Fosinopril

Identification

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Name

Fosinopril

Accession Number

DB00492  (APRD00526)

Type

Small Molecule

Groups

Approved

Description

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Fosinopril (DB00492)

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Synonyms

• Fosenopril
• Fosinopril

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Fosinopril sodium	NW2RTH6T2N	88889-14-9	TVTJZMHAIQQZTL-UHFFFAOYSA-M

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Fosinoprilat	prodrug	S312EY6ZT8	95399-71-6	WOIWWYDXDVSWAZ-RTWAWAEBSA-N

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Fosinopril	Tablet	20 mg	Oral	Sanis Health Inc	2017-04-11	Not applicable
Fosinopril	Tablet	10 mg	Oral	Sanis Health Inc	2017-04-11	Not applicable
Fosinopril Tablets	Tablet	10 mg	Oral	Ranbaxy Inc.	Not applicable	Not applicable
Fosinopril Tablets	Tablet	20 mg	Oral	Ranbaxy Inc.	Not applicable	Not applicable
Fosinopril-10	Tablet	10 mg	Oral	Pro Doc Limitee	2008-10-23	Not applicable
Fosinopril-20	Tablet	20 mg	Oral	Pro Doc Limitee	2008-10-23	Not applicable
Monopril	Tablet	20 mg/1	Oral	Bristol Myers Squibb	2008-12-15	2010-06-30
Monopril	Tablet	10 mg/1	Oral	Bristol Myers Squibb	2008-12-15	2010-09-30
Monopril	Tablet	20 mg/1	Oral	Physicians Total Care, Inc.	2008-12-15	2011-05-31
Monopril	Tablet	10 mg/1	Oral	Physicians Total Care, Inc.	2008-12-15	2011-05-31

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Apo-fosinopril	Tablet	20 mg	Oral	Apotex Corporation	2005-04-27	Not applicable
Apo-fosinopril	Tablet	10 mg	Oral	Apotex Corporation	2005-04-27	Not applicable
Ava-fosinopril	Tablet	20 mg	Oral	Avanstra Inc	2011-11-28	2014-08-21
Ava-fosinopril	Tablet	10 mg	Oral	Avanstra Inc	2011-11-28	2014-08-21
FOSINOPRIL Na	Tablet	20 mg/1	Oral	Apotex Corporation	2005-05-18	2016-05-31
FOSINOPRIL Na	Tablet	10 mg/1	Oral	Apotex Corporation	2005-05-18	2016-05-31
FOSINOPRIL Na	Tablet	40 mg/1	Oral	Apotex Corporation	2005-05-18	2016-05-31
Fosinopril Sodium	Tablet	20 mg/1	Oral	Aphena Pharma Solutions Tennessee, Inc.	2004-04-23	Not applicable
Fosinopril Sodium	Tablet	40 mg/1	Oral	A-S Medication Solutions	2007-09-17	Not applicable
Fosinopril Sodium	Tablet	40 mg/1	Oral	St. Marys Medical Park Pharmacy	2014-05-22	2016-08-31

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Application Number
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Product Code
Product Code
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Ranbaxy Inc.	2004-12-20	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Rising Health, Llc	2009-07-09	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	bryant ranch prepack	2009-07-09	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Heritage	2011-11-15	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Ranbaxy Inc.	2004-12-20	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	2005-11-15	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Aurobindo Pharma Limited	2009-07-09	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Eon Labs, Inc.	2005-09-28	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (10 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Heritage	2011-11-15	Not applicable
Fosinopril Sodium and Hydrochlorothiazide	Fosinopril sodium (20 mg/1) + Hydrochlorothiazide (12.5 mg/1)	Tablet	Oral	Teva	2011-03-02	2011-03-02

International/Other Brands

Acecor (SPA (Czech Republic)) / Staril (BMS (United Kingdom))

Categories

• ACE Inhibitors and Diuretics
• Acids
• Acids, Acyclic
• Acids, Noncarboxylic
• Agents Acting on the Renin-Angiotensin System
• Agents causing angioedema
• Agents causing hyperkalemia
• Amino Acids
• Amino Acids, Cyclic
• Amino Acids, Peptides, and Proteins
• Angiotensin-Converting Enzyme Inhibitors
• Antihypertensive Agents
• Cardiovascular Agents
• Drugs that are Mainly Renally Excreted
• Enzyme Inhibitors
• Hypotensive Agents
• Imines
• Imino Acids
• Organophosphorus Compounds
• Phosphinic Acids
• Phosphorus Acids
• Phosphorus Compounds
• Proline
• Protease Inhibitors

UNII

R43D2573WO

CAS number

98048-97-6

Weight

Average: 563.672
Monoisotopic: 563.301189823

Chemical Formula

C₃₀H₄₆NO₇P

InChI Key

BIDNLKIUORFRQP-XYGFDPSESA-N

InChI

InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39-/m1/s1

IUPAC Name

(2S,4S)-4-cyclohexyl-1-{2-[(R)-[(1S)-2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic acid

SMILES

CCC(=O)O[C@@H](O[P@](=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C

Pharmacology

Indication

For treating mild to moderate hypertension, use as an adjunct in treating congestive heart failure, and may be used to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Associated Conditions

• Diabetic Nephropathies
• Heart Failure
• High Blood Pressure (Hypertension)

Pharmacodynamics

Following oral administration, fosinopril is rapidly and completely hydrolyzed to its principle active metabolite, fosinoprilat. Hydrolysis is thought to occur in the gastrointestinal mucosa and liver. Fosinoprilat is a competitive inhibitor of ACE, a peptidyl dipeptidase that is part of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may further sustain the effects of fosinoprilat by causing increased vasodilation and decreased blood pressure.

