General Information of Drug (ID: DMIKQH5)

Drug Name
Hydroxyprogesterone Drug Info
Synonyms Delalutin (TN); Proluton depot (TN)
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1]
Cross-matching ID
PubChem CID
6238
ChEBI ID
CHEBI:17252
CAS Number
CAS 68-96-2
TTD Drug ID
DMIKQH5
INTEDE Drug ID
DR0839

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DME
DOT
Drug Status:
Approved 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 [7]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [8]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [9]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [10]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [11]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [12]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [13]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [14]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [8]
Verapamil DMA7PEW Angina pectoris BA40 Approved [15]
⏷ 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 [16]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [17]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [18]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [19]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [20]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [21]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [22]
Metronidazole DMTIVEN Abscess Approved [23]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [24]
Ethanol DMDRQZU Chronic pain MG30 Approved [25]
⏷ 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 [26]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [27]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [28]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [29]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [30]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [31]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [32]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [33]
Verapamil DMA7PEW Angina pectoris BA40 Approved [34]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [29]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Steroid 21-hydroxylase (CYP21A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [35]
Drug(s) Affected By Androgen receptor (AR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [36]
Nilutamide DMFN07X Prostate cancer 2C82.0 Approved [36]
Hydroxyflutamide DMGIZF5 Prostate cancer 2C82.0 Approved [36]
Enzalutamide DMGL19D Prostate cancer 2C82.0 Approved [37]
Bicalutamide DMZMSPF Prostate cancer 2C82.0 Approved [38]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [39]
Drospirenone DM1A9W3 Acne vulgaris ED80 Approved [40]
Nitrendipine DM21C09 Hypertension BA00-BA04 Approved [41]
Selenium DM25CGV N. A. N. A. Approved [42]
Spironolactone DM2AQ5N Chronic heart failure BD1Z Approved [43]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Etretinate DM2CZFA Keratosis ED56 Approved [44]
FADROZOLE DM3C5GZ Breast cancer 2C60-2C65 Approved [45]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [46]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [47]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [48]
Testosterone DM7HUNW Hot flushes GA30 Approved [48]
Pyruvic acid DM7Q41G Malnutrition 5B50-5B71 Approved [49]
Topiramate DM82Z30 Alcohol dependence 6C40.2 Approved [50]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [50]
ABIRATERONE DM8V75C Prostate cancer 2C82.0 Approved [51]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [3]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [2]
Steroid 21-hydroxylase (CYP21A2) DE0JMZ5 CP21A_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Gene/Protein Processing [5]
Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1) OTZKVLVJ CP17A_HUMAN Regulation of Drug Effects [6]

