Details of the Drug

General Information of Drug (ID: DMJ0QOW)

Drug Name

Rilpivirine

Synonyms

500287-72-9; TMC278; Edurant; TMC 278; UNII-FI96A8X663; R278474; TMC-278; 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile; CHEBI:68606; FI96A8X663; R 278474; 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile; (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile; (E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile; W-202888; RPV; Mu O-conotoxin

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus infection	1C62	Approved	[1]
Pain	MG30-MG3Z	Investigative	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

366.4

Logarithm of the Partition Coefficient (xlogp)

4.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 2235 +/- 851 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 247 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 3-4 h [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance: The total clearance of drug is 6.89-8.66 L/h [3]
Elimination: Rilpivirine is 85% eliminated in the feces and 6.1% eliminated in the urine [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 34 - 55 hours [6]
Metabolism: The drug is metabolized via the CYP3A4 and CYP3A5 to the hydroxylated metabolites [7]
Vd: The volume of distribution (Vd) of drug is 152-173 L [3]

Chemical Identifiers

Formula: C22H18N6
IUPAC Name: 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
Canonical SMILES: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N
InChI: InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
InChIKey: YIBOMRUWOWDFLG-ONEGZZNKSA-N

Cross-matching ID

PubChem CID: 6451164
ChEBI ID: CHEBI:68606
CAS Number: 500287-72-9
DrugBank ID: DB08864
TTD ID: D0T6WN
INTEDE ID: DR1424
ACDINA ID: D00594

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 Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Inhibitor	[8]
Voltage-gated sodium channel alpha Nav1.8 (SCN10A)	TT90XZ8	SCNAA_HUMAN	Inhibitor	[2]

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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	[9]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[10]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[11]
UDP-glucuronosyltransferase 1A4 (UGT1A4)	DELOY3P	UD14_HUMAN	Substrate	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Human immunodeficiency virus infection

ICD Disease Classification

1C62

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Voltage-gated sodium channel alpha Nav1.8 (SCN10A)	DTT	SCN10A	9.89E-01	-0.16	-0.31
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DME	UGT1A1	3.80E-01	-9.11E-03	-3.47E-02
Mephenytoin 4-hydroxylase (CYP2C19)	DME	CYP2C19	1.65E-02	-4.37E-02	-7.84E-02
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	6.90E-01	2.35E-02	7.88E-02

