General Information of Drug (ID: DMUNTE3)

Drug Name
Estradiol Drug Info
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
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1] , [2] , [3] , [4] , [5]
Therapeutic Class
Estrogens
Cross-matching ID
PubChem CID
5757
ChEBI ID
CHEBI:16469
CAS Number
CAS 17916-67-5
TTD Drug ID
DMUNTE3
VARIDT Drug ID
DR00129
INTEDE Drug ID
DR0007
ACDINA Drug ID
D00246

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [23]
Progesterone DMUY35B Premature labour JB00 Approved [24]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [25]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [26]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [27]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [28]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [29]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [24]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [30]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [31]
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Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [32]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [33]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [34]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [35]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [36]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [28]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [37]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [38]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [39]
Sorafenib DMS8IFC Hepatocellular carcinoma 2C12.02 Approved [40]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [41]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [42]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [43]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [44]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [45]
Mycophenolate mofetil DMPQAGE Organ transplant rejection NE84 Approved [46]
Metronidazole DMTIVEN Amoebiasis 1A36 Approved [47]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [48]
Ethanol DMDRQZU Chronic pain MG30 Approved [49]
Atorvastatin DMF28YC Cardiovascular disease BA00-BE2Z Approved [50]
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Drug(s) Metabolized By Cytochrome P450 1A1 (CYP1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [51]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [52]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [53]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [37]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [54]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [55]
Erythromycin DM4K7GQ Bacterial infection 1A00-1C4Z Approved [56]
Riboflavin DM8YMWE Acne vulgaris ED80 Approved [57]
Mercaptopurine DMTM2IK Acute lymphoblastic leukaemia 2A85 Approved [58]
Nicotine DMWX5CO Nicotine dependence 6C4A.2 Approved [59]
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Drug(s) Metabolized By Sulfotransferase 1A1 (SULT1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [60]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [61]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [62]
Aspirin DM672AH Myocardial infarction BA41-BA43 Approved [63]
Warfarin DMJYCVW Atrial fibrillation BC81.3 Approved [64]
Cholic acid DM7OKQV Peroxisomal disorder 5C57 Approved [65]
Liothyronine DM6IR3P Hypothyroidism 5A00 Approved [66]
Epinephrine DM3KJBC Allergy 4A80-4A85 Approved [67]
Benzyl alcohol DMBVYDI Head and body lice 1G00.0 Approved [68]
Teicoplanin DMAQ2LK Bacterial infection 1A00-1C4Z Approved [69]
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Drug(s) Metabolized By Cytochrome P450 3A5 (CYP3A5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [70]
Progesterone DMUY35B Premature labour JB00 Approved [71]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [72]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [73]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [74]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [75]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [76]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [77]
Sorafenib DMS8IFC Hepatocellular carcinoma 2C12.02 Approved [15]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [78]
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Drug(s) Metabolized By Thiopurine methyltransferase (TPMT)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methotrexate DM2TEOL leukaemia 2A60-2B33 Approved [79]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [80]
Mercaptopurine DMTM2IK Acute lymphoblastic leukaemia 2A85 Approved [81]
Ergotidine DM78IME Respiratory allergy 4A80 Approved [82]
Vitamin C DMXJ7O8 Vitamin C deficiency 5B56 Approved [83]
Cefazolin DMPDYFR Bacterial infection 1A00-1C4Z Approved [84]
Epinephrine DM3KJBC Allergy 4A80-4A85 Approved [85]
Levodopa DMN3E57 Parkinson disease 8A00.0 Approved [86]
Thioguanine DM7NKEV Acute myeloid leukaemia 2A60 Approved [87]
Azathioprine DMMZSXQ Organ transplant rejection NE84 Approved [88]
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Drug(s) Metabolized By Cytochrome P450 3A7 (CYP3A7)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [89]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [15]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [15]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [90]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [91]
Sorafenib DMS8IFC Hepatocellular carcinoma 2C12.02 Approved [15]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [15]
Irinotecan DMP6SC2 Colorectal cancer 2B91.Z Approved [15]
Metronidazole DMTIVEN Amoebiasis 1A36 Approved [92]
Atorvastatin DMF28YC Cardiovascular disease BA00-BE2Z Approved [93]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C8 (CYP2C8)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [32]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [16]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [90]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [94]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [95]
Sorafenib DMS8IFC Hepatocellular carcinoma 2C12.02 Approved [96]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [16]
Mycophenolate mofetil DMPQAGE Organ transplant rejection NE84 Approved [97]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [98]
