General Information of Drug (ID: DMC3JST)

Drug Name
Clorazepate
Synonyms
Chlorazepate; Tranxene; Cchlorazepic acid; Chlorazepic acid; Clorazepate dipotassium; Clorazepic acid; Clorazepic acid [BAN]; Gen-xene; Novo-Clopate; Tranxene (Cherazepate dipotasium); Tranxene (TN); Novo-Clopate (TN); (Chloromethyl)(dimethyl)(tridecyloxy)silane; 7-Chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid; 7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid; 7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid
Indication
Disease Entry ICD 11 Status REF
Anxiety disorder 6B00-6B0Z Approved [1], [2]
Therapeutic Class
Hypnotics and Sedatives
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 314.72
Topological Polar Surface Area (xlogp) 3.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
91% of drug becomes completely available to its intended biological destination(s) [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.1 mL/min/kg [5]
Elimination
0.5% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 40 - 50 hours [5]
Metabolism
The drug is metabolized via the liver [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 5.44685 micromolar/kg/day [7]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.2 L/kg [5]
Chemical Identifiers
Formula
C16H11ClN2O3
IUPAC Name
7-chloro-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-3-carboxylic acid
Canonical SMILES
C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)C(=O)O
InChI
InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)
InChIKey
XDDJGVMJFWAHJX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2809
ChEBI ID
CHEBI:3761
CAS Number
23887-31-2
DrugBank ID
DB00628
TTD ID
D0P3JU
INTEDE ID
DR0358
ACDINA ID
D00143

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Translocator protein (TSPO) TTPTXIN TSPO_HUMAN Modulator [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME
DE4LYSA CP3A4_HUMAN Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Clorazepate (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Sodium bicarbonate DMMU6BJ Minor Altered absorption of Clorazepate due to GI dynamics variation caused by Sodium bicarbonate. Acidosis [5C73] [25]
Oliceridine DM6MDCF Major Additive CNS depression effects by the combination of Clorazepate and Oliceridine. Acute pain [MG31] [26]
Dalfopristin DM4LTKV Moderate Decreased metabolism of Clorazepate caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [27]
Clarithromycin DM4M1SG Moderate Decreased metabolism of Clorazepate caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [28]
Lapatinib DM3BH1Y Moderate Decreased metabolism of Clorazepate caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [29]
Dihydrocodeine DMB0FWL Major Additive CNS depression effects by the combination of Clorazepate and Dihydrocodeine. Chronic pain [MG30] [26]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Clorazepate and Olopatadine. Conjunctiva disorder [9A60] [30]
Propofol DMB4OLE Moderate Additive CNS depression effects by the combination of Clorazepate and Propofol. Corneal disease [9A76-9A78] [31]
Alfentanil DMVO0UB Major Additive CNS depression effects by the combination of Clorazepate and Alfentanil. Corneal disease [9A76-9A78] [26]
Remifentanil DMZTXCH Major Additive CNS depression effects by the combination of Clorazepate and Remifentanil. Corneal disease [9A76-9A78] [26]
Mifepristone DMGZQEF Moderate Decreased metabolism of Clorazepate caused by Mifepristone mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [32]
Ivacaftor DMZC1HS Moderate Decreased metabolism of Clorazepate caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [33]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Clorazepate and Ethanol. Cystitis [GC00] [34]
MK-8228 DMOB58Q Moderate Decreased metabolism of Clorazepate caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [35]
Aprepitant DM053KT Moderate Decreased metabolism of Clorazepate caused by Aprepitant mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [36]
Nefazodone DM4ZS8M Moderate Decreased metabolism of Clorazepate caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [37]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Clorazepate and Esketamine. Depression [6A70-6A7Z] [30]
SODIUM CITRATE DMHPD2Y Minor Altered absorption of Clorazepate due to GI dynamics variation caused by SODIUM CITRATE. Discovery agent [N.A.] [25]
Stiripentol DMMSDOY Moderate Decreased metabolism of Clorazepate caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [38]
Fosphenytoin DMOX3LB Moderate Increased metabolism of Clorazepate caused by Fosphenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [39]
Rufinamide DMWE60C Moderate Increased metabolism of Clorazepate caused by Rufinamide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [32]
