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darunavir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
HIV protease inhibitors	4143	206361-99-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: darunavir darunavir ethanolate prezista TMC-114 TMC 114 darunavir ethnolate	An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS. There was some evidence of in vitro activity against SARS-CoV-2, but no clinical trial data was found to support use in the treatment of COVID-19. Molecular weight: 547.67 Formula: C27H37N3O7S CLOGP: 2.89 LIPINSKI: 1 HAC: 10 HDO: 3 TPSA: 140.42 ALOGS: -3.91 ROTB: 11 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

darunavir
darunavir ethanolate
prezista
TMC-114
TMC 114
darunavir ethnolate

An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS. There was some evidence of in vitro activity against SARS-CoV-2, but no clinical trial data was found to support use in the treatment of COVID-19.

Molecular weight: 547.67
Formula: C27H37N3O7S
CLOGP: 2.89
LIPINSKI: 1
HAC: 10
HDO: 3
TPSA: 140.42
ALOGS: -3.91
ROTB: 11

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1.20	g	O

ADMET properties:

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Property	Value	Reference
CL (Clearance)	7.81 mL/min/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	37 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	20.87 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	15 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	1.20 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.15 mg/mL	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.05 %	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
Feb. 12, 2007	EMA	Janssen-Cilag International NV
June 23, 2006	FDA	JANSSEN PRODS
Nov. 22, 2007	PMDA	Janssen Pharmaceutical K.K.

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FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Exposure during pregnancy	935.38	27.75	451	8699	155096	63324776
Foetal exposure during pregnancy	837.66	27.75	270	8880	31692	63448180
Abortion spontaneous	741.99	27.75	272	8878	46923	63432949
Maternal exposure during pregnancy	356.17	27.75	276	8874	219786	63260086
Virologic failure	281.38	27.75	63	9087	1799	63478073
Premature labour	244.75	27.75	85	9065	12419	63467453
Premature baby	237.07	27.75	95	9055	20640	63459232
Live birth	214.39	27.75	94	9056	25536	63454336
Drug interaction	209.51	27.75	208	8942	228923	63250949
Treatment noncompliance	204.02	27.75	102	9048	37223	63442649

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome	526.58	15.47	185	16022	8574	34932150
Foetal exposure during pregnancy	474.95	15.47	266	15941	37835	34902889
Lipodystrophy acquired	412.59	15.47	122	16085	3222	34937502
Drug interaction	338.37	15.47	466	15741	225480	34715244
Mitochondrial toxicity	309.19	15.47	93	16114	2606	34938118
Progressive external ophthalmoplegia	294.46	15.47	78	16129	1357	34939367
Virologic failure	294.06	15.47	95	16112	3385	34937339
Eyelid ptosis	247.14	15.47	95	16112	5671	34935053
Viral mutation identified	179.69	15.47	63	16144	2891	34937833
Blood HIV RNA increased	169.86	15.47	49	16158	1181	34939543

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome	620.99	16.19	199	18823	13642	79711724
Drug interaction	572.02	16.19	592	18430	414591	79310775
Virologic failure	563.29	16.19	142	18880	4049	79721317
Abortion spontaneous	538.63	16.19	218	18804	29289	79696077
Lipodystrophy acquired	534.28	16.19	137	18885	4188	79721178
Exposure during pregnancy	510.40	16.19	311	18711	100821	79624545
Viral mutation identified	407.87	16.19	108	18914	3750	79721616
Mitochondrial toxicity	376.57	16.19	97	18925	3017	79722349
Progressive external ophthalmoplegia	350.84	16.19	79	18943	1366	79724000
Pathogen resistance	282.45	16.19	112	18910	14230	79711136

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J05AE10	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Protease inhibitors
ATC	J05AR14	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR22	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
ATC	J05AR26	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Antivirals for treatment of HIV infections, combinations
CHEBI has role	CHEBI:35660	HIV protease inhibitors
CHEBI has role	CHEBI:36044	antiviral drugs
FDA EPC	N0000175889	Protease Inhibitor
FDA MoA	N0000000246	HIV Protease Inhibitors
FDA MoA	N0000182137	Cytochrome P450 2D6 Inhibitors
FDA MoA	N0000190114	Cytochrome P450 3A Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Human immunodeficiency virus infection	indication	86406008	DOID:526
Coronavirus infection	off-label use	186747009
Hypercholesterolemia	contraindication	13644009
Cirrhosis of liver	contraindication	19943007	DOID:5082
Hereditary factor VIII deficiency disease	contraindication	28293008	DOID:12134
Hereditary factor IX deficiency disease	contraindication	41788008	DOID:12259
Hepatic failure	contraindication	59927004
Chronic type B viral hepatitis	contraindication	61977001
Diabetes mellitus	contraindication	73211009	DOID:9351
Hyperglycemia	contraindication	80394007	DOID:4195

