NAV

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
Similar Structures
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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofMultidrug resistant hiv-1 infection••••••••••••••••••• •••••••• •••••••• ••••••••••••••••
Adjunct therapy in treatment ofMultidrug 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

TargetActionsOrganism
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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of Lenacapavir can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Lenacapavir.
AbrocitinibThe serum concentration of Lenacapavir can be increased when it is combined with Abrocitinib.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Lenacapavir.
AcenocoumarolThe 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

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Product Ingredients
IngredientUNIICASInChI Key
Lenacapavir sodiumBDT58WJ9WE2283356-12-5SSXPGMNGIORJAQ-PZNXWHLTSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SunlencaInjection; Kit463.5 mg/1.5mLSubcutaneousGilead Sciences2022-12-22Not applicableUS flag
SunlencaTablet, film coated300 mgOralGilead Sciences Ireland Unlimited Company2022-08-29Not applicableEU flag
SunlencaSolution309 mg / mLSubcutaneousGilead Sciences2023-03-15Not applicableCanada flag
SunlencaTablet, film coated300 mg/1OralGilead Sciences2022-12-22Not applicableUS flag
SunlencaTablet300 mgOralGilead Sciences2023-03-15Not applicableCanada flag

Categories

ATC Codes
J05AX31 — Lenacapavir
Drug Categories
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]
ChemSpider
81367881
RxNav
2625651
ChEMBL
CHEMBL4594438
PDBe Ligand
QNG
Wikipedia
Lenacapavir
PDB Entries
6v2f / 6vkv / 7rhn / 7rj2 / 7rj4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Active Not RecruitingPreventionHIV Pre-Exposure Prophylaxis1
3Active Not RecruitingTreatmentHIV Pre-Exposure Prophylaxis1
3RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionSubcutaneous464 mg
Injection; kitSubcutaneous463.5 mg/1.5mL
SolutionSubcutaneous309 mg / mL
TabletOral300 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral300 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10654827No2020-05-192037-08-17US flag
US9951043No2018-04-242034-02-28US flag
US11267799No2018-08-162038-08-16US flag
US10071985No2018-09-112037-08-17US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00357 mg/mLALOGPS
logP6.47ALOGPS
logP6.4Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)6.69Chemaxon
pKa (Strongest Basic)1.91Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area157.94 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity231.27 m3·mol-1Chemaxon
Polarizability83.29 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0000000094-cbb657f99feb3aeb9ade
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ls-9020031304-fcde1a2f8047b5cafb77
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000000091-c160c3fc30c83da17ddd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0g30-9030134303-bea4ba0179debf1141a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1020401492-0ccf3fa300fe99a01a3f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00c0-7090200001-4e9fde025533e988dbfc
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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insights and accelerate drug research.
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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]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
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
  1. EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]
Details2. UDP-glucuronosyltransferase 1-1
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
  1. EMA Approved Drug Products: Sunlenca (lenacapavir) Subcutaneous Injection or Oral Tablets [Link]

Transporters

Details1. P-glycoprotein 1
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
  1. 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