Details of the Drug

General Information of Drug (ID: DMN3GCH)

Drug Name

Darunavir

Synonyms

206361-99-1; TMC114; Prezista; TMC-114; UIC-94017; Darunavirum; TMC 114; Darunavirum [INN-Latin]; UNII-YO603Y8113; AIDS073035; CHEMBL1323; (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE; CHEBI:367163; Darunavir-d9; YO603Y8113; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate; NCGC00168773-01; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl; Darunavirum; Darunavir [USAN]; UIC 94017; Prezista(TM); UIC-96017; Darunavir (USAN/INN); Carbamic acid, [(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester; {(1S,2R)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester; [(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester; N-((1S,2R)-3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(330)oct-2-yloxy)carboxamide; [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate; (3-((4-aminobenzenesulfonyl)isobutylamino)-1-benzyl-2-hydroxypropyl)carbamic acid hexahydrofuro(2,3-b)furan-3-yl ester; (3R,3aS,6aR)-Hexahydrofuro(2,3-b)furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate; (3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate; (3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus infection	1C62	Approved	[1]
Human immunodeficiency virus-1 infection	1C62	Phase 3	[2]
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Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

547.7

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 8.1 mg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 6 days [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability: The bioavailability of drug is 73-80% [3]
Clearance: The clearance of drug is 32.8 L/h [5]
Elimination: A mass balance study in healthy volunteers demonstrated that after single dose administration of 400 mg 14C-darunavir, given with 100 mg ritonavir, approximately 79.5% and 13.9% of the administered dose of radiolabeled darunavir was obtained in the feces and urine, respectively [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 15 hours [6]
Metabolism: The drug is metabolized via the hepatic cytochrome enzymes (mainly CYP3A) [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 20.8672 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.05% [9]
Vd: The volume of distribution (Vd) of drug is 206.5 L [10]
Water Solubility: The ability of drug to dissolve in water is measured as 0.15 mg/mL [4]

Chemical Identifiers

Formula: C27H37N3O7S
IUPAC Name: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
Canonical SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
InChI: InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
InChIKey: CJBJHOAVZSMMDJ-HEXNFIEUSA-N

Cross-matching ID

PubChem CID: 213039
ChEBI ID: CHEBI:367163
CAS Number: 206361-99-1
DrugBank ID: DB01264
TTD ID: D03IGH
VARIDT ID: DR00514
INTEDE ID: DR0420
ACDINA ID: D00170

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Protease (HIV PR)	TT5FNQT	POL_HV1B1	Modulator	[11]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[12]
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DT3D8F0	SO1B1_HUMAN	Substrate	[13]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[14]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[15]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Darunavir

