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All progestins are not created equal
Abstract
A variety of progestins are available for therapeutic use. It is convenient to classify them into those related in chemical structure to progesterone or testosterone. Progestins related to progesterone can be subdivided into pregnanes and 19-norpregnanes, whereas those related to testosterone can be subdivided into those with and without a 17-ethinyl group. 17-Ethinylated progestins consist of the families of norethindrone (estranes) and levonorgestrel (13-ethylgonanes). Progestins administered orally undergo extensive hepatic first pass metabolism primarily by reduction and conjugation, and in most instances, relatively high progestin doses are required for therapeutic use. There are limited reliable data on the pharmacokinetics of most progestins. Some progestins are prodrugs, requiring transformation prior to exhibiting progestational activity. Qualitative and quantitative tests utilizing either human or animal species have been used to establish progestin potency. However, profound differences in progestational activity are often observed between human and animal tissues. Also, there is a misconception about androgenicity of progestins due largely to extrapolation of data from rat studies to the human. Progestins differ widely in their chemical structures, structure-function relationships, metabolism, pharmacokinetics, and potencies; they are not created equal.
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“Progestogens are primarily metabolized by the liver largely to form pregnanediols and pregnanolones [336,337].”
From Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: a comprehensive review (2019) · cites this paper as [337]
Citations
Cites
Reproductive Endocrinology: Physiology, Pathophysiology and Clinical Management.
(1986) · Annals of Internal Medicine · doi:10.7326/0003-4819-105-3-484_1 · Cited by 413
Drospirenone: pharmacology and pharmacokinetics of a unique progestogen
Krattenmacher, R. (2000) · Contraception · doi:10.1016/s0010-7824(00)00133-5 · Cited by 375
Treatment of the Postmenopausal Woman
Løbo, R. A., Taylor, A. E., & Schlechte, J. (1995) · The Endocrinologist · doi:10.1097/00019616-199501000-00012 · Cited by 194
Simon, J. A., Robinson, D. E., Andrews, M. C., Hildebrand, J. R., Rocci, M. L., Blake, R. E., & Hodgen, G. D. (1993) · Fertility and Sterility · doi:10.1016/s0015-0282(16)56031-2 · Cited by 151
Assessment of the potency of orally administered progestins in women
King, R. J. B., & Whitehead, M. I. (1986) · Fertility and Sterility · doi:10.1016/s0015-0282(16)49880-8 · Cited by 127
Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids
Stanczyk, F. Z., & Roy, S. (1990) · Contraception · doi:10.1016/0010-7824(90)90093-b · Cited by 122
Phillips, A., Demarest, K. T., Hahn, D. W., Wong, F. A., & McGuire, J. L. (1990) · Contraception · doi:10.1016/0010-7824(90)90039-x · Cited by 119
Effect of low-dose oral contraceptives on androgenic markers and acne
Thorneycroft, I. H., Stanczyk, F. Z., Bradshaw, K. D., Ballagh, S. A., Nichols, M. D. N., & Weber, M. E. (1999) · Contraception · doi:10.1016/s0010-7824(99)00093-1 · Cited by 112
Pharmacokinetics and Potency of Progestins used for Hormone Replacement Therapy and Contraception
Stanczyk, F. Z. (2002) · Reviews in Endocrine and Metabolic Disorders · doi:10.1023/a:1020072325818 · Cited by 108
Kuhnz, W., Heuner, A., Humpel, M., Seifert, W., & Michaelis, K. (1997) · Contraception · doi:10.1016/s0010-7824(97)00174-1 · Cited by 106
Flagged first, then by citations
3 of the 37 references couldn’t be matched to a known paper.
Research works printed but not linked: 5
- Stanczyk, 1989, Pharmacokinetics of progestogens, Int. Proc. J., 1, 11
- Stanczyk, 1996, Introduction: structure–function relationships, metabolism, pharmacokinetics and potency of progestins, Drugs Today, 32, 1
- Kuhnz, 1993, Systemic availability of levonorgestrel after single oral administration of a norgestimate-containing oral contraceptive to 12 women, Contraception, 47, 283
- Oettel, 1995, A 19-norprogestin without a 17α-ethinyl group. I. Dienogest from a pharmacokinetic point of view, Drugs Today, 31, 499
- Teichman AT. Levonorgestrel, vol. 43. Stuart-George Thieme Verlag; 1990.
Cited by
Sorted by citations
Fournier, A., Berrino, F., & Clavel-Chapelon, F. (2007) · Breast Cancer Research and Treatment · doi:10.1007/s10549-007-9523-x · Cited by 693
“However, small structural changes in progestagens may considerably alter their effects [2,3].”
