 1 study of enzalutamide was initiated in July 2007. Compared to the average time of 10 to 15 years for a drug to go from pre-clinical to clinical studies, enzalutamide was developed relatively rapidly.7
- Type
- Small Molecule
- Groups
- Approved
- Structure
- 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 castration-resistant prostate cancer, metastatic castration-sensitive prostate cancer (mCSPC), and non-metastatic castration-sensitive prostate cancer (nmCSPC) with biochemical recurrence at high risk for metastasis (high-risk BCR).13 It is also used in combination with talazoparib for the treatment of adult patients with HRR gene-mutated mCRPC.12
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 Castration resistant prostate cancer •••••••••••• •••••••• •••••• Treatment of Metastatic castration sensitive prostate cancer •••••••••••• •••••••• ••••••••• ••••••••• ••••••• Treatment of Metastatic castration sensitive prostate cancer •••••••••••• •••••••••••• ••••• •••••••• ••••••• •••••••• ••••••••••• ••••••• ••••••• ••••••• Used in combination to treat Metastatic castration-resistant prostate cancer (mcrpc) Regimen in combination with: Talazoparib (DB11760) •••••••••••• ••••• ••• •••• •••••••• Treatment of Metastatic castration-sensitive prostate cancer •••••••••••• •••••••• •••••• - 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
Enzalutamide is a second-generation antiandrogen that blocks the activity of androgen and androgen receptor (AR) in prostate cancer. AR activity and prostate cancer progression are closely related due to the normal physiology of prostate cells, providing the rationale for androgen deprivation therapy (ADT).4 However, resistance will eventually arise after the commencement of ADT in 2-3 years due to the accumulation of mutations, including constitutively active mutation, AR overexpression, and changes in AR splicing variants.5,1 Enzalutamide was therefore designed to exploit these mutations.3 In vitro experiments in human prostate cancer cell line VCaP showed that enzalutamide can suppress cell growth and induce apoptosis while other antiandrogens like bicalutamide did not.3
Clinical trials on prostate cancer patients indicated that enzalutamide can lead to a decrease in serum PSA for at least 12 weeks, although this response can be short-lived and thus resulting in enzalutamide resistance.6,3 Patients receiving enzalutamide also had a 37% decreased in the risk of death compared to placebo.2
- Mechanism of action
Enzalutamide is a competitive androgen receptor (AR) inhibitor that has a threefold inhibition on the androgen signaling pathway without significant AR agonist activity.9,1 It inhibits androgen binding to its receptor, androgen receptor nuclear translocation, and subsequent interaction with chromosomal DNA to upregulate oncogenes.1,2 Enzalutamide binds to the AR with 5 to 8-fold greater affinity than first-generation antiandrogens such as bicalutamide and only 2-3 fold reduced affinity than the natural ligand dihydrotestosterone.3 Molecular docking showed that enzalutamide binds to the ligand binding domain of the AR distinctive from that of bicalutamide.1
Target Actions Organism AAndrogen receptor inhibitorHumans - Absorption
The median Tmax is 1 hour (0.5 to 3 hours) following a single 160 mg dose of capsules and 2 hours (0.5 to 6 hours) following a single 160 mg dose of tablets.9 Enzalutamide achieves steady-state by Day 28 and its AUC accumulates approximately 8.3-fold relative to a single dose. At steady-state, the mean (%CV) maximum concentration (Cmax) for enzalutamide and N-desmethyl enzalutamide is 16.6 µg/mL (23%) and 12.7 µg/mL (30%), respectively, and the mean (%CV) minimum concentrations (Cmin) are 11.4 µg/mL (26%) and 13.0 µg/mL (30%), respectively.9
- Volume of distribution
The mean (%CV) volume of distribution after a single oral dose is 110 L (29%).9
- Protein binding
Enzalutamide is 97% to 98% bound to plasma proteins, primarily albumin. N-desmethyl enzalutamide is 95% bound to plasma proteins.9
- Metabolism
Enzalutamide is metabolized by CYP2C8 and CYP3A4. CYP2C8 is primarily responsible for the formation of the active metabolite (N-desmethyl enzalutamide). Carboxylesterase 1 metabolizes N-desmethyl enzalutamide and enzalutamide to the inactive carboxylic acid metabolite.9
