Lenacapavir
Identification
- Summary
Lenacapavir is a first-in-class capsid inhibitor being investigated for use in HIV-1 treatment.
- Generic Name
- Lenacapavir
- DrugBank Accession Number
- DB15673
- Background
HIV/AIDS remains an area of concern despite the introduction of numerous successful therapies, mainly due to the emergence of multidrug resistance and patient difficulty in adhering to treatment regimens.1,2 Lenacapavir is a first-in-class capsid inhibitor that demonstrates picomolar HIV-1 inhibition as a monotherapy in vitro, little to no cross-resistance with existing antiretroviral agents, and extended pharmacokinetics with subcutaneous dosing.1,2,3,5
Lenacapavir was first globally approved on August 22, 2022 by the European Commission to treat adults with multi-drug resistant HIV infection.7 On December 22, 2022, it was also approved by the FDA.9
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 968.28
Monoisotopic: 967.1435188 - Chemical Formula
- C39H32ClF10N7O5S2
- Synonyms
- Lenacapavir
- External IDs
- GS-CA1
Pharmacology
- Indication
Lenacapavir, in combination with other antiretroviral(s), is indicated for the treatment of multidrug-resistant human immunodeficiency virus type 1 (HIV-1) infection in heavily treatment-experienced adults who are experiencing a failure of their current antiretroviral regimen due to resistance, intolerance, or safety considerations.6,8
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Multidrug resistant hiv-1 infection •••••••••••• ••••• •• •••••••• •••••••• ••••••• ••••••••• Adjunct therapy in treatment of Multidrug resistant hiv-1 infection •••••••••••• ••••• •• •••••••• •••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Lenacapavir is an antiviral drug with an extended pharmacokinetic profile. Lenacapavir works against the HIV-1 virus by inhibiting viral replication: it interferes with a number of essential steps of the viral lifecycle, including viral uptake, assembly, and release.6 Single subcutaneous doses ≥100 mg in healthy volunteers resulted in plasma concentrations exceeding the 95% effective concentration (EC95) for ≥12 weeks while doses ≥300 mg exceeded the EC95 for ≥24 weeks. In treatment-naive HIV-1-infected patients, a single subcutaneous dose of 20-450 mg resulted in a mean maximum log10-transformed reduction in plasma HIV-1 RNA of 1.35-2.20 by the ninth-day post-injection.2
- Mechanism of action
HIV-1 co-opts various host factors during its replicative cycle, including during host cell entry, nuclear integration, replication, and virion assembly. Following the initial fusion with the host cell membrane, the viral capsid is released into the host cell cytoplasm. The capsid comprises approximately 250 hexamers and exactly 12 pentamers, each composed of monomeric capsid proteins (CA). Each CA monomer has an N-terminal and C-terminal domain (NTD/CTD) and offers an interaction surface for host cell machinery. Several important protein-protein interaction interfaces occur between CA monomers in the assembled multimers; the binding constants of these proteins are substantially lower for assembled multimers than individual capsid monomers.1
To facilitate HIV-1 genomic integration, the capsid must cross the nuclear envelope, for which it utilizes the nuclear pore complex (NPC). Two host proteins shown to be essential for capsid nuclear entry that directly bind to the capsid are cleavage and polyadenylation specificity factor subunit 6 (CPSF6) and nucleoporin 153 (Nup153, an NPC protein present on the nucleoplasmic face of the complex).1 Both proteins bind the same phenylalanine-glycine binding pocket between the NTD and CTD of neighbouring CA monomers in multimeric CA assemblies.1,2,3,4
Lenacapavir contains a difluorobenzyl ring that occupies the same binding pocket as CPSF6/Nup153, overlapping with the benzyl group of F321 in CPSF6 and F1417 in Nup153 in the overlayed structures.1,2,3,4 Crystal structures of lenacapavir bound to CA hexamers reveal that six lenacapavir molecules bind to each hexamer, establishing extensive hydrophobic interactions, two cation-π interactions, and seven hydrogen bonds, contacting ~2,000 Å2 of buried protein surface area.2,3 Strong binding of lenacapavir, therefore competitively interrupts capsid interactions with CPSF6 and Nup153. In vitro HIV-1 replication inhibition experiments in a variety of cell lines show EC50 values of ~12-314 pM, with greater efficacy against early steps over later steps.2,3 At very low concentrations (0.5 nM), lenacapavir inhibits viral nuclear entry, while at higher concentrations (5-50 nM), it additionally inhibits viral DNA synthesis and reverse transcription.3 As CPSF6 and Nup153 are essential for nuclear entry, it is likely that lenacapavir binding inhibits these interactions and blocks capsid nuclear entry.
