Details of the Drug

General Information of Drug (ID: DMCT3I8)

Drug Name
Ifosfamide
Synonyms
Cyfos; Holoxan; Ifex; Ifosfamid; Ifosfamida; Ifosfamidum; Ifosphamide; Ifsofamide; Iphosphamid; Iphosphamide; Isoendoxan; Isofosfamide; Isophosphamide; Isosfamide; Mitoxana; Naxamide; Ifosfamide Sterile; Iso Endoxan; A 4942; ASTA Z 4942; Holoxan 1000; MJF 9325; Z 4942; Z4942; I-Phosphamide; IFEX (TN); Ifex (TN); Ifosfamida [INN-Spanish]; Ifosfamidum [INN-Latin]; Iphosphamid(e); Iso-Endoxan; MJF-9325; Mitoxana (TN); NPFAPI-04; Z-4942; Mitoxana, Ifex, Ifosfamide; Ifosfamide (JAN/USP/INN); Ifosfamide [USAN:INN:BAN:JAN]; N,N-Bis(beta-chloroethyl)-amino-N',O-propylene-phosphoric acid ester diamide; N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide; N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylen ephosphoric acid diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylene phosphoric acid ester diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide; N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid; N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid [German]; N-(2-Chloroethyl)-N-(3-(2-chloroethyl)-2-oxido-1,3,2-oxazaphosphinan-2-yl)amine; (+-)-Ifosfamid; (+-)-Ifosphamide; (+-)-Tetrahydro-N,3-bis(2-chloroethyl)-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; (D,L)-Ifosfamide; (R,S)-Ifosphamide; (R,S)-N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; 1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide; 1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide; 2,3-(N,N(sup 1)-Bis(2-chloroethyl)diamido)-1,3,2-oxazaphosphoridinoxyd; 2,3-N,N(sup 1)-Bis(2-chloroethyl)diamido-1,3,2-oxazaphosphoridinoxyd; 2H-1,3,2-Oxazaphosphorin-2-amine, N,3-bis(2-chloroethyl)tetrahydro-, 2-oxide; 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide; 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide (8CI); 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide; 3,} 2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)perhydro-2H-1,3,2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2H-1,3,2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2H-1,3,2-oxazaphosphorineoxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1], [2]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 261.079
Topological Polar Surface Area (xlogp) 0.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
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
92% 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
10% 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 7 - 15 hours [5]
Metabolism
The drug is metabolized via the hepatic [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 113.5897 micromolar/kg/day [7]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [5]
Vd
The volume of distribution (Vd) of drug is 0.64 L/kg [8]
Water Solubility
The ability of drug to dissolve in water is measured as 100 mg/mL [3]
Chemical Identifiers
Formula
C7H15Cl2N2O2P
IUPAC Name
N,3-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
Canonical SMILES
C1CN(P(=O)(OC1)NCCCl)CCCl
InChI
InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
InChIKey
HOMGKSMUEGBAAB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3690
ChEBI ID
CHEBI:5864
CAS Number
3778-73-2
DrugBank ID
DB01181
TTD ID
D02TLO
INTEDE ID
DR0855
ACDINA ID
D01151

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human Deoxyribonucleic acid (hDNA) TTUTN1I NOUNIPROTAC Modulator [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [10]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [11]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [12]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [13]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [14]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [15]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [14]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [16]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [10]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Substrate [12]
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 Same Disease as Ifosfamide
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
LEE011 DMMX75K Moderate Decreased metabolism of Ifosfamide caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [85]
Coadministration of a Drug Treating the Disease Different from Ifosfamide (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Decreased renal excretion of Ifosfamide caused by Remdesivir mediated nephrotoxicity. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [86]
Arn-509 DMT81LZ Moderate Increased metabolism of Ifosfamide caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [87]
Inotersen DMJ93CT Major Increased risk of nephrotoxicity by the combination of Ifosfamide and Inotersen. Amyloidosis [5D00] [87]
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Ifosfamide and Roflumilast. Asthma [CA23] [87]
Dalfopristin DM4LTKV Moderate Decreased metabolism of Ifosfamide caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [88]
Sparfloxacin DMB4HCT Minor Decreased absorption of Ifosfamide due to intestinal mucosa variation caused by Sparfloxacin. Bacterial infection [1A00-1C4Z] [89]
ABT-492 DMJFD2I Minor Decreased absorption of Ifosfamide due to intestinal mucosa variation caused by ABT-492. Bacterial infection [1A00-1C4Z] [89]
