General Information of Drug (ID: DM8MC6O)

Drug Name
Estradiol Valerate Drug Info
Synonyms Delestrogen
Indication
Disease Entry ICD 11 Status REF
Hormone replacement therapy 8E01 Approved [1]
Cross-matching ID
PubChem CID
13791
ChEBI ID
CHEBI:31561
CAS Number
CAS 979-32-8
TTD Drug ID
DM8MC6O
INTEDE Drug ID
DR0644

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Drug(s) Targeting Estrogen receptor (ESR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [8]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [9]
Estrone DM5T6US Acne vulgaris ED80 Approved [9]
Estradiol Acetate DM07U2A Hormone replacement therapy 8E01 Approved [2]
Estradiol Cypionate DM27Z5T Hormone replacement therapy 8E01 Approved [2]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [10]
Raloxifene DMDKF3M Osteoporosis FB83.0 Approved [11]
Ospemifene DMC4GEI Dyspareunia GA12 Approved [12]
Toremifene DMQYUWG Breast cancer 2C60-2C65 Approved [13]
Mestranol DMG3F94 Contraception QA21 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [24]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [25]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [26]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [27]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [28]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [29]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [31]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [32]
⏷ 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 [33]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [4]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [34]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [35]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [36]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [38]
Metronidazole DMTIVEN Abscess Approved [39]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [40]
Ethanol DMDRQZU Chronic pain MG30 Approved [41]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A5 (CYP3A5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [42]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [43]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [44]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [7]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [45]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [46]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [47]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [48]
Verapamil DMA7PEW Angina pectoris BA40 Approved [49]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [7]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A7 (CYP3A7)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [50]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [7]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [7]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [7]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [51]
Verapamil DMA7PEW Angina pectoris BA40 Approved [52]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [7]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [7]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [7]
Metronidazole DMTIVEN Abscess Approved [53]
⏷ 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 Adenocarcinoma 2D40 Approved [24]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [54]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [54]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [51]
Verapamil DMA7PEW Angina pectoris BA40 Approved [55]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [56]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [57]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [54]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [58]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [59]
⏷ 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 Amenorrhea GA20.0 Approved [60]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [61]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [62]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [51]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [63]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [51]
Verapamil DMA7PEW Angina pectoris BA40 Approved [64]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [65]
Estrone DM5T6US Acne vulgaris ED80 Approved [3]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [66]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [67]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [60]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [68]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [69]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [51]
Verapamil DMA7PEW Angina pectoris BA40 Approved [70]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [71]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [66]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [72]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [59]
⏷ Show the Full List of 10 Drug(s)

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 Modulator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [5]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [6]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [7]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [5]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [7]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
3 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
4 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
5 Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54.
6 Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals. Drug Metab Dispos. 2006 Sep;34(9):1606-14.
7 Drug Interactions Flockhart Table
8 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.
9 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
10 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
11 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).
12 Clinical pipeline report, company report or official report of Shionogi (2011).
13 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.
14 Short-term effects of environmentally relevant concentrations of EDC mixtures on Mytilus galloprovincialis digestive gland. Aquat Toxicol. 2008 May 30;87(4):272-9.
15 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
20 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
23 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.
24 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.
25 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.
26 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
27 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
28 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
29 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
30 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.
31 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
32 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
33 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
34 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
35 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.
36 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.
37 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.
38 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
39 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.
40 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.
41 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
42 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.
43 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.
44 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.
45 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.
46 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
47 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
48 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
49 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
50 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.
51 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
52 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
53 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.
54 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
55 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
56 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
57 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.
58 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
59 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
60 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.
61 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
62 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.
63 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
64 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
65 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.
66 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
67 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.
68 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
69 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
70 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.
71 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.
72 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.