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Article: Ritonavir: 25 Years' Experience of Concomitant Medication Management. A Narrative Review.

Quercia, Romina / Di Perri, Giovanni / Pein, Carolina / Bodie, Jennifer / Singh, Ravi Shankar P / Hendrick, Victoria / Boffito, Marta

Infectious diseases and therapy

2024

Abstract: Ritonavir is a potent inhibitor of the cytochrome P450 3A4 enzyme and is commonly used as a pharmacokinetic (PK) enhancer in antiviral therapies because it increases bioavailability of concomitantly administered antivirals. Decades of experience with ... ...

Abstract	Ritonavir is a potent inhibitor of the cytochrome P450 3A4 enzyme and is commonly used as a pharmacokinetic (PK) enhancer in antiviral therapies because it increases bioavailability of concomitantly administered antivirals. Decades of experience with ritonavir-enhanced HIV therapies and, more recently, COVID-19 therapies demonstrate that boosting doses of ritonavir are well tolerated, with an established safety profile. The mechanisms of PK enhancement by ritonavir result in the potential for drug-drug interactions (DDIs) with several classes of drugs, thus making co-medication management an important consideration with enhanced antiviral therapies. However, rates of DDIs with contraindicated medications are low, suggesting these risks are manageable by infectious disease specialists who have experience with the use of PK enhancers. In this review, we provide an overview of ritonavir's mechanisms of action and describe approaches and resources available to mitigate adverse events and manage concomitant medication in both chronic and short-term settings.
Language	English
Publishing date	2024-04-12
Publishing country	New Zealand
Document type	Journal Article ; Review
ZDB-ID	2701611-0
ISSN	2193-6382 ; 2193-8229
ISSN (online)	2193-6382
ISSN	2193-8229
DOI	10.1007/s40121-024-00959-6
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Article ; Online: Dosing recommendation of nirmatrelvir/ritonavir using an integrated population pharmacokinetic analysis.

Chan, Phylinda L S / Singh, Ravi Shankar P / Cox, Donna S / Shi, Haihong / Damle, Bharat / Nicholas, Timothy

CPT: pharmacometrics & systems pharmacology

2023 Volume 12, Issue 12, Page(s) 1897–1910

Abstract: Protease inhibitor nirmatrelvir coadministered with ritonavir as a pharmacokinetic enhancer (PAXLOVID™; Pfizer Inc) became the first orally bioavailable antiviral agent granted Emergency Use Authorization in the United States in patients ≥12 years old ... ...

Abstract	Protease inhibitor nirmatrelvir coadministered with ritonavir as a pharmacokinetic enhancer (PAXLOVID™; Pfizer Inc) became the first orally bioavailable antiviral agent granted Emergency Use Authorization in the United States in patients ≥12 years old with mild to moderate coronavirus disease 2019 (COVID-19). This population pharmacokinetic analysis used pooled plasma nirmatrelvir concentrations from eight completed phase I and II/III studies to characterize nirmatrelvir pharmacokinetics when coadministered with ritonavir in adults with/without COVID-19. Influence of covariates (e.g., formulation, dose, COVID-19) was examined using a stepwise forward selection (α = 0.05) and backward elimination (α = 0.001) approach. Simulations with 5000 subjects for each age and weight group and renal function category were performed to support dosing recommendations of nirmatrelvir/ritonavir for adults with COVID-19 and guide dose adjustments for specific patient populations (e.g., renal insufficiency, pediatrics). The final model was a two-compartment model with first-order absorption, including allometric scaling of body weight and dose-dependent absorption (power function on relative bioavailability). Nirmatrelvir clearance (CL) increased proportionally to body surface area-normalized creatinine CL (nCLCR) up to 70 ml/min/1.73 m
MeSH term(s)	Adult ; Humans ; Child ; Ritonavir ; Antiviral Agents ; Benzodiazepines ; COVID-19
Chemical Substances	Ritonavir (O3J8G9O825) ; Antiviral Agents ; Benzodiazepines (12794-10-4)
Language	English
Publishing date	2023-10-06
Publishing country	United States
Document type	Journal Article
ZDB-ID	2697010-7
ISSN	2163-8306 ; 2163-8306
ISSN (online)	2163-8306
ISSN	2163-8306
DOI	10.1002/psp4.13039
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Article ; Online: Effect of Hepatic Impairment on the Pharmacokinetics of Nirmatrelvir/Ritonavir, the First Oral Protease Inhibitor for the Treatment of COVID-19.