Lenacapavir may have additional effects beyond blocking interactions with host cell factors. Lenacapavir increases the rate and extent of CA assembly, dramatically extends the lifetime of assembled CA structures, even at high salt concentrations, and alters assembled capsid morphology.2,3 The stabilizing concentration is ~1:1, closely mimicking the observed binding stoichiometry to isolated CA hexamers. Further analysis suggests that lenacapavir binding alters intra- and inter-hexamer interactions, altering the structure and stability of the resulting assemblies.3
Serial passage of HIV-1 in increasing concentrations of lenacapavir resulted in the appearance of major resistance mutations Q67H and N74D, which remain sensitive to other antiretroviral drugs. Extended passage resulted in the additional mutations L56I, M66I, K70N, N74S, and T107N. All identified resistance mutations map to the lenacapavir binding site, and all but the Q67H variant show reduced replication capacity in vitro.2 Additional studies have shown no lenacapavir resistance in variants associated with resistance to other antiretrovirals or naturally occurring polymorphisms, suggesting a very low potential for cross-resistance in combination therapy.5
Target Actions Organism AGag-Pol polyprotein inhibitor- Absorption
Following subcutaneous administration, lenacapavir is slowly released but completely absorbed, with peak plasma concentrations occurring at 84 days post-dose. Absolute bioavailability following oral administration is low, approximately 6 to 10%. Tmax after oral administration is about four hours. The mean steady-state Cmax (%CV) is 97.2 (70.3) ng/ mL following oral and subcutaneous administration.6
According to population pharmacokinetics analysis, lenacapavir exposures (AUCtau, Cmax and Ctrough) were 29% to 84% higher in heavily treatment-experienced patients with an HIV-1 infection compared to subjects without an HIV-1 infection. A low-fat meal had negligible effects on drug absorption.6
- Volume of distribution
The steady state volume of distribution was 976 L in heavily treatment-experienced patients with an HIV-1 infection.6
- Protein binding
In vitro, lenacapavir is approximately 99.8% bound to plasma proteins.6
- Metabolism
Metabolism played a lesser role in lenacapavir elimination. It undergoes CYP3A4- and UGT1A1-mediated oxidation, N-dealkylation, hydrogenation, amide hydrolysis, glucuronidation, hexose conjugation, pentose conjugation, and glutathione conjugation. The metabolites of lenacapavir have not been fully characterized. No single circulating metabolite accounted for >10% of plasma drug-related exposure.6
- Route of elimination
Following a single intravenous dose of radiolabelled-lenacapavir in healthy subjects, 76% of the total radioactivity was recovered from feces and less than 1% from urine. Unchanged lenacapavir was the predominant moiety in plasma (69%) and feces (33%).6
- Half-life
The median half-life ranged from 10 to 12 days following following oral administration, and 8 to 12 weeks following subcutaneous administration.6
- Clearance
Lenacapavir clearance was 3.62 L/h in heavily treatment experienced patients with HIV-1 infection.6
- Adverse Effects
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- Toxicity