Alpelisib DMEXMYK Moderate Increased metabolism of Ifosfamide caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [87]
Iodipamide DMXIQYS Major Increased risk of nephrotoxicity by the combination of Ifosfamide and Iodipamide. Cholelithiasis [DC11] [90]
MK-8228 DMOB58Q Moderate Decreased metabolism of Ifosfamide caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [91]
Cenobamate DMGOVHA Moderate Increased metabolism of Ifosfamide caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [92]
Stiripentol DMMSDOY Moderate Decreased metabolism of Ifosfamide caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [93]
Rufinamide DMWE60C Moderate Increased metabolism of Ifosfamide caused by Rufinamide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [87]
Fosamprenavir DM4W9B3 Moderate Decreased metabolism of Ifosfamide caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [94]
Darunavir DMN3GCH Moderate Decreased metabolism of Ifosfamide caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [95]
Teriflunomide DMQ2FKJ Major Additive myelosuppressive effects by the combination of Ifosfamide and Teriflunomide. Hyper-lipoproteinaemia [5C80] [96]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Ifosfamide and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [86]
Berotralstat DMWA2DZ Moderate Decreased metabolism of Ifosfamide caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [97]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Ifosfamide and Denosumab. Low bone mass disorder [FB83] [98]
Ceritinib DMB920Z Moderate Decreased metabolism of Ifosfamide caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [87]
PF-06463922 DMKM7EW Moderate Increased metabolism of Ifosfamide caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [99]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Ifosfamide and Tecfidera. Multiple sclerosis [8A40] [100]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Ifosfamide and Siponimod. Multiple sclerosis [8A40] [86]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Ifosfamide and Fingolimod. Multiple sclerosis [8A40] [101]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Ifosfamide and Ocrelizumab. Multiple sclerosis [8A40] [102]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Ifosfamide and Ozanimod. Multiple sclerosis [8A40] [87]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive myelosuppressive effects by the combination of Ifosfamide and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [103]
Abametapir DM2RX0I Moderate Decreased metabolism of Ifosfamide caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [104]
Lefamulin DME6G97 Moderate Decreased metabolism of Ifosfamide caused by Lefamulin mediated inhibition of CYP450 enzyme. Pneumonia [CA40] [105]
Enzalutamide DMGL19D Moderate Increased metabolism of Ifosfamide caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [106]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Ifosfamide and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [107]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Ifosfamide and Canakinumab. Rheumatoid arthritis [FA20] [108]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Ifosfamide and Rilonacept. Rheumatoid arthritis [FA20] [108]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Ifosfamide and Golimumab. Rheumatoid arthritis [FA20] [109]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Ifosfamide when combined with Anthrax vaccine. Sepsis [1G40-1G41] [110]
Pitolisant DM8RFNJ Moderate Increased metabolism of Ifosfamide caused by Pitolisant mediated induction of CYP450 enzyme. Somnolence [MG42] [87]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Ifosfamide caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [111]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Ifosfamide and Plazomicin. Urinary tract infection [GC08] [86]
Valganciclovir DMS2IUH Moderate Increased risk of nephrotoxicity by the combination of Ifosfamide and Valganciclovir. Virus infection [1A24-1D9Z] [86]
⏷ 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
Water E00035 962 Solvent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Ifosfamide 3gm/vial injectable 3gm/vial Injectable Injection
Ifosfamide 1gm/vial injectable 1gm/vial Injectable Injection
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: 7201).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076078.
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 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
9 Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35.
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 CYP2C9 polymorphisms in human tumors. Anticancer Res. 2006 Jan-Feb;26(1A):299-305.
12 Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66.
13 Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92.
14 Enhanced cyclophosphamide and ifosfamide activation in primary human hepatocyte cultures: response to cytochrome P-450 inducers and autoinduction by oxazaphosphorines. Cancer Res. 1997 May 15;57(10):1946-54.
15 A novel distal enhancer module regulated by pregnane X receptor/constitutive androstane receptor is essential for the maximal induction of CYP2B6 gene expression. J Biol Chem. 2003 Apr 18;278(16):14146-52.
16 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
17 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.