Singh, Ravi Shankar P / LaBadie, Robert R / Toussi, Sima S / Shi, Haihong / Berg, Jolene Kay / Neutel, Joel M / Aggarwal, Sudeepta

Journal of clinical pharmacology

2023 Volume 64, Issue 2, Page(s) 145–154

Abstract: Nirmatrelvir, a novel, potent, orally bioavailable severe acute respiratory syndrome coronavirus 2 main protease inhibitor, coadministered with ritonavir for pharmacokinetic (PK) enhancement is licensed for the treatment of mild to moderate COVID-19 in ... ...

Abstract	Nirmatrelvir, a novel, potent, orally bioavailable severe acute respiratory syndrome coronavirus 2 main protease inhibitor, coadministered with ritonavir for pharmacokinetic (PK) enhancement is licensed for the treatment of mild to moderate COVID-19 in individuals at increased risk of progression to severe disease. Cytochrome P450 3A4 is the primary metabolic enzyme responsible for nirmatrelvir metabolism; however, when cytochrome P450 3A4 is inhibited by ritonavir, nirmatrelvir is primarily excreted, unchanged, in urine. Because of intended use of nirmatrelvir among individuals with hepatic impairment, this Phase 1 study (NCT05005312) evaluated the effects of hepatic impairment on nirmatrelvir PK parameters to assess the potential need for any dose adjustments in this population. Participants with normal hepatic function or moderate hepatic impairment (n = 8 each) were administered a single 100-mg nirmatrelvir dose, with 100 mg of ritonavir administered 12 hours before, together with, and 12 and 24 hours after nirmatrelvir. Nirmatrelvir median plasma concentrations and systemic exposure measured by area under the plasma concentration-time curve from time zero extrapolated to infinite time and maximum observed plasma concentration values were comparable in both groups. Nirmatrelvir/ritonavir had an acceptable safety profile in both groups, and no clinically significant changes in laboratory measurements, vital signs, or electrocardiogram assessments were observed. Based on these results, no dose adjustment is deemed necessary in patients with moderate hepatic impairment and, by extension, in patients with mild hepatic impairment.
MeSH term(s)	Humans ; Ritonavir ; Protease Inhibitors/therapeutic use ; COVID-19 ; COVID-19 Drug Treatment ; Antiviral Agents/pharmacokinetics ; Liver Diseases/metabolism ; Cytochrome P-450 Enzyme System
Chemical Substances	Ritonavir (O3J8G9O825) ; Protease Inhibitors ; Antiviral Agents ; Cytochrome P-450 Enzyme System (9035-51-2)
Language	English
Publishing date	2023-10-24
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	188980-1
ISSN	1552-4604 ; 0091-2700 ; 0021-9754
ISSN (online)	1552-4604
ISSN	0091-2700 ; 0021-9754
DOI	10.1002/jcph.2353
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Article ; Online: A Comprehensive Review of the Clinical Pharmacokinetics, Pharmacodynamics, and Drug Interactions of Nirmatrelvir/Ritonavir.

Gerhart, Jacqueline / Cox, Donna S / Singh, Ravi Shankar P / Chan, Phylinda L S / Rao, Rohit / Allen, Richard / Shi, Haihong / Masters, Joanna C / Damle, Bharat

Clinical pharmacokinetics

2024 Volume 63, Issue 1, Page(s) 27–42

Abstract: Nirmatrelvir is a potent and selective inhibitor of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease that is used as an oral antiviral coronavirus disease 2019 (COVID-19) treatment. To sustain unbound systemic trough ... ...

