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Identification
NameFenoterol
Accession NumberDB01288
TypeSmall Molecule
GroupsApproved
DescriptionAn adrenergic beta-2 agonist that is used as a bronchodilator and tocolytic. [PubChem]
Structure
Thumb
Synonyms
1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane
1-(P-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3',5'-dihydroxyphenyl))ethyl)aminopropane
3,5-Dihydroxy-alpha-(((P-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcohol
5-{1-hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diol
Fenoterolum
Phenoterol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Berotec 1mg/mlsolution1 mginhalationBoehringer Ingelheim (Canada) Ltd Ltee1982-12-312008-12-16Canada
Berotec Aem 100mcg/dosemetered-dose aerosol100 mcginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1992-12-312007-11-02Canada
Berotec Forte Metered Aermetered-dose aerosol0.2 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1977-12-311997-08-14Canada
Berotec Tab 2.5mgtablet2.5 mgoralBoehringer Ingelheim (Canada) Ltd Ltee1979-12-312000-07-31Canada
Berotec Udv Inhalation Solution 0.25mg/mlsolution0.25 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1994-12-312005-02-10Canada
Berotec Udv Inhalation Soluton 0.625mg/mlsolution0.625 mginhalation; oralBoehringer Ingelheim (Canada) Ltd Ltee1994-12-312004-07-16Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AlveofenPrieto
BerotecBoehringer Ingelheim
Berotec NBoehringer Ingelheim
CenfenolCenter
PartusistenBoehringer Ingelheim
Brand mixtures
NameLabellerIngredients
Duovent UdvBoehringer Ingelheim (Canada) Ltd Ltee
Salts
Name/CASStructureProperties
Fenoterol hydrobromide
ThumbNot applicableDBSALT001185
Categories
UNII22M9P70OQ9
CAS number13392-18-2
WeightAverage: 303.3529
Monoisotopic: 303.147058165
Chemical FormulaC17H21NO4
InChI KeyInChIKey=LSLYOANBFKQKPT-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3
IUPAC Name
5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diol
SMILES
CC(CC1=CC=C(O)C=C1)NCC(O)C1=CC(O)=CC(O)=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Resorcinol
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFenoterol is used for the treatment of asthma.
PharmacodynamicsFenoterol is a beta agonist designed to open up the airways to the lungs by decreasing bronchconstriction.
Mechanism of actionBeta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier-0.9294
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7292
P-glycoprotein inhibitor INon-inhibitor0.9064
P-glycoprotein inhibitor IINon-inhibitor0.946
Renal organic cation transporterNon-inhibitor0.7992
CYP450 2C9 substrateNon-substrate0.7004
CYP450 2D6 substrateNon-substrate0.7055
CYP450 3A4 substrateNon-substrate0.625
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.8609
CarcinogenicityNon-carcinogens0.9011
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity2.1550 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.813
hERG inhibition (predictor II)Non-inhibitor0.7963
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutioninhalation1 mg
Metered-dose aerosolinhalation; oral100 mcg
Metered-dose aerosolinhalation; oral0.2 mg
Tabletoral2.5 mg
Solutioninhalation; oral0.25 mg
Solutioninhalation; oral0.625 mg
Solutioninhalation; oral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point222-223Zeile, K., Thoma, O. and Mentrup, A,; U.S. Patent 3,341,593; September 12, 1967; assigned to Boehringer lngelheim GmbH, Germany.
Predicted Properties
PropertyValueSource
Water Solubility0.162 mg/mLALOGPS
logP1.36ALOGPS
logP1.47ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.85ChemAxon
pKa (Strongest Basic)9.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area92.95 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85 m3·mol-1ChemAxon
Polarizability31.75 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Zeile, K., Thoma, O. and Mentrup, A,; U.S. Patent 3,341,593; September 12, 1967; assigned to Boehringer lngelheim GmbH, Germany.

General ReferencesNot Available
External Links
ATC CodesR03AL01R03CC04R03AC04G02CA03
AHFS Codes
  • 12:12.08.12
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINEThe risk or severity of adverse effects can be increased when 7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE is combined with Fenoterol.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Fenoterol.
AlprenololAlprenolol may decrease the bronchodilatory activities of Fenoterol.
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Fenoterol.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Fenoterol.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Fenoterol.
AtenololAtenolol may decrease the bronchodilatory activities of Fenoterol.
AtomoxetineAtomoxetine may increase the hypertensive activities of Fenoterol.
AtosibanThe risk or severity of adverse effects can be increased when Fenoterol is combined with Atosiban.
BendroflumethiazideFenoterol may increase the hypokalemic activities of Bendroflumethiazide.
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Fenoterol.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Fenoterol.
BetahistineThe therapeutic efficacy of Fenoterol can be decreased when used in combination with Betahistine.
BetaxololBetaxolol may decrease the bronchodilatory activities of Fenoterol.
BisoprololBisoprolol may decrease the bronchodilatory activities of Fenoterol.
BopindololBopindolol may decrease the bronchodilatory activities of Fenoterol.
BumetanideFenoterol may increase the hypokalemic activities of Bumetanide.
BupranololBupranolol may decrease the bronchodilatory activities of Fenoterol.
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Fenoterol.
CarteololCarteolol may decrease the bronchodilatory activities of Fenoterol.
CeliprololThe risk or severity of adverse effects can be increased when Fenoterol is combined with Celiprolol.
ChlorothiazideFenoterol may increase the hypokalemic activities of Chlorothiazide.
ChlorphentermineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Chlorphentermine.