References

1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Prevention of preterm delivery with 17-hydroxyprogesterone caproate: pharmacologic considerations. Semin Perinatol. 2014 Dec;38(8):516-22.
3 The glucuronidation of Delta4-3-Keto C19- and C21-hydroxysteroids by human liver microsomal and recombinant UDP-glucuronosyltransferases (UGTs): 6alpha- and 21-hydroxyprogesterone are selective substrates for UGT2B7. Drug Metab Dispos. 2007 Mar;35(3):363-70.
4 Functional characterization of two novel point mutations in the CYP21 gene causing simple virilizing forms of congenital adrenal hyperplasia due to 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2005 Jan;90(1):445-54.
5 Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. Environ Health Perspect. 2011 Aug;119(8):1142-8. doi: 10.1289/ehp.1002952. Epub 2011 May 4.
6 Steroidogenic disruptive effects of the serotonin-noradrenaline reuptake inhibitors duloxetine, venlafaxine and tramadol in the H295R cell assay and in a recombinant CYP17 assay. Toxicol In Vitro. 2018 Mar;47:63-71.
7 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.
8 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
9 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.
10 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
11 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.
12 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.
13 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
14 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.
15 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.
16 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
17 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
18 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
19 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.
20 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.
21 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.
22 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
23 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.
24 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.
25 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
26 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.
27 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.
28 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.
29 Drug Interactions Flockhart Table
30 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.
31 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
32 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
33 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
34 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
35 Human cytochrome P450 21A2, the major steroid 21-hydroxylase: structure of the enzyme progesterone substrate complex and rate-limiting C-H bond cleavage. J Biol Chem. 2015 May 22;290(21):13128-43.
36 TBECH, 1,2-dibromo-4-(1,2 dibromoethyl) cyclohexane, alters androgen receptor regulation in response to mutations associated with prostate cancer. Toxicol Appl Pharmacol. 2016 Sep 15;307:91-101. doi: 10.1016/j.taap.2016.07.018. Epub 2016 Jul 27.
37 Targeting chromatin binding regulation of constitutively active AR variants to overcome prostate cancer resistance to endocrine-based therapies. Nucleic Acids Res. 2015 Jul 13;43(12):5880-97. doi: 10.1093/nar/gkv262. Epub 2015 Apr 23.
38 Possible role of adaptive mutation in resistance to antiandrogen in prostate cancer cells. Prostate. 2005 Nov 1;65(3):268-75. doi: 10.1002/pros.20282.
39 Effects of the environmental estrogens bisphenol A, o,p'-DDT, p-tert-octylphenol and coumestrol on apoptosis induction, cell proliferation and the expression of estrogen sensitive molecular parameters in the human breast cancer cell line MCF-7. J Steroid Biochem Mol Biol. 2002 Jan;80(1):61-70. doi: 10.1016/s0960-0760(01)00173-x.
40 Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform. Toxicology. 2017 Jun 15;385:48-58. doi: 10.1016/j.tox.2017.05.001. Epub 2017 May 4.
41 Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Sci Rep. 2014 Sep 26;4:6437. doi: 10.1038/srep06437.
42 Prostate specific antigen expression is down-regulated by selenium through disruption of androgen receptor signaling. Cancer Res. 2004 Jan 1;64(1):19-22. doi: 10.1158/0008-5472.can-03-2789.
43 Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals. Toxicology. 2004 Feb 15;195(2-3):177-86. doi: 10.1016/j.tox.2003.09.012.
44 Retinoids and retinol differentially regulate steroid biosynthesis in ovarian theca cells isolated from normal cycling women and women with polycystic ovary syndrome. J Clin Endocrinol Metab. 2005 Aug;90(8):4858-65. doi: 10.1210/jc.2005-0330. Epub 2005 May 24.
45 Synthesis and evaluation of (pyridylmethylene)tetrahydronaphthalenes/-indanes and structurally modified derivatives: potent and selective inhibitors of aldosterone synthase. J Med Chem. 2005 Mar 10;48(5):1563-75.
46 Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. J Mol Endocrinol. 2004 Apr;32(2):425-36.
47 Use of organ culture to study the human fetal testis development: effect of retinoic acid. J Clin Endocrinol Metab. 2006 Jul;91(7):2696-703.
48 Inhibition of CYP17 expression by adrenal androgens and transforming growth factor beta in adrenocortical cells. Acta Biochim Pol. 2004;51(4):907-17.
49 Phosphorylation of CtBP1 by cAMP-dependent protein kinase modulates induction of CYP17 by stimulating partnering of CtBP1 and 2. J Biol Chem. 2008 Mar 14;283(11):6925-34. doi: 10.1074/jbc.M708432200. Epub 2008 Jan 9.
50 Effects of anticonvulsants on human p450c17 (17alpha-hydroxylase/17,20 lyase) and 3beta-hydroxysteroid dehydrogenase type 2. Epilepsia. 2005 Mar;46(3):444-8.
51 A fission yeast-based test system for the determination of IC50 values of anti-prostate tumor drugs acting on CYP21. J Enzyme Inhib Med Chem. 2006 Oct;21(5):547-56.