Identification

Name
Enzalutamide
Accession Number
DB08899  (DB05094)
Type
Small Molecule
Groups
Approved
Description

Enzalutamide is an androgen receptor inhibitor for the treatment of castration-resistant prostate cancer. FDA approved on August 31, 2012.

Structure
Thumb
Synonyms
Not Available
External IDs
MDV 3100 / MDV-3100 / MDV3100
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
XtandiCapsule40 mgOralAstellas Pharma Inc2013-06-07Not applicableCanada
XtandiCapsule40 mg/1OralAstellas Pharma US, Inc.2012-08-31Not applicableUs
XtandiCapsule40 mgOralAstellas Pharma Europe Bv2013-06-21Not applicableEu
Categories
UNII
93T0T9GKNU
CAS number
915087-33-1
Weight
Average: 464.436
Monoisotopic: 464.093009286
Chemical Formula
C21H16F4N4O2S
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

Pharmacology

Indication

Enzalutamide is indicated for the treatment of patients with metastatic castration-resistant prostate cancer who have previously received docetaxel.

Associated Conditions
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.

TargetActionsOrganism
AAndrogen receptor
inhibitor
Human
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)

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
DrugInteraction
16-BromoepiandrosteroneThe serum concentration of 16-Bromoepiandrosterone can be decreased when it is combined with Enzalutamide.
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be decreased when it is combined with Enzalutamide.
5-androstenedioneThe serum concentration of 5-androstenedione can be decreased when it is combined with Enzalutamide.
AbemaciclibThe serum concentration of Abemaciclib can be decreased when it is combined with Enzalutamide.
AbirateroneThe serum concentration of Abiraterone can be decreased when it is combined with Enzalutamide.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Enzalutamide.
AcenocoumarolThe serum concentration of Acenocoumarol can be decreased when it is combined with Enzalutamide.
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Enzalutamide.
AcetazolamideThe metabolism of Enzalutamide can be decreased when combined with Acetazolamide.
Acetyl sulfisoxazoleThe metabolism of Enzalutamide can be decreased when combined with Acetyl sulfisoxazole.
Food Interactions
Not Available