BackgroundProgesterone receptors: form and function in brain
Brinton, R. D., Thompson, R. F., Foy, M. R., Baudry, M., Wang, J., Finch, C. E., Morgan, T. E., Pike, C. J., Mack, W. J., Stanczyk, F. Z., et al. (2008) · Frontiers in Neuroendocrinology · doi:10.1016/j.yfrne.2008.02.001 · Cited by 675
“anes (20 carbons) (see Tables 1 and 2) [258].”
Schiffer, L., Barnard, L., Baranowski, E. S., Gilligan, L. C., Taylor, A. E., Arlt, W., Shackleton, C. H. L., & Storbeck, K.-H. (2019) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2019.105439 · Cited by 450
“Progestogens are primarily metabolized by the liver largely to form pregnanediols and pregnanolones [336,337].”
Stanczyk, F. Z., Hapgood, J. P., Winer, S., & Mishell, D. R. (2013) · Endocrine Reviews · doi:10.1210/er.2012-1008 · Cited by 429
“The biological activity of a progestogen changes considerably, depending on its chemical structure, particularly with respect to pharmacokinetics and potency (5).”
BackgroundInfluentialContraception Selection, Effectiveness, and Adverse Effects
Teal, S. B., & Edelman, A. B. (2021) · JAMA · doi:10.1001/jama.2021.21392 · Cited by 371
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Trabert, B. L., Sherman, M. E., Kannan, N., & Stanczyk, F. Z. (2019) · Endocrine Reviews · doi:10.1210/endrev/bnz001 · Cited by 273
Africander, D., Verhoog, N. J. D., & Hapgood, J. P. (2011) · Steroids · doi:10.1016/j.steroids.2011.03.001 · Cited by 244
Guennoun, R., Labombarda, F., Deniselle, M. C. G., Lière, P., Nicola, A. F. D., & Schumacher, M. (2014) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2014.09.001 · Cited by 232
Progesterone Synthesis in the Nervous System: Implications for Myelination and Myelin Repair
Schumacher, M., Hussain, R., Gago, N., Oudinet, J., Mattern, C., & Ghoumari, A. M. (2012) · Frontiers in Neuroscience · doi:10.3389/fnins.2012.00010 · Cited by 233
“However, it is important to call here attention to the fact that not all synthetic progestins are the same, and that they belong to different classes with very distinct pharmacological properties and actions (Stanczyk, 2003; Hapgood et al., 2004; Schumacher et al., 2007, 2008).”
BackgroundSteroid Hormones and Their Action in Women's Brains: The Importance of Hormonal Balance
Río, J. P. D., Alliende, M. I., Molina, N., Serrano, F. G., Molina, S., & Pilar Vigil, P. (2018) · Frontiers in Public Health · doi:10.3389/fpubh.2018.00141 · Cited by 235
“term progestin refers to synthetic progesterone (111).”
Fournier, A., Fabre, A., Mesrine, S., Boutron‐Ruault, M., Berrino, F., & Clavel‐Chapelon, F. (2008) · Journal of Clinical Oncology · doi:10.1200/jco.2007.13.4338 · Cited by 187
Pharmacokinetic Drug Interactions Involving 17??-Ethinylestradiol
Zhang, H., Cui, D., Wang, B., Han, Y., Balimane, P. V., Yang, Z., Sinz, M., & Rodrigues, A. D. (2007) · Clinical Pharmacokinetics · doi:10.2165/00003088-200746020-00003 · Cited by 174
The Challenge Presented by Progestins in Ecotoxicological Research: A Critical Review
Kumar, V., Johnson, A. C., Trubiroha, A., Tumová, J., Ihara, M., Grabic, R., Kloas, W., Tanaka, H., & Kroupová, H. K. (2015) · Environmental Science & Technology · doi:10.1021/es5051343 · Cited by 170
Progestagens for human use, exposure and hazard assessment for the aquatic environment
Besse, J.-P., & Garric, J. (2009) · Environmental Pollution · doi:10.1016/j.envpol.2009.06.012 · Cited by 145
“Metabolism data 193 194 Metabolism and pharmacokinetic data for progestins are limited (Stanczyk, 2003).”
