Details of the Drug
General Information of Drug (ID: DMUNTE3)
Drug Name |
Estradiol
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Synonyms |
Aerodiol; Alora; Altrad; Aquadiol; Bardiol; Climaderm; Climara; Compudose; Corpagen; Dermestril; Destradiol; Dihydrofolliculin; Dihydromenformon; Dihydrotheelin; Dihydroxyesterin; Dihydroxyestrin; Dihydroxyoestrin; Dimenformon; Diogyn; Diogynets; Divigel; Elestrin; Encore; Esclim; Estrace; Estraderm; Estradiolo; Estradiolum; Estradot; Estraldine; Estrasorb; Estreva; Estrifam; Estring; Estroclim; Estrodiolum; Estrogel; Estrovite; Evamist; Evorel; Extrasorb; Femanest; Femestral; Femestrol; Fempatch; Femtran; Follicyclin; Gelestra; Ginedisc; Ginosedol; GynPolar; Gynergon; Gynestrel; Gynodiol; Gynoestryl; Innofem; Lamdiol; Macrodiol; Macrol; Menest; Menorest; Microdiol; Nordicol; Oesclim; Oestergon; Oestradiol; Oestradiolum; Oestrogel; Oestroglandol; Oestrogynal; Ovahormon; Ovasterol; Ovastevol; Ovociclina; Ovocyclin; Ovocycline; Ovocylin; Perlatanol; Polyestradiol; Primofol; Profoliol; Progynon; Syndiol; Systen; Tradelia; Trocosone; Vagifem; Vivelle; Zerella; Zesteem; Zesteen; Zumenon; Climara Forte; Component of Menrium; Estraderm MX; Estraderm TTS; Estradiolo [DCIT]; Estradiolum [INN]; Estring vaginal ring; Estrofem Forte; Oestradiol Berco; Oestradiol R; Progynon DH; Sandrena Gel; Sisare Gel; Trial SAT; CMC_11154; Compudose 200; Compudose 365; E 2; E 8875; E0025; Epiestriol 50; Estraderm TTS 100; Estraderm TTS 50; Estrapak 50; Estroclim 50; Estrofem 2; Sandrena 1; [3H]]estradiol; Activella (TN); Alora (TN); Alpha-Oestradiol; AngeliQ (TN); B-Estradiol; Beta-Estradiol; Beta-Oestradiol; Beta-estradiol; Cis-Estradiol; Cis-Oestradiol; Climara (TN); D-Estradiol; D-Oestradiol; Divigel (TN); E(sub 2); Elestrin (TN); Estrace (TN); Estraderm (TN); Estraderm TTS (TN); Estradiol [USAN:INN]; Estradiol acetate (TN); Estradiol cypionate (TN); Estradiol valerate (TN); Estradiol-17 beta; Estradiol-17beta; Estrasorb (TN); Estrasorb Topical (TN); Estring (TN); Estrofem (TN); Estrogel (TN); EvaMist (TN); Femring (TN); Innofem (TN); Menostar (TN); Oestradiol-17beta; Progynon-DH; Progynova (TN); S-21400; SK-Estrogens; SL-1100; VIVELLE-DOT; Vagifem (TN); Vivelle (TN); [3H]-estradiol; Estradiol-17-beta; Estradiol-3,17beta; Oestradiol-17-beta; Vivelle-Dot (TN); D-3,17beta-Estradiol; [2,4,6,7-3H]-E2; 17 beta-Estradiol; 17-.BETA.-Estradiol; 17-beta-OH-estradiol; 17-beta-estradiol; 17.beta.-Estradiol; 17.beta.-Oestradiol; 17b-Oestradiol; 17beta oestradiol; 17beta-Estradiol; 17beta-Oestradiol; 3,17-beta-Estradiol; 3,17-beta-Oestradiol; 3,17.beta.-Estradiol; 3,17beta-Estradiol
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Indication |
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Therapeutic Class |
Estrogens
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Drug Type |
Small molecular drug
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Structure |
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3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 272.4 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 4 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 0 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 2 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 2 | |||||||||||||||||||
ADMET Property |
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Chemical Identifiers |
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Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
![]() Drug Therapeutic Target (DTT) |
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![]() Drug Transporter (DTP) |
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![]() Drug-Metabolizing Enzyme (DME) |
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Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Expression Atlas of This Drug
The Studied Disease | Breast cancer | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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ICD Disease Classification | 2C60-2C65 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Molecular Expression Atlas (MEA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Same Disease as Estradiol
Coadministration of a Drug Treating the Disease Different from Estradiol (Comorbidity)
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) 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: 1013). | ||||
---|---|---|---|---|---|
2 | Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77. | ||||
3 | Regulation of the estrogen receptor in MCF-7 cells by estradiol. Mol Endocrinol. 1988 Dec;2(12):1157-62. | ||||
4 | Estradiol regulates estrogen receptor mRNA stability. J Steroid Biochem Mol Biol. 1998 Aug;66(3):113-20. | ||||
5 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | ||||
6 | BDDCS applied to over 900 drugs | ||||
7 | Pharmacokinetic and pharmacologic variation between different estrogen products. J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x. | ||||
8 | Tubic-Grozdanis M, Hilfinger JM, Amidon GL, Kim JS, Kijek P, Staubach P, Langguth P: Pharmacokinetics of the CYP 3A substrate simvastatin following administration of delayed versus immediate release oral dosage forms. Pharm Res. 2008 Jul;25(7):1591-600. doi: 10.1007/s11095-007-9519-6. Epub 2008 Jan 24. | ||||
9 | 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 | ||||
