References
- Omura T (1999) Forty years of cytochrome P450. Biochem Biophys Res Commun 266:690-698. https://doi.org/10.1006/bbrc.1999.1887
- Guengerich FP (2022) Roles of cytochrome P450 enzymes in pharmacology and toxicology: past, present, and future. Adv Pharmacol 95:1-47. https://doi.org/10.1016/bs.apha.2021.12.001
- Guengerich FP (2004) Cytochrome P450: what have we learned and what are the future issues? Drug Metab Rev 36:159-197. https://doi.org/10.1081/dmr-120033996
- Guengerich FP (2006) Cytochrome P450s and other enzymes in drug metabolism and toxicity. AAPS J 8:E101-E111. https://doi.org/10.1208/aapsj080112
- Adhya D, Annuario E, Lancaster MA, Price J, Baron-Cohen S, Srivastava DP (2018) Understanding the role of steroids in typical and atypical brain development: advantages of using a "brain in a dish" approach. J Neuroendocrinol 3:e12547. https://doi.org/10.1111/jne.12547
- Yaghjyan L, Colditz GA (2011) Estrogens in the breast tissue: a systematic review. Cancer Causes Control 22:529-540. https://doi.org/10.1007/s10552-011-9729-4
- Basu S, Tindall DJ (2010) Androgen action in prostate cancer. Horm Cancer 1:223-228. https://doi.org/10.1007/s12672-010-0044-4
- Lacroix A, Feelders RA, Stratakis CA, Nieman LK (2015) Cushing's syndrome. Lancet 386:913-927. https://doi.org/10.1016/s0140-6736(14)61375-1
- Miller WL, Auchus RJ (2011) The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders. Endocr Rev 32:81-151. https://doi.org/10.1210/er.2010-0013
- Karimaa M, Riikonen R, Kettunen H, Taavitsainen P, Ramela M, Chrusciel M, Karlsson S, Rummakko P, Simola O, Wohlfahrt G, Hakulinen P, Vuorela A, Joensuu H, Utriainen T, Fizazi K, Oksala R (2022) First-in-class small molecule to inhibit CYP11A1 and steroid hormone biosynthesis. Mol Cancer Ther 21:1765-1776. https://doi.org/10.1158/1535-7163.Mct-22-0115
- Strushkevich N, MacKenzie F, Cherkesova T, Grabovec I, Usanov S, Park HW (2011) Structural basis for pregnenolone biosynthesis by the mitochondrial monooxygenase system. Proc Natl Acad Sci U S A 108:10139-10143. https://doi.org/10.1073/pnas.1019441108
- Potter GA, Barrie SE, Jarman M, Rowlands MG (1995) Novel steroidal inhibitors of human cytochrome P45017 alpha (17 alpha-hydroxylase-C17,20-lyase): potential agents for the treatment of prostatic cancer. J Med Chem 38:2463-2471. https://doi.org/10.1021/jm00013a022
- DeVore NM, Scott EE (2012) Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001. Nature 482:116-119. https://doi.org/10.1038/nature10743
- Bonomo S, Hansen CH, Petrunak EM, Scott EE, Styrishave B, Jorgensen FS, Olsen L (2016) Promising tools in prostate cancer research: selective non-steroidal cytochrome P450 17A1 inhibitors. Sci Rep 6:29468. https://doi.org/10.1038/srep29468
- Attard G, Reid AH, Yap TA, Raynaud F, Dowsett M, Settatree S, Barrett M, Parker C, Martins V, Folkerd E, Clark J, Cooper CS, Kaye SB, Dearnaley D, Lee G, de Bono JS (2008) Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven. J Clin Oncol 26:4563-4571. https://doi.org/10.1200/jco.2007.15.9749
- Guengerich FP (2023) Cytochrome P450 enzymes as drug targets in human disease. Drug Metab Dispos DMD-MR-2023-001431. https://doi.org/10.1124/dmd.123.001431 [Online ahead of print]
- Auchus RJ, Yu MK, Nguyen S, Mundle SD (2014) Use of prednisone with abiraterone acetate in metastatic castration-resistant prostate cancer. Oncologist 19:1231-1240. https://doi.org/10.1634/theoncologist.2014-0167
