Details of the Drug

General Information of Drug (ID: DM70IK5)

Drug Name
Marinol
Synonyms
Dronabinol; TETRAHYDROCANNABINOL; delta9-Tetrahydrocannabinol; delta9-THC; Deltanyne; Dronabinolum; delta-9-tetrahydrocannabinol; Abbott 40566; delta-9-THC; delta(9)-THC; 1972/8/3; delta1-THC; delta(sup 1)-Thc; delta(sup 9)-Thc; 1-trans-delta-9-Tetrahydrocannabinol; THC; Namisol; Dronabinolum [Latin]; 9-tetrahydrocannabinol; delta(9)-Tetrahydrocannabinol; delta(1)-Tetrahydrocannabinol; (-)-delta9-trans-Tetrahydrocannabinol; delta1-Tetrahydrocannabinol; 1-trans-delta9-Tetrahydrocannabinol; delta(9)-Tetrahydrocannibinol; SP; Compassia; Ganja; Hashish; Marincap; MaxEPA; Omegaven; Promega; Relivar; Sonergx; Tetranabinex; Cannabis resin; Drona binol; QCD 84924; SP 104; Tetrahydrocannabinol delta9; CAT-310; DELTA1-THC; DELTA1-Tetrahydrocannabinol;DELTA9-THC; DRG-0138; Delta-THC; Delta1-THC; Delta1-Tetrahydrocannabinol; Delta9-THC; Delta9-Tetrahydrocannabinol; Delta9-Tetrahydrocannabinol solution; Dronabinol [USAN:INN]; Marinol (TN); Pro-Mega;QCD-84924; Trans-tetrahydrocannabinol; DELTA9-trans-Tetrahydrocannabinol; Delta(1)-THC; Delta(1)-Tetrahydrocannabinol; Delta(9)-THC; Delta(9)-Tetrahydrocannabinol; Delta(9)-Tetrahydrocannibinol; Delta(sup 1)-Tetrahydrocannabinol; Delta(sup 1)-Thc; Delta(sup 9)-Tetrahydrocannabinol; Delta(sup 9)-Thc; Delta(sup9)-THC; Delta-9-THC; Delta-9-tetrahydrocannabinol; Delta1-Tetrahydrocannabinol (VAN); Delta9-Tetrahydrocannabinol (VAN); Delta9-trans-Tetrahydrocannabinol; Dronabinol (USP/INN); Omega-3-Fatty acid; THC-delta-9; Trans-delta9-Tetrahydrocannabinol; Cannabinol, tetrahydro-(6CI); Fish oils, n-3 fatty acid-high; Fish oils, omega-3 fatty acid-high; L-delta(sup 1)-tetrahydrocannabinol; L-delta1-trans-Tetrahydrocannabinol; L-trans-delta9-Tetrahydrocannabinol; Trans-delta-9-Tetrahydrocannabinol; Cannabinol, Delta1-tetrahydro-(7CI); Fats and Glyceridic oils, fish, n-3 fatty acid-high; L-delta1-Tetrahydrocannabinol; Trans-DELTA9-Tetrahydrocannabinol; L-delta1-trans-Tetrahydrocannabinol;L-trans-delta9-Tetrahydrocannabinol; Tetrahydrocannabinols (-)-delta1-3,4-trans-form; (-)-DELTA1-Tetrahydrocannabinol; (-)-DELTA9-THC; (-)-DELTA9-Tetrahydrocannabinol; (-)-DELTA9-trans-Tetrahydrocannabinol; (-)-delta(sup9)-trans-Tetrahydrocannabinol; (-)-3,4-trans-Delta1-Tetrahydrocannabinol; (-)-delta(sup 1)-3,4-trans-Tetrahydrocannabinol; (-)-delta1-Tetrahydrocannabinol; (-)-delta9-(trans)-Tetrahydrocannabinol; (-)-delta9-Tetrahydrocannabinol; (-)-trans-DELTA9-Tetrahydrocannabinol; (-)-trans-Delta1-Tetrahydrocannabinol; (-)-trans-Delta9-THC; (-)-trans-delta9-Tetrahydrocannabinol; (L)-delta1-Tetrahydrocannabinol; (l)-delta(sup 1)-Tetrahydrocannabinol; (l)-delta1-Tetrahydrocannabinol; 1-trans-delta(sup9)-tetrahydrocannabinol; 1-trans-D9-Tetrahydrocannabinol; 1-trans-delta(sup 9)-Tetrahydrocannabinol; 14C-DELTA1-Tetrahydrocannabinol; 6H-Dibenzo; 9-delta-Tetrahydrocannabinol; 9-ene-Tetrahydrocannabinol; Delta(9)-tetrahydrocannabinol
Indication
Disease Entry ICD 11 Status REF
Anorexia nervosa cachexia 6B80 Approved [1]
Chemotherapy-induced nausea MD90 Phase 2/3 [2]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 314.5
Topological Polar Surface Area (xlogp) 7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.2 mL/min/kg [4]
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 4 hours [4]
Metabolism
The drug is metabolized via the liver [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.9086 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.05% [4]
Vd
The volume of distribution (Vd) of drug is 10 L/kg [7]
Chemical Identifiers
Formula
C21H30O2
IUPAC Name
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Canonical SMILES
CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O
InChI
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1
InChIKey
CYQFCXCEBYINGO-IAGOWNOFSA-N
Cross-matching ID
PubChem CID