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
MK-1439	DM215WE	Minor	Decreased metabolism of Darunavir caused by MK-1439 mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Fostemsavir	DM50ILT	Moderate	Decreased metabolism of Darunavir caused by Fostemsavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[17]
Dolutegravir	DMCZGRE	Minor	Increased metabolism of Darunavir caused by Dolutegravir mediated induction of UGT.	Human immunodeficiency virus disease [1C60-1C62]	[18]
Rilpivirine	DMJ0QOW	Moderate	Decreased metabolism of Darunavir caused by Rilpivirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[19]
Maraviroc	DMTL94F	Major	Decreased metabolism of Darunavir caused by Maraviroc mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[20]
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Coadministration of a Drug Treating the Disease Different from Darunavir (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[21]
Midostaurin	DMI6E0R	Moderate	Decreased metabolism of Darunavir caused by Midostaurin mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[22]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Darunavir caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[23]
Gilteritinib	DMTI0ZO	Moderate	Decreased metabolism of Darunavir caused by Gilteritinib mediated inhibition of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[24]
Oliceridine	DM6MDCF	Major	Decreased metabolism of Darunavir caused by Oliceridine mediated inhibition of CYP450 enzyme.	Acute pain [MG31]	[25]
Ivabradine	DM0L594	Major	Decreased metabolism of Darunavir caused by Ivabradine mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[21]
Dronedarone	DMA8FS5	Major	Decreased metabolism of Darunavir caused by Dronedarone mediated inhibition of CYP450 enzyme.	Angina pectoris [BA40]	[21]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[26]
Cariprazine	DMJYDVK	Moderate	Decreased metabolism of Darunavir caused by Cariprazine mediated inhibition of CYP450 enzyme.	Bipolar disorder [6A60]	[27]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Darunavir and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[28]
Talazoparib	DM1KS78	Moderate	Decreased clearance of Darunavir due to the transporter inhibition by Talazoparib.	Breast cancer [2C60-2C6Y]	[24]
Ixabepilone	DM2OZ3G	Moderate	Decreased metabolism of Darunavir caused by Ixabepilone mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[29]
HKI-272	DM6QOVN	Major	Decreased metabolism of Darunavir caused by HKI-272 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[30]
LY2835219	DM93VBZ	Moderate	Decreased metabolism of Darunavir caused by LY2835219 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[31]
Esterified estrogens	DM9KZDO	Moderate	Decreased metabolism of Darunavir caused by Esterified estrogens mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[19]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Darunavir caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[32]
Palbociclib	DMD7L94	Moderate	Decreased metabolism of Darunavir caused by Palbociclib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[24]
Quinestrol	DMJ6H1Z	Moderate	Decreased metabolism of Darunavir caused by Quinestrol mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[19]
Cabazitaxel	DMPAZHC	Moderate	Decreased metabolism of Darunavir caused by Cabazitaxel mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[33]
Bosutinib	DMTI8YE	Major	Decreased metabolism of Darunavir caused by Bosutinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[21]
Macitentan	DMP79A1	Moderate	Decreased metabolism of Darunavir caused by Macitentan mediated inhibition of CYP450 enzyme.	Cardiovascular disease [BA00-BE2Z]	[34]
PF-04449913	DMSB068	Moderate	Decreased metabolism of Darunavir caused by PF-04449913 mediated inhibition of CYP450 enzyme.	Chronic myelomonocytic leukaemia [2A40]	[35]
Revefenacin	DMMP5SI	Moderate	Decreased clearance of Darunavir due to the transporter inhibition by Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[36]
Indacaterol	DMQJHR7	Minor	Decreased metabolism of Darunavir caused by Indacaterol mediated inhibition of CYP450 enzyme.	Chronic obstructive pulmonary disease [CA22]	[37]
Dihydrocodeine	DMB0FWL	Moderate	Decreased metabolism of Darunavir caused by Dihydrocodeine mediated inhibition of CYP450 enzyme.	Chronic pain [MG30]	[19]
Levonorgestrel	DM1DP7T	Moderate	Decreased metabolism of Darunavir caused by Levonorgestrel mediated inhibition of CYP450 enzyme.	Contraceptive management [QA21]	[19]
Ulipristal	DMBNI20	Minor	Decreased metabolism of Darunavir caused by Ulipristal mediated inhibition of CYP450 enzyme.	Contraceptive management [QA21]	[24]
Mestranol	DMG3F94	Moderate	Decreased metabolism of Darunavir caused by Mestranol mediated inhibition of CYP450 enzyme.	Contraceptive management [QA21]	[19]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Darunavir caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[24]
Ivacaftor	DMZC1HS	Major	Decreased metabolism of Darunavir caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[24]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Darunavir caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[38]
Rivaroxaban	DMQMBZ1	Moderate	Decreased metabolism of Darunavir caused by Rivaroxaban mediated inhibition of CYP450 enzyme.	Deep vein thrombosis [BD71]	[21]
Vilazodone	DM4LECQ	Moderate	Decreased metabolism of Darunavir caused by Vilazodone mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[39]
OPC-34712	DMHG57U	Major	Decreased metabolism of Darunavir caused by OPC-34712 mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[40]
Polatuzumab vedotin	DMF6Y0L	Moderate	Decreased metabolism of Darunavir caused by Polatuzumab vedotin mediated inhibition of CYP450 enzyme.	Diffuse large B-cell lymphoma [2A81]	[41]