There is limited information available regarding the acute toxicity and overdose of lenacapavir. If overdose occurs the patient must be monitored for signs or symptoms of adverse reactions. Treatment of overdose with lenacapavir consists of general supportive measures including monitoring of vital signs as well as observation of the clinical status of the patient. As lenacapavir is highly protein bound, it is unlikely to be significantly removed by dialysis.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Lenacapavir can be increased when it is combined with Abametapir. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Lenacapavir. Abrocitinib The serum concentration of Lenacapavir can be increased when it is combined with Abrocitinib. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Lenacapavir. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Lenacapavir. - Food Interactions
- Take with or without food. Oral lenacapavir should be taken orally with or without food, as food has negligible effects on drug absorption.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Lenacapavir sodium BDT58WJ9WE 2283356-12-5 SSXPGMNGIORJAQ-PZNXWHLTSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Sunlenca Tablet, film coated 300 mg Oral Gilead Sciences Ireland Unlimited Company 2022-08-29 Not applicable EU Sunlenca Injection; Kit 463.5 mg/1.5mL Subcutaneous Gilead Sciences 2022-12-22 Not applicable US Sunlenca Solution 309 mg / mL Subcutaneous Gilead Sciences 2023-03-15 Not applicable Canada Sunlenca Tablet, film coated 300 mg/1 Oral Gilead Sciences 2022-12-22 Not applicable US Sunlenca Injection, solution 464 mg Subcutaneous Gilead Sciences Ireland Unlimited Company 2022-08-29 Not applicable EU
Categories
- ATC Codes
- J05AX31 — Lenacapavir
- Drug Categories
- Anti-HIV Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Heterocyclic Compounds, Fused-Ring
- P-glycoprotein substrates
- Pyrazoles
- UGT1A1 Substrates
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- A9A0O6FB4H
- CAS number
- 2189684-44-2
- InChI Key
- BRYXUCLEHAUSDY-WEWMWRJBSA-N
- InChI
- InChI=1S/C39H32ClF10N7O5S2/c1-36(2,63(3,59)60)10-9-21-5-6-22(23-7-8-26(40)30-32(23)57(17-37(43,44)45)54-35(30)55-64(4,61)62)31(51-21)27(13-18-11-19(41)14-20(42)12-18)52-28(58)16-56-34-29(33(53-56)39(48,49)50)24-15-25(24)38(34,46)47/h5-8,11-12,14,24-25,27H,13,15-17H2,1-4H3,(H,52,58)(H,54,55)/t24-,25+,27-/m0/s1
- IUPAC Name
- N-[(1S)-1-{3-[4-chloro-3-methanesulfonamido-1-(2,2,2-trifluoroethyl)-1H-indazol-7-yl]-6-(3-methanesulfonyl-3-methylbut-1-yn-1-yl)pyridin-2-yl}-2-(3,5-difluorophenyl)ethyl]-2-[(2S,4R)-5,5-difluoro-9-(trifluoromethyl)-7,8-diazatricyclo[4.3.0.0^{2,4}]nona-1(6),8-dien-7-yl]acetamide
- SMILES
- [H][C@]12C[C@@]1([H])C(F)(F)C1=C2C(=NN1CC(=O)N[C@@H](CC1=CC(F)=CC(F)=C1)C1=NC(=CC=C1C1=CC=C(Cl)C2=C1N(CC(F)(F)F)N=C2NS(C)(=O)=O)C#CC(C)(C)S(C)(=O)=O)C(F)(F)F
References
- General References
- Zhuang S, Torbett BE: Interactions of HIV-1 Capsid with Host Factors and Their Implications for Developing Novel Therapeutics. Viruses. 2021 Mar 5;13(3). pii: v13030417. doi: 10.3390/v13030417. [Article]
- Link JO, Rhee MS, Tse WC, Zheng J, Somoza JR, Rowe W, Begley R, Chiu A, Mulato A, Hansen D, Singer E, Tsai LK, Bam RA, Chou CH, Canales E, Brizgys G, Zhang JR, Li J, Graupe M, Morganelli P, Liu Q, Wu Q, Halcomb RL, Saito RD, Schroeder SD, Lazerwith SE, Bondy S, Jin D, Hung M, Novikov N, Liu X, Villasenor AG, Cannizzaro CE, Hu EY, Anderson RL, Appleby TC, Lu B, Mwangi J, Liclican A, Niedziela-Majka A, Papalia GA, Wong MH, Leavitt SA, Xu Y, Koditek D, Stepan GJ, Yu H, Pagratis N, Clancy S, Ahmadyar S, Cai TZ, Sellers S, Wolckenhauer SA, Ling J, Callebaut C, Margot N, Ram RR, Liu YP, Hyland R, Sinclair GI, Ruane PJ, Crofoot GE, McDonald CK, Brainard DM, Lad L, Swaminathan S, Sundquist WI, Sakowicz R, Chester AE, Lee WE, Daar ES, Yant SR, Cihlar T: Clinical targeting of HIV capsid protein with a long-acting small molecule. Nature. 2020 Aug;584(7822):614-618. doi: 10.1038/s41586-020-2443-1. Epub 2020 Jul 1. [Article]
