Identification

Name
Nilutamide
Accession Number
DB00665  (APRD00150)
Type
Small Molecule
Groups
Approved
Description

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.

Structure
Thumb
Synonyms
  • 5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin
  • Nilutamida
  • Nilutamide
  • Nilutamidum
External IDs
RU 23908 / RU-23908
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnandronTablet50 mgOralSanofi Aventis1997-08-20Not applicableCanada
Anandron - Tab 100mgTablet100 mgOralAventis Pharma Ltd.1997-08-202003-07-22Canada
Anandron Tab 100mgTablet100 mgOralRoussel Canada Inc.1992-12-311996-09-09Canada
Anandron Tab 100mgTablet100 mgOralHoechst Roussel Canada Inc.1992-12-311999-08-11Canada
Anandron Tab 50mgTablet50 mgOralRoussel Canada Inc.1992-12-311996-09-09Canada
Anandron Tab 50mgTablet50 mgOralHoechst Roussel Canada Inc.1994-12-311999-08-11Canada
NilandronTablet150 mg/1OralSanofi Aventis1996-09-19Not applicableUs
NilandronTablet150 mg/1OralConcordia Pharmaceuticals, Inc2013-07-15Not applicableUs
NilandronTablet150 mg/1OralCovis Pharmaceuticals, Inc.2013-07-152017-08-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NilutamideTablet150 mg/1OralANI Pharmaceuticals, Inc.2016-07-18Not applicableUs
International/Other Brands
Nilandron
Categories
UNII
51G6I8B902
CAS number
63612-50-0
Weight
Average: 317.2207
Monoisotopic: 317.062340438
Chemical Formula
C12H10F3N3O4
InChI Key
XWXYUMMDTVBTOU-UHFFFAOYSA-N
InChI
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
IUPAC Name
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
SMILES
CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

Pharmacology

Indication

For use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).

Structured Indications
Pharmacodynamics

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide.

Mechanism of action

Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis.

TargetActionsOrganism
AAndrogen receptor
antagonist
Human
Absorption

Rapidly and completely absorbed, yielding high and persistent plasma concentrations.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days.

Route of elimination

Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days.

Half life

38.0-59.1 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Nilutamide can be decreased when combined with Abiraterone.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Nilutamide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Nilutamide.Experimental
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Nilutamide.Approved
ArmodafinilThe metabolism of Nilutamide can be decreased when combined with Armodafinil.Approved, Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Nilutamide.Approved, Investigational
BortezomibThe metabolism of Nilutamide can be decreased when combined with Bortezomib.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Nilutamide.Approved
Capromab pendetideNilutamide may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CarbamazepineThe metabolism of Nilutamide can be increased when combined with Carbamazepine.Approved, Investigational
ChloramphenicolThe metabolism of Nilutamide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Nilutamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Nilutamide.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Nilutamide.Approved
CimetidineThe metabolism of Nilutamide can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Nilutamide can be decreased when combined with Citalopram.Approved
ClotrimazoleThe metabolism of Nilutamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Nilutamide.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Nilutamide.Experimental
DabrafenibThe serum concentration of Nilutamide can be decreased when it is combined with Dabrafenib.Approved
DelavirdineThe metabolism of Nilutamide can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Nilutamide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Nilutamide.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Nilutamide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Nilutamide.Approved, Investigational
EfavirenzThe metabolism of Nilutamide can be decreased when combined with Efavirenz.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Nilutamide can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Nilutamide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Nilutamide can be decreased when combined with Etravirine.Approved
FluconazoleThe metabolism of Nilutamide can be decreased when combined with Fluconazole.Approved
FluoxetineThe metabolism of Nilutamide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Nilutamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Nilutamide can be increased when combined with Fosphenytoin.Approved
GemfibrozilThe metabolism of Nilutamide can be decreased when combined with Gemfibrozil.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Nilutamide.Experimental
IndinavirThe metabolism of Nilutamide can be decreased when combined with Indinavir.Approved
IsoniazidThe metabolism of Nilutamide can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Nilutamide can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Nilutamide.Experimental
LobeglitazoneThe metabolism of Nilutamide can be decreased when combined with Lobeglitazone.Approved
LopinavirThe metabolism of Nilutamide can be increased when combined with Lopinavir.Approved
LuliconazoleThe serum concentration of Nilutamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Nilutamide can be decreased when it is combined with Lumacaftor.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Nilutamide.Experimental
MoclobemideThe metabolism of Nilutamide can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Nilutamide can be decreased when combined with Modafinil.Approved, Investigational
NelfinavirThe metabolism of Nilutamide can be decreased when combined with Nelfinavir.Approved
NicardipineThe metabolism of Nilutamide can be decreased when combined with Nicardipine.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Nilutamide.Experimental
OmeprazoleThe metabolism of Nilutamide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Nilutamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Nilutamide.Approved, Vet Approved
PantoprazoleThe metabolism of Nilutamide can be decreased when combined with Pantoprazole.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Nilutamide.Experimental
PhenytoinThe metabolism of Nilutamide can be increased when combined with Phenytoin.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Nilutamide.Experimental
RifampicinThe metabolism of Nilutamide can be increased when combined with Rifampicin.Approved
SertralineThe metabolism of Nilutamide can be decreased when combined with Sertraline.Approved
StiripentolThe metabolism of Nilutamide can be decreased when combined with Stiripentol.Approved
TiclopidineThe metabolism of Nilutamide can be decreased when combined with Ticlopidine.Approved
TopiramateThe metabolism of Nilutamide can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Nilutamide can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Nilutamide.Approved, Investigational
VoriconazoleThe metabolism of Nilutamide can be decreased when combined with Voriconazole.Approved, Investigational
ZucapsaicinThe metabolism of Nilutamide can be decreased when combined with Zucapsaicin.Approved
Food Interactions
  • Avoid alcohol.
  • Take before breakfast.