16078
ChEBI ID
CHEBI:66964
CAS Number
1972-08-3
DrugBank ID
DB00470
TTD ID
D0P1FO
INTEDE ID
DR0548
ACDINA ID
D00217

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Agonist [8], [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [10]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [11]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [12]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [13]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [14]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Anorexia nervosa cachexia
ICD Disease Classification 6B80
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cannabinoid receptor 1 (CB1) DTT CNR1 5.59E-02 -0.22 -0.45
Cannabinoid receptor 1 (CB1) DTT CNR1 7.68E-01 -0.06 -0.46
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 6.24E-01 6.79E-02 2.28E-01
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 2.82E-01 -4.18E-02 -2.80E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 7.39E-01 1.54E-02 4.74E-02
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 4.64E-02 -8.21E-02 -7.11E-01
Cytochrome P450 1A1 (CYP1A1) DME CYP1A1 2.32E-01 -3.66E-02 -1.30E-01
Cytochrome P450 1A1 (CYP1A1) DME CYP1A1 6.55E-01 1.27E-02 8.44E-02
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 8.99E-01 -6.93E-03 -1.36E-02
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 9.21E-01 7.31E-03 6.10E-02
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.66E-01 4.25E-02 1.20E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 4.75E-01 5.15E-02 3.64E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 3.26E-01 1.33E-01 1.12E-01
Prostaglandin G/H synthase 1 (COX-1) DME PTGS1 2.34E-01 4.46E-02 4.03E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Marinol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Lapatinib DM3BH1Y Moderate Decreased metabolism of Marinol caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [64]
Alpelisib DMEXMYK Moderate Increased metabolism of Marinol caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [65]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Marinol and Olopatadine. Conjunctiva disorder [9A60] [66]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Marinol and Ethanol. Cystitis [GC00] [66]
Aprepitant DM053KT Moderate Increased metabolism of Marinol caused by Aprepitant mediated induction of CYP450 enzyme. Depression [6A70-6A7Z] [67]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Marinol and Esketamine. Depression [6A70-6A7Z] [68]
Oxcarbazepine DM5PU6O Moderate Increased metabolism of Marinol caused by Oxcarbazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [69]
Brimonidine DMQLT4N Moderate Additive CNS depression effects by the combination of Marinol and Brimonidine. Glaucoma [9C61] [70]
Rifapentine DMCHV4I Moderate Increased metabolism of Marinol caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [71]
Delavirdine DM3NF5G Minor Decreased metabolism of Marinol caused by Delavirdine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [72]
Efavirenz DMC0GSJ Moderate Increased metabolism of Marinol caused by Efavirenz mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [73]
Etravirine DMGV8QU Moderate Increased metabolism of Marinol caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [74]
Ritonavir DMU764S Minor Increased metabolism of Marinol caused by Ritonavir mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [75]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Marinol and Polyethylene glycol. Irritable bowel syndrome [DD91] [76]
Brigatinib DM7W94S Moderate Increased metabolism of Marinol caused by Brigatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [77]
PF-06463922 DMKM7EW Moderate Increased metabolism of Marinol caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [68]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Marinol and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [78]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Marinol and Lasmiditan. Migraine [8A80] [79]
