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We Have Some Trouble with Special Characters and Displaying Monographs We have some trouble with special characters and displaying monographs. 22.09.2018 ATC code: G03HB01 Classification: PRP - Probably porphyrinogenic Substance: Cyproterone and estrogen Rationale for risk classification: Estrogens and progestogens are considered as potentially porphyrinogenic substances and are known to have caused porphyric attacks in susceptible carriers of acute porphyria. Both pharmacodynamic and pharmacokinetic properties can explain the triggering effect in acute porphyria. Studies have shown that these hormones can affect CYP enzymes by induction and mechanism-based inhibition. Although these effects are described to a limited extent in drug-drug interactions studies in general, it is likely that they have a role in a probable upregulation of the heme biosynthesis. Chemical description: 17-alpha-hydroxy-progesterone derivative. Therapeutic characteristics: Androgen in combination with estrogen used for systemic treatment of moderate to severe acne related to androgen-sensitivity (with or without seborrhea) and/or hirsutism, in women of reproductive age. This combination also prevents conception. Cyproterone has potent antiandrogen, gestagen and antigonadotropic activities. It is administered orally. Side effects or other pharmacodynamic effetcs of relevance to acute porphyria: A suggested hypothesis for the porphyrinogenic potential of progestins (Thunell 2016) is that they activate the mPR?-PGRMC2 receptor complex (Thomas 2013), which is accompanied by heme binding (Rohe 2009), and may therefore result in a heme drain. A decreased cellular heme pool may then upregulate ALAS-1 (Besur 2014). In addition, the heme-sensing receptor, Rev-erb-?, will sense the decreased level of the regulatory heme pool and reduce its repressor effect on PGC-1? (Wu 2009). PGC-1? may then co-activate FoxO1 and NRF-1, with subsequent induction of the ALAS-1 gene (Handschin 2005). Copyright 2007-2018 The Drug Database. All rights reserved.Page 1/8 An in vitro study found that estrogens might directly activate ALAS-1 (Du Plessis 2009). In the presence of estrogen, the estrogen receptor-? (ER-?) binds to estrogen receptor elements (ERE) in the ALAS-1 promotor and results in an elevated transcription of ALAS-1 and thereby causing a subsequent increase in the rate of the entire heme biosynthesis pathway. Metabolism and pharmacokinetics: Ethinyl estradiol is mainly metabolized via hydroxylation by CYP3A4 and CYP2C9 (Guengerich 1990, Wang 2004). Ethinyl estradiol is listed as an activator of hPXR by several references (Honkakoski 2003, Kretschmer 2005, Mnif 2007), but one in vitro study found that ethinyl estradiol only moderately transactivate hPXR, and this was seen at concentrations > 10 µM (Zhang 2007). Since this is well above concentrations obtained clinically the authors concluded that PXR activation is unlikely to be clinically relevant. Ethinyl estradiol contains an acetylenic group that has shown to cause mechanism-based inactivation of CYP enzymes (Ortiz 1980). In vitro studies suggest that ethinyl estradiol is a mechanism-based inhibitor of CYP3A4 through covalent attachment of the modified heme to the apoprotein (Guengerich 1988, Lin 2002) and CYP2B6 (Kent 2002). In vivo studies showed only minor and clinically insignificant effects on CYP 3A4 activity by oral contraceptives containing ethinylestradiol and progestin (Belle 2002, Palovaara 2000). The lack of observed significant effects on CYP 3A4 in vivo may partly be explained by PXR induction being counteracted and masked by a concurrent CYP inhibition, and this phenomenon has been discussed by Wei et al. for other drugs (Wei 2016). Ethinyl estradiol was found to be an in vitro inhibitor of CYP2C9 and CYP2C19 (Laine 2003), and the CYP2C19 inhibitory action is supported by in vivo studies (Hägg 2001, Palovaara 2003). Cyproterone acetate is metabolised by various pathways, including hydroxylations and conjugations. The main metabolite in human plasma is the 15ß-hydroxy derivative. Based on in vitro inhibition studies, an inhibition of the cytochrome P450 enzymes CYP2C8, 2C9, 2C19, 3A4 and 2D6 is possible at high Copyright 2007-2018 The Drug Database. All rights reserved.Page 2/8 cyproterone acetate doses of 100mg three times per day (SPC Anrdocur). Like other synthetic progestogens, cyproterone is an activator of PXR (Lehmann1998, Schuetz 1998, Kliewer 1998). Progestogens and estradiol are not listed as significant inducers of CYP 3A4 in most interaction databases (Preissner 2010, NOMA, Lexi-Interact, The Danish Health and Medicines Authority, Micromedex). Results from clinical studies suggest that the increased hormonal levels in pregnancy have the potential to alter hepatic cytochrome P450 drug metabolism (Anderson 2005). Also, in vitro studies have shown increased CYP mRNA after exposing hepatocytes to progesterone and estradiol levels equal to the high hormonal levels typically seen in the third trimester of pregnancy (Choi 2013). Hormonal therapy generally leads to