ChlorthalidoneFenoterol may increase the hypokalemic activities of Chlorthalidone.
ClenbuterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Clenbuterol.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Fenoterol.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Fenoterol.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Fenoterol.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Fenoterol.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Fenoterol.
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Fenoterol.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Fenoterol.
DoxofyllineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Fenoterol.
EphedrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Fenoterol.
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Fenoterol.
EsmololEsmolol may decrease the bronchodilatory activities of Fenoterol.
Etacrynic acidFenoterol may increase the hypokalemic activities of Etacrynic acid.
EtilefrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Etilefrine.
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Fenoterol.
FurosemideFenoterol may increase the hypokalemic activities of Furosemide.
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Fenoterol.
HydrochlorothiazideFenoterol may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideFenoterol may increase the hypokalemic activities of Hydroflumethiazide.
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Fenoterol is combined with Hydroxyamphetamine hydrobromide.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Fenoterol.
IndapamideFenoterol may increase the hypokalemic activities of Indapamide.
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Fenoterol.
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Fenoterol.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Fenoterol.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Fenoterol.
IsoxsuprineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Isoxsuprine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Fenoterol.
LinezolidLinezolid may increase the hypertensive activities of Fenoterol.
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Fenoterol.
MephentermineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Mephentermine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenoterol.
MethamphetamineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fenoterol.
MethyclothiazideFenoterol may increase the hypokalemic activities of Methyclothiazide.
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Fenoterol.
MetolazoneFenoterol may increase the hypokalemic activities of Metolazone.
MetoprololMetoprolol may decrease the bronchodilatory activities of Fenoterol.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Fenoterol.
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Fenoterol.
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Fenoterol.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Fenoterol.
NabiloneNabilone may increase the tachycardic activities of Fenoterol.
NadololNadolol may decrease the bronchodilatory activities of Fenoterol.
NebivololNebivolol may decrease the bronchodilatory activities of Fenoterol.
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Fenoterol.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Fenoterol.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Fenoterol.
NylidrinThe risk or severity of adverse effects can be increased when Fenoterol is combined with Nylidrin.
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Fenoterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Fenoterol.
OxprenololOxprenolol may decrease the bronchodilatory activities of Fenoterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Fenoterol.
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Fenoterol.
PenbutololPenbutolol may decrease the bronchodilatory activities of Fenoterol.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Fenoterol.
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Fenoterol.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Fenoterol.
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Fenoterol.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Fenoterol.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Fenoterol.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Fenoterol.
PindololPindolol may decrease the bronchodilatory activities of Fenoterol.
PiretanideFenoterol may increase the hypokalemic activities of Piretanide.
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Fenoterol.
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Fenoterol.
PolythiazideFenoterol may increase the hypokalemic activities of Polythiazide.
ProcaterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Procaterol.
PropranololPropranolol may decrease the bronchodilatory activities of Fenoterol.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Fenoterol.
PseudoephedrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pseudoephedrine.
QuinethazoneFenoterol may increase the hypokalemic activities of Quinethazone.
RacepinephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Racepinephrine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Fenoterol.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Fenoterol.
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Fenoterol.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Fenoterol.
SotalolSotalol may decrease the bronchodilatory activities of Fenoterol.
SynephrineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Synephrine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Fenoterol.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Fenoterol.
TetryzolineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Tetryzoline.
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Fenoterol.
TimololTimolol may decrease the bronchodilatory activities of Fenoterol.
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Fenoterol.
TorasemideFenoterol may increase the hypokalemic activities of Torasemide.
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Fenoterol.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Fenoterol.
TrichlormethiazideFenoterol may increase the hypokalemic activities of Trichlormethiazide.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Fenoterol.
TyramineThe risk or severity of adverse effects can be increased when Fenoterol is combined with Tyramine.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. de Vries B, Roffel AF, Zaagsma J, Meurs H: Effect of fenoterol-induced constitutive beta(2)-adrenoceptor activity on contractile receptor function in airway smooth muscle. Eur J Pharmacol. 2001 Nov 23;431(3):353-9. [PubMed:11730729 ]
  2. Boterman M, Smits SR, Meurs H, Zaagsma J: Protein kinase C potentiates homologous desensitization of the beta2-adrenoceptor in bovine tracheal smooth muscle. Eur J Pharmacol. 2006 Jan 4;529(1-3):151-6. Epub 2005 Dec 1. [PubMed:16324695 ]
  3. Marone G, Ambrosio G, Bonaduce D, Genovese A, Triggiani M, Condorelli M: Inhibition of IgE-mediated histamine release from human basophils and mast cells by fenoterol. Int Arch Allergy Appl Immunol. 1984;74(4):356-61. [PubMed:6203844 ]
  4. Coqueret O, Demarquay D, Lagente V: Role of cyclic AMP in the modulation of IgE production by the beta 2-adrenoceptor agonist, fenoterol. Eur Respir J. 1996 Feb;9(2):220-5. [PubMed:8777955 ]
  5. Bouillon T, Meineke I, Port R, Hildebrandt R, Gunther K, Gundert-Remy U: Concentration-effect relationship of the positive chronotropic and hypokalaemic effects of fenoterol in healthy women of childbearing age. Eur J Clin Pharmacol. 1996;51(2):153-60. [PubMed:8911881 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [PubMed:14730417 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular Weight:
43518.615 Da
References
  1. Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [PubMed:14730417 ]
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Drug created on June 28, 2007 09:56 / Updated on August 17, 2016 12:23