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- 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 the dose as unchanged enzalutamide and 1% as N-desmethyl enzalutamide).11
- 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.9
- Clearance
The mean apparent clearance (CL/F) of enzalutamide after a single dose is 0.56 L/h (0.33 to 1.02 L/h).9
- 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
In an embryo-fetal developmental toxicity study in mice, enzalutamide caused developmental toxicity when administered at oral doses of 10 or 30 mg/kg/day throughout the period of organogenesis (gestational days 6-15). Findings included embryo-fetal lethality (increased post-implantation loss and resorptions) and decreased anogenital distance at ≥ 10 mg/kg/day, and cleft palate and absent palatine bone at 30 mg/kg/day. Doses of 30 mg/kg/day caused maternal toxicity. The doses tested in mice (1, 10, and 30 mg/kg/day) resulted in systemic exposures (AUC) of approximately 0.04, 0.4, and 1.1 times, respectively, the exposures in patients. Enzalutamide did not cause developmental toxicity in rabbits when administered throughout the period of organogenesis (gestational days 6-18) at dose levels up to 10 mg/kg/day (approximately 0.4 times the exposures in patients based on AUC).9
In a pharmacokinetic study in pregnant rats with a single oral 30 mg/kg enzalutamide administration on gestation day 14, enzalutamide and/or its metabolites were present in the fetus at a Cmax that was approximately 0.3 times the concentration found in maternal plasma and occurred 4 hours after administration.9
Based on animal studies, XTANDI may impair fertility in males of reproductive potential. Advise male patients with female partners of reproductive potential to use effective contraception during treatment and for 3 months after the last dose of XTANDI.9
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.9
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 serum concentration of 1,2-Benzodiazepine can be decreased when it is combined with Enzalutamide. Abacavir 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. Abemaciclib The serum concentration of Abemaciclib can be decreased when it is combined with Enzalutamide. - 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
- 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.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Xtandi Tablet 40 mg/1 Oral Astellas Pharma US, Inc. 2020-08-04 Not applicable US Xtandi Tablet 40 mg/1 Oral Astellas Pharma US, Inc. 2020-08-04 Not applicable US Xtandi Tablet, film coated 40 mg Oral Astellas Pharma Europe Bv 2020-12-16 Not applicable EU Xtandi Capsule 40 mg/1 Oral Astellas Pharma US, Inc. 2012-08-31 Not applicable US Xtandi Capsule 40 mg/1 Oral Astellas Pharma US, Inc. 2012-08-31 Not applicable US
Categories
- ATC Codes
- L02BB04 — Enzalutamide
- Drug Categories
- Amides
- Androgen Receptor Antagonists
- Androgen Receptor Inhibitors
- Antiandrogens
- Antiandrogens, non-steroidal
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Benzene Derivatives
- 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)
- Affected organisms
- Humans and other mammals
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
- Schalken J, Fitzpatrick JM: Enzalutamide: targeting the androgen signalling pathway in metastatic castration-resistant prostate cancer. BJU Int. 2016 Feb;117(2):215-25. doi: 10.1111/bju.13123. Epub 2015 Jun 6. [Article]
- Saad F: Evidence for the efficacy of enzalutamide in postchemotherapy metastatic castrate-resistant prostate cancer. Ther Adv Urol. 2013 Aug;5(4):201-10. doi: 10.1177/1756287213490054. [Article]
- Tran C, Ouk S, Clegg NJ, Chen Y, Watson PA, Arora V, Wongvipat J, Smith-Jones PM, Yoo D, Kwon A, Wasielewska T, Welsbie D, Chen CD, Higano CS, Beer TM, Hung DT, Scher HI, Jung ME, Sawyers CL: Development of a second-generation antiandrogen for treatment of advanced prostate cancer. Science. 2009 May 8;324(5928):787-90. doi: 10.1126/science.1168175. Epub 2009 Apr 9. [Article]
- Heinlein CA, Chang C: Androgen receptor in prostate cancer. Endocr Rev. 2004 Apr;25(2):276-308. doi: 10.1210/er.2002-0032. [Article]
- Fujita K, Nonomura N: Role of Androgen Receptor in Prostate Cancer: A Review. World J Mens Health. 2019 Sep;37(3):288-295. doi: 10.5534/wjmh.180040. Epub 2018 Sep 10. [Article]
- Tan MH, Li J, Xu HE, Melcher K, Yong EL: Androgen receptor: structure, role in prostate cancer and drug discovery. Acta Pharmacol Sin. 2015 Jan;36(1):3-23. doi: 10.1038/aps.2014.18. Epub 2014 Jun 9. [Article]