References

General References
  1. 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
ChEBI
68534
ChEMBL
CHEMBL1082407
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Enzalutamide
ATC Codes
L02BB04 — Enzalutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (393 KB)
MSDS
Download (89.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentClear Cell Renal Cell Carcinoma / Stage I Renal Cell Cancer1
1Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
1Active Not RecruitingTreatmentBladder Cancers / Renal Pelvis Cancer / Transitional Cell Carcinoma / Ureteral Cancer / Urethral Cancer1
1Active Not RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)1
1Active Not RecruitingTreatmentMalignant Neoplasm of Pancreas1
1Active Not RecruitingTreatmentNeoplasms / Solid Cancers1
1Active Not RecruitingTreatmentProstate Cancer2
1Active Not RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
1CompletedNot AvailableDrug-Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics1
1CompletedNot AvailableHealthy Volunteers / Kidney Diseases / Pharmacokinetics of MDV31001
1CompletedBasic ScienceCastration Resistant Prostate Cancer (CRPC) / Healthy Volunteers / MDV3100 / Relative Bioavailability1
1CompletedBasic ScienceDrug-Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics of Enzalutamide1
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of MDV31001
1CompletedBasic ScienceNormal Hepatic Function / Severe Hepatic Impairment1
1CompletedBasic SciencePharmacokinetics of Caffeine / Pharmacokinetics of Dextromethorphan / Prostate Cancer1
1CompletedBasic SciencePharmacokinetics of Enzalutamide / Prostate Cancer1
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentCastration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Adenocarcinoma1
1CompletedTreatmentCastration Resistant Prostate Cancer (CRPC) / Pharmacokinetics of MDV31001
1CompletedTreatmentHormone Refractory Prostate Cancer / Prostate Cancer1
1CompletedTreatmentProstate Cancer1
1Not Yet RecruitingBasic ScienceCerebrovascular Circulation1
1Not Yet RecruitingTreatmentCastration Resistant Prostate Cancer (CRPC) / Hormone Receptor Positive Advanced Breast Cancer / Human Epidermal Receptor 2 Negative Advanced Breast Cancer / Metastatic Breast Cancer (MBC)1
1Not Yet RecruitingTreatmentMalignant Neoplasm of Breast1
1Not Yet RecruitingTreatmentProstate Cancer1
1RecruitingOtherProstate Cancer1
1RecruitingTreatmentAdvanced Solid Tumors / Cancer, Breast / Prostate Cancer1
1RecruitingTreatmentCancers1
1RecruitingTreatmentCastration Resistant Prostate Cancer (CRPC) / Prostate Cancer1
1RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer / Prostatic Neoplasms1
1RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentMetastatic Hormone Refractory Prostate Cancer1
1WithdrawnTreatmentCancers1
1, 2Active Not RecruitingTreatmentEstrogen Receptor Negative / Estrogen Receptor Positive / HER2/Neu Negative / Progesterone Receptor Negative / Progesterone Receptor Positive / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma1
1, 2Active Not RecruitingTreatmentMetastatic Castrate-Resistant Prostate Cancer1
1, 2CompletedTreatmentCastration Resistant Prostate Cancer (CRPC) / Prostate Cancer / Prostate Neoplasms1
1, 2RecruitingTreatmentAdvanced Solid Tumors / Metastatic Castration Resistant Prostate Cancer1
1, 2RecruitingTreatmentCastration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer / Stage IV Prostate Cancer AJCC v71
1, 2RecruitingTreatmentHepatocellular,Carcinoma1
1, 2RecruitingTreatmentHormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Prostate Carcinoma Metastatic in the Bone / Stage IV Prostate Cancer1
1, 2RecruitingTreatmentHormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
1, 2RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer2
1, 2RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer (mCRPC)1
1, 2RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
2Active Not RecruitingOtherMetastatic Castration Resistant Prostate Cancer1
2Active Not RecruitingTreatmentAdenocarcinoma of the Prostate1
2Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
2Active Not RecruitingTreatmentAdenocarcinoma, Prostate / High Risk Prostate Cancer / Prostate Cancer1
2Active Not RecruitingTreatmentAdvanced Breast Cancer / HER2 Amplified / Human Epidermal Growth Factor Receptor 2 (HER2)1
2Active Not RecruitingTreatmentAdvanced Hepatocellular Carcinoma1
2Active Not RecruitingTreatmentAdvanced, Androgen Receptor Positive Triple Negative Breast Cancer1
2Active Not RecruitingTreatmentCancer, Breast1
2Active Not RecruitingTreatmentCastration Resistant Metastatic Prostate Cancer1
2Active Not RecruitingTreatmentCastration Resistant Prostate Cancer (CRPC) / Prostate Carcinoma Metastatic to the Bone1
2Active Not RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)1
2Active Not RecruitingTreatmentCastration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / PSA Progression / Recurrent Prostate Carcinoma / Stage IV Prostate Adenocarcinoma / Stage IV Prostate Adenocarcinoma AJCC v7 / Stage IV Prostate Cancer1
2Active Not RecruitingTreatmentHormone-Refractory Prostate Cancer1
2Active Not RecruitingTreatmentIntermediate Risk Prostate Cancer1
2Active Not RecruitingTreatmentMetastatic Castration-Resistant Prostatic Cancer1
2Active Not RecruitingTreatmentPelvic Nodal / Prostatic Neoplasms1
2Active Not RecruitingTreatmentProstate Cancer12
2Active Not RecruitingTreatmentProstate Carcinoma Metastatic to the Bone1
2CompletedBasic ScienceMetastatic Hormone Refractory Prostate Cancer1
2CompletedTreatmentAndrogen Receptor Abnormal / DNA / Prostate Cancer1
2CompletedTreatmentCastration-Resistant Prostate Cancer (CRPC)1
2CompletedTreatmentCastration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1
2CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
2CompletedTreatmentMetastatic Hormone Refractory Prostate Cancer1
2CompletedTreatmentMetastatic Progressive Castration-resistant Prostate Cancer1
2CompletedTreatmentNon-metastatic, Hormone naïve Prostate Cancer1
2CompletedTreatmentProstate Cancer4
2CompletedTreatmentProstatic Neoplasms2
2Not Yet RecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1
2Not Yet RecruitingTreatmentCastration-Resistant Prostate Carcinoma / Prostate Carcinoma Metastatic in the Bone / Stage IV Prostate Cancer1
2Not Yet RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer / Prostate Neoplasms1
2RecruitingOtherMetastatic Castrate-resistant Prostate (CRPC) Cancer1