- Ryan CJ, Smith MR, Fong L, Rosenberg JE, Kantoff P, Raynaud F, Martins V, Lee G, Kheoh T, Kim J, Molina A, Small EJ (2010) Phase I clinical trial of the CYP17 inhibitor abiraterone acetate demonstrating clinical activity in patients with castration-resistant prostate cancer who received prior ketoconazole therapy. J Clin Oncol 28:1481-1488. https://doi.org/10.1200/jco.2009.24.1281
- Bhatt MR, Khatri Y, Rodgers RJ, Martin LL (2017) Role of cytochrome b5 in the modulation of the enzymatic activities of cytochrome P450 17α-hydroxylase/17,20-lyase (P450 17A1). J Steroid Biochem Mol Biol 170:2-18. https://doi.org/10.1016/j.jsbmb.2016.02.033
- Lee G-H, Kim V, Lee S-G, Jeong E, Kim C, Lee Y-B, Kim D (2024) Catalytic enhancements in cytochrome P450 2C19 by cytochrome b5. Toxicol Res 40:215-222. https://doi.org/10.1007/s43188-023-00219-8
- Kim D, Kim V, McCarty KD, Guengerich FP (2021) Tight binding of cytochrome b(5) to cytochrome P450 17A1 is a critical feature of stimulation of C21 steroid lyase activity and androgen synthesis. J Biol Chem 296:100571. https://doi.org/10.1016/j.jbc.2021.100571
- Geller DH, Auchus RJ, Miller WL (1999) P450c17 mutations R347H and R358Q selectively disrupt 17,20-lyase activity by disrupting interactions with P450 oxidoreductase and cytochrome b5. Mol Endocrinol 13:167-175. https://doi.org/10.1210/mend.13.1.0219
- Gonzalez E, Guengerich FP (2017) Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1. J Biol Chem 292:13168-13185. https://doi.org/10.1074/jbc.M117.794917
- Katagiri M, Kagawa N, Waterman MR (1995) The role of cytochrome b5 in the biosynthesis of androgens by human P450c17. Arch Biochem Biophys 317:343-347. https://doi.org/10.1006/abbi.1995.1173
- Peng HM, Im SC, Pearl NM, Turcu AF, Rege J, Waskell L, Auchus RJ (2016) Cytochrome b5 activates the 17,20-lyase activity of human cytochrome P450 17A1 by increasing the coupling of NADPH consumption to androgen production. Biochemistry 55:4356-4365. https://doi.org/10.1021/acs.biochem.6b00532
- Estrada DF, Laurence JS, Scott EE (2013) Substrate-modulated cytochrome P450 17A1 and cytochrome b5 interactions revealed by NMR. J Biol Chem 288:17008-17018. https://doi.org/10.1074/jbc.M113.468926
- Estrada DF, Skinner AL, Laurence JS, Scott EE (2014) Human cytochrome P450 17A1 conformational selection: modulation by ligand and cytochrome b5. J Biol Chem 289:14310-14320. https://doi.org/10.1074/jbc.M114.560144
- Auchus RJ, Lee TC, Miller WL (1998) Cytochrome b5 augments the 17,20-lyase activity of human P450c17 without direct electron transfer. J Biol Chem 273:3158-3165. https://doi.org/10.1074/jbc.273.6.3158
- Kok RC, Timmerman MA, Wolfenbuttel KP, Drop SL, de Jong FH (2010) Isolated 17,20-lyase deficiency due to the cytochrome b5 mutation W27X. J Clin Endocrinol Metab 95:994-999. https://doi.org/10.1210/jc.2008-1745
- Malikova J, Brixius-Anderko S, Udhane SS, Parween S, Dick B, Bernhardt R, Pandey AV (2017) CYP17A1 inhibitor abiraterone, an anti-prostate cancer drug, also inhibits the 21-hydroxylase activity of CYP21A2. J Steroid Biochem Mol Biol 174:192-200. https://doi.org/10.1016/j.jsbmb.2017.09.007