Exjade DMHPRWG Moderate Decreased metabolism of Marinol caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [80]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Marinol and Thalidomide. Multiple myeloma [2A83] [81]
Nilotinib DM7HXWT Moderate Decreased metabolism of Marinol caused by Nilotinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [82]
Modafinil DMYILBE Minor Increased metabolism of Marinol caused by Modafinil mediated induction of CYP450 enzyme. Narcolepsy [7A20] [83]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Marinol and Bupropion. Nicotine use disorder [6C4A] [84]
Levomethadyl Acetate DM06HG5 Major Additive CNS depression effects by the combination of Marinol and Levomethadyl Acetate. Opioid use disorder [6C43] [85]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Marinol and Apraclonidine. Optic nerve disorder [9C40] [70]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Marinol caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [86]
Dextropropoxyphene DM23HCX Major Decreased metabolism of Marinol caused by Dextropropoxyphene mediated inhibition of CYP450 enzyme. Pain [MG30-MG3Z] [87]
Buprenorphine DMPRI8G Major Additive CNS depression effects by the combination of Marinol and Buprenorphine. Pain [MG30-MG3Z] [88]
Biperiden DME78OA Moderate Additive CNS depression effects by the combination of Marinol and Biperiden. Parkinsonism [8A00] [89]
Abametapir DM2RX0I Moderate Decreased metabolism of Marinol caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [90]
Lefamulin DME6G97 Moderate Decreased metabolism of Marinol caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [91]
Bosentan DMIOGBU Moderate Increased metabolism of Marinol caused by Bosentan mediated induction of CYP450 enzyme. Pulmonary hypertension [BB01] [92]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Marinol and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [93]
Larotrectinib DM26CQR Moderate Decreased metabolism of Marinol caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [68]
Armodafinil DMGB035 Minor Increased metabolism of Marinol caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [83]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Marinol caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [94]
Tizanidine DMR2IQ4 Moderate Additive CNS depression effects by the combination of Marinol and Tizanidine. Tonus and reflex abnormality [MB47] [95]
Sirolimus DMGW1ID Moderate Increased plasma concentrations of Marinol and Sirolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [93]
Tacrolimus DMZ7XNQ Moderate Increased plasma concentrations of Marinol and Tacrolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [93]
⏷ Show the Full List of 39 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
Allura red AC dye E00338 33258 Colorant
FD&C blue no. 1 E00263 19700 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Quinoline yellow WS E00309 24671 Colorant
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Eisenoxyd E00585 56841934 Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Water E00035 962 Solvent
⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Dronabinol 2.5 mg capsule 2.5 mg Oral Capsule Oral
Dronabinol 5 mg capsule 5 mg Oral Capsule Oral
Dronabinol 10 mg capsule 10 mg Oral Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018651.
2 Clinical pipeline report, company report or official report of INSYS Therapeutics.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Ciccolini J, Serdjebi C, Peters GJ, Giovannetti E: Pharmacokinetics and pharmacogenetics of Gemcitabine as a mainstay in adult and pediatric oncology: an EORTC-PAMM perspective. Cancer Chemother Pharmacol. 2016 Jul;78(1):1-12. doi: 10.1007/s00280-016-3003-0. Epub 2016 Mar 23.