Abstract	Nirmatrelvir is a potent and selective inhibitor of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease that is used as an oral antiviral coronavirus disease 2019 (COVID-19) treatment. To sustain unbound systemic trough concentrations above the antiviral in vitro 90% effective concentration value (EC
MeSH term(s)	Humans ; Ritonavir/pharmacology ; Ritonavir/therapeutic use ; Pandemics ; Drug Interactions ; COVID-19 ; Antiviral Agents/pharmacology ; Antiviral Agents/therapeutic use ; Nitriles ; Drug Combinations ; Leucine ; Proline ; Lactams
Chemical Substances	nirmatrelvir and ritonavir drug combination ; Ritonavir (O3J8G9O825) ; Antiviral Agents ; Nitriles ; Drug Combinations ; Leucine (GMW67QNF9C) ; Proline (9DLQ4CIU6V) ; Lactams
Language	English
Publishing date	2024-01-04
Publishing country	Switzerland
Document type	Journal Article ; Review ; Research Support, N.I.H., Extramural
ZDB-ID	197627-8
ISSN	1179-1926 ; 0312-5963
ISSN (online)	1179-1926
ISSN	0312-5963
DOI	10.1007/s40262-023-01339-y
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Article ; Online: Oral tyrosine kinase 2 inhibitor PF-06826647 demonstrates efficacy and an acceptable safety profile in participants with moderate-to-severe plaque psoriasis in a phase 2b, randomized, double-blind, placebo-controlled study.

Tehlirian, Christopher / Singh, Ravi Shankar P / Pradhan, Vivek / Roberts, Erika S / Tarabar, Sanela / Peeva, Elena / Vincent, Michael S / Gale, Jeremy D

Journal of the American Academy of Dermatology

2022 Volume 87, Issue 2, Page(s) 333–342

Abstract: Background: Psoriasis treatments lack durable efficacy and have inconvenient administration, highlighting the need for new therapies.: Objective: To evaluate the efficacy and safety of tyrosine kinase 2 inhibitor, PF-06826647, in moderate-to-severe ... ...

Abstract	Background: Psoriasis treatments lack durable efficacy and have inconvenient administration, highlighting the need for new therapies. Objective: To evaluate the efficacy and safety of tyrosine kinase 2 inhibitor, PF-06826647, in moderate-to-severe plaque psoriasis. Methods: This phase 2b, double-blind study randomized participants to oral, once-daily PF-06826647 (1:1:2:2:2) 50:100:200:400 mg:placebo (16 weeks), then 200 or 400 mg (24 weeks) (NCT03895372). The primary end point was a proportion of participants achieving psoriasis area severity index (PASI) 90 at week 16. Secondary end points (PASI50/75/90/100; Physician's Global Assessment) and safety were assessed to week 40. Results: Overall, 178 participants were treated. A significantly greater proportion of participants (risk difference % [90% CI]) achieved PASI90 in the 200-mg (33.0 [18.0, 47.1], P = .0004) and 400-mg (46.5 [30.6, 60.6], P < .0001; week 16) groups versus placebo. Significant increases from placebo were observed for all secondary end points (200 and 400 mg; weeks 6-16; P < .05); increases were evident to week 40 (categorical data). PF-06826647 was well tolerated and most treatment-emergent adverse events were mild/moderate. Eighteen participants discontinued due to treatment-emergent adverse events (14 arising from laboratory abnormalities). Limitations: Limitations included the large proportion of White males and non-placebo-controlled extension. Conclusion: PF-06826647 200 and 400 mg once daily showed significant efficacy versus placebo at week 16 and was well tolerated over 40 weeks.
MeSH term(s)	Double-Blind Method ; Humans ; Protein Kinase Inhibitors/adverse effects ; Protein Kinase Inhibitors/therapeutic use ; Psoriasis/diagnosis ; Psoriasis/drug therapy ; Severity of Illness Index ; TYK2 Kinase/antagonists & inhibitors ; Treatment Outcome
Chemical Substances	Protein Kinase Inhibitors ; TYK2 Kinase (EC 2.7.10.2)
Language	English
Publishing date	2022-04-06
Publishing country	United States
Document type	Journal Article ; Randomized Controlled Trial ; Research Support, Non-U.S. Gov't
ZDB-ID	603641-7
ISSN	1097-6787 ; 0190-9622
ISSN (online)	1097-6787
ISSN	0190-9622
DOI	10.1016/j.jaad.2022.03.059
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Article ; Online: A Phase 1 Study to Assess Mass Balance and Absolute Bioavailability of Zimlovisertib in Healthy Male Participants Using a