- Speiser PW, Azziz R, Baskin LS, Ghizzoni L, Hensle TW, Merke DP, Meyer-Bahlburg HF, Miller WL, Montori VM, Oberfeld SE, Ritzen M, White PC (2010) Congenital adrenal hyperplasia due to steroid 21-hydroxylase deficiency: an Endocrine Society clinical practice guideline. J Clin Endocrinol Metab 95:4133-4160. https://doi.org/10.1210/jc.2009-2631
- Fehl C, Vogt CD, Yadav R, Li K, Scott EE, Aube J (2018) Structure-based design of inhibitors with improved selectivity for steroidogenic cytochrome P450 17A1 over cytochrome P450 21A2. J Med Chem 61:4946-4960. https://doi.org/10.1021/acs.jmedchem.8b00419
- Bhatnagar AS (2007) The discovery and mechanism of action of letrozole. Breast Cancer Res Treat 105(Suppl 1):7-17. https://doi.org/10.1007/s10549-007-9696-3
- Ghosh D, Lo J, Morton D, Valette D, Xi J, Griswold J, Hubbell S, Egbuta C, Jiang W, An J, Davies HM (2012) Novel aromatase inhibitors by structure-guided design. J Med Chem 55:8464-8476. https://doi.org/10.1021/jm300930n
- Evans TR, Di Salle E, Ornati G, Lassus M, Benedetti MS, Pianezzola E, Coombes RC (1992) Phase I and endocrine study of exemestane (FCE 24304), a new aromatase inhibitor, in postmenopausal women. Cancer Res 52:5933-5939 https://doi.org/10.1016/0960-0760(92)90198-R
- Lipton A, Demers LM, Harvey HA, Kambic KB, Grossberg H, Brady C, Adlercruetz H, Trunet PF, Santen RJ (1995) Letrozole (CGS 20267). A phase I study of a new potent oral aromatase inhibitor of breast cancer. Cancer 75:2132-2138. https://doi.org/10.1002/1097-0142(19950415)75:8%3c2132::aid-cncr2820750816%3e3.0.co;2-u
- Plourde PV, Dyrof M, Dowsett M, Demers L, Yates R, Webster A (1995) ARIMIDEX: a new oral, once-a-day aromatase inhibitor. J Steroid Biochem Mol Biol 53:175-179. https://doi.org/10.1016/0960-0760(95)00045-2
- Mojaddami A, Sakhteman A, Fereidoonnezhad M, Faghih Z, Najdian A, Khabnadideh S, Sadeghpour H, Rezaei Z (2017) Binding mode of triazole derivatives as aromatase inhibitors based on docking, protein ligand interaction fingerprinting, and molecular dynamics simulation studies. Res Pharm Sci 12:21-30. https://doi.org/10.4103/1735-5362.199043
- Simpson ER (2003) Sources of estrogen and their importance. J Steroid Biochem Mol Biol 86:225-230. https://doi.org/10.1016/s0960-0760(03)00360-1
- Sasano H, Uzuki M, Sawai T, Nagura H, Matsunaga G, Kashimoto O, Harada N (1997) Aromatase in human bone tissue. J Bone Miner Res 12:1416-1423. https://doi.org/10.1359/jbmr.1997.12.9.1416
- Khosla S, Oursler MJ, Monroe DG (2012) Estrogen and the skeleton. Trends Endocrinol Metab 23:576-581. https://doi.org/10.1016/j.tem.2012.03.008
- Cheung AM, Tile L, Cardew S, Pruthi S, Robbins J, Tomlinson G, Kapral MK, Khosla S, Majumdar S, Erlandson M, Scher J, Hu H, Demaras A, Lickley L, Bordeleau L, Elser C, Ingle J, Richardson H, Goss PE (2012) Bone density and structure in healthy postmenopausal women treated with exemestane for the primary prevention of breast cancer: a nested substudy of the MAP.3 randomised controlled trial. Lancet Oncol 13:275-284. https://doi.org/10.1016/s1470-2045(11)70389-8
- Perez EA, Josse RG, Pritchard KI, Ingle JN, Martino S, Findlay BP, Shenkier TN, Tozer RG, Palmer MJ, Shepherd LE, Liu S, Tu D, Goss PE (2006) Effect of letrozole versus placebo on bone mineral density in women with primary breast cancer completing 5 or more years of adjuvant tamoxifen: a companion study to NCIC CTG MA.17. J Clin Oncol 24:3629-3635. https://doi.org/10.1200/jco.2005.05.4882