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.67	acidic
pKa2	1.64	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
150MG;800MG	PREZCOBIX	JANSSEN PRODS	N205395	Jan. 29, 2015	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV INFECTION IN ADULTS AND PEDIATRIC PATIENTS WEIGHING AT LEAST 40KG USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE
150MG;800MG	PREZCOBIX	JANSSEN PRODS	N205395	Jan. 29, 2015	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV INFECTION USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV-1 INFECTION USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE IN ADULTS WHO ARE VIROLOGICALLY SUPPRESSED ON A STABLE ANTIRETROVIRAL REGIMEN FOR AT LEAST 6 MONTHS
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV-1 INFECTION USING A COMPOSITION CONTAINING A PHARMACOKINETIC ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENASE IN ADULTS WHO HAVE NO PRIOR ANTIRETROVIRAL TREATMENT HISTORY
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV-1 INFECTION USING A COMPOSITION CONTAINING A PK ENHANCER THAT INHIBITS CY P450 MONOXYGENASE IN ADULTS AND PEDIATRIC PATIENTS WEIGHING AT LEAST 40KG WHO ARE VIROLOGICALLY SUPPRESSED ON A STABLE ARV REGIMEN FOR AT LEAST 6 MONTHS
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TREATMENT OF HIV-1 INFECTION USING A COMPOSITION CONTAINING A PK ENHANCER THAT INHIBITS CY P450 MONOXYGENASE IN ADULTS AND PEDIATRIC PATIENTS WEIGHING AT LEAST 40KG WHO HAVE NO PRIOR ARV TREATMENT HISTORY
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TX OF HIV1 INFECTION USING A COMPOSITION CONTAINING A PK ENHANCER THAT INHIBITS CY P450 MONOXYGENASE IN ADULTS & PEDIATRIC PATIENTS AT LEAST 40KG HAVING NO PRIOR ARV TX HISTORY OR ARE VIROLOGICALLY SUPPRESSED ON A STABLE ARV REGIMEN FOR AT LEAST 6 MO
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8148374	Sept. 3, 2029	TX OF HIV-1 INFECTION USING A COMPOSITION CONTAINING A PK ENHANCER THAT INHIBITS CYTOCHROME P450 MONOOXYGENATES IN ADULTS WHO HAVE NO PRIOR ANTIRETROVIRAL TX HISTORY OR ARE VIROLOGICALLY SUPPRESSED ON A STABLE ANTIRETROVIRAL REGIMEN FOR AT LEAST 6 MONTHS
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8754065	Aug. 15, 2032	TREATMENT OF HIV-1 INFECTION IN ADULTS AND PEDIATRIC PATIENTS WEIGHING AT LEAST 40 KG WHO HAVE NO PRIOR ANTIRETROVIRAL TREATMENT HISTORY OR ARE VIROLOGICALLY SUPPRESSED ON A STABLE ANTIRETROVIRAL REGIMEN FOR AT LEAST 6 MONTHS
150MG;800MG;200MG;EQ 10MG BASE	SYMTUZA	JANSSEN PRODS	N210455	July 17, 2018	RX	TABLET	ORAL	8754065	Aug. 15, 2032	TREATMENT OF HIV-1 INFECTION IN ADULTS WHO HAVE NO PRIOR ANTIRETROVIRAL TREATMENT HISTORY OR ARE VIROLOGICALLY SUPPRESSED ON A STABLE ANTIRETROVIRAL REGIMEN FOR AT LEAST 6 MONTHS

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
800MG	DARUNAVIR	LUPIN LTD	A202073	Sept. 29, 2022	RX	TABLET	ORAL	Nov. 28, 2023	PATENT CHALLENGE

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	5.18	CHEMBL
Pol polyprotein	Enzyme		Q72874_9HIV1	INHIBITOR	Ki	10.85	CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein		POL_HV1BR		Ki	9.66	WOMBAT-PK
Protease	Enzyme		Q9YQ12_9HIV1		IC50	10.21	CHEMBL
Protease	Unclassified		O90781_9PLVG		Ki	10.96	CHEMBL
Protease	Unclassified		Q9YQ30_9PLVG		Ki	10.82	CHEMBL

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External reference:

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ID	Source
017	PDB_CHEM_ID
011599	NDDF
011600	NDDF
11243	IUPHAR_LIGAND_ID
213039	PUBCHEM_CID
21619	MMSL
310017	MMSL
4025441	VUID
4025441	VANDF
4025493	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
PREZCOBIX	HUMAN PRESCRIPTION DRUG LABEL	2	50090-1723	TABLET, FILM COATED	800 mg	ORAL	NDA	29 sections
PREZCOBIX	HUMAN PRESCRIPTION DRUG LABEL	2	59676-575	TABLET, FILM COATED	800 mg	ORAL	NDA	30 sections
PREZCOBIX	HUMAN PRESCRIPTION DRUG LABEL	2	59676-575	TABLET, FILM COATED	800 mg	ORAL	NDA	30 sections
PREZCOBIX	HUMAN PRESCRIPTION DRUG LABEL	2	59676-575	TABLET, FILM COATED	800 mg	ORAL	NDA	30 sections
PREZCOBIX	HUMAN PRESCRIPTION DRUG LABEL	2	59676-575	TABLET, FILM COATED	800 mg	ORAL	NDA	30 sections
PREZISTA	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0672	TABLET, FILM COATED	400 mg	ORAL	NDA	31 sections
PREZISTA	HUMAN PRESCRIPTION DRUG LABEL	1	53808-0773	TABLET, FILM COATED	600 mg	ORAL	NDA	31 sections
PREZISTA	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5969	TABLET, FILM COATED	400 mg	ORAL	NDA	31 sections
PREZISTA	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6369	TABLET, FILM COATED	600 mg	ORAL	NDA	31 sections
PREZISTA	HUMAN PRESCRIPTION DRUG LABEL	1	59676-562	TABLET, FILM COATED	600 mg	ORAL	NDA	31 sections

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