Ethotoin DMXWOCP Moderate Increased metabolism of Clorazepate caused by Ethotoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [39]
Boceprevir DMBSHMF Moderate Decreased metabolism of Clorazepate caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [40]
Telaprevir DMMRV29 Moderate Decreased metabolism of Clorazepate caused by Telaprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [41]
Isoniazid DM5JVS3 Moderate Decreased metabolism of Clorazepate caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [32]
Rifampin DMA8J1G Minor Increased metabolism of Clorazepate caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [42]
Rifapentine DMCHV4I Moderate Increased metabolism of Clorazepate caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [43]
Fosamprenavir DM4W9B3 Moderate Decreased metabolism of Clorazepate caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [44]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Clorazepate caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [45]
Saquinavir DMG814N Moderate Decreased metabolism of Clorazepate caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [46]
Etravirine DMGV8QU Moderate Increased metabolism of Clorazepate caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [47]
Didanosine DMI2QPE Minor Altered absorption of Clorazepate due to GI dynamics variation caused by Didanosine. Human immunodeficiency virus disease [1C60-1C62] [25]
Amprenavir DMLMXE0 Moderate Decreased metabolism of Clorazepate caused by Amprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [44]
Darunavir DMN3GCH Moderate Decreased metabolism of Clorazepate caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [48]
Conivaptan DM1V329 Moderate Decreased metabolism of Clorazepate caused by Conivaptan mediated inhibition of CYP450 enzyme. Hypo-osmolality/hyponatraemia [5C72] [49]
Probenecid DMMFWOJ Minor Decreased metabolism of Clorazepate caused by Probenecid. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [50]
Brigatinib DM7W94S Moderate Increased metabolism of Clorazepate caused by Brigatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [51]
PF-06463922 DMKM7EW Moderate Increased metabolism of Clorazepate caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [32]
Selpercatinib DMZR15V Moderate Decreased metabolism of Clorazepate caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [52]
Idelalisib DM602WT Moderate Decreased metabolism of Clorazepate caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [53]
IPI-145 DMWA24P Moderate Decreased metabolism of Clorazepate caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [54]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Clorazepate caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [32]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Clorazepate and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [51]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Clorazepate and Lasmiditan. Migraine [8A80] [55]
Exjade DMHPRWG Moderate Decreased metabolism of Clorazepate caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [56]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Clorazepate and Flibanserin. Mood disorder [6A60-6E23] [30]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Clorazepate and Thalidomide. Multiple myeloma [2A83] [30]
Fedratinib DM4ZBK6 Moderate Decreased metabolism of Clorazepate caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [57]
Dasatinib DMJV2EK Moderate Decreased metabolism of Clorazepate caused by Dasatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [46]
Modafinil DMYILBE Minor Increased metabolism of Clorazepate caused by Modafinil mediated induction of CYP450 enzyme. Narcolepsy [7A20] [58]
Teduglutide DMYOAKS Moderate Altered absorption of Clorazepate caused by Teduglutide. Neonatal malabsorption syndrome [KB89] [59]
Levomethadyl Acetate DM06HG5 Major Additive CNS depression effects by the combination of Clorazepate and Levomethadyl Acetate. Opioid use disorder [6C43] [26]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Clorazepate and Apraclonidine. Optic nerve disorder [9C40] [60]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Clorazepate caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [61]
Pentazocine DM1XBHS Major Additive CNS depression effects by the combination of Clorazepate and Pentazocine. Pain [MG30-MG3Z] [26]
Dextropropoxyphene DM23HCX Major Additive CNS depression effects by the combination of Clorazepate and Dextropropoxyphene. Pain [MG30-MG3Z] [62]
Oxymorphone DM65AGJ Major Additive CNS depression effects by the combination of Clorazepate and Oxymorphone. Pain [MG30-MG3Z] [26]