- Menon MP, Higano CS: Enzalutamide, a second generation androgen receptor antagonist: development and clinical applications in prostate cancer. Curr Oncol Rep. 2013 Apr;15(2):69-75. doi: 10.1007/s11912-013-0293-9. [Article]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (January 2022) [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
- Health Canada Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use 2022 [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (August 2012) [Link]
- FDA Approved Drug Products: TALZENNA (talazoparib) capsules, for oral use (June 2023) [Link]
- FDA Approved Drug Products: XTANDI® (enzalutamide) capsules/tablet, for oral use (November 2023) [Link]
- External Links
- Human Metabolome Database
- HMDB0251831
- 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
- FDA label
- Download (393 KB)
- MSDS
- Download (89.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Castration Resistant Prostatic Neoplasms 1 4 Active Not Recruiting Treatment Metastatic Castration-Resistant Prostate Cancer (mCRPC) 2 4 Completed Treatment Metastatic Castration-Resistant Prostate Cancer (mCRPC) 2 4 Completed Treatment Metastatic Prostate Cancer 1 4 Completed Treatment Prostate Cancer 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, liquid filled Oral 53.55 mg Capsule Oral Capsule Oral 40 mg/1 Capsule Oral 40.000 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 Oral 40 mg Tablet, coated Oral 80 mg Capsule, liquid filled Oral 40.0 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8183274 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 US11839689 No 2013-09-11 2033-09-11 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 201 ºC L43242 water solubility Insoluble FDA label logP 3.0 L43242 - 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) -1.6 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 42.69 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 200.69005 predictedDeepCCS 1.0 (2019) [M+H]+ 203.0856 predictedDeepCCS 1.0 (2019) [M+Na]+ 208.99814 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
References
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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. [Article]
- Poondru S, Ghicavii V, Khosravan R, Manchandani P, Heo N, Moy S, Wojtkowski T, Patton M, Haas GP: Effect of enzalutamide on PK of P-gp and BCRP substrates in cancer patients: CYP450 induction may not always predict overall effect on transporters. Clin Transl Sci. 2022 May;15(5):1131-1142. doi: 10.1111/cts.13229. Epub 2022 Feb 4. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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. [Article]
- FDA table of interactions [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (August 2012) [Link]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
- Enzalutamide FDA label [File]
- Xtandi Monograph [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
- Ezalutamide FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Hutson PR: Enzalutamide: A Step Towards Pharmacokinetic-Based Dosing in Men with Metastatic Castration-Resistant Prostate Cancer. Clin Pharmacokinet. 2015 Oct;54(10):989-91. doi: 10.1007/s40262-015-0293-z. [Article]
- Poondru S, Ghicavii V, Khosravan R, Manchandani P, Heo N, Moy S, Wojtkowski T, Patton M, Haas GP: Effect of enzalutamide on PK of P-gp and BCRP substrates in cancer patients: CYP450 induction may not always predict overall effect on transporters. Clin Transl Sci. 2022 May;15(5):1131-1142. doi: 10.1111/cts.13229. Epub 2022 Feb 4. [Article]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
- Enzalutamide FDA Review [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- No
- Actions
- Binder
- 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
References
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Poondru S, Ghicavii V, Khosravan R, Manchandani P, Heo N, Moy S, Wojtkowski T, Patton M, Haas GP: Effect of enzalutamide on PK of P-gp and BCRP substrates in cancer patients: CYP450 induction may not always predict overall effect on transporters. Clin Transl Sci. 2022 May;15(5):1131-1142. doi: 10.1111/cts.13229. Epub 2022 Feb 4. [Article]
- FDA Approved Drug Products: Xtandi (enzalutamide) capsules/tablets for oral use (September 2022) [Link]
Drug created at June 05, 2013 05:12 / Updated at February 20, 2024 23:54