2RecruitingSupportive CareAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2RecruitingTreatmentAdenocarcinoma of the Prostate2
2RecruitingTreatmentAdenocarcinoma, Prostate / Prostate Cancer1
2RecruitingTreatmentAdvanced Epithelial Ovarian / Fallopian Tubes / Primary Peritoneal Carcinoma / Recurrent Epithelial Ovarian1
2RecruitingTreatmentBone Metastases / Castration-Resistant Prostate Cancer (CRPC)1
2RecruitingTreatmentBone Metastases / Prostate Cancer1
2RecruitingTreatmentCancer of the Ovary1
2RecruitingTreatmentCancer of the Prostate / Prostate Cancer1
2RecruitingTreatmentCancer, Breast3
2RecruitingTreatmentCancer, Breast / Early Stage / Triple Negative Breast Cancer (TNBC)1
2RecruitingTreatmentEndometrial Cancers1
2RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer / Metastatic Castration-Resistant Prostate Cancer (mCRPC)1
2RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer3
2RecruitingTreatmentPrimary Breast Cancer AR+ve TNBN / Primary Breast Cancer ER+ve1
2RecruitingTreatmentProstate Cancer9
2RecruitingTreatmentProstatic Neoplasms1
2RecruitingTreatmentSalivary Cancer1
2TerminatedPreventionBladder Cancers1
2WithdrawnTreatmentLocalized Prostate Cancer / Prostate Cancer1
2WithdrawnTreatmentMetastatic Castration Resistant Prostate Cancer1
2, 3RecruitingTreatmentCastration-resistant Prostate Cancer Patients With Oligometastases1
2, 3RecruitingTreatmentMetastasis / Metastatic Hormone Refractory Prostate Cancer1
2, 3RecruitingTreatmentProstate Cancer1
3Active Not RecruitingTreatmentAdenocarcinoma of the Prostate / Hormone-Resistant Prostate Cancer / Recurrent Prostate Cancer / Stage IV Prostate Cancer1
3Active Not RecruitingTreatmentCancer of the Prostate / Hormone Sensitive Prostate Cancer / Prostate Cancer1
3Active Not RecruitingTreatmentCancer of the Prostate / Nonmetastatic Castration-Resistant Prostate Cancer / Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
3Active Not RecruitingTreatmentMetastatic Hormone Sensitive Prostate Cancer1
3Active Not RecruitingTreatmentProgressive Metastatic Prostate Cancer1
3Active Not RecruitingTreatmentProstate Cancer1
3Active Not RecruitingTreatmentProstatic Neoplasms2
3CompletedTreatmentCastration-Resistant Prostate Cancer (CRPC)1
3RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
3RecruitingTreatmentProstate Cancer1
3RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
3TerminatedTreatmentProstate Cancer1
3WithdrawnTreatmentCancer, Breast1
4Active Not RecruitingTreatmentMetastatic Castration-Resistant Prostate Cancer (mCRPC)1
4Active Not RecruitingTreatmentProstate Cancer2
4CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
4RecruitingSupportive CareCastration-Resistant Prostatic Cancer / Hormone-Refractory Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
4RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
4RecruitingTreatmentMetastatic Hormone Refractory Prostate Cancer1
4TerminatedTreatmentMetastatic Castration Resistant Prostate Cancer1
Not AvailableActive Not RecruitingNot AvailableAdenocarcinoma, Prostate / Castration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / PSA Progression / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
Not AvailableActive Not RecruitingNot AvailableCastration-Resistant Prostate Cancer (CRPC)1
Not AvailableActive Not RecruitingNot AvailableMetastatic Castration Resistant Prostate Cancer1
Not AvailableActive Not RecruitingNot AvailableProstate Cancer1
Not AvailableActive Not RecruitingNot AvailableProstatic Neoplasms, Castration-Resistant1
Not AvailableActive Not RecruitingTreatmentAdenocarcinoma of the Prostate / Castration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / Metastatic Prostate Carcinoma in the Soft Tissue / Metastatic Prostatic Adenocarcinoma / Prostate Carcinoma Metastatic in the Bone / PSA Progression / Recurrent Prostate Cancer / Recurrent Prostate Carcinoma / Stage III Prostate Adenocarcinoma / Stage IV Prostate Adenocarcinoma / Stage IV Prostate Cancer1
Not AvailableActive Not RecruitingTreatmentProstate Cancer1
Not AvailableApproved for MarketingNot AvailableMetastatic Castration Resistant Prostate Cancer1
Not AvailableCompletedNot AvailableMetastatic Castration Resistant Prostate Cancer1
Not AvailableRecruitingTreatmentAdenocarcinoma, Prostate / Hormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Stage IV Prostate Cancer1
Not AvailableRecruitingTreatmentAnn Arbor Stage I Mantle Cell Lymphoma / Ann Arbor Stage II Mantle Cell Lymphoma / Ann Arbor Stage III Mantle Cell Lymphoma / Ann Arbor Stage IV Mantle Cell Lymphoma / Recurrent Mantle Cell Lymphoma / Refractory Mantle Cell Lymphoma / Stage I Mantle Cell Lymphoma / Stage II Mantle Cell Lymphoma / Stage III Mantle Cell Lymphoma / Stage IV Mantle Cell Lymphoma1
Not AvailableRecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)1
Not AvailableTerminatedTreatmentProstate Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral40 mg
CapsuleOral40 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8183274No2006-05-152026-05-15Us
US9126941No2006-05-152026-05-15Us
US7709517No2007-08-132027-08-13Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityInsoluble FDA label
Predicted Properties
PropertyValueSource
Water Solubility0.00136 mg/mLALOGPS
logP3.75ALOGPS
logP4.16ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)13.05ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.44 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.48 m3·mol-1ChemAxon
Polarizability42.71 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9356
Blood Brain Barrier+0.8514
Caco-2 permeable+0.5219
P-glycoprotein substrateNon-substrate0.7609
P-glycoprotein inhibitor IInhibitor0.6464
P-glycoprotein inhibitor IIInhibitor0.5693
Renal organic cation transporterNon-inhibitor0.899
CYP450 2C9 substrateNon-substrate0.7447
CYP450 2D6 substrateNon-substrate0.8061
CYP450 3A4 substrateSubstrate0.5589
CYP450 1A2 substrateNon-inhibitor0.5613
CYP450 2C9 inhibitorInhibitor0.7126
CYP450 2D6 inhibitorNon-inhibitor0.9148
CYP450 2C19 inhibitorInhibitor0.6882
CYP450 3A4 inhibitorInhibitor0.6184
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6711
Ames testNon AMES toxic0.683
CarcinogenicityNon-carcinogens0.7232
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4319 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Inhibitor0.7079
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0321900000-b1c610c4a717fdea030e