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Rilpivirine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Fostemsavir	DM50ILT	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Fostemsavir.	Human immunodeficiency virus disease [1C60-1C62]	[12]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Rilpivirine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[13]
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Coadministration of a Drug Treating the Disease Different from Rilpivirine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Rilpivirine and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Metreleptin	DM1NOEK	Moderate	Increased metabolism of Rilpivirine caused by Metreleptin mediated induction of CYP450 enzyme.	Acute diabete complication [5A2Y]	[13]
Ivosidenib	DM8S6T7	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Ivosidenib.	Acute myeloid leukaemia [2A60]	[14]
Arn-509	DMT81LZ	Major	Increased metabolism of Rilpivirine caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[15]
Gilteritinib	DMTI0ZO	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Gilteritinib.	Acute myeloid leukaemia [2A60]	[16]
Ivabradine	DM0L594	Major	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Ivabradine.	Angina pectoris [BA40]	[17]
Bedaquiline	DM3906J	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[18]
Levalbuterol	DM5YBO1	Moderate	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Levalbuterol.	Asthma [CA23]	[19]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Rilpivirine and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[20]
Eribulin	DM1DX4Q	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Eribulin.	Breast cancer [2C60-2C6Y]	[21]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Rilpivirine caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
Palbociclib	DMD7L94	Moderate	Decreased metabolism of Rilpivirine caused by Palbociclib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[13]
PF-04449913	DMSB068	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and PF-04449913.	Chronic myelomonocytic leukaemia [2A40]	[22]
Olodaterol	DM62B78	Moderate	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Olodaterol.	Chronic obstructive pulmonary disease [CA22]	[23]
Vilanterol	DMF5EK1	Moderate	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Vilanterol.	Chronic obstructive pulmonary disease [CA22]	[19]
Osilodrostat	DMIJC9X	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Osilodrostat.	Cushing syndrome [5A70]	[17]
Lumacaftor	DMCLWDJ	Major	Increased metabolism of Rilpivirine caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[24]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Rilpivirine caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[13]
SODIUM CITRATE	DMHPD2Y	Moderate	Decreased absorption of Rilpivirine due to altered gastric pH caused by SODIUM CITRATE.	Discovery agent [N.A.]	[15]
Deutetrabenazine	DMUPFLI	Moderate	Additive CNS depression effects by the combination of Rilpivirine and Deutetrabenazine.	Dystonic disorder [8A02]	[25]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Rilpivirine caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[13]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Rilpivirine and Cannabidiol.	Epileptic encephalopathy [8A62]	[17]
Tazemetostat	DMWP1BH	Moderate	Increased metabolism of Rilpivirine caused by Tazemetostat mediated induction of CYP450 enzyme.	Follicular lymphoma [2A80]	[13]
Boceprevir	DMBSHMF	Moderate	Decreased metabolism of Rilpivirine caused by Boceprevir mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[26]
ABT-450	DMFW860	Major	Decreased metabolism of Rilpivirine caused by ABT-450 mediated inhibition of CYP450 enzyme.	Hepatitis virus infection [1E50-1E51]	[15]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Rilpivirine and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[27]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Rilpivirine and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[21]
Sodium zirconium cyclosilicate	DMCSLZ4	Moderate	Decreased absorption of Rilpivirine due to altered gastric pH caused by Sodium zirconium cyclosilicate.	Hyperkalaemia [5C76]	[17]
Lesinurad	DMUR64T	Moderate	Increased metabolism of Rilpivirine caused by Lesinurad mediated induction of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[13]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Rilpivirine caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[13]
Suvorexant	DM0E6S3	Moderate	Decreased metabolism of Rilpivirine caused by Suvorexant mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[13]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[17]
Glycerol phenylbutyrate	DMDGRQO	Moderate	Increased metabolism of Rilpivirine caused by Glycerol phenylbutyrate mediated induction of CYP450 enzyme.	Liver disease [DB90-DB9Z]	[13]
Crizotinib	DM4F29C	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Crizotinib.	Lung cancer [2C25]	[28]
Brigatinib	DM7W94S	Moderate	Increased metabolism of Rilpivirine caused by Brigatinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[13]
Ceritinib	DMB920Z	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Ceritinib.	Lung cancer [2C25]	[21]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Rilpivirine caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[29]
Osimertinib	DMRJLAT	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Osimertinib.	Lung cancer [2C25]	[30]
Selpercatinib	DMZR15V	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Selpercatinib.	Lung cancer [2C25]	[17]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Rilpivirine and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[31]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Rilpivirine and Idelalisib.	Mature B-cell leukaemia [2A82]	[32]
Vemurafenib	DM62UG5	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Vemurafenib.	Melanoma [2C30]	[21]
LGX818	DMNQXV8	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and LGX818.	Melanoma [2C30]	[33]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Rilpivirine caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[13]
Siponimod	DM2R86O	Major	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Siponimod.	Multiple sclerosis [8A40]	[13]
Fingolimod	DM5JVAN	Major	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Fingolimod.	Multiple sclerosis [8A40]	[21]
Ozanimod	DMT6AM2	Major	Increased risk of ventricular arrhythmias by the combination of Rilpivirine and Ozanimod.	Multiple sclerosis [8A40]	[34]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Rilpivirine caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[13]
Entrectinib	DMMPTLH	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Entrectinib.	Non-small cell lung cancer [2C25]	[13]
Rucaparib	DM9PVX8	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Rucaparib.	Ovarian cancer [2C73]	[21]
Triclabendazole	DMPWGBR	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Triclabendazole.	Parasitic worm infestation [1F90]	[21]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Rilpivirine caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[35]
Macimorelin	DMQYJIR	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Macimorelin.	Pituitary gland disorder [5A60-5A61]	[36]
Lefamulin	DME6G97	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Lefamulin.	Pneumonia [CA40]	[37]
Enzalutamide	DMGL19D	Major	Increased metabolism of Rilpivirine caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[15]
Relugolix	DMK7IWL	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Relugolix.	Prostate cancer [2C82]	[17]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Rilpivirine caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[13]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Rilpivirine caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[17]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Rilpivirine caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[13]
LEE011	DMMX75K	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and LEE011.	Solid tumour/cancer [2A00-2F9Z]	[21]
Pitolisant	DM8RFNJ	Moderate	Increased risk of prolong QT interval by the combination of Rilpivirine and Pitolisant.	Somnolence [MG42]	[17]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Rilpivirine caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[38]
Cabozantinib	DMIYDT4	Major	Increased risk of prolong QT interval by the combination of Rilpivirine and Cabozantinib.	Thyroid cancer [2D10]	[17]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Rilpivirine caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[13]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Carmellose sodium	E00625	Not Available	Disintegrant
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polysorbate 20	E00664	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
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⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Rilpivirine 25 mg tablet	25 mg	Oral Tablet	Oral
Rilpivirine Hydrochloride eq 25mg base tablet	eq 25mg base	Tablet	Oral

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References

1	2011 FDA drug approvals. Nat Rev Drug Discov. 2012 Feb 1;11(2):91-4.
2	Structures of muO-conotoxins from Conus marmoreus. I nhibitors of tetrodotoxin (TTX)-sensitive and TTX-resistant sodium channels in mammalian senso... J Biol Chem. 2004 Jun 11;279(24):25774-82.
3	Australian Government: Australian Public Assessment Report for Rilpivirine
4	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
5	FDA Approved Drug Products: Edurant (rilpivirine) oral tablets
6	Safety, efficacy, and pharmacokinetics of rilpivirine: systematic review with an emphasis on resource-limited settings. HIV AIDS (Auckl). 2011;3:35-44. doi: 10.2147/HIV.S14559. Epub 2011 Apr 28.
7	Duffey H, Firszt R: Management of acute attacks of hereditary angioedema: role of ecallantide. J Blood Med. 2015 Apr 16;6:115-23. doi: 10.2147/JBM.S66825. eCollection 2015.
8	Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
9	Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7.
10	Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79.
11	Population pharmacokinetics and pharmacogenetics analysis of rilpivirine in HIV-1-infected individuals. Antimicrob Agents Chemother. 2016 Dec 27;61(1).
12	Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC.
13	Cerner Multum, Inc. "Australian Product Information.".
14	Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA.
15	Product Information. Edurant (rilpivirine). Tibotec Pharmaceuticals, Titusville, NJ.
16	Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL.
17	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
18	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
19	Product Information. Arcapta Neohaler (indacaterol). Novartis Pharmaceuticals, East Hanover, NJ.
20	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
21	Canadian Pharmacists Association.
22	Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
23	Bengtsson B, Fagerstrom PO "Extrapulmonary effects of terbutaline during prolonged administration." Clin Pharmacol Ther 31 (1982): 726-32. [PMID: 7042176]
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25	Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
26	Product Information. Victrelis (boceprevir). Schering-Plough Corporation, Kenilworth, NJ.
27	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
28	Product Information. Xalkori (crizotinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
29	Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
30	Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
31	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]
32	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
33	Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
34	Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
35	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
36	Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.
37	Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
38	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.