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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Lenacapavir (DB15673)

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Weight

Average: 968.28
Monoisotopic: 967.1435188

Chemical Formula

C₃₉H₃₂ClF₁₀N₇O₅S₂

Synonyms

• Lenacapavir

External IDs

• GS-CA1

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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

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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		••••••••••••	•••••	•• •••••••• •••••••• •••••••	••••••

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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 Ų 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%. T_max after oral administration is about four hours. The mean steady-state C_max (%CV) is 97.2 (70.3) ng/ mL following oral and subcutaneous administration.⁶

According to population pharmacokinetics analysis, lenacapavir exposures (AUC_tau, C_max and C_trough) 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

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Not Available

Interactions

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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.

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• Withdrawn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

Drug	Interaction
Integrate drug-drug interactions in your software
Abametapir	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.

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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
Sunlenca	Injection; Kit	463.5 mg/1.5mL	Subcutaneous	Gilead Sciences	2022-12-22	Not applicable
Sunlenca	Solution	309 mg / mL	Subcutaneous	Gilead Sciences	2023-03-15	Not applicable
Sunlenca	Tablet, film coated	300 mg/1	Oral	Gilead Sciences	2022-12-22	Not applicable
Sunlenca	Injection, solution	464 mg	Subcutaneous	Gilead Sciences Ireland Unlimited Company	2022-08-29	Not applicable

Categories

ATC Codes

J05AX31 — Lenacapavir

• J05AX — Other antivirals
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

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

1. 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]
2. 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]
3. 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]
4. 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]
5. 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]
6. EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
7. Gilead Press Releases: Gilead Announces First Global Regulatory Approval of Sunlenca® (Lenacapavir), the Only Twice-Yearly HIV Treatment Option [Link]
8. FDA Approved Drug Products: SUNLENCA (lenacapavir) tablets, for oral use or injection, for subcutaneous use [Link]
9. 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

RxNav

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
US9951043	No	2018-04-24	2034-02-28
US11267799	No	2018-08-16	2038-08-16
US10071985	No	2018-09-11	2037-08-17

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

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kr-0000000094-cbb657f99feb3aeb9ade
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00ls-9020031304-fcde1a2f8047b5cafb77
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0000000091-c160c3fc30c83da17ddd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0g30-9030134303-bea4ba0179debf1141a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-1020401492-0ccf3fa300fe99a01a3f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00c0-7090200001-4e9fde025533e988dbfc

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Gag-Pol polyprotein

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

1. 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]
2. 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]
3. 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]
4. 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]
5. EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]

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Drug created at April 20, 2020 15:47 / Updated at November 01, 2023 05:14