Ibuprofen DM8VCBE Pain MG30-MG3Z Approved [99]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [100]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [101]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [90]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [102]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [90]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [103]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [104]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [105]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [106]
Pravastatin DM6A0X7 Hypercholesterolaemia 5C80.0 Approved [107]
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Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Bacterial infection 1A00-1C4Z Approved [108]
Progesterone DMUY35B Premature labour JB00 Approved [100]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [109]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [90]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [110]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [54]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [106]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [111]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [98]
Ibuprofen DM8VCBE Pain MG30-MG3Z Approved [90]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1B1 (CYP1B1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [112]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [37]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [55]
Erythromycin DM4K7GQ Bacterial infection 1A00-1C4Z Approved [56]
Rosuvastatin DMMIQ7G Hypercholesterolaemia 5C80.0 Approved [113]
Vitamin A DMJ2AH4 Night blindness 9D45 Approved [114]
Caffeine DMKBJWP Orthostatic hypotension BA21 Approved [115]
Melatonin DMKWFBT Insomnia 7A00-7A0Z Approved [116]
Theophylline DMRJFN9 Chronic obstructive pulmonary disease CA22 Approved [115]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [117]
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Drug(s) Metabolized By Farnesol dehydrogenase (AKR1B15)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [20]
Testosterone cypionate DMC1TEV Testosterone deficiency 5A81.1 Approved [20]
Androsterone DMITJAK N. A. N. A. Phase 3 [20]
Nitrobenzaldehyde DM4UHB5 Discovery agent N.A. Investigative [118]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Testosterone cypionate DMC1TEV Testosterone deficiency 5A81.1 Approved [21]
Drug(s) Transported By P-glycoprotein 1 (ABCB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Bacterial infection 1A00-1C4Z Approved [119]
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [120]
Methotrexate DM2TEOL leukaemia 2A60-2B33 Approved [121]
Folic acid DMEMBJC Folate-deficiency anemia 3A02.Y Approved [122]
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [121]
Cisplatin DMRHGI9 Solid tumour/cancer 2A00-2F9Z Approved [121]
Progesterone DMUY35B Premature labour JB00 Approved [123]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [121]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [124]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [125]
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Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [126]
Methotrexate DM2TEOL leukaemia 2A60-2B33 Approved [127]
Folic acid DMEMBJC Folate-deficiency anemia 3A02.Y Approved [128]
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [129]
Cisplatin DMRHGI9 Solid tumour/cancer 2A00-2F9Z Approved [130]
Progesterone DMUY35B Premature labour JB00 Approved [7]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [131]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [132]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [133]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [134]
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Drug(s) Targeting Estrogen receptor (ESR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [135]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [6]
Estradiol valerate DM8MC6O Hormone replacement therapy 8E01 Approved [136]
Estradiol acetate DM07U2A Hormone replacement therapy 8E01 Approved [136]
Estradiol cypionate DM27Z5T Hormone replacement therapy 8E01 Approved [136]
Ethinyl estradiol DMODJ40 Female hypogonadism GA30.6 Approved [137]
Raloxifene DMDKF3M Osteoporosis FB83.0 Approved [138]
Ospemifene DMC4GEI Dyspareunia GA12 Approved [139]
Toremifene DMQYUWG Breast cancer 2C60-2C65 Approved [140]
Mestranol DMG3F94 Contraception QA21 Approved [141]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Agonist [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [7]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [9]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [10]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [11]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [12]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [13]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [14]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [15]
Cytochrome P450 1B1 (CYP1B1) DE9QHP6 CP1B1_HUMAN Substrate [11]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [16]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [15]
Sulfotransferase 1A1 (SULT1A1) DEYWLRK ST1A1_HUMAN Substrate [17]
Thiopurine methyltransferase (TPMT) DEFQ8VO TPMT_HUMAN Substrate [18]
Lactoperoxidase (LPO) DEHX1DZ PERL_HUMAN Substrate [19]
Farnesol dehydrogenase (AKR1B15) DER0XCH AK1BF_HUMAN Substrate [20]
Dehydrogenase/reductase retSDR3 (HSD17B14) DEGTB1K DHB14_HUMAN Substrate [21]
UDP-glucuronosyltransferase 2B28 (UGT2B28) DEB7I4M UDB28_HUMAN Substrate [22]

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 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
7 Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51.
8 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
9 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
10 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.
11 Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
12 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
13 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
14 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
15 Drug Interactions Flockhart Table
16 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
17 Proposed role of the sulfotransferase/sulfatase pathway in modulating yolk steroid effects. Integr Comp Biol. 2008 Sep;48(3):419-27.
18 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.
19 The metabolism of 17 beta-estradiol by lactoperoxidase: a possible source of oxidative stress in breast cancer. Carcinogenesis. 1994 Nov;15(11):2637-43.