Singh, Ravi Shankar P / Dowty, Martin E / Salganik, Mikhail / Brodfuehrer, Joanne I / Walker, Gregory S / Sharma, Raman / Beebe, Jean S / Danto, Spencer I

Clinical pharmacology in drug development

2022 Volume 11, Issue 7, Page(s) 815–825

Abstract: Zimlovisertib (PF-06650833) is a selective, reversible inhibitor of interleukin-1 receptor-associated kinase 4 (IRAK4) with anti-inflammatory effects. This phase 1, open-label, fixed-sequence, two-period, single-dose study aimed to evaluate the mass ... ...

Abstract	Zimlovisertib (PF-06650833) is a selective, reversible inhibitor of interleukin-1 receptor-associated kinase 4 (IRAK4) with anti-inflammatory effects. This phase 1, open-label, fixed-sequence, two-period, single-dose study aimed to evaluate the mass balance and excretion rate of zimlovisertib in healthy male participants using a
MeSH term(s)	Administration, Oral ; Biological Availability ; Feces ; Healthy Volunteers ; Humans ; Male
Language	English
Publishing date	2022-05-04
Publishing country	United States
Document type	Clinical Trial, Phase I ; Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2649010-9
ISSN	2160-7648 ; 2160-763X
ISSN (online)	2160-7648
ISSN	2160-763X
DOI	10.1002/cpdd.1109
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Article ; Online: Patient Centric Microsampling to Support Paxlovid Clinical Development: Bridging and Implementation.

Wan, Katty / Kavetska, Olga / Damle, Bharat / Shi, Haihong / Cox, Donna S / Oladoyinbo, Olayide / Chan, Phylinda / Singh, Ravi Shankar P / Craft, Susan / Berthier, Erwin / Corrigan, Brian

Clinical pharmacology and therapeutics

2023 Volume 115, Issue 1, Page(s) 42–51

Abstract: Nirmatrelvir is a potent and selective severe acute respiratory syndrome-coronavirus 2 (SARS-CoV-2) main protease inhibitor. Nirmatrelvir co-packaged with ritonavir (as PAXLOVID) received US Food and Drug Administration (FDA) Emergency Use Authorization ( ...

Abstract	Nirmatrelvir is a potent and selective severe acute respiratory syndrome-coronavirus 2 (SARS-CoV-2) main protease inhibitor. Nirmatrelvir co-packaged with ritonavir (as PAXLOVID) received US Food and Drug Administration (FDA) Emergency Use Authorization (EUA) on December 22, 2021, as an oral treatment for coronavirus disease 2019 (COVID-19) and subsequent new drug application approval on May 25, 2023. Pharmacokinetic (PK) capillary blood sampling at-home using Tasso-M20 micro-volumetric sampling device was implemented in the program, including three phase II/III outpatient and several clinical pharmacology studies supporting the EUA. The at-home sampling complemented venous blood sampling procedures to enrich the PK dataset, to decrease the need for patients' site visit for PK sampling, and to allow different sampling approaches for flexibility and convenience. To demonstrate concordance/equivalence, bridging between venous plasma and Tasso dried blood results was conducted by comparing concentrations and derived PK parameters from both sampling approaches. In addition, a two-compartment population PK model was utilized to bridge the plasma and Tasso data by estimating the PK parameters using blood-to-plasma ratio as a slope parameter. Operational challenges were successfully managed to implement at-home PK sampling in global phase II/III trials. Sample quality was generally very good with less than 3% samples deemed as "not usable" from over 800 samples collected in all the studies. Experience gained from sites and patients will guide future broader implementations.
MeSH term(s)	United States ; Humans ; Lactams ; Leucine ; Ritonavir ; Patient-Centered Care
Chemical Substances	nirmatrelvir and ritonavir drug combination ; Lactams ; Leucine (GMW67QNF9C) ; Ritonavir (O3J8G9O825)
Language	English
Publishing date	2023-09-05
Publishing country	United States
Document type	Journal Article
ZDB-ID	123793-7
ISSN	1532-6535 ; 0009-9236
ISSN (online)	1532-6535
ISSN	0009-9236
DOI	10.1002/cpt.3025
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Article ; Online: Disposition of Nirmatrelvir, an Orally Bioavailable Inhibitor of SARS-CoV-2 3C-Like Protease, across Animals and Humans.