Levorphanol DMGS80V Major Additive CNS depression effects by the combination of Clorazepate and Levorphanol. Pain [MG30-MG3Z] [26]
Dezocine DMJDB0Y Major Additive CNS depression effects by the combination of Clorazepate and Dezocine. Pain [MG30-MG3Z] [26]
Nalbuphine DMOSQGU Major Additive CNS depression effects by the combination of Clorazepate and Nalbuphine. Pain [MG30-MG3Z] [26]
Buprenorphine DMPRI8G Major Additive CNS depression effects by the combination of Clorazepate and Buprenorphine. Pain [MG30-MG3Z] [63]
Hydrocodone DMQ2JO5 Major Additive CNS depression effects by the combination of Clorazepate and Hydrocodone. Pain [MG30-MG3Z] [26]
Abametapir DM2RX0I Moderate Decreased metabolism of Clorazepate caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [64]
Lefamulin DME6G97 Moderate Decreased metabolism of Clorazepate caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [29]
Enzalutamide DMGL19D Moderate Increased metabolism of Clorazepate caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [65]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Clorazepate and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [66]
Fentanyl DM8WAHT Major Additive CNS depression effects by the combination of Clorazepate and Fentanyl. Sensation disturbance [MB40] [26]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Clorazepate caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [32]
Armodafinil DMGB035 Minor Increased metabolism of Clorazepate caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [58]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Clorazepate caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [67]
Tizanidine DMR2IQ4 Moderate Additive CNS depression effects by the combination of Clorazepate and Tizanidine. Tonus and reflex abnormality [MB47] [30]
Sirolimus DMGW1ID Moderate Increased plasma concentrations of Clorazepate and Sirolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [66]
Tacrolimus DMZ7XNQ Moderate Increased plasma concentrations of Clorazepate and Tacrolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [66]
Amiodarone DMUTEX3 Minor Potentiate the pharmacologic effects by the combination of Clorazepate and Amiodarone. Ventricular tachyarrhythmia [BC71] [68]
⏷ Show the Full List of 74 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
FD&C blue no. 2 E00446 2723854 Colorant
Potassium chloride E00074 4873 Tonicity agent
FD&C red no. 3 E00629 Not Available Colorant
Magnesium oxide E00232 14792 Anticaking agent; Diluent; Emulsifying agent; Glidant; Tonicity agent
Magnesium stearate E00208 11177 lubricant
Potassium carbonate E00211 11430 Alkalizing agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Clorazepate 15 mg tablet 15 mg Oral Tablet Oral
Clorazepate 3.75 mg tablet 3.75 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7548).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 071852.
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
7 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
8 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
9 In vitro drug allergy detection system incorporating human liver microsomes in chlorazepate-induced skin rash: drug-specific proliferation associated with interleukin-5 secretion. Br J Dermatol. 2001 Feb;144(2):316-20.
10 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
11 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
12 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
13 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
14 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
15 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
16 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
17 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
18 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
19 Translocator protein (18 kDa) mediates the pro-growth effects of diazepam on Ehrlich tumor cells in vivo. Eur J Pharmacol. 2010 Jan 25;626(2-3):131-8.
20 Comparison of five benzodiazepine-receptor agonists on buprenorphine-induced mu-opioid receptor regulation. J Pharmacol Sci. 2009 May;110(1):36-46.
21 Effects of the combination of metyrapone and oxazepam on cocaine and food self-administration in rats. Pharmacol Biochem Behav. 2008 Nov;91(1):181-9.
22 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2879).
23 Effects of benzodiazepines and non-benzodiazepine compounds on the GABA-induced response in frog isolated sensory neurones. Br J Pharmacol. 1989 Nov;98(3):735-40.
24 New hypnotics: perspectives from sleep physiology. Vertex. 2007 Jul-Aug;18(74):294-9.
25 Greenblatt DJ, Allen MD, MacLaughlin DS, Harmatz JS, Shader RI "Diazepam absorption: effect of antacids and food." Clin Pharmacol Ther 24 (1978): 600-9. [PMID: 699484]