a much lower plasma concentration relative to the levels of endogenous hormones in pregnancy and may explain the lack of observed significant effects of administered hormones on CYP 3A4 in vivo. However, since both ethinyl estradiol and the progestin component have the potential to induce ALAS1 through PXR activation and at the same time cause mechanism-based inhibition of CYP 3A4, this may explain the absence of observed pharmacokinetic drug-drug interactions. For an evaluation of the porphyrinogenicity of these drugs it is important to realize that the inhibitory effect can mask the inductive power and that an increased de novo synthesis of CYP enzymes can take place irrespective of negative results from in vivo DDI-studies. The effects of concomitant induction and inhibition have in general been discussed by Wei et al. for other drugs (Wei 2016). An increased de novo synthesis of CYP enzymes, although masked, will give an upregulation of ALAS-1and thereby a higher flux through the heme biosynthesis. Such a mechanism can possibly in part explain the observed porphyrinogenic effects of these drugs. Studies have shown that women with acute porphyria have an altered 5alfa-reductase steroid metabolism and it is suggested that this may lead to a diversion from the 5 alfa reductase pathway to formation of 5beta steroid metabolites that may be more potent inductors of ALAS1 (Innala 2012, Anderson 1979, Jacobs 2005). EPNET drug reports: Uneventful use reported in 2 patients with acute porphyria. References: Andersson C, Innala E, et al. Acute intermittent porphyria in women: clinical expression, use and experience of exogenous sex hormones. A population-based study in northern Sweden. J Intern Med. 2003 Copyright 2007-2018 The Drug Database. All rights reserved.Page 3/8 Aug;254(2):176-83. Anderson GD. Pregnancy-induced changes in pharmacokinetics: a mechanistic-based approach. Clin Pharmacokinet. 2005;44(10):989-1008. Anderson KE, Bradlow HL, et al. Studies in porphyria. VIII. Relationship of the 5 alpha-reductive metabolism of steroid hormones to clinical expression of the genetic defect in acute intermittent porphyria. Am J Med. 1979 Apr;66(4):644-50. Belle DJ, Callaghan JT, et al. The effects of an oral contraceptive containing ethinyloestradiol and norgestrel on CYP3A activity. Br J Clin Pharmacol. 2002 Jan;53(1):67-74. Besur S, Hou W, et al. Clinically important features of porphyrin and heme metabolism and the porphyrias. Metabolites. 2014 Nov 3;4(4):977-1006. Bonkovsky HL, Maddukuri VC et al. Acute porphyrias in the USA: features of 108 subjects from porphyrias consortium. Am J Med. 2014 Dec;127(12):1233-41. Choi S-Y, Koh KH, et al. Isoform-spesific regulation of cytochrome P450 expression by estradiol and progesterone. Drug Metab Dispos 2013 Feb. 41:253-269. Du Plessis N, Kimberg M, et al. Functional analysis of the 5' regulatory region of the 5-aminolevulinate synthase (ALAS1) gene in response to estrogen. Cell Mol Biol (Noisy-le-grand). 2009 Jul 1;55(2):20-30. Guengerich FP. Oxidation of 17 alpha-ethynylestradiol by human liver cytochrome P-450. Mol Pharmacol. 1988 May;33(5):500-8.’ Guengerich FP. Metabolism of 17 alpha-ethynylestradiol in humans. Life Sci. 1990;47(22):1981-8. Copyright 2007-2018 The Drug Database. All rights reserved.Page 4/8 Handschin C, Lin J, et al. Nutritional regulation of hepatic heme biosynthesis and porphyria through PGC-1alpha. Cell. 2005 Aug 26;122(4):505-15. Honkakoski P1, Sueyoshi T, et al. Drug-activated nuclear receptors CAR and PXR. Ann Med. 2003;35(3):172-82. Hägg S, Spigset O, et al. Influence of gender and oral contraceptives on CYP2D6 and CYP2C19 activity in healthy volunteers. Br J Clin Pharmacol. 2001 Feb;51(2):169-73. Innala E, Bäckström T et al. Women with acute intermittent porphyria have a defect in 5?-steroid production during the menstrual cycle. Acta Obstet Gynecol Scand. 2012 Dec;91(12):1445-52. Jacobs MN, Nolan GT, Hood SR. Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). Toxicol Appl Pharmacol. 2005 Dec 1;209(2):123-33 Kauppinen R, Mustajoki P. Prognosis of acute porphyria: occurrence of acute attacks, precipitating factors, and associated diseases. Medicine (Baltimore). 1992 Jan;71(1):1-13. Kent UM, Mills DE, et al. Effect of 17-alpha-ethynylestradiol on activities of cytochrome P450 2B (P450 2B) enzymes: characterization of inactivation of P450s 2B1 and 2B6 and identification of metabolites. J Pharmacol Exp Ther. 2002 Feb;300(2):549-58. Kent UM, Mills DE, et al. Effect of 17-alpha-ethynylestradiol on activities of cytochrome P450 2B (P450 2B) enzymes: characterization of inactivation of P450s 2B1 and 2B6 and identification of metabolites. J Pharmacol Exp Ther. 2002 Feb;300(2):549-58. Kliewer SA, Moore JT, et al. An orphan nuclear receptor activated by pregnanes defines a novel steroid signaling pathway. Cell. 1998 Jan 9;92(1):73-82. Kretschmer XC1, Baldwin WS. CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. Copyright 2007-2018 The Drug Database. All rights reserved.Page 5/8 2005 Aug 15;155(3):111-28 Laine K, Yasar U, et al.
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