[3H]estrone-3-sulphate	DMGPF0N	Moderate	Decreased metabolism of Darunavir caused by [3H]estrone-3-sulphate mediated inhibition of CYP450 enzyme.	Discovery agent [N.A.]	[19]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Darunavir caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[23]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Darunavir caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[24]
Fosphenytoin	DMOX3LB	Major	Increased metabolism of Darunavir caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[42]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Darunavir caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[23]
Cannabidiol	DM0659E	Minor	Decreased metabolism of Darunavir caused by Cannabidiol mediated inhibition of CYP450 enzyme.	Epileptic encephalopathy [8A62]	[24]
Bay 80-6946	DMLOS5R	Moderate	Decreased metabolism of Darunavir caused by Bay 80-6946 mediated inhibition of CYP450 enzyme.	Follicular lymphoma [2A80]	[43]
Tazemetostat	DMWP1BH	Major	Decreased metabolism of Darunavir caused by Tazemetostat mediated inhibition of CYP450 enzyme.	Follicular lymphoma [2A80]	[44]
Solifenacin	DMG592Q	Moderate	Decreased metabolism of Darunavir caused by Solifenacin mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[45]
Mirabegron	DMS1GYT	Minor	Decreased metabolism of Darunavir caused by Mirabegron mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[46]
Ripretinib	DM958QB	Moderate	Decreased metabolism of Darunavir caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[21]
Avapritinib	DMK2GZX	Major	Decreased metabolism of Darunavir caused by Avapritinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[24]
Colchicine	DM2POTE	Major	Decreased metabolism of Darunavir caused by Colchicine mediated inhibition of CYP450 enzyme.	Gout [FA25]	[47]
Simeprevir	DMLUA9D	Major	Decreased metabolism of Darunavir caused by Simeprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[21]
Daclatasvir	DMSFK9V	Moderate	Decreased metabolism of Darunavir caused by Daclatasvir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[21]
GS-9857	DMYU6P5	Moderate	Decreased clearance of Darunavir due to the transporter inhibition by GS-9857.	Hepatitis virus infection [1E50-1E51]	[48]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[49]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Darunavir and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[50]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Darunavir and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[42]
BMS-201038	DMQTAGO	Major	Decreased metabolism of Darunavir caused by BMS-201038 mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[21]
Aliskiren	DM1BV7W	Moderate	Decreased metabolism of Darunavir caused by Aliskiren mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[42]
Levamlodipine	DM92S6N	Moderate	Decreased metabolism of Darunavir caused by Levamlodipine mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[42]
Suvorexant	DM0E6S3	Major	Decreased metabolism of Darunavir caused by Suvorexant mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[51]
Amobarbital	DM0GQ8N	Moderate	Increased metabolism of Darunavir caused by Amobarbital mediated induction of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[23]
Tasimelteon	DMLOQ1V	Moderate	Decreased metabolism of Darunavir caused by Tasimelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[52]
ITI-007	DMUQ1DO	Major	Decreased metabolism of Darunavir caused by ITI-007 mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[53]
Naloxegol	DML0B41	Major	Decreased metabolism of Darunavir caused by Naloxegol mediated inhibition of CYP450 enzyme.	Large intestine motility disorder [DB32]	[21]
Pemigatinib	DM819JF	Major	Decreased metabolism of Darunavir caused by Pemigatinib mediated inhibition of CYP450 enzyme.	Liver cancer [2C12]	[24]
Crizotinib	DM4F29C	Moderate	Decreased metabolism of Darunavir caused by Crizotinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[54]
Brigatinib	DM7W94S	Major	Decreased metabolism of Darunavir caused by Brigatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[21]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Darunavir caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[55]
Lurbinectedin	DMEFRTZ	Major	Decreased metabolism of Darunavir caused by Lurbinectedin mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[56]
Osimertinib	DMRJLAT	Moderate	Decreased metabolism of Darunavir caused by Osimertinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[57]
Pralsetinib	DMWU0I2	Moderate	Decreased metabolism of Darunavir caused by Pralsetinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[58]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Darunavir caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[59]
Selpercatinib	DMZR15V	Major	Decreased metabolism of Darunavir caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[24]
Artemether	DM48QOT	Major	Decreased metabolism of Darunavir caused by Artemether mediated inhibition of CYP450 enzyme.	Malaria [1F40-1F45]	[21]
Hydroxychloroquine	DMSIVND	Moderate	Decreased metabolism of Darunavir caused by Hydroxychloroquine mediated inhibition of CYP450 enzyme.	Malaria [1F40-1F45]	[21]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[60]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Idelalisib.	Mature B-cell leukaemia [2A82]	[61]
GDC-0199	DMH0QKA	Major	Decreased metabolism of Darunavir caused by GDC-0199 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[21]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Darunavir caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[62]
Ibrutinib	DMHZCPO	Major	Decreased metabolism of Darunavir caused by Ibrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[63]