10 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
11 | Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201. | ||||
12 | Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. | ||||
13 | Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. | ||||
14 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
15 | 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. | ||||
16 | Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94. | ||||
17 | Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8. | ||||
18 | CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6. | ||||
19 | Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. | ||||
20 | Drug Interactions Flockhart Table | ||||
21 | Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. | ||||
22 | Proposed role of the sulfotransferase/sulfatase pathway in modulating yolk steroid effects. Integr Comp Biol. 2008 Sep;48(3):419-27. | ||||
23 | Influence of estradiol-17 beta and progesterone on catechol-O-methyltransferase and monoamine oxidase activities in uterine artery and myometrium of ovariectomized pigs. Arch Vet Pol. 1993;33(1-2):29-37. | ||||
24 | The metabolism of 17 beta-estradiol by lactoperoxidase: a possible source of oxidative stress in breast cancer. Carcinogenesis. 1994 Nov;15(11):2637-43. | ||||
25 | Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates. J Biol Chem. 2015 Mar 6;290(10):6531-45. | ||||
26 | Expression patterns of 17beta-hydroxysteroid dehydrogenase 14 in human tissues. Horm Metab Res. 2012 Dec;44(13):949-56. | ||||
27 | Isolation and characterization of the UGT2B28 cDNA encoding a novel human steroid conjugating UDP-glucuronosyltransferase. Biochemistry. 2001 Apr 3;40(13):3869-81. | ||||
28 | 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. | ||||
29 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
30 | 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. | ||||
31 | 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. | ||||
32 | 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. | ||||
33 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
34 | 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. | ||||
35 | 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. | ||||
36 | Cytochrome P450 3A4-mediated interaction of diclofenac and quinidine. Drug Metab Dispos. 2000 Sep;28(9):1043-50. | ||||
37 | 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. | ||||
38 | Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8. | ||||
39 | Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. | ||||
40 | PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. | ||||
41 | The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184. | ||||
42 | 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. | ||||
43 | Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. | ||||
44 | Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509. | ||||
45 | Ontogeny and sorafenib metabolism. Clin Cancer Res. 2012 Oct 15;18(20):5788-95. | ||||
46 | Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900. | ||||
47 | Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731. | ||||
48 | UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80. | ||||
49 | Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90. | ||||
50 | Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36. | ||||
51 | Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9. | ||||
52 | Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. | ||||
53 | Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4. | ||||
54 | Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32. | ||||
55 | Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. Drug Metab Dispos. 2007 Aug;35(8):1315-24. | ||||
56 | 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. | ||||
57 | 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. | ||||
58 | 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. | ||||
59 | 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. | ||||
60 | A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6. | ||||
61 | Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72. | ||||
62 | 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. | ||||
63 | Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62. | ||||
64 | Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. | ||||
65 | Progestagenic effects of tibolone are target gene-specific in human endometrial cells. J Soc Gynecol Investig. 2006 Sep;13(6):459-65. | ||||
66 | Tamoxifen-induced adduct formation and cell stress in human endometrial glands. Drug Metab Dispos. 2010 Jan;38(1):200-7. | ||||
67 | Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. | ||||
68 | Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53. | ||||
69 | Natural products isolated from Mexican medicinal plants: novel inhibitors of sulfotransferases, SULT1A1 and SULT2A1. Phytomedicine. 2001 Nov;8(6):481-8. | ||||
70 | Kinetic analysis of bile acid sulfation by stably expressed human sulfotransferase 2A1 (SULT2A1). Xenobiotica. 2010 Mar;40(3):184-94. | ||||
71 | Characterization of human liver thermostable phenol sulfotransferase (SULT1A1) allozymes with 3,3',5-triiodothyronine as the substrate. J Endocrinol. 2001 Dec;171(3):525-32. | ||||
72 | Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3'-phosphoadenosine 5'-phosphate. Biochem Biophys Res Commun. 2005 Sep 23;335(2):417-23. | ||||