Eng, Heather / Dantonio, Alyssa L / Kadar, Eugene P / Obach, R Scott / Di, Li / Lin, Jian / Patel, Nandini C / Boras, Britton / Walker, Gregory S / Novak, Jonathan J / Kimoto, Emi / Singh, Ravi Shankar P / Kalgutkar, Amit S

Drug metabolism and disposition: the biological fate of chemicals

2022 Volume 50, Issue 5, Page(s) 576–590

Abstract: The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) 3C-like protease inhibitor PF-07321332 (nirmatrelvir), in combination with ritonavir (Paxlovid), was recently granted emergency use authorization by multiple regulatory agencies for the ... ...

Abstract	The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) 3C-like protease inhibitor PF-07321332 (nirmatrelvir), in combination with ritonavir (Paxlovid), was recently granted emergency use authorization by multiple regulatory agencies for the treatment of coronavirus disease 2019 (COVID-19) in adults and pediatric patients. Disposition studies on nirmatrelvir in animals and in human reagents, which were used to support clinical studies, are described herein. Plasma clearance was moderate in rats (27.2 ml/min per kg) and monkeys (17.1 ml/min per kg), resulting in half-lives of 5.1 and 0.8 hours, respectively. The corresponding oral bioavailability was moderate in rats (34%-50%) and low in monkeys (8.5%), primarily due to oxidative metabolism along the gastrointestinal tract in this species. Nirmatrelvir demonstrated moderate plasma protein binding in rats, monkeys, and humans with mean unbound fractions ranging from 0.310 to 0.478. The metabolism of nirmatrelvir was qualitatively similar in liver microsomes and hepatocytes from rats, monkeys, and humans; prominent metabolites arose via cytochrome P450 (CYP450)-mediated oxidations on the P1 pyrrolidinone ring, P2 6,6-dimethyl-3-azabicyclo[3.1.0]hexane, and the tertiary-butyl group at the P3 position. Reaction phenotyping studies in human liver microsomes revealed that CYP3A4 was primarily responsible (fraction metabolized = 0.99) for the oxidative metabolism of nirmatrelvir. Minor clearance mechanisms involving renal and biliary excretion of unchanged nirmatrelvir were also noted in animals and in sandwich-cultured human hepatocytes. Nirmatrelvir was a reversible and time-dependent inhibitor as well as inducer of CYP3A activity in vitro. First-in-human pharmacokinetic studies have demonstrated a considerable boost in the oral systemic exposure of nirmatrelvir upon coadministration with the CYP3A4 inhibitor ritonavir, consistent with the predominant role of CYP3A4 in nirmatrelvir metabolism. SIGNIFICANCE STATEMENT: The manuscript describes the preclinical disposition, metabolism, and drug-drug interaction potential of PF-07321332 (nirmatrelvir), an orally active peptidomimetic-based inhibitor of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) 3CL protease, which has been granted emergency use authorization by multiple regulatory agencies around the globe for the treatment of coronavirus disease 2019 (COVID-19) in COVID-19-positive adults and pediatric patients who are at high risk for progression to severe COVID-19, including hospitalization or death.
MeSH term(s)	Administration, Oral ; Animals ; COVID-19/drug therapy ; Child ; Cytochrome P-450 CYP3A/metabolism ; Haplorhini ; Humans ; Lactams ; Leucine ; Microsomes, Liver/metabolism ; Nitriles ; Peptide Hydrolases/metabolism ; Proline ; Rats ; Ritonavir/metabolism ; SARS-CoV-2
Chemical Substances	Lactams ; Nitriles ; nirmatrelvir (7R9A5P7H32) ; Proline (9DLQ4CIU6V) ; Cytochrome P-450 CYP3A (EC 1.14.14.1) ; Peptide Hydrolases (EC 3.4.-) ; Leucine (GMW67QNF9C) ; Ritonavir (O3J8G9O825)
Language	English
Publishing date	2022-02-13
Publishing country	United States
Document type	Journal Article
ZDB-ID	186795-7
ISSN	1521-009X ; 0090-9556
ISSN (online)	1521-009X
ISSN	0090-9556
DOI	10.1124/dmd.121.000801
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Article ; Online: Metabolism and Excretion of Nirmatrelvir in Humans Using Quantitative Fluorine Nuclear Magnetic Resonance Spectroscopy: A Novel Approach for Accelerating Drug Development.