Vemurafenib	DM62UG5	Moderate	Increased metabolism of Darunavir caused by Vemurafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[23]
Selumetinib	DMC7W6R	Major	Decreased metabolism of Darunavir caused by Selumetinib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[64]
LGX818	DMNQXV8	Major	Decreased metabolism of Darunavir caused by LGX818 mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[65]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Darunavir caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[23]
Rimegepant	DMHOAUG	Moderate	Decreased metabolism of Darunavir caused by Rimegepant mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[66]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Darunavir caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[67]
Flibanserin	DM70DTN	Major	Decreased metabolism of Darunavir caused by Flibanserin mediated inhibition of CYP450 enzyme.	Mood disorder [6A60-6E23]	[68]
Panobinostat	DM58WKG	Moderate	Decreased metabolism of Darunavir caused by Panobinostat mediated inhibition of CYP450 enzyme.	Multiple myeloma [2A83]	[69]
Deflazacort	DMV0RNS	Major	Decreased metabolism of Darunavir caused by Deflazacort mediated inhibition of CYP450 enzyme.	Muscular dystrophy [8C70]	[24]
Fedratinib	DM4ZBK6	Minor	Decreased metabolism of Darunavir caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[24]
Ruxolitinib	DM7Q98D	Minor	Decreased metabolism of Darunavir caused by Ruxolitinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[24]
Entrectinib	DMMPTLH	Major	Decreased metabolism of Darunavir caused by Entrectinib mediated inhibition of CYP450 enzyme.	Non-small cell lung cancer [2C25]	[21]
S-297995	DM26IH8	Moderate	Decreased metabolism of Darunavir caused by S-297995 mediated inhibition of CYP450 enzyme.	Opioid use disorder [6C43]	[24]
Olaparib	DM8QB1D	Major	Decreased metabolism of Darunavir caused by Olaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[21]
Istradefylline	DM20VSK	Moderate	Decreased metabolism of Darunavir caused by Istradefylline mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[70]
Pimavanserin	DMR7IVC	Moderate	Decreased metabolism of Darunavir caused by Pimavanserin mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[71]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Darunavir caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[72]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Darunavir caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[73]
Lonafarnib	DMGM2Z6	Major	Decreased metabolism of Darunavir caused by Lonafarnib mediated inhibition of CYP450 enzyme.	Premature ageing appearance [LD2B]	[74]
Darolutamide	DMV7YFT	Minor	Decreased metabolism of Darunavir caused by Darolutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[75]
Silodosin	DMJSBT6	Moderate	Decreased metabolism of Darunavir caused by Silodosin mediated inhibition of CYP450 enzyme.	Prostate hyperplasia [GA90]	[76]
Everolimus	DM8X2EH	Major	Decreased clearance of Darunavir due to the transporter inhibition by Everolimus.	Renal cell carcinoma [2C90]	[77]
Axitinib	DMGVH6N	Moderate	Decreased metabolism of Darunavir caused by Axitinib mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[24]
Temsirolimus	DMS104F	Moderate	Decreased metabolism of Darunavir caused by Temsirolimus mediated inhibition of CYP450 enzyme.	Renal cell carcinoma [2C90]	[78]
Ciclesonide	DM2NA4K	Moderate	Decreased metabolism of Darunavir caused by Ciclesonide mediated inhibition of CYP450 enzyme.	Respiratory system disease [CB40-CB7Z]	[79]
Upadacitinib	DM32B5U	Moderate	Decreased metabolism of Darunavir caused by Upadacitinib mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[80]
Tofacitinib	DMBS370	Moderate	Decreased metabolism of Darunavir caused by Tofacitinib mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[21]
Iloperidone	DM6AUFY	Moderate	Decreased metabolism of Darunavir caused by Iloperidone mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[19]
Avanafil	DM75CXN	Major	Decreased metabolism of Darunavir caused by Avanafil mediated inhibition of CYP450 enzyme.	Sexual dysfunction [HA00-HA01]	[81]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Darunavir caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[82]
LDE225	DMM9F25	Major	Decreased metabolism of Darunavir caused by LDE225 mediated inhibition of CYP450 enzyme.	Skin cancer [2C30-2C37]	[83]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Darunavir caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[24]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Darunavir caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[21]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Darunavir and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[24]
Armodafinil	DMGB035	Minor	Decreased metabolism of Darunavir caused by Armodafinil mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[21]
Pitolisant	DM8RFNJ	Moderate	Increased metabolism of Darunavir caused by Pitolisant mediated induction of CYP450 enzyme.	Somnolence [MG42]	[24]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Darunavir caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[84]
Apixaban	DM89JLN	Moderate	Decreased metabolism of Darunavir caused by Apixaban mediated inhibition of CYP450 enzyme.	Thrombosis [DB61-GB90]	[21]
Brilinta	DMBR01X	Moderate	Decreased metabolism of Darunavir caused by Brilinta mediated inhibition of CYP450 enzyme.	Thrombosis [DB61-GB90]	[24]
Cabozantinib	DMIYDT4	Moderate	Decreased metabolism of Darunavir caused by Cabozantinib mediated inhibition of CYP450 enzyme.	Thyroid cancer [2D10]	[85]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Darunavir caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[23]
Fluticasone	DMGCSVF	Moderate	Decreased metabolism of Darunavir caused by Fluticasone mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[21]
-----------