18 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
19 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.
20 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
21 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.
22 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.
23 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
24 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.
25 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.
26 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
27 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
28 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.
29 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
30 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
31 Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95.
32 Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81.
33 Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
34 Drug Interactions Flockhart Table
35 Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8.
36 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
37 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
38 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
39 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
40 The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. J Steroid Biochem Mol Biol. 1993 Jan;44(1):61-7.
41 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
42 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.
43 Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8.
44 Targeted antipeptide antibodies to cytochrome P450 2C18 based on epitope mapping of an inhibitory monoclonal antibody to P450 2C51. Arch Biochem Biophys. 1997 Feb 15;338(2):157-64.
45 Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes. Chem Res Toxicol. 1996 Mar;9(2):365-73.
46 CYP2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos. 2000 Aug;28(8):865-8.
47 Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51.
48 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
49 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
50 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
51 Interaction of sorafenib and cytochrome P450 isoenzymes in patients with advanced melanoma: a phase I/II pharmacokinetic interaction study. Cancer Chemother Pharmacol. 2011 Nov;68(5):1111-8.
52 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
53 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.
54 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
55 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.
56 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
57 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
58 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.
59 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
60 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
61 Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52.
62 Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96.
63 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
64 Drugs that may have potential CYP2B6 interactions.
65 Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24.
66 Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4.
67 PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70.
68 Application of the relative activity factor approach in scaling from heterologously expressed cytochromes p450 to human liver microsomes: studies on amitriptyline as a model substrate. J Pharmacol Exp Ther. 2001 Apr;297(1):326-37.
69 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.
70 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
71 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
72 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.
73 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.
74 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.
75 Cisplatin and DNA repair in cancer chemotherapy.Trends Biochem Sci.1995 Oct;20(10):435-9.
76 Structures of oxaliplatin-oligonucleotide adducts from DNA.J Mass Spectrom.2012 Oct;47(10):1282-93.
77 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12.
78 O6-methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int J Cancer. 1998 Sep 11;77(6):919-22.
79 Inhibition of carboplatin-induced DNA interstrand cross-link repair by gemcitabine in patients receiving these drugs for platinum-resistant ovarian cancer.Clin Cancer Res.2010 Oct 1;16(19):4899-905.
80 DNA intrastrand cross-link at the 5'-GA-3' sequence formed by busulfan and its role in the cytotoxic effect. Cancer Sci. 2004 May;95(5):454-8.
81 Brca2/Xrcc2 dependent HR, but not NHEJ, is required for protection against O(6)-methylguanine triggered apoptosis, DSBs and chromosomal aberrations... DNA Repair (Amst). 2009 Jan 1;8(1):72-86.
82 Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Ther. 1999 Sep;83(3):181-215.
83 Predicting the myelotoxicity of chemotherapy: the use of pretreatment O6-methylguanine-DNA methyltransferase determination in peripheral blood mono... Melanoma Res. 2011 Dec;21(6):502-8.
84 Alkylation of DNA by melphalan in relation to immunoassay of melphalan-DNA adducts: characterization of mono-alkylated and cross-linked products fr... Chem Biol Interact. 1990;73(2-3):183-94.
85 DSouza DL, Levasseur LM, Nezamis J, Robbins DK, Simms L, Koch KM "Effect of alosetron on the pharmacokinetics of alprazolam." J Clin Pharmacol 41 (2001): 452-4. [PMID: 11304902]
86 Cerner Multum, Inc. "Australian Product Information.".
87 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
88 Product Information. Synercid (dalfopristin-quinupristin) Rhone-Poulenc Rorer, Collegeville, PA.
89 Johnson EJ, MacGowan AP, Potter MN, et al "Reduced absorption of oral ciprofloxacin after chemotherapy for haematological malignancy." J Antimicrob Chemother 25 (1990): 837-42. [PMID: 2373666]
90 Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
91 Product Information. Prevymis (letermovir). Merck & Company Inc, Whitehouse Station, NJ.
92 Product Information. Xcopri (cenobamate). SK Life Science, Inc., Paramus, NJ.
93 EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
94 Product Information. Agenerase (amprenavir). Glaxo Wellcome, Research Triangle Pk, NC.
95 Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ.
96 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
97 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
98 Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
99 Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
100 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
101 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
102 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
103 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
104 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
105 Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
106 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]
107 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
108 Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
109 Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
110 CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058]
111 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.