73 | Sulfation of benzyl alcohol by the human cytosolic sulfotransferases (SULTs): a systematic analysis. J Appl Toxicol. 2016 Sep;36(9):1090-4. | ||||
74 | The 2.7 A resolution structure of the glycopeptide sulfotransferase Teg14. Acta Crystallogr D Biol Crystallogr. 2010 Dec;66(Pt 12):1278-86. | ||||
75 | 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. | ||||
76 | 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. | ||||
77 | 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. | ||||
78 | 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. | ||||
79 | Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8. | ||||
80 | Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94. | ||||
81 | Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000. | ||||
82 | Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71. | ||||
83 | 16Alpha-hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis. 1998 May;19(5):867-72. | ||||
84 | Genetics of rheumatoid arthritis. Mayo Clin Proc. 2006 Jan;81(1):94-101. | ||||
85 | Polymorphism of estrogen metabolism genes and cataract. Med Hypotheses. 2004;63(3):494-7. | ||||
86 | The degree of myelosuppression during maintenance therapy of adolescents with B-lineage intermediate risk acute lymphoblastic leukemia predicts risk of relapse. Leukemia. 2010 Apr;24(4):715-20. | ||||
87 | Histamine-N-methyl transferase polymorphism and risk for multiple sclerosis. Eur J Neurol. 2010 Feb;17(2):335-8. | ||||
88 | Ascorbic acid inhibits spinal meningeal catechol-o-methyl transferase in vitro, markedly increasing epinephrine bioavailability. Anesthesiology. 1997 Feb;86(2):405-9. | ||||
89 | Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in human tissue: possible relationship to hypoprothrombinemia. Drug Metab Dispos. 2002 Oct;30(10):1123-8. | ||||
90 | Adrenal catecholamines and their metabolism in the vitamin A deficient rat. Ann Nutr Metab. 1983;27(3):220-7. | ||||
91 | Reduced 3-O-methyl-dopa levels in OCD patients and their unaffected parents is associated with the low activity M158 COMT allele. Am J Med Genet B Neuropsychiatr Genet. 2010 Mar 5;153B(2):542-548. | ||||
92 | Usefulness of thiopurine methyltransferase and thiopurine metabolite analysis in clinical practice in patients with inflammatory bowel diseases. Acta Gastroenterol Belg. 2010 Jul-Sep;73(3):331-5. | ||||
93 | Nodular regenerative liver hyperplasia as a complication of azathioprine-containing immunosuppressive treatment for Crohn's disease. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):398-402. | ||||
94 | 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. | ||||
95 | Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. | ||||
96 | Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66. | ||||
97 | 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. | ||||
98 | Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers. | ||||
99 | Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75. | ||||
100 | Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92. | ||||
101 | 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. | ||||
102 | PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. | ||||
103 | Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. | ||||
104 | Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. | ||||
105 | 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. | ||||
106 | Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4. | ||||
107 | Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076. | ||||
108 | Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. | ||||
109 | 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. | ||||
110 | A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7. | ||||
111 | A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63. | ||||
112 | In vitro comparative inhibition profiles of major human drug metabolising cytochrome P450 isozymes (CYP2C9, CYP2D6 and CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol. 1996;50(3):209-15. | ||||
113 | 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. | ||||
114 | Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91. | ||||
115 | 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. | ||||
116 | 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. | ||||
117 | Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. | ||||
118 | Pharmacokinetics of rosuvastatin when coadministered with rifampicin in healthy males: a randomized, single-blind, placebo-controlled, crossover study. Clin Ther. 2008 Jul;30(7):1283-9. | ||||
119 | Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7. | ||||
120 | Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22. | ||||
121 | Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. | ||||
122 | Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41. | ||||
123 | Functional expression of novel human and murine AKR1B genes. Chem Biol Interact. 2011 May 30;191(1-3):177-84. | ||||
124 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | ||||
125 | MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. | ||||
126 | Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64. | ||||
127 | Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31. | ||||
128 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | ||||