⏷ Show the Full List of 120 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Sunset yellow FCF	E00255	17730	Colorant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
--------------------


⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Darunavir 400 mg tablet	400 mg	Oral Tablet	Oral
Darunavir 600 mg tablet	600 mg	Oral Tablet	Oral
Darunavir 800 mg tablet	800 mg	Oral Tablet	Oral
Darunavir 150 mg tablet	150 mg	Oral Tablet	Oral
Darunavir 75 mg tablet	75 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3	FDA Approves ILUMYA (tildrakizumab-asmn) for the Treatment of Adults with Moderate-To-Severe Plaque Psoriasis Who Are Candidates for Systemic Therapy or Phototherapy
4	BDDCS applied to over 900 drugs
5	Vermeir M, Lachau-Durand S, Mannens G, Cuyckens F, van Hoof B, Raoof A: Absorption, metabolism, and excretion of darunavir, a new protease inhibitor, administered alone and with low-dose ritonavir in healthy subjects. Drug Metab Dispos. 2009 Apr;37(4):809-20. doi: 10.1124/dmd.108.024109. Epub 2009 Jan 8.
6	Darunavir: pharmacokinetics and drug interactions. Antivir Ther. 2008;13(1):1-13.
7	FDA Approved Drug Products: Prezista (darunavir) oral tablets/suspension
8	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
10	Larson KB, Cressey TR, Yogev R, Wiznia A, Hazra R, Jean-Philippe P, Graham B, Gonzalez A, Britto P, Carey VJ, Acosta EP: Pharmacokinetics of Once-Daily Darunavir/Ritonavir With and Without Etravirine in Human Immunodeficiency Virus-Infected Children, Adolescents, and Young Adults. J Pediatric Infect Dis Soc. 2016 Jun;5(2):131-7. doi: 10.1093/jpids/piu142. Epub 2015 Jan 28.
11	2006 drug approvals: finding the niche. Nat Rev Drug Discov. 2007 Feb;6(2):99-101.
12	P-glycoprotein mediates efflux transport of darunavir in human intestinal Caco-2 and ABCB1 gene-transfected renal LLC-PK1 cell lines. Biol Pharm Bull. 2009 Sep;32(9):1588-93.
13	Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
14	Impact of drug transporters on cellular resistance towards saquinavir and darunavir. J Antimicrob Chemother. 2010 Nov;65(11):2319-28.
15	Drug interactions with new and investigational antiretrovirals. Clin Pharmacokinet. 2009;48(4):211-41.
16	Product Information. Pifeltro (doravirine). Merck & Company Inc, Whitehouse Station, NJ.
17	Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC.
18	Product Information. Tivicay (dolutegravir). ViiV Healthcare, Research Triangle Park, NC.
19	Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ.
20	Product Information. Selzentry (maraviroc). Pfizer U.S. Pharmaceuticals Group, New York, NY.
21	Cerner Multum, Inc. "Australian Product Information.".
22	Dutreix C, Munarini F, Lorenzo S, Roesel J, Wang Y "Investigation into CYP3A4-mediated drug-drug interactions on midostaurin in healthy volunteers." Cancer Chemother Pharmacol 72 (2013): 1223-34. [PMID: 24085261]
23	Acosta EP, Henry K, Baken L, Page LM, Fletcher CV "Indinavir concentrations and antiviral effect." Pharmacotherapy 19 (1999): 708-12. [PMID: 10391416]
24	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
25	Product Information. Olinvyk (oliceridine). Trevena Inc, Chesterbrook, PA.
26	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
27	Product Information. Vraylar (cariprazine). Actavis Pharma, Inc., Parsippany, NJ.
28	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
29	Product Information. Ixempra (ixabepilone). Bristol-Myers Squibb, Princeton, NJ.
30	Abbas R, Hug BA, Leister C, Burns J, Sonnichsen D "Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects." Br J Clin Pharmacol 71 (2011): 522-7. [PMID: 21395644]
31	Product Information. Verzenio (abemaciclib). Lilly, Eli and Company, Indianapolis, IN.
32	Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
33	Product Information. Jevtana (cabazitaxel). sanofi-aventis , Bridgewater, NJ.
34	Product Information. Opsumit (macitentan). Actelion Pharmaceuticals US Inc, South San Francisco, CA.
35	Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