Mechanism of action

There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Fosinoprilat, the active metabolite of fosinopril, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Fosinoprilat also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors.

Target	Actions	Organism
AAngiotensin-converting enzyme	inhibitor	Humans

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Contraindications

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Absorption

Average absolute absorption is 36%. The primary site of absorption is the proximal small intestine (duodenum/jejunum). Food slows the rate of absorption with no effect on the extent of absorption.

Volume of distribution

Not Available

Protein binding

Fosinoprilat is ≥95% protein bound

Metabolism

Since fosinoprilat is not biotransformed after intravenous administration, fosinopril, not fosinoprilat, appears to be the precursor for the glucuronide and p-hydroxy metabolites.

• Fosinopril
  Fosinoprilat

Route of elimination

After oral administration of radiolabeled fosinopril, approximately half of the absorbed dose is excreted in the urine and the remainder is excreted in the feces.

Half life

12 hours

Clearance

• 26 - 39 mL/min [healthy]

Toxicity

Human overdoses of fosinopril have not been reported, but the most common manifestation of human fosinopril overdosage is likely to be hypotension. Oral doses of fosinopril at 2600 mg/kg in rats were associated with significant lethality. The most common adverse effects include dizzines, cough, fatigue, and headache.

Affected organisms

• Humans and other mammals

Pathways

Pathway	Category
Fosinopril Action Pathway	Drug action
Fosinopril Metabolism Pathway	Drug metabolism

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The therapeutic efficacy of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid can be increased when used in combination with Fosinopril.
1-benzylimidazole	1-benzylimidazole may decrease the antihypertensive activities of Fosinopril.
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Fosinopril.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Fosinopril.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Fosinopril.
4-Methoxyamphetamine	4-Methoxyamphetamine may decrease the antihypertensive activities of Fosinopril.
5-methoxy-N,N-dimethyltryptamine	5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Fosinopril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Fosinopril.
Abacavir	Fosinopril may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abediterol	Abediterol may decrease the antihypertensive activities of Fosinopril.

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Extended Description
Extended Description
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Severity
Severity
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Food Interactions

• Do not take calcium, aluminum, magnesium or iron supplements, or antacids within 2 hours of taking this medication.
• Fosinopril may decrease the excretion of potassium. Salt substitutes containing potassium may increase the risk of hyperkalemia.
• Herbs that may attenuate the antihypertensive effect of fosinopril include: bayberry, blue cohash, cayenne, ephedra, ginger, ginseng (American), kola and licorice.
• High salt intake may attenuate the antihypertensive effect of fosinopril.
• Take without regard to meals.

References

Synthesis Reference

Sandra Gallego Pato, Antonio Palomo Coll, Francisco Palomo Nicolau, "Preparation of crystalline polymorphs of fosinopril sodium." U.S. Patent US20050010054, issued January 13, 2005.

US20050010054

General References

1. David D, Jallad N, Germino FW, Willett MS, de Silva J, Weidner SM, Mills DJ: A Comparison of the Cough Profile of Fosinopril and Enalapril in Hypertensive Patients with a History of ACE Inhibitor-Associated Cough. Am J Ther. 1995 Oct;2(10):806-813. [PubMed:11854791]
2. Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. [PubMed:11329095]

External Links

Human Metabolome Database

HMDB0014635

KEGG Drug

D00622

KEGG Compound

C07016

PubChem Compound

55891

PubChem Substance

46506495

ChemSpider

7875352

ChEBI

5163

ChEMBL

CHEMBL3039598

Therapeutic Targets Database

DAP000582

PharmGKB

PA449710

Wikipedia

Fosinopril

ATC Codes

C09BA09 — Fosinopril and diuretics

• C09BA — ACE inhibitors and diuretics
• C09B — ACE INHIBITORS, COMBINATIONS
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

C09AA09 — Fosinopril

• C09AA — ACE inhibitors, plain
• C09A — ACE INHIBITORS, PLAIN
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

AHFS Codes

• 24:32.04 — Angiotensin-converting Enzyme Inhibitors

FDA label

Download (206 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Prevention	Cardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension)	1
2	Completed	Treatment	Diabetic Nephropathies	1
3	Completed	Prevention	Cardiovascular Disease (CVD) / Kidney Diseases / Microalbuminuria	1
3	Recruiting	Treatment	Chronic Kidney Disease Requiring Chronic Dialysis / Hyperphosphataemia	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Treatment	High Blood Pressure (Hypertension) / Induction of intra-operative hypotension	1
4	Not Yet Recruiting	Treatment	Chronic Kidney Disease (CKD)	1
Not Available	Completed	Not Available	Healthy Volunteers	4
Not Available	Completed	Treatment	Diabetes Mellitus (DM) / Hypertension,Essential	1
Not Available	Unknown Status	Treatment	Angiotensin II Type 1 Receptor Blockers / Angiotensin-Converting Enzyme Inhibitors / Kidney Insufficiency, Chronic / Proteinuria	1