129 | Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50. | ||||
130 | Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers. Pharm Res. 2003 Aug;20(8):1200-9. | ||||
131 | Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25. | ||||
132 | Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43. | ||||
133 | The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9. | ||||
134 | Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10. | ||||
135 | Inhibiting the function of ABCB1 and ABCG2 by the EGFR tyrosine kinase inhibitor AG1478. Biochem Pharmacol. 2009 Mar 1;77(5):781-93. | ||||
136 | The phytoestrogen genistein enhances multidrug resistance in breast cancer cell lines by translational regulation of ABC transporters. Cancer Lett. 2016 Jun 28;376(1):165-72. | ||||
137 | Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7. | ||||
138 | Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2. | ||||
139 | Characterization of 3-methoxy flavones for their interaction with ABCG2 as suggested by ATPase activity. Biochim Biophys Acta. 2014 Nov;1838(11):2929-38. | ||||
140 | Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86. | ||||
141 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | ||||
142 | 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8. | ||||
143 | 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: 620). | ||||
144 | Clinical pipeline report, company report or official report of Shionogi (2011). | ||||
145 | Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81. | ||||
146 | Short-term effects of environmentally relevant concentrations of EDC mixtures on Mytilus galloprovincialis digestive gland. Aquat Toxicol. 2008 May 30;87(4):272-9. | ||||
147 | Product Information. Tykerb (lapatinib). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
148 | Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA. | ||||
149 | Baciewicz AM "Oral contraceptive drug interactions." Ther Drug Monit 7 (1985): 26-35. [PMID: 2859674] | ||||
150 | Product Information. Ambien (zolpidem). sanofi-aventis, Bridgewater, NJ. | ||||
151 | Back DJ, Breckenridge AM, Crawford FE, MacIver M, Orne ML, Rowe PH "Interindividual variation and drug interactions with hormonal steroid contraceptives." Drugs 21 (1981): 46-61. [PMID: 7009137] | ||||
152 | Devenport MH, Crook D, Wynn V, Lees LJ "Metabolic effects of low-dose fluconazole in healthy female users and non-users of oral contraceptives." Br J Clin Pharmacol 27 (1989): 851-9. [PMID: 2547410] | ||||
153 | Gardner MJ, Tornatore KM, Jusko WJ, Kanarkowski R "Effects of tobacco smoking and oral contraceptive use on theophylline disposition." Br J Clin Pharmacol 16 (1983): 271-80. [PMID: 6626419] | ||||
154 | Cerner Multum, Inc. "Australian Product Information.". | ||||
155 | Product Information. Ketek (telithromycin). Aventis Pharmaceuticals, Bridgewater, NJ. | ||||
156 | Product Information. Lipitor (atorvastatin). Parke-Davis, Morris Plains, NJ. | ||||
157 | Notelovitz M "Oral contraception and coagulation." Clin Obstet Gynecol 28 (1985): 73-83. [PMID: 3987135] | ||||
158 | Product Information. Kalydeco (ivacaftor). Vertex Pharmaceuticals, Cambridge, MA. | ||||
159 | Adson DE, Kotlyar M "A probable interaction between a very low-dose oral contraceptive and the antidepressant nefazodone: a case report." J Clin Psychopharmacol 21 (2001): 618-9. [PMID: 11763013] | ||||
160 | EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.". | ||||
161 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
162 | Product Information. Dantrium (dantrolene). Procter and Gamble Pharmaceutic, Cincinnati, OH. | ||||
163 | Product Information. Tazverik (tazemetostat). Epizyme, Inc, Cambridge, MA. | ||||
164 | Product Information. Victrelis (boceprevir). Schering-Plough Corporation, Kenilworth, NJ. | ||||
165 | Product Information. Norvir (ritonavir). Abbott Pharmaceutical, Abbott Park, IL. | ||||
166 | Product Information. Incivek (telaprevir). Vertex Pharmaceuticals, Cambridge, MA. | ||||
167 | Product Information. Aptivus (tipranavir). Boehringer-Ingelheim, Ridgefield, CT. | ||||
168 | Product Information. Fortovase (saquinavir) Roche Laboratories, Nutley, NJ. | ||||
169 | Product Information. Prezista (darunavir). Ortho Biotech Inc, Bridgewater, NJ. | ||||
170 | Product Information. Vaprisol (conivaptan). Cumberland Pharmaceuticals Inc, Nashville, TN. | ||||
171 | Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC. | ||||
172 | Product Information. Alunbrig (brigatinib). Ariad Pharmaceuticals Inc, Cambridge, MA. | ||||
173 | Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA. | ||||
174 | Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
175 | Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
176 | Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ. | ||||
177 | EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.". | ||||
178 | Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ. | ||||
179 | Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA. | ||||
180 | Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA. | ||||
181 | Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL. | ||||
182 | Product Information. Oxbryta (voxelotor). Global Blood Therapeutics, Inc., South San Francisco, CA. | ||||
183 | 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] | ||||
184 | Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA. | ||||