36	Product Information. Nexletol (bempedoic acid). Esperion Therapeutics, Ann Arbor, MI.
37	Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
38	Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
39	Product Information. Viibryd (vilazodone). Trovis Pharmaceuticals LLC, New Haven, CT.
40	Product Information. Rexulti (brexpiprazole). Otsuka American Pharmaceuticals Inc, Rockville, MD.
41	Product Information. Polivy (polatuzumab vedotin). Genentech, South San Francisco, CA.
42	Canadian Pharmacists Association.
43	Product Information. Aliqopa (copanlisib). Bayer Pharmaceutical Inc, West Haven, CT.
44	Product Information. Tazverik (tazemetostat). Epizyme, Inc, Cambridge, MA.
45	Product Information. VESIcare (solifenacin). GlaxoSmithKline, Research Triangle Park, NC.
46	Product Information. Myrbetriq (mirabegron). Astellas Pharma US, Inc, Deerfield, IL.
47	Akdag I, Ersoy A, Kahvecioglu S, Gullulu M, Dilek K "Acute colchicine intoxication during clarithromycin administration in patients with chronic renal failure." J Nephrol 19 (2006): 515-7. [PMID: 17048210]
48	Product Information. Vosevi (sofosbuvir/velpatasvir/voxilaprevir). Gilead Sciences, Foster City, CA.
49	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
50	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
51	Product Information. Belsomra (suvorexant). Merck & Company Inc, Whitehouse Station, NJ.
52	Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
53	Product Information. Caplyta (lumateperone). Intra-Cellular Therapies, Inc., New York, NY.
54	Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
55	Product Information. Zykadia (ceritinib). Novartis Pharmaceuticals, East Hanover, NJ.
56	Product Information. Zepzelca (lurbinectedin). Jazz Pharmaceuticals, Palo Alto, CA.
57	Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
58	Product Information. Gavreto (pralsetinib). Blueprint Medicines Corporation, Cambridge, MA.
59	Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
60	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
61	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
62	Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
63	Product Information. Imbruvica (ibrutinib). Pharmacyclics Inc, Sunnyvale, CA.
64	Product Information. Koselugo (selumetinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
65	Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
66	Product Information. Nurtec ODT (rimegepant). Biohaven Pharmaceuticals, New Haven, CT.
67	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
68	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
69	Hamberg P, Woo MM, Chen LC, et al. "Effect of ketoconazole-mediated CYP3A4 inhibition on clinical pharmacokinetics of panobinostat (LBH589), an orally active histone deacetylase inhibitor." Cancer Chemother Pharmacol 68 (2011): 805-13. [PMID: 21706316]
70	Product Information. Nourianz (istradefylline). Kyowa Kirin, Inc, Bedminster, NJ.
71	Product Information. Nuplazid (pimavanserin). Accelis Pharma, East Windsor, NJ.
72	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
73	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
74	Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
75	Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
76	Product Information. Rapaflo (silodosin). Watson Pharmaceuticals, Corona, CA.
77	Product Information. Afinitor (everolimus). Novartis Pharmaceuticals, East Hanover, NJ.
78	Product Information. Torisel (temsirolimus). Wyeth-Ayerst Laboratories, Philadelphia, PA.
79	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
80	Product Information. Rinvoq (upadacitinib). AbbVie US LLC, North Chicago, IL.
81	Product Information. Stendra (avanafil). Vivus Inc, Mountain View, CA.
82	Product Information. Oxbryta (voxelotor). Global Blood Therapeutics, Inc., South San Francisco, CA.
83	Product Information. Odomzo (sonidegib). Novartis Pharmaceuticals, East Hanover, NJ.
84	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
85	Product Information. Cometriq (cabozantinib). Exelixis Inc, S San Francisco, CA.