- Eastell R, Adams JE, Coleman RE, Howell A, Hannon RA, Cuzick J, Mackey JR, Beckmann MW, Clack G (2008) Efect of anastrozole on bone mineral density: 5-year results from the anastrozole, tamoxifen, alone or in combination trial 18233230. J Clin Oncol 26:1051-1057. https://doi.org/10.1200/jco.2007.11.0726
- Pivonello R, Fleseriu M, Newell-Price J, Bertagna X, Findling J, Shimatsu A, Gu F, Auchus R, Leelawattana R, Lee EJ, Kim JH, Lacroix A, Laplanche A, O'Connell P, Tauchmanova L, Pedroncelli AM, Biller BMK (2020) Effcacy and safety of osilodrostat in patients with Cushing's disease (LINC 3): a multicentre phase III study with a double-blind, randomised withdrawal phase. Lancet Diabetes Endocrinol 8:748-761. https://doi.org/10.1016/s2213-8587(20)30240-0
- Fleseriu M, Pivonello R, Elenkova A, Salvatori R, Auchus RJ, Feelders RA, Geer EB, Greenman Y, Witek P, Cohen F, Biller BMK (2019) Effcacy and safety of levoketoconazole in the treatment of endogenous Cushing's syndrome (SONICS): a phase 3, multicentre, open-label, single-arm trial. Lancet Diabetes Endocrinol 7:855-865. https://doi.org/10.1016/s2213-8587(19)30313-4
- Valentin-Goyco J, Liu J, Peng HM, Oommen J, Auchus RJ (2023) Selectivity of osilodrostat as an inhibitor of human steroidogenic cytochromes P450. J Steroid Biochem Mol Biol 231:106316. https://doi.org/10.1016/j.jsbmb.2023.106316
- Bogman K, Schwab D, Delporte ML, Palermo G, Amrein K, Mohr S, De Vera Mudry MC, Brown MJ, Ferber P (2017) Preclinical and early clinical profile of a highly selective and potent oral inhibitor of aldosterone synthase (CYP11B2). Hypertension 69:189-196. https://doi.org/10.1161/hypertensionaha.116.07716
- Freeman MW, Halvorsen YD, Marshall W, Pater M, Isaacsohn J, Pearce C, Murphy B, Alp N, Srivastava A, Bhatt DL, Brown MJ (2023) Phase 2 trial of baxdrostat for treatment-resistant hypertension. N Engl J Med 388:395-405. https://doi.org/10.1056/NEJMoa2213169
- Lafn LJ, Rodman D, Luther JM, Vaidya A, Weir MR, Rajicic N, Slingsby BT, Nissen SE (2023) Aldosterone synthase inhibition with lorundrostat for uncontrolled hypertension: the target-HTN randomized clinical trial. JAMA 330:1140-1150. https://doi.org/10.1001/jama.2023.16029
- Amaral C, Varela C, Azevedo M, da Silva ET, Roleira FM, Chen S, Correia-da-Silva G, Teixeira N (2013) Effects of steroidal aromatase inhibitors on sensitive and resistant breast cancer cells: aromatase inhibition and autophagy. J Steroid Biochem Mol Biol 135:51-59. https://doi.org/10.1016/j.jsbmb.2012.12.017
- Lu Q, Liu Y, Long BJ, Grigoryev D, Gimbel M, Brodie A (1999) The effect of combining aromatase inhibitors with antiestrogens on tumor growth in a nude mouse model for breast cancer. Breast Cancer Res Treat 57:183-192. https://doi.org/10.1023/a:1006225601046
- Creemers SG, Feelders RA, de Jong FH, Franssen GJH, de Rijke YB, van Koetsveld PM, Hofand LJ (2019) Osilodrostat is a potential novel steroidogenesis inhibitor for the treatment of cushing syndrome: an in vitro study. J Clin Endocrinol Metab 104:3437-3449. https://doi.org/10.1210/jc.2019-00217
- Creemers SG, Feelders RA, de Jong FH, Franssen GJH, de Rijke YB, van Koetsveld PM, Hofand LJ (2021) Levoketoconazole, the 2S,4R enantiomer of ketoconazole, a new steroidogenesis inhibitor for cushing's syndrome treatment. J Clin Endocrinol Metab 106:e1618-e1630. https://doi.org/10.1210/clinem/dgaa989