- Bester SM, Wei G, Zhao H, Adu-Ampratwum D, Iqbal N, Courouble VV, Francis AC, Annamalai AS, Singh PK, Shkriabai N, Van Blerkom P, Morrison J, Poeschla EM, Engelman AN, Melikyan GB, Griffin PR, Fuchs JR, Asturias FJ, Kvaratskhelia M: Structural and mechanistic bases for a potent HIV-1 capsid inhibitor. Science. 2020 Oct 16;370(6514):360-364. doi: 10.1126/science.abb4808. [Article]
- Singh K, Gallazzi F, Hill KJ, Burke DH, Lange MJ, Quinn TP, Neogi U, Sonnerborg A: GS-CA Compounds: First-In-Class HIV-1 Capsid Inhibitors Covering Multiple Grounds. Front Microbiol. 2019 Jun 20;10:1227. doi: 10.3389/fmicb.2019.01227. eCollection 2019. [Article]
- Margot N, Ram R, Rhee M, Callebaut C: Absence of Lenacapavir (GS-6207) Phenotypic Resistance in HIV Gag Cleavage Site Mutants and in Isolates with Resistance to Existing Drug Classes. Antimicrob Agents Chemother. 2021 Feb 17;65(3). pii: AAC.02057-20. doi: 10.1128/AAC.02057-20. Print 2021 Feb 17. [Article]
- EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
- Gilead Press Releases: Gilead Announces First Global Regulatory Approval of Sunlenca® (Lenacapavir), the Only Twice-Yearly HIV Treatment Option [Link]
- FDA Approved Drug Products: SUNLENCA (lenacapavir) tablets, for oral use or injection, for subcutaneous use [Link]
- Gilead: Sunlenca® (lenacapavir) Receives FDA Approval as a First-in-Class, Twice-Yearly Treatment Option for People Living With Multi-Drug Resistant HIV [Link]
- External Links
- ChemSpider
- 81367881
- 2625651
- ChEMBL
- CHEMBL4594438
- PDBe Ligand
- QNG
- Wikipedia
- Lenacapavir
- PDB Entries
- 6v2f / 6vkv / 7rhn / 7rj2 / 7rj4
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Active Not Recruiting Prevention HIV Pre-Exposure Prophylaxis 1 3 Active Not Recruiting Treatment HIV Pre-Exposure Prophylaxis 1 2 Active Not Recruiting Treatment Human Immunodeficiency Virus (HIV) Infections 1 2 Completed Treatment Human Immunodeficiency Virus Type 1 (HIV-1) Infection 1 2 Recruiting Prevention HIV Pre-Exposure Prophylaxis 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Subcutaneous 464 mg Injection; kit Subcutaneous 463.5 mg/1.5mL Solution Subcutaneous 309 mg / mL Tablet Oral 300 mg Tablet, film coated Oral 300 mg Tablet, film coated Oral 300 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US10654827 No 2020-05-19 2037-08-17 US US9951043 No 2018-04-24 2034-02-28 US US11267799 No 2018-08-16 2038-08-16 US US10071985 No 2018-09-11 2037-08-17 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00357 mg/mL ALOGPS logP 6.47 ALOGPS logP 6.4 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 6.69 Chemaxon pKa (Strongest Basic) 1.91 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 157.94 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 231.27 m3·mol-1 Chemaxon Polarizability 83.29 Å3 Chemaxon Number of Rings 7 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Lenacapavir specifically binds to the interface between capsid (p24; CA) monomers in assembled capsid structures. The capsid protein is one of several cleavage products resulting from this polyprotein.