20 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.
21 Expression patterns of 17beta-hydroxysteroid dehydrogenase 14 in human tissues. Horm Metab Res. 2012 Dec;44(13):949-56.
22 Isolation and characterization of the UGT2B28 cDNA encoding a novel human steroid conjugating UDP-glucuronosyltransferase. Biochemistry. 2001 Apr 3;40(13):3869-81.
23 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.
24 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
25 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.
26 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.
27 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.
28 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
29 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.
30 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.
31 Cytochrome P450 3A4-mediated interaction of diclofenac and quinidine. Drug Metab Dispos. 2000 Sep;28(9):1043-50.
32 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.
33 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.
34 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
35 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
36 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
37 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.
38 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
39 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
40 Ontogeny and sorafenib metabolism. Clin Cancer Res. 2012 Oct 15;18(20):5788-95.
41 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
42 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
43 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.
44 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.
45 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.
46 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
47 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.
48 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.
49 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
50 Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. Drug Metab Dispos. 2007 Aug;35(8):1315-24.
51 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.
52 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.
53 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.
54 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.
55 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
56 Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
57 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.
58 Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62.
59 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
60 Progestagenic effects of tibolone are target gene-specific in human endometrial cells. J Soc Gynecol Investig. 2006 Sep;13(6):459-65.
61 Tamoxifen-induced adduct formation and cell stress in human endometrial glands. Drug Metab Dispos. 2010 Jan;38(1):200-7.
62 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.
63 Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53.
64 Natural products isolated from Mexican medicinal plants: novel inhibitors of sulfotransferases, SULT1A1 and SULT2A1. Phytomedicine. 2001 Nov;8(6):481-8.
65 Kinetic analysis of bile acid sulfation by stably expressed human sulfotransferase 2A1 (SULT2A1). Xenobiotica. 2010 Mar;40(3):184-94.
66 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.
67 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.
68 Sulfation of benzyl alcohol by the human cytosolic sulfotransferases (SULTs): a systematic analysis. J Appl Toxicol. 2016 Sep;36(9):1090-4.
69 The 2.7 A resolution structure of the glycopeptide sulfotransferase Teg14. Acta Crystallogr D Biol Crystallogr. 2010 Dec;66(Pt 12):1278-86.
70 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.
71 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.
72 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.
73 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.
74 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
75 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
76 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
77 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
78 16Alpha-hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis. 1998 May;19(5):867-72.
79 Genetics of rheumatoid arthritis. Mayo Clin Proc. 2006 Jan;81(1):94-101.
80 Polymorphism of estrogen metabolism genes and cataract. Med Hypotheses. 2004;63(3):494-7.
81 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.
82 Histamine-N-methyl transferase polymorphism and risk for multiple sclerosis. Eur J Neurol. 2010 Feb;17(2):335-8.
83 Ascorbic acid inhibits spinal meningeal catechol-o-methyl transferase in vitro, markedly increasing epinephrine bioavailability. Anesthesiology. 1997 Feb;86(2):405-9.
84 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.
85 Adrenal catecholamines and their metabolism in the vitamin A deficient rat. Ann Nutr Metab. 1983;27(3):220-7.
86 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.
87 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.
88 Nodular regenerative liver hyperplasia as a complication of azathioprine-containing immunosuppressive treatment for Crohn's disease. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):398-402.
89 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.
90 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
91 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
92 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.
93 Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers.
94 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
95 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
96 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.
97 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
98 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
99 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.
100 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.
101 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
102 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
103 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
104 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.
105 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
106 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
107 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.
108 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.
109 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
110 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.
111 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.
112 Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13.
113 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.
114 Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7.
115 Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22.
116 Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94.
117 Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41.
118 Functional expression of novel human and murine AKR1B genes. Chem Biol Interact. 2011 May 30;191(1-3):177-84.
119 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
120 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
121 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.
122 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
123 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
124 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.
125 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.
126 Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25.
127 Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43.
128 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.
129 Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10.
130 Inhibiting the function of ABCB1 and ABCG2 by the EGFR tyrosine kinase inhibitor AG1478. Biochem Pharmacol. 2009 Mar 1;77(5):781-93.
131 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.
132 Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7.
133 Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2.
134 Characterization of 3-methoxy flavones for their interaction with ABCG2 as suggested by ATPase activity. Biochim Biophys Acta. 2014 Nov;1838(11):2929-38.
135 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.
136 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
137 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
138 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).
139 Clinical pipeline report, company report or official report of Shionogi (2011).
140 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.
141 Short-term effects of environmentally relevant concentrations of EDC mixtures on Mytilus galloprovincialis digestive gland. Aquat Toxicol. 2008 May 30;87(4):272-9.