Singh, Ravi Shankar P / Walker, Gregory S / Kadar, Eugene P / Cox, Loretta M / Eng, Heather / Sharma, Raman / Bergman, Arthur J / Van Eyck, Lien / Hackman, Frances / Toussi, Sima S / Kalgutkar, Amit S / Obach, R Scott

Clinical pharmacology and therapeutics

2022 Volume 112, Issue 6, Page(s) 1201–1206

Abstract: Typically human absorption, distribution, metabolism, and excretion (ADME) studies are executed using radiolabeled (e.g., carbon-14) material, the synthesis of which is a time-consuming activity. In this study, we were able to assess the metabolism and ... ...

Abstract	Typically human absorption, distribution, metabolism, and excretion (ADME) studies are executed using radiolabeled (e.g., carbon-14) material, the synthesis of which is a time-consuming activity. In this study, we were able to assess the metabolism and excretion of unlabeled nirmatrelvir (PF-07321332) within the first-in-human study via a novel application of quantitative fluorine (
MeSH term(s)	Humans ; Fluorine ; Carbon Radioisotopes ; Drug Development ; Magnetic Resonance Spectroscopy ; Administration, Oral
Chemical Substances	Fluorine (284SYP0193) ; nirmatrelvir (7R9A5P7H32) ; Carbon Radioisotopes
Language	English
Publishing date	2022-06-29
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123793-7
ISSN	1532-6535 ; 0009-9236
ISSN (online)	1532-6535
ISSN	0009-9236
DOI	10.1002/cpt.2683
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Article ; Online: Innovative Randomized Phase I Study and Dosing Regimen Selection to Accelerate and Inform Pivotal COVID-19 Trial of Nirmatrelvir.

Singh, Ravi Shankar P / Toussi, Sima S / Hackman, Frances / Chan, Phylinda L / Rao, Rohit / Allen, Richard / Van Eyck, Lien / Pawlak, Sylvester / Kadar, Eugene P / Clark, Frances / Shi, Haihong / Anderson, Annaliesa S / Binks, Michael / Menon, Sandeep / Nucci, Gianluca / Bergman, Arthur

Clinical pharmacology and therapeutics

2022 Volume 112, Issue 1, Page(s) 101–111

Abstract: Coronavirus disease 2019 (COVID-19) is a continued leading cause of hospitalization and death. Safe, efficacious COVID-19 antivirals are needed urgently. Nirmatrelvir (PF-07321332), the first orally bioavailable, severe acute respiratory syndrome- ... ...

Abstract	Coronavirus disease 2019 (COVID-19) is a continued leading cause of hospitalization and death. Safe, efficacious COVID-19 antivirals are needed urgently. Nirmatrelvir (PF-07321332), the first orally bioavailable, severe acute respiratory syndrome-coronavirus 2 (SARS-CoV-2) M
MeSH term(s)	Antiviral Agents/pharmacokinetics ; Humans ; Lactams ; Leucine ; Nitriles ; Proline ; Ritonavir ; SARS-CoV-2 ; COVID-19 Drug Treatment
Chemical Substances	Antiviral Agents ; Lactams ; Nitriles ; nirmatrelvir (7R9A5P7H32) ; Proline (9DLQ4CIU6V) ; Leucine (GMW67QNF9C) ; Ritonavir (O3J8G9O825)
Language	English
Publishing date	2022-05-04
Publishing country	United States
Document type	Clinical Trial, Phase I ; Journal Article ; Randomized Controlled Trial ; Research Support, Non-U.S. Gov't
ZDB-ID	123793-7
ISSN	1532-6535 ; 0009-9236
ISSN (online)	1532-6535
ISSN	0009-9236
DOI	10.1002/cpt.2603
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