BackgroundBedaiwy, M. A., Allaire, C., & Alfaraj, S. (2017) · Fertility and Sterility · doi:10.1016/j.fertnstert.2016.12.024 · Cited by 126
Bakken, K. S., Fournier, A., Lund, E., Waaseth, M., Dumeaux, V., Clavel‐Chapelon, F., Fabre, A., Hémon, B., Rinaldi, S., Chajès, V., et al. (2010) · International Journal of Cancer · doi:10.1002/ijc.25314 · Cited by 143
Selective Progesterone Receptor Modulators—Mechanisms and Therapeutic Utility
Islam, M. S., Afrin, S., Jones, S. I., & Segars, J. (2020) · Endocrine Reviews · doi:10.1210/endrev/bnaa012 · Cited by 143
Allen, N. E., Tsilidis, K. K., Key, T. J., Dossus, L., Kaaks, R., Lund, E., Bakken, K. S., Gavrilyuk, O. N., Overvad, K., Tjønneland, A. M., et al. (2010) · American Journal of Epidemiology · doi:10.1093/aje/kwq300 · Cited by 141
Comparative Pathology of Mammary Gland Cancers in Domestic and Wild Animals
Munson, L., & Moresco, A. (2007) · Breast Disease · doi:10.3233/bd-2007-28102 · Cited by 137
“When high dose progestins are administered concurrently with estrogens, mammary cancers do arise in dogs [39,61,84] One factor to be considered in comparing the results of these studies is that progestins differ in relative potencies; MGA is approximately 100X [30,119]and MPA approximately 50X the potency of progester…”
The Influence of Oral Contraceptives on Athletic Performance in Female Athletes
Burrows, M., & Peters, C. E. (2007) · Sports Medicine · doi:10.2165/00007256-200737070-00001 · Cited by 122
Hormonal Contraception and HIV-1 Acquisition: Biological Mechanisms
Hapgood, J. P., Kaushic, C., & Hel, Z. (2018) · Endocrine Reviews · doi:10.1210/er.2017-00103 · Cited by 120
“All other relative binding affinities and all other progestin biological activities in preclinical models were taken from references (32, 38).”
BackgroundHormonal modulation of the immune system — A spotlight on the role of progestogens
Tan, I. J., Peeva, E., & Zandman‐Goddard, G. (2015) · Autoimmunity Reviews · doi:10.1016/j.autrev.2015.02.004 · Cited by 117
Association of Surgical Risk With Exogenous Hormone Use in Transgender Patients
Boskey, E. R., Taghinia, A. H., & Ganor, O. (2018) · JAMA Surgery · doi:10.1001/jamasurg.2018.4598 · Cited by 101
Kissow, J., Jacobsen, K. J., Gunnarsson, T. P., Jessen, S., & Hostrup, M. (2022) · Sports Medicine · doi:10.1007/s40279-022-01679-y · Cited by 101
Progesterone to prevent spontaneous preterm birth
Romero, R. J., Yeo, L., Chaemsaithong, P., Chaiworapongsa, T., & Hassan, S. S. (2013) · Seminars in Fetal and Neonatal Medicine · doi:10.1016/j.siny.2013.10.004 · Cited by 103
Ajo, P., Preis, S., Vornamo, T., Mänttäri, M., Kallioinen, M., & Louhi‐Kultanen, M. (2018) · Journal of environmental chemical engineering · doi:10.1016/j.jece.2018.02.007 · Cited by 97
“A comprehensive list of identified and theoretical metabolites of progesterone can be found in the article by Stanczyk [52].”
BackgroundInternational society of sports nutrition position stand: nutritional concerns of the female athlete
Sims, S. T., Kerksick, C. M., Smith-Ryan, A. E., Janse de Jonge, X. A. K., Hirsch, K. R., Arent, S. M., Hewlings, S. J., Kleiner, S. M., Bustillo, E., Tartar, J. L., et al. (2023) · Journal of the International Society of Sports Nutrition · doi:10.1080/15502783.2023.2204066 · Cited by 129
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Butterworth, R. F. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2015.11.006 · Cited by 90
Metabolism and pharmacokinetics of contraceptive steroids in obese women: a review
Edelman, A. B., Cherala, G., & Stanczyk, F. Z. (2010) · Contraception · doi:10.1016/j.contraception.2010.04.016 · Cited by 90
“However, as stated earlier, there is wide intersubject variability in their blood levels and pharmacokinetic parameters [28].”
