The DOI matches its Crossref record; 34 of the 37 references it cites were found in a registry or an index.
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.
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Drospirenone: pharmacology and pharmacokinetics of a unique progestogen
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Treatment of the Postmenopausal Woman
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Assessment of the potency of orally administered progestins in women
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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
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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.
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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
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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