Taxonomy

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
Phenylimidazolidine / Alpha-amino acid or derivatives / Trifluoromethylbenzene / N-phenylthiourea / 2-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzonitrile / Benzoyl
show 29 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
benzamides, nitrile, imidazolidinone, monofluorobenzenes, (trifluoromethyl)benzenes, thiocarbonyl compound (CHEBI:68534)

Targets

Details
1. Androgen receptor
Kind
Protein
Organism
Human
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
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. 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]
  2. Enzalutamide FDA label [File]
  3. Xtandi Monograph [File]
Kind
Protein
Organism
Human
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
  1. 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]
  2. Ezalutamide FDA label [File]
Kind
Protein
Organism
Human
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
  1. Enzalutamide FDA Review [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Benoist GE, Hendriks RJ, Mulders PF, Gerritsen WR, Somford DM, Schalken JA, van Oort IM, Burger DM, van Erp NP: Pharmacokinetic Aspects of the Two Novel Oral Drugs Used for Metastatic Castration-Resistant Prostate Cancer: Abiraterone Acetate and Enzalutamide. Clin Pharmacokinet. 2016 Nov;55(11):1369-1380. doi: 10.1007/s40262-016-0403-6. [PubMed:27106175]
  2. Xtandi [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
  1. Xtandi monograph [File]

Carriers

Kind
Protein
Organism
Human
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

Transporters

Kind
Protein
Organism
Human
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 16, 2018 08:40