BackgroundInfluentialLiu, L., Zhao, L., She, H., Chen, S., Wang, J. M., Wong, C., McClure, K., Sitruk-Ware, R. L., & Brinton, R. D. (2010) · Endocrinology · doi:10.1210/en.2010-0005 · Cited by 90
Progesterone and progestins: neuroprotection and myelin repair
Schumacher, M., Sitruk-Ware, R. L., & Nicola, A. F. D. (2008) · Current Opinion in Pharmacology · doi:10.1016/j.coph.2008.10.002 · Cited by 92
Fu, X., Giretti, M. S., Baldacci, C., Garibaldi, S., Flamini, M. I., Sanchez, A. M., Gadducci, A., Genazzani, A. R., & Simoncini, T. (2008) · PLoS ONE · doi:10.1371/journal.pone.0002790 · Cited by 85
“The pharmacological properties of progestins are not equal [13, 14 ].”
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Perry, G. A. (2016) · Theriogenology · doi:10.1016/j.theriogenology.2016.04.051 · Cited by 83
Romero, R. J., & Stanczyk, F. Z. (2013) · American Journal of Obstetrics and Gynecology · doi:10.1016/j.ajog.2013.04.027 · Cited by 82
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Ahboucha, S., & Butterworth, R. F. (2007) · Neurochemistry International · doi:10.1016/j.neuint.2007.05.004 · Cited by 81
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Noh, J. J., Maskarinec, G., Pagano, I., Cheung, L. W. K., & Stanczyk, F. Z. (2005) · The Breast · doi:10.1016/j.breast.2005.04.014 · Cited by 81
Liu, S., Chen, H., Xu, X., Liu, S., Sun, K., Zhao, J., & Ying, G. (2014) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2014.09.039 · Cited by 82
Shifren, J. L., Rifai, N., Desindes, S., McIlwain, M., Doros, G. D., & Mazer, N. A. (2008) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jc.2007-2193 · Cited by 81
“In comparison to medroxyprogesterone acetate, norethisterone acetate, and levonorgestrel,oralmicronizedprogesteronewouldbeexpected to have minimal androgenicity, and a negligible effect on the inflammation and hepatic parameters in this study (32, 33 ).”
BackgroundEdelman, A. B., Cherala, G., Blue, S. W., Erikson, D. W., & Jensen, J. T. (2016) · Contraception · doi:10.1016/j.contraception.2016.03.006 · Cited by 77
“LNG is a highly bound drug, mainly to SHBG, with only a small fraction unbound (2–3%) [15,16].”
BackgroundPolycystic ovary syndrome: A review for dermatologists
Housman, E., & Reynolds, R. V. (2014) · Journal of the American Academy of Dermatology · doi:10.1016/j.jaad.2014.05.007 · Cited by 78
Grøntvedt, T. V., Grebe, N. M., Kennair, L. E. O., & Gangestad, S. W. (2016) · Evolution and Human Behavior · doi:10.1016/j.evolhumbehav.2016.10.006 · Cited by 74
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Piette, P. C. M. (2020) · Best Practice & Research Clinical Obstetrics & Gynaecology · doi:10.1016/j.bpobgyn.2020.06.002 · Cited by 76
Hormonal contraception and obesity
Simmons, K. B., & Edelman, A. B. (2016) · Fertility and Sterility · doi:10.1016/j.fertnstert.2016.07.1094 · Cited by 73
Role of CYP3A in Oral Contraceptives Clearance
Zhang, N., Shon, J., Kim, M., Yu, C., Zhang, L., Huang, S. M., Lee, L., Tran, D. C., & Li, L. (2017) · Clinical and Translational Science · doi:10.1111/cts.12499 · Cited by 68
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Jaakkola, S., Lyytinen, H. K., Pukkala, ., & Ylikorkala, O. (2009) · Obstetrics and Gynecology · doi:10.1097/aog.0b013e3181bea950 · Cited by 65
Simone, J., Bogue, E. A., Bhatti, D. L., Day, L. E., Farr, N. A., Grossman, A. M., & Holmes, P. V. (2015) · Psychoneuroendocrinology · doi:10.1016/j.psyneuen.2015.08.015 · Cited by 64
Jaakkola, S., Lyytinen, H. K., Dyba, T. A., Ylikorkala, O., & Pukkala, . (2010) · International Journal of Cancer · doi:10.1002/ijc.25762 · Cited by 62
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BackgroundHormonal Contraception and Depression: Updated Evidence and Implications in Clinical Practice
Fruzzetti, F., & Fidecicchi, T. (2020) · Clinical Drug Investigation · doi:10.1007/s40261-020-00966-8 · Cited by 67
“It is converted to 5β-LNG, 3α-LNG, and 3β,5α-LNG, with also less anxiolytic effects [60].”
