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William F. Coleman Wellesley College Wellesley, MA 02481
The Molecules of Oral Contraceptives William F. Coleman Department of Chemistry, Wellesley College, Wellesley, Massachusetts 02481
[email protected] w This paper contains enhanced objects available on the Internet at http://pubs.acs.org/jchemeduc. n
JCE Featured Molecules for July 2010
In her Research Advances article this month, Angela King summarizes a paper describing the discovery of the female sex hormone progesterone in plants (1). Progesterone was included in the molecule collection in November 2008 (2), and this month we add a number of additional steroidal hormones to the collection. This column is being written on May 9, 2010, the 50th anniversary of the FDA's decision to approve the first female oral contraceptive for sale in the United States. This first formulation, known commercially as Enovid, consisted of a mixture of an estrogen, mestranol, and a progestin, norethynodrel (Figure 1). A number of other so-called combination oral contraceptives have been in use over the years, pills that contain an estrogen and a progestin. Many of these pill formulations contain ethinyl estradiol in combination with progestins, including norethisterone, norethisterone acetate, norgestimate, levonorgestrel (also used alone in higher amounts in the emergency contraceptive known as Plan B), drospirenone, etonogestrel, and norelgestromin. All of these molecules, as well as the female sex hormones estradiol, estriol, and estrone, are included in the collection (Table 1), and 3D, rotatable images in MOL format of all the molecules are available in the HTML version of this paper. Aspects of the topic of oral contraceptives are relevant to a variety of chemistry courses. Students at all levels should be
Figure 1. Molecules of the first oral contraceptive formulation, known commercially as Enovid: mestranol (an estrogen) and norethynodrel (a progestin).
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familiar with the basic steroid structure and its significance in human biochemistry. Biochemistry students certainly should understand the detailed mechanism of action of a number of steroidal hormones, and organic chemistry students should be Table 1. Molecules of Oral Contraceptives Added to JCE Featured Molecules Collection Featured Molecule
Description
desogestrel
a progestin used in combination oral contraceptives
dienogest
a progestin used in combination oral contraceptives
drospirenone
a progestin used in combination oral contraceptives
estradiol
female steroid sex hormone (one of the three major naturally occurring estrogens in women)
estradiol valerate
oral version of estradiol
estriol
female steroid sex hormone (one of the three major naturally occurring estrogens in women)
estrone
female steroid sex hormone (one of the three major naturally occurring estrogens in women)
ethinyl estradiol
an estrogen used in combination oral contraceptives (orally active synthetic steroidal estrogen)
etonogestrel
a progestin used in combination oral contraceptives
levonorgestrel
a progestin used in combination oral contraceptives and also used alone in higher amounts in the emergency contraceptive known as Plan B
mestranol
an estrogen used in Enovid, one of the first oral contraceptives
norelgestromin
a progestin used in combination oral contraceptives
norethisterone
a progestin used in combination oral contraceptives
norethisterone acetate
a progestin used in combination oral contraceptives
norethynodrel
a progestin used in Enovid, one of the first oral contraceptives
norgestimate
a progestin used in combination oral contraceptives
progesterone
steroid hormone
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Vol. 87 No. 7 July 2010 pubs.acs.org/jchemeduc r 2010 American Chemical Society and Division of Chemical Education, Inc. 10.1021/ed100494g Published on Web 05/19/2010
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able to predict transformations from one structure to another. But it is in courses that touch on the interaction between chemistry and the broader society that offer the richest array of possibilities. From the social and political work of Margaret Sanger to the groundbreaking synthetic work of Carl Djerassi and others, the promise of female oral contraceptives was both anticipated and the subject of intense debate. Students could follow the social history of contraception from Sanger through Kathryn McCormick, Gregory Pincus, and John Rock, to the work of synthetic chemists and the pharmaceutical industry (3-6). There are many ethical questions to address, and a seemingly endless debate over the health effects of oral contraceptives. On May 7, 2010, the FDA announced approval of a new oral contraceptive that will be sold under the trade name Natazia, which contains a mixture of estradiol valerate and dienogest (7). However, as was noted in a National Public Radio report on the 50th anniversary, some things never change: there is still no male oral contraceptive (8). Literature Cited 1. King, A. Research Advances: Elastic Salt, and Plant Progesterone. J. Chem. Educ. 2010, 87, DOI: 10.1021/ed100382j.
r 2010 American Chemical Society and Division of Chemical Education, Inc.
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2. JCE Featured Molecules from June 2002 through December 2009 are available at the JCE Digital Library, http://www.jce.divched.org/ JCEWWW/Features/MonthlyMolecules/ (accessed May 2010). 3. Djerassi, C. This Man's Pill: Reflections on the 50th Birthday of the Pill; Oxford University Press: New York, 2004. (The difference in dates for the 50th anniversary reflects the fact that Djerassi's early work on contraception was done in Mexico, and preceded FDA approval in the United States by six years.) 4. Djerassi, C. The Pill, Pygmy Chimps, and Degas' Horse; Basic Books: New York, 1998. 5. May, E. T. America and the Pill: A History of Promise, Peril, and Liberation; Basic Books: New York, 2010. 6. Gibbs, N. The Pill at 50: Sex, Freedom and Paradox. Time, April 22, 2010, available at http://www.time.com/time/health/ article/0,8599,1983712,00.html (accessed May 2010). 7. Thomson Reuters News Agency Online Health Article. FDA Approves New Birth Control Pill Natazia. http://www.reuters. com/article/idUSTRE64640Z20100507 (accessed May 2010). 8. National Public Radio Staff. The Pill Turns 50. Originally broadcast on National Public Radio's Weekend Edition news program on May 9, 2010; audio streaming and transcript are available at http://www.npr.org/templates/story/story.php?storyId=126646877 (accessed May 2010).
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