26 US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
27 Product Information. Synercid (dalfopristin-quinupristin) Rhone-Poulenc Rorer, Collegeville, PA.
28 Mattila MJ, Idanpaanheikkila JJ, Tornwall M, Vanakoski J "Oral single doses of erythromycin and roxithromycin may increase the effects of midazolam on human performance." Pharmacol Toxicol 73 (1993): 180-5. [PMID: 8265524]
29 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
30 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
31 McClune S, McKay AC, Wright PM, et al "Synergistic interaction between midazolam and propofol." Br J Anaesth 69 (1992): 240-5. [PMID: 1389840]
32 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
33 Lilja JJ, Kivisto KT, Neuvonen PJ "Grapefruit juice-simvastatin interaction: Effect on serum concentrations of simvastatin, simvastatin acid, and HMG-CoA reductase inhibitors." Clin Pharmacol Ther 64 (1998): 477-83. [PMID: 9834039]
34 Divoll M, Greenblatt DJ, Lacasse Y, Shader RI "Benzodiazepine overdosage: plasma concentrations and clinical outcome." Psychopharmacology (Berl) 73 (1981): 381-3. [PMID: 6789361]
35 Product Information. Prevymis (letermovir). Merck &amp Company Inc, Whitehouse Station, NJ.
36 Dresser GK, Spence JD, Bailey DG "Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition." Clin Pharmacokinet 38 (2000): 41-57. [PMID: 10668858]
37 Barbhaiya RH, Shukla UA, Kroboth PD, Greene DS "Coadministration of nefazodone and benzodiazepines: 2. a pharmacokinetic interaction study with triazolam." J Clin Psychopharmacol 15 (1995): 320-6. [PMID: 8830062]
38 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
39 Murphy A, Wilbur K "Phenytoin-diazepam interaction." Ann Pharmacother 37 (2003): 659-63. [PMID: 12708941]
40 Product Information. Victrelis (boceprevir). Schering-Plough Corporation, Kenilworth, NJ.
41 Product Information. Incivek (telaprevir). Vertex Pharmaceuticals, Cambridge, MA.
42 Ochs HR, Greenblatt DJ, Roberts GM, Dengler HJ "Diazepam interaction with antituberculosis drugs." Clin Pharmacol Ther 29 (1981): 671-8. [PMID: 7214796]
43 Product Information. Priftin (rifapentine). Hoechst Marion-Roussel Inc, Kansas City, MO.
44 Product Information. Agenerase (amprenavir). Glaxo Wellcome, Research Triangle Pk, NC.
45 Bailey DG, Dresser GK "Natural products and adverse drug interactions." Can Med Assoc J 170 (2004): 1531-2. [PMID: 15136542]
46 Cerner Multum, Inc. "Australian Product Information.".
47 Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
48 Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ.
49 Gunston GD, Mehta U "Potentially serious drug interactions with grapefruit juice." S Afr Med J 90 (2000): 41. [PMID: 10721388]
50 Abernethy DR, Greenblatt DJ, Ameer B, Shader RI "Probenecid impairment of acetaminophen and lorazepam clearance: direct inhibition of ether glucuronide formation." J Pharmacol Exp Ther 234 (1985): 345-9. [PMID: 4020675]
51 Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):.
52 Product Information. Retevmo (selpercatinib). Lilly, Eli and Company, Indianapolis, IN.
53 Bailey DG, Malcolm J, Arnold O, Spence JD "Grapefruit juice-drug interactions." Br J Clin Pharmacol 46 (1998): 101-10. [PMID: 9723817]
54 Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
55 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
56 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
57 Bailey DG, Arnold JMO, Spence JD "Grapefruit juice and drugs - how significant is the interaction." Clin Pharmacokinet 26 (1994): 91-8. [PMID: 8162660]
58 Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]
59 Hukkinen SK, Varhe A, Olkkola KT, Neuvonen PJ "Plasma concentrations of triazolam are increased by concomitant ingestion of grapefruit juice." Clin Pharmacol Ther 58 (1995): 127-31. [PMID: 7648762]
60 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
61 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
62 Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
63 Schuman-Olivier Z, Hoeppner BB, Weiss RD, Borodovsky J, Shaffer HJ, Albanese MJ "Benzodiazepine use during buprenorphine treatment for opioid dependence: clinical and safety outcomes." Drug Alcohol Depend 132 (2013): 580-6. [PMID: 23688843]
64 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
65 Benoist G, van Oort I, et al "Drug-drug interaction potential in men treated with enzalutamide: Mind the gap." Br J Clin Pharmacol 0 (2017): epub. [PMID: 28881501]
66 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
67 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
68 Kerin NZ, Aragon E, Faitel K, Frumin H, Rubenfire M "Long-term efficacy and toxicity of high- and low-dose amiodarone regimens." J Clin Pharmacol 29 (1989): 418-23. [PMID: 2661600]