BackgroundProgestogens and brain: An update
Pluchino, N., Cubeddu, A., Giannini, A., Merlini, S., Cela, V., Angioni, S. L., & Genazzani, A. R. (2009) · Maturitas · doi:10.1016/j.maturitas.2008.11.023 · Cited by 61
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Bick, A. J., Toit, R. L.-D., Skosana, S. B., Africander, D., & Hapgood, J. P. (2020) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2020.107789 · Cited by 60
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García-Sáenz, M. R., Ibarra‐Salce, R., Pozos-Varela, F. J., Mena-Ureta, T. S., Flores-Villagómez, S., Santana-Mata, M. A., Aguilar, R. D. L. S., Uribe-Cortés, D., & Ferreira‐Hermosillo, A. (2023) · Journal of Clinical Medicine · doi:10.3390/jcm12103388 · Cited by 60
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BackgroundAhboucha, S., Pomier–Layrargues, G., Mamer, O., & Butterworth, R. F. (2006) · Neurochemistry International · doi:10.1016/j.neuint.2006.02.002 · Cited by 60
Schwartz, E., & Holtorf, K. (2008) · Primary Care Clinics in Office Practice · doi:10.1016/j.pop.2008.07.015 · Cited by 59
“The molecular difference between these two types of hormone formulations affect their actions in the human body.(2,4,7,10) In 2001, a literature review by Stanczyk(5) scrutinized the various estrogen preparations available on the market.”
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Coombes, Z., Yadav, V., McCoubrey, L. E., Freire, C., Basit, A. W., Conlan, R. S., & González, D. (2020) · Pharmaceutics · doi:10.3390/pharmaceutics12080760 · Cited by 58
“Known metabolites of LNG include several tetrahydro- and hydroxy- derivatives, in addition to sulfate and glucuronide conjugations produced during phase II hepatic metabolism [42,44].”
BackgroundBray, J. D., Jelinsky, S. A., Ghatge, R. P., Bray, J. A., Tunkey, C. D., Saraf, K. A., Jacobsen, B. M., Richer, J. K., Brown, E. L., Winneker, R. C., et al. (2005) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2005.06.032 · Cited by 59
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Dalgaard, L. B., Dalgas, U., Andersen, J. L., Rossen, N. B., Møller, A. B., Stødkilde-Jørgensen, H., Jørgensen, J. O., Kovanen, V., Couppé, C., Langberg, H., et al. (2019) · Frontiers in Physiology · doi:10.3389/fphys.2019.00824 · Cited by 58
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BackgroundThe other side of progestins: effects in the brain.
Giatti, S., Melcangi, R., & Pesaresi, M. (2016) · Journal of Molecular Endocrinology · doi:10.1530/jme-16-0061 · Cited by 53
“…plasma binding proteins that bind steroids (i.e., albumin, corticosteroid-binding globulin (CBG), and sex hormone binding globulin (SHBG)) (Hammond 2002, Schindler et al. 2003) as well as by the metabolism of progestins, which can result in compounds that have different activities (Stanczyk 2003).”
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Abenhaim, H. A., Suissa, S., Azoulay, L., Spence, A. R., Czuzoj‐Shulman, N., & Tulandi, T. (2022) · Obstetrics and Gynecology · doi:10.1097/aog.0000000000004723 · Cited by 57
Kroupová, H. K., Trubiroha, A., Lorenz, C., Contardo‐Jara, V., Lutz, I., Grabic, R., Kocour, M., & Kloas, W. (2014) · Aquatic Toxicology · doi:10.1016/j.aquatox.2014.05.008 · Cited by 57
Degradation of Norgestrel by Bacteria from Activated Sludge: Comparison to Progesterone
Liu, S., Ying, G., Liu, Y.-S., Peng, F., & He, L.-Y. (2013) · Environmental Science & Technology · doi:10.1021/es304688g · Cited by 53
Tsilidis, K. K., Allen, N. E., Key, T. J., Dossus, L., Kaaks, R., Bakken, K. S., Lund, E., Fournier, A., Dahm, C. C., Overvad, K., et al. (2011) · Cancer Causes & Control · doi:10.1007/s10552-011-9782-z · Cited by 53
“For estrogen-only users, analyses were performed by constituent (estradiol compounds, conjugated equine estrogens) and route of administration (cutaneous, oral), and for estrogen plus progestin users, by progestin constituent (micronized [natural] progesterone, progesterone derivatives, testosterone derivatives) [8],…”
Sonneveld, E., Pieterse, B., Schoonen, W. G. E. J., & van der Burg, B. (2010) · Toxicology in Vitro · doi:10.1016/j.tiv.2010.11.018 · Cited by 51
Norethisterone and its acetate – what’s so special about them?
