Pharmacokinetic drug interactions involving 17alpha-ethinylestradiol: a new look at an old drug

Clin Pharmacokinet. 2007;46(2):133-57. doi: 10.2165/00003088-200746020-00003.

Abstract

17alpha-Ethinylestradiol (EE) is widely used as the estrogenic component of oral contraceptives (OC). In vitro and in vivo metabolism studies indicate that EE is extensively metabolised, primarily via intestinal sulfation and hepatic oxidation, glucuronidation and sulfation. Cytochrome P450 (CYP)3A4-mediated EE 2-hydroxylation is the major pathway of oxidative metabolism of EE. For some time it has been known that inducers of drug-metabolising enzymes (such as the CYP3A4 inducer rifampicin [rifampin]) can lead to breakthrough bleeding and contraceptive failure. Conversely, inhibitors of drug-metabolising enzymes can give rise to elevated EE plasma concentrations and increased risks of vascular disease and hypertension. In vitro studies have also shown that EE inhibits a number of human CYP enzymes, such as CYP2C19, CYP3A4 and CYP2B6. Consequently, there are numerous reports in the literature describing EE-containing OC formulations as perpetrators of pharmacokinetic drug interactions. Because EE may participate in multiple pharmacokinetic drug interactions as either a victim or perpetrator, pharmaceutical companies routinely conduct clinical drug interaction studies with EE-containing OCs when evaluating new chemical entities in development. It is therefore critical to understand the mechanisms underlying these drug interactions. Such an understanding can enable the interpretation of clinical data and lead to a greater appreciation of the profile of the drug by physicians, clinicians and regulators. This article summarises what is known of the drug-metabolising enzymes and transporters governing the metabolism, disposition and excretion of EE. An effort is made to relate this information to known clinical drug-drug interactions. The inhibition and induction of drug-metabolising enzymes by EE is also reviewed.

Publication types

  • Review

MeSH terms

  • Biotransformation
  • Contraceptives, Oral / pharmacokinetics*
  • Contraceptives, Oral / pharmacology
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / biosynthesis
  • Cytochrome P-450 Enzyme System / metabolism*
  • Drug Interactions
  • Enzyme Induction / drug effects
  • Enzyme Inhibitors / pharmacokinetics*
  • Enzyme Inhibitors / pharmacology
  • Ethinyl Estradiol / pharmacokinetics*
  • Ethinyl Estradiol / pharmacology
  • Food-Drug Interactions
  • Glucuronides / metabolism
  • Glucuronosyltransferase / antagonists & inhibitors
  • Glucuronosyltransferase / metabolism*
  • Humans
  • Isoenzymes / metabolism
  • Membrane Transport Proteins / metabolism
  • Models, Biological
  • Oxidation-Reduction
  • Progestins / pharmacology
  • Sulfotransferases / antagonists & inhibitors
  • Sulfotransferases / metabolism*
  • Sulfuric Acid Esters / metabolism

Substances

  • Contraceptives, Oral
  • Cytochrome P-450 Enzyme Inhibitors
  • Enzyme Inhibitors
  • Glucuronides
  • Isoenzymes
  • Membrane Transport Proteins
  • Progestins
  • Sulfuric Acid Esters
  • Ethinyl Estradiol
  • Cytochrome P-450 Enzyme System
  • Glucuronosyltransferase
  • Sulfotransferases