- General Function
- Zinc ion binding
- Specific Function
- Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
- Gene Name
- gag-pol
- Uniprot ID
- P04585
- Uniprot Name
- Gag-Pol polyprotein
- Molecular Weight
- 162041.05 Da
References
- Zhuang S, Torbett BE: Interactions of HIV-1 Capsid with Host Factors and Their Implications for Developing Novel Therapeutics. Viruses. 2021 Mar 5;13(3). pii: v13030417. doi: 10.3390/v13030417. [Article]
- Link JO, Rhee MS, Tse WC, Zheng J, Somoza JR, Rowe W, Begley R, Chiu A, Mulato A, Hansen D, Singer E, Tsai LK, Bam RA, Chou CH, Canales E, Brizgys G, Zhang JR, Li J, Graupe M, Morganelli P, Liu Q, Wu Q, Halcomb RL, Saito RD, Schroeder SD, Lazerwith SE, Bondy S, Jin D, Hung M, Novikov N, Liu X, Villasenor AG, Cannizzaro CE, Hu EY, Anderson RL, Appleby TC, Lu B, Mwangi J, Liclican A, Niedziela-Majka A, Papalia GA, Wong MH, Leavitt SA, Xu Y, Koditek D, Stepan GJ, Yu H, Pagratis N, Clancy S, Ahmadyar S, Cai TZ, Sellers S, Wolckenhauer SA, Ling J, Callebaut C, Margot N, Ram RR, Liu YP, Hyland R, Sinclair GI, Ruane PJ, Crofoot GE, McDonald CK, Brainard DM, Lad L, Swaminathan S, Sundquist WI, Sakowicz R, Chester AE, Lee WE, Daar ES, Yant SR, Cihlar T: Clinical targeting of HIV capsid protein with a long-acting small molecule. Nature. 2020 Aug;584(7822):614-618. doi: 10.1038/s41586-020-2443-1. Epub 2020 Jul 1. [Article]
- Bester SM, Wei G, Zhao H, Adu-Ampratwum D, Iqbal N, Courouble VV, Francis AC, Annamalai AS, Singh PK, Shkriabai N, Van Blerkom P, Morrison J, Poeschla EM, Engelman AN, Melikyan GB, Griffin PR, Fuchs JR, Asturias FJ, Kvaratskhelia M: Structural and mechanistic bases for a potent HIV-1 capsid inhibitor. Science. 2020 Oct 16;370(6514):360-364. doi: 10.1126/science.abb4808. [Article]
- Singh K, Gallazzi F, Hill KJ, Burke DH, Lange MJ, Quinn TP, Neogi U, Sonnerborg A: GS-CA Compounds: First-In-Class HIV-1 Capsid Inhibitors Covering Multiple Grounds. Front Microbiol. 2019 Jun 20;10:1227. doi: 10.3389/fmicb.2019.01227. eCollection 2019. [Article]
- EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
Drug created at April 20, 2020 15:47 / Updated at November 01, 2023 05:14