Huvinen, E., Holopainen, E., & Heikinheimo, O. (2020) · BMJ Sexual & Reproductive Health · doi:10.1136/bmjsrh-2020-200619 · Cited by 50
Meendering, J. R., Torgrimson, B. N., Miller, N. P., Kaplan, P., & Minson, C. T. (2008) · American Journal of Physiology-Heart and Circulatory Physiology · doi:10.1152/ajpheart.01314.2007 · Cited by 47
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BackgroundPharmacodynamics of combined estrogen-progestin oral contraceptives: 2. effects on hemostasis
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BackgroundBraden, B. B., Andrews, M. G., Acosta, J. I., Mennenga, S. E., Lavery, C. N., & Bimonte‐Nelson, H. A. (2016) · Behavioural Brain Research · doi:10.1016/j.bbr.2016.06.053 · Cited by 46
Polycystic ovary syndrome: A review for dermatologists
Buzney, E. A., Sheu, J., Buzney, C. D., & Reynolds, R. V. (2014) · Journal of the American Academy of Dermatology · doi:10.1016/j.jaad.2014.05.009 · Cited by 47
Perry, G. A. (2011) · Journal of Animal Science · doi:10.2527/jas.2011-4572 · Cited by 46
Salazar, M. G. S., Lerma-Ortiz, A., Hooks, G. M., Ashley, A. K., & Ashley, R. L. (2016) · Gene · doi:10.1016/j.gene.2016.06.044 · Cited by 45
“Indeed, the pharmacological properties of progestins vary depending on their parent compound in which they were synthesized from, leading to disparities in biological activities (Schindler, Campagnoli, Druckmann et al., 2003, Stanczyk, 2003).”
BackgroundEthinyl estradiol-to-desogestrel ratio impacts endothelial function in young women
Meendering, J. R., Torgrimson, B. N., Miller, N. P., Kaplan, P., & Minson, C. T. (2008) · Contraception · doi:10.1016/j.contraception.2008.07.025 · Cited by 45
“Each progestin can have dramatically different effects on the body based on the parent molecule from which it was created, its chemical structure, pharmacokinetics, activity and specificity to given receptors [24–27].”
Naturally Occurring and Melengestrol Acetate-associated Reproductive Tract Lesions in Zoo Canids
Moresco, A., Munson, L., & Gardner, I. A. (2009) · Veterinary Pathology · doi:10.1354/vp.08-vp-0293-m-fl · Cited by 43
Association of Estrogen and Progestin Potency of Oral Contraceptives With Ovarian Carcinoma Risk
Lurie, G., Thompson, P. J., McDuffie, K., Carney, M. E., Terada, K. Y., & Goodman, M. T. (2007) · Obstetrics and Gynecology · doi:10.1097/01.aog.0000255664.48970.e6 · Cited by 44
Effects of Female Reproductive Hormones on Sports Performance
Lebrun, C. M., Joyce, S., & Constantini, N. (2013) · Humana Press eBooks · doi:10.1007/978-1-62703-314-5_16 · Cited by 49
Contraceptive progestins with androgenic properties stimulate breast epithelial cell proliferation
Shamseddin, M., Martino, F. D., Constantin, C., Scabia, V., Lancelot, A., László, C., Ayyanan, A., Battista, L., Raffoul, W., Gailloud‐Matthieu, M., et al. (2021) · EMBO Molecular Medicine · doi:10.15252/emmm.202114314 · Cited by 45
“They also vary in bioavailability, efficacy, and have different binding affinities for the sex hormone-binding globulin (SHBG) and corticosteroid-binding globulin (CBG) bound to which these hydrophobic substances travel in the bloodstream (Stanczyk, 2002, 2003 ) .”
Petit-Topin, I., Turque, N., Fagart, J., Fay, M., Ulmann, A., Gainer, E., & Rafestin-Oblin, M. E. (2009) · Molecular Pharmacology · doi:10.1124/mol.108.054312 · Cited by 43
“Many progestins have been developed for contraception, menopausal hormone therapy, and treatment of gynecological diseases (Schindler et al., 2003; Stanczyk, 2003; SitrukWare, 2004, 2007).”
BackgroundCardiovascular effects of medroxyprogesterone acetate and progesterone: a case of mistaken identity?