References

General References
  1. Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. [PubMed:12686822]
  2. Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. [PubMed:17576447]
External Links
Human Metabolome Database
HMDB14803
KEGG Drug
D00965
KEGG Compound
C08164
PubChem Compound
4493
PubChem Substance
46505381
ChemSpider
4337
BindingDB
50135912
ChEBI
7573
ChEMBL
CHEMBL1274
Therapeutic Targets Database
DAP000302
PharmGKB
PA450632
IUPHAR
2864
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nilutamide
ATC Codes
L02BB02 — Nilutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer1
2CompletedTreatmentProstate Cancer2
2TerminatedTreatmentProstate Cancer1
2, 3RecruitingTreatmentStage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma1
3CompletedTreatmentProstate Cancer3
3Unknown StatusTreatmentProstate Cancer1

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
Packagers
Dosage forms
FormRouteStrength
TabletOral50 mg
TabletOral100 mg
TabletOral150 mg/1
Prices
Unit descriptionCostUnit
Nilandron 150 mg tablet18.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00419 mg/mLALOGPS
logP1.74ALOGPS
logP2.25ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area95.23 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.23 m3·mol-1ChemAxon
Polarizability25.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8491
Caco-2 permeable-0.5254
P-glycoprotein substrateNon-substrate0.637
P-glycoprotein inhibitor INon-inhibitor0.8572
P-glycoprotein inhibitor IINon-inhibitor0.9314
Renal organic cation transporterNon-inhibitor0.9567
CYP450 2C9 substrateNon-substrate0.7776
CYP450 2D6 substrateNon-substrate0.8934
CYP450 3A4 substrateNon-substrate0.527
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8293
Ames testAMES toxic0.6671
CarcinogenicityNon-carcinogens0.6032
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity3.0768 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9684
hERG inhibition (predictor II)Non-inhibitor0.8734
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azolidines
Sub Class
Imidazolidines
Direct Parent
Phenylhydantoins
Alternative Parents
Phenylimidazolidines / Trifluoromethylbenzenes / Alpha amino acids and derivatives / Nitrobenzenes / Nitroaromatic compounds / N-acyl ureas / Dicarboximides / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organic oxoazanium compounds
show 8 more
Substituents
3-phenylhydantoin / Phenylimidazolidine / Alpha-amino acid or derivatives / Trifluoromethylbenzene / Nitrobenzene / Nitroaromatic compound / N-acyl urea / Ureide / Monocyclic benzene moiety / Benzenoid
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
C-nitro compound, imidazolidinone, (trifluoromethyl)benzenes (CHEBI:7573)

Targets

Details
1. Androgen receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
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
  1. Raynaud JP: Antiandrogens in combination with LH-RH agonists in prostate cancer. Am J Clin Oncol. 1988;11 Suppl 2:S132-47. [PubMed:3071951]
  2. Moguilewsky M, Bertagna C, Hucher M: Pharmacological and clinical studies of the antiandrogen Anandron. J Steroid Biochem. 1987;27(4-6):871-5. [PubMed:3320565]
  3. Raynaud JP, Bonne C, Moguilewsky M, Lefebvre FA, Belanger A, Labrie F: The pure antiandrogen RU 23908 (Anandron), a candidate of choice for the combined antihormonal treatment of prostatic cancer: a review. Prostate. 1984;5(3):299-311. [PubMed:6374639]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  5. Labrie F: Hormonal therapy of prostate cancer. Prog Brain Res. 2010;182:321-41. doi: 10.1016/S0079-6123(10)82014-X. [PubMed:20541672]
  6. Schasfoort EM, Van De Beek C, Newling DW: Safety and efficacy of a non-steroidal anti-androgen, based on results of a post marketing surveillance of nilutamide. Prostate Cancer Prostatic Dis. 2001;4(2):112-117. [PubMed:12497048]
  7. Kaisary AV, Iversen P, Tyrrell CJ, Carroll K, Morris T: Is there a role for antiandrogen monotherapy in patients with metastatic prostate cancer? Prostate Cancer Prostatic Dis. 2001;4(4):196-203. [PubMed:12497018]
  8. Kolvenbag GJ, Furr BJ, Blackledge GR: Receptor affinity and potency of non-steroidal antiandrogens: translation of preclinical findings into clinical activity. Prostate Cancer Prostatic Dis. 1998 Dec;1(6):307-314. [PubMed:12496872]
  9. Brawer MK, Crawford ED, Labrie F, Mendoza-Valdes A, Miller PD, Petrylak DP: Androgen deprivation and other treatments for advanced prostate cancer. Rev Urol. 2001;3 Suppl 2:S59-68. [PubMed:16986000]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Berger V, Berson A, Wolf C, Chachaty C, Fau D, Fromenty B, Pessayre D: Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol. 1992 Feb 4;43(3):654-7. [PubMed:1311586]
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 09:34