6 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
7 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
8 Emerging strategies for exploiting cannabinoid receptor agonists as medicines. Br J Pharmacol. 2009 Feb;156(3):397-411.
9 Central side-effects of therapies based on CB1 cannabinoid receptor agonists and antagonists: focus on anxiety and depression. Best Pract Res Clin Endocrinol Metab. 2009 Feb;23(1):133-44.
10 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.
11 CYP2C-catalyzed delta9-tetrahydrocannabinol metabolism: kinetics, pharmacogenetics and interaction with phenytoin. Biochem Pharmacol. 2005 Oct 1;70(7):1096-103.
12 Increasing the intracellular availability of all-trans retinoic acid in neuroblastoma cells. Br J Cancer. 2005 Feb 28;92(4):696-704.
13 Inhibition of cyclosporine and tetrahydrocannabinol metabolism by cannabidiol in mouse and human microsomes. Xenobiotica. 1996 Mar;26(3):275-84.
14 Health control over the feeding of troops on the Western and 3d Belorussian Fronts during the Great Patriotic War years. Voen Med Zh. 1975 Jun;(6):86-8.
15 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.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 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.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 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.
20 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.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 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.
23 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
24 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
25 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
26 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
27 The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
28 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
29 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
30 Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30.
31 Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74.
32 Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
33 Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies. J Med Chem. 1994 Mar 18;37(6):860-7.
34 The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
35 Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
36 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
37 Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
38 Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81.
39 Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62.
40 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
41 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
42 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
43 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
44 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
45 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
46 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
47 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
48 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
49 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
50 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
51 Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
52 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
53 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.
54 Novel 1',1'-chain substituted hexahydrocannabinols: 9-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid r... J Med Chem. 2010 Oct 14;53(19):6996-7010.
55 Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism. J Med Chem. 2008 Nov 13;51(21):6970-9.
56 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
57 Emerging drugs for obesity: linking novel biological mechanisms to pharmaceutical pipelines. Expert Opin Emerg Drugs. 2005 Aug;10(3):643-60.
58 Clinical pipeline report, company report or official report of AstraZeneca (2009).
59 Company report (Gwpharm)
60 Surinabant, a selective cannabinoid receptor type 1 antagonist, inhibits 9-tetrahydrocannabinol-induced central nervous system and heart rate effects in humans.Br J Clin Pharmacol.2013 Jul;76(1):65-77.
61 Clinical pipeline report, company report or official report of Bird Rock Bio.
62 Clinical pipeline report, company report or official report of Affimed Therapeutics.
63 Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis. Expert Opin Emerg Drugs. 2009 Mar;14(1):43-65.
64 Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ.
65 Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
66 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
67 Product Information. Emend (aprepitant). Merck & Company Inc, West Point, PA.
68 Cerner Multum, Inc. "Australian Product Information.".
69 Product Information. Trileptal (oxcarbazepine) Novartis Pharmaceuticals, East Hanover, NJ.
70 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
71 Product Information. Priftin (rifapentine). Hoechst Marion-Roussel Inc, Kansas City, MO.
72 Barry M, Mulcahy F, Merry C, Gibbons S, Back D "Pharmacokinetics and potential interactions amongst antiretroviral agents used to treat patients with HIV infection." Clin Pharmacokinet 36 (1999): 289-304. [PMID: 10320951]
73 Product Information. Sustiva (efavirenz). DuPont Pharmaceuticals, Wilmington, DE.
74 Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
75 Product Information. Norvir (ritonavir). Abbott Pharmaceutical, Abbott Park, IL.
76 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
77 Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
78 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
79 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
80 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
81 Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
82 Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
83 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]
84 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
85 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
86 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
87 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]
88 Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
89 Product Information. Artane (trihexyphenidyl). Lederle Laboratories, Wayne, NJ.
90 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
91 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
92 Product Information. Tracleer (bosentan). Acetelion Pharmaceuticals US, Inc, South San Francisco, CA.
93 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
94 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.
95 Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.