Hermsmeyer, R. K., Thompson, T. L., Pohost, G. M., & Kaski, J. C. (2008) · Nature Clinical Practice Cardiovascular Medicine · doi:10.1038/ncpcardio1234 · Cited by 40
“There is, however, only one unique, naturally occurring hormone known as progesterone, which is a specific chemical entity that belongs to the class of progestins”
BackgroundWillibald, M., Bayer, G., Stahlhut, V., Poschmann, G., Stühler, K., Gierke, B., Pawlak, M., Seeger, H., Mueck, A. O., Niederacher, D., et al. (2017) · Oncotarget · doi:10.18632/oncotarget.19819 · Cited by 38
“However, they differ from their molecule of origin and from each other in metabolism, pharmacokinetics, pharmacodynamics, potency and binding affinity to progesterone receptor (PR), causing different effects in breast cells [13,14].”
The neurosteroid system: an emerging therapeutic target for hepatic encephalopathy
Ahboucha, S., & Butterworth, R. F. (2007) · Metabolic Brain Disease · doi:10.1007/s11011-007-9065-2 · Cited by 38
“Some precursors of NS, including pregnenolone and progesterone, are normally metabolized by the liver (Stanczyk 2003).”
BackgroundMagnetic Resonance Imaging (MRI) of hormone-induced breast changes in young premenopausal women
Clendenen, T. V., Kim, S., Moy, L. P., Wan, L. S., Rusinek, H., Stanczyk, F. Z., Pike, M. C., & Zeleniuch‐Jacquotte, A. (2012) · Magnetic Resonance Imaging · doi:10.1016/j.mri.2012.06.022 · Cited by 38
“We studied a single OC formulation because the type and dose of hormones differ across formulations [29] and may have variable effects on the breast tissue.”
BackgroundFu, X., Giretti, M. S., Goglia, L., Flamini, M. I., Sanchez, A. M., Baldacci, C., Garibaldi, S., Sitruk-Ware, R. L., Genazzani, A. R., & Simoncini, T. (2008) · BMC Cancer · doi:10.1186/1471-2407-8-166 · Cited by 39
“The pharmacological properties of progestins vary depending on the parent molecule from which they are derived, leading to considerable variations of the full spectrum of biological activities [2,6].”
BackgroundMeendering, J. R., Torgrimson, B. N., Miller, N. P., Kaplan, P., & Minson, C. T. (2010) · Contraception · doi:10.1016/j.contraception.2010.03.009 · Cited by 36
The role of progestins in treating the pain of endometriosis
Surrey, E. S. (2006) · Journal of Minimally Invasive Gynecology · doi:10.1016/j.jmig.2006.06.008 · Cited by 36
Oral progesterone for the prevention of recurrent preterm birth: systematic review and metaanalysis
Boelig, R. C., Corte, L. D., Ashoush, S. A., McKenna, D. S., Saccone, G., Rajaram, S., & Berghella, V. (2019) · American Journal of Obstetrics & Gynecology MFM · doi:10.1016/j.ajogmf.2019.03.001 · Cited by 35
Progress in progestin-based therapies for neurological disorders
Sitruk-Ware, R. L., Bonsack, B., Brinton, R. D., Schumacher, M., Kumar, N., Lee, J.-Y., Castelli, V., Corey, S., Coats, A. B., Sadanandan, N., et al. (2020) · Neuroscience & Biobehavioral Reviews · doi:10.1016/j.neubiorev.2020.12.007 · Cited by 36
Do progestins contribute to (anti-)androgenic activities in aquatic environments?
Šauer, P., Bořík, A., Golovko, O., Grabic, R., Staňová, A. V., Valentová, O., Stará, A., Šandová, M., & Kroupová, H. K. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2018.06.104 · Cited by 33
Effects of Combination Oral Contraceptives on Strength Development in Women Athletes
Nichols, A. W., Hetzler, R. K., Villanueva, R. J., Stickley, C. D., & Kimura, I. F. (2008) · The Journal of Strength and Conditioning Research · doi:10.1519/jsc.0b013e31817ae1f3 · Cited by 33
“For example, levonorgestrol and norethindrone have been shown to have both androgenic and antiandrogenic properties (36).”