Pharmacoeconomics

Manufacturers

• Apotex inc etobicoke site
• Invagen pharmaceuticals inc
• Ranbaxy laboratories ltd
• Sandoz inc
• Teva pharmaceuticals usa inc
• Watson laboratories inc
• Watson laboratories inc florida
• Bristol myers squibb co pharmaceutical research institute

Packagers

• Apotex Inc.
• A-S Medication Solutions LLC
• Atlantic Biologicals Corporation
• Blu Pharmaceuticals LLC
• Bristol-Myers Squibb Co.
• Cobalt Pharmaceuticals Inc.
• Deca Pharmaceuticals LLC
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Eon Labs
• Glenmark Generics Ltd.
• InvaGen Pharmaceuticals Inc.
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Murfreesboro Pharmaceutical Nursing Supply
• Neuman Distributors Inc.
• Nucare Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Princeton Pharmaceutical Products Inc.
• Ranbaxy Laboratories
• Resource Optimization and Innovation LLC
• Teva Pharmaceutical Industries Ltd.
• Va Cmop Dallas
• Watson Pharmaceuticals

Dosage forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Tablet	Oral	40 mg/1
Tablet	Oral	10 mg
Tablet	Oral	20 mg

Prices

Unit description	Cost	Unit
Monopril HCT 10-12.5 mg tablet	1.71USD	tablet
Monopril 10 mg tablet	1.68USD	tablet
Monopril 40 mg tablet	1.67USD	tablet
Monopril 20 mg tablet	1.62USD	tablet
Fosinopril Sodium-HCTZ 10-12.5 mg tablet	1.61USD	tablet
Fosinopril Sodium-HCTZ 20-12.5 mg tablet	1.61USD	tablet
Fosinopril sodium 20 mg tablet	1.25USD	tablet
Fosinopril sodium 40 mg tablet	1.25USD	tablet
Fosinopril sodium 10 mg tablet	1.21USD	tablet
Monopril 20 mg Tablet	1.1USD	tablet
Monopril 10 mg Tablet	0.91USD	tablet
Apo-Fosinopril 20 mg Tablet	0.61USD	tablet
Fosinopril 20 mg Tablet	0.61USD	tablet
Jamp-Fosinopril 20 mg Tablet	0.61USD	tablet
Mylan-Fosinopril 20 mg Tablet	0.61USD	tablet
Novo-Fosinopril 20 mg Tablet	0.61USD	tablet
Ran-Fosinopril 20 mg Tablet	0.61USD	tablet
Apo-Fosinopril 10 mg Tablet	0.51USD	tablet
Fosinopril 10 mg Tablet	0.51USD	tablet
Jamp-Fosinopril 10 mg Tablet	0.51USD	tablet
Mylan-Fosinopril 10 mg Tablet	0.51USD	tablet
Novo-Fosinopril 10 mg Tablet	0.51USD	tablet
Ran-Fosinopril 10 mg Tablet	0.51USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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US5006344	No	1991-04-09	2010-01-10

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Filed On
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	149-153 °C	Not Available
water solubility	Insoluble	Not Available
logP	6.3	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00101 mg/mL	ALOGPS
logP	4.71	ALOGPS
logP	5.62	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å2	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.12 m3·mol-1	ChemAxon
Polarizability	61.83 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9532
Blood Brain Barrier	-	0.667
Caco-2 permeable	-	0.6561
P-glycoprotein substrate	Substrate	0.6165
P-glycoprotein inhibitor I	Inhibitor	0.7161
P-glycoprotein inhibitor II	Non-inhibitor	0.6774
Renal organic cation transporter	Non-inhibitor	0.812
CYP450 2C9 substrate	Non-substrate	0.7028
CYP450 2D6 substrate	Non-substrate	0.8128
CYP450 3A4 substrate	Substrate	0.6729
CYP450 1A2 substrate	Non-inhibitor	0.8913
CYP450 2C9 inhibitor	Non-inhibitor	0.7438
CYP450 2D6 inhibitor	Non-inhibitor	0.9004
CYP450 2C19 inhibitor	Non-inhibitor	0.5725
CYP450 3A4 inhibitor	Non-inhibitor	0.7303
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6376
Ames test	Non AMES toxic	0.7141
Carcinogenicity	Non-carcinogens	0.8025
Biodegradation	Not ready biodegradable	0.8102
Rat acute toxicity	2.8211 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9534
hERG inhibition (predictor II)	Non-inhibitor	0.5918

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Taxonomy

Classification

Not classified

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Drug created on June 13, 2005 07:24 / Updated on July 15, 2019 20:11