BackgroundBasis of melengestrol acetate action as a progestin
Perry, G. A., Welshons, W. V., Bott, R. C., & Smith, M. F. (2004) · Domestic Animal Endocrinology · doi:10.1016/j.domaniend.2004.07.002 · Cited by 33
Fournier, A., Berrino, F., & Clavel‐Chapelon, F. (2007) · Breast Cancer Research and Treatment · doi:10.1007/s10549-007-9604-x · Cited by 33
Maritz, M. F., Ray, R. M., Bick, A. J., Tomasicchio, M., Woodland, J. G., Govender, Y., Avenant, C., & Hapgood, J. P. (2018) · PLoS ONE · doi:10.1371/journal.pone.0196043 · Cited by 33
Neuroactive steroids and fatigue severity in patients with primary biliary cirrhosis and hepatitis C
Ahboucha, S., Butterworth, R. F., Pomier–Layrargues, G., Vincent, C., Hassoun, Z., & Baker, G. B. (2008) · Neurogastroenterology & Motility · doi:10.1111/j.1365-2982.2007.01080.x · Cited by 31
Influence of Progestin Bioactivity on Cutaneous Vascular Responses to Passive Heating
Houghton, B. L., Holowatz, L. A., & Minson, C. T. (2005) · Medicine & Science in Sports & Exercise · doi:10.1249/01.mss.0000150075.81511.fe · Cited by 31
Malik, M., Britten, J., Cox, J. M., Patel, A. D., & Catherino, W. H. (2015) · Fertility and Sterility · doi:10.1016/j.fertnstert.2015.09.006 · Cited by 30
Tsilidis, K. K., Allen, N. E., Key, T. J., Sanjoaquin, M. A., Bakken, K. S., Berrino, F., Fournier, A., Lund, E., Overvad, K., Olsen, A., et al. (2010) · International Journal of Cancer · doi:10.1002/ijc.25504 · Cited by 30
Impact of Metabolism on the Safety of Estrogen Therapy
Prókai-Tátrai, K., & Prókai, L. (2005) · Annals of the New York Academy of Sciences · doi:10.1196/annals.1347.018 · Cited by 31
Hormonal contraception and breast cancer
Westhoff, C. L., & Pike, M. C. (2018) · Contraception · doi:10.1016/j.contraception.2018.05.002 · Cited by 30
Mishra, R. G., Hermsmeyer, R. K., Miyagawa, K., Sarrel, P. M., Uchida, B. T., Stanczyk, F. Z., Burry, K. A., Illingworth, D. R., & Nordt, F. J. (2005) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jc.2004-1557 · Cited by 29
“bioidentical (54,55), will greatly enhance these preventive and therapeutic strategies.”
BackgroundModeling hormonal contraception in female rats: A framework for studies in behavioral neurobiology
Lacasse, J. M., Gomez‐Perales, E. L., & Brake, W. G. (2022) · Frontiers in Neuroendocrinology · doi:10.1016/j.yfrne.2022.101020 · Cited by 29
Does the Progestogen Used in Combined Hormonal Contraception Affect Venous Thrombosis Risk?
Han, L. L., & Jensen, J. T. (2015) · Obstetrics and Gynecology Clinics of North America · doi:10.1016/j.ogc.2015.07.007 · Cited by 27
Romualdi, D., Cicco, S. D., Busacca, M., Gagliano, D., Lanzone, A., & Guido, M. (2013) · Journal of Endocrinological Investigation · doi:10.1007/bf03346756 · Cited by 26
Metadata
- Authors
- Stanczyk, F. Z.
- Affiliations
- University of Southern California (US)
- Corresponding author
- Stanczyk, Frank Z
- ORCID
- Stanczyk, Frank Z
- Venue
- Steroids
- Publisher
- Elsevier BV
- Published
- 2003-11
- Volume
- 68
- Issue
- 10-13
- Pages
- 879-890
- ISSN
- 0039-128X (ISSN-L)
- OpenAlex
- W2037043326
- Cited by
- 226
- References
- 37
- Citations by year
- 2026: 5 · 2025: 11 · 2024: 5 · 2023: 5 · 2022: 13 · 2021: 7 · 2020: 11 · 2019: 15 · 2018: 15 · 2017: 9 · 2016: 9 · 2015: 11 · 2014: 11 · 2013: 15 · 2012: 8
- FWCI
- 2.47
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Steroids (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Endocrinology › Estrogen and related hormone effects
- Health Sciences › Medicine › Public Health, Environmental and Occupational Health › Reproductive Health and Contraception
- Health Sciences › Medicine › Endocrinology, Diabetes and Metabolism › Adrenal Hormones and Disorders
- Keywords
- progestins, progesterone derivatives, testosterone derivatives, pregnane derivatives, norethisterone, levonorgestrel, hepatic first-pass metabolism, prodrugs, structure-function relationship, androgenic activity, pharmacokinetics
- MeSH terms
- Animals, Female, Humans, Liver, Models, Chemical, Norethindrone, Pregnanes, Progestins, Structure-Activity Relationship, Time Factors, Levonorgestrel, Rats
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