ORGANIC CHEMISTRY I

CHM 258
NO 11: ETHINYL ESTRADIOL IN BIRTH
CONTROL PILLS.

NAME MUHAMAD SYAMEL AMRI BIN SHAMSUL AZUMI

STUDENT ID 2018220274

GROUP AS1203_I

TITLE NO 11: ETHINYL ESTRADIOL IN BIRTH

CONTROL PILLS
DATE OF SUBMISSION 21/10/ 2019

LECTURER’S NAME ROSMAWATI BINTI ABDUL AZIZ

Introduction.

Ethinyl estradiol also known as 17-ethinyl-3,17-estradiol is a semisynthetic estrogen

medication. The molecular formula for this compound is C20H24O2 and the molecular weight is
296.4 g/mol. The IUPAC name for this compound is (8R,9S,13S,14S,17R)-17-ethynyl-13-
methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol. The source
of ethinyl estradiol is from estradiol. Ethinyl estradiol is a synthetic form of estradiol. In the
making of ethinyl estradiol, the estradiol which is 17alpha-ethynylestradiol is a 3-hydroxy
steroid that will be substituted by an ethynyl group at position 17. It is a xenoestrogen
synthesized from estradiol and has been shown to exhibit high estrogenic potency when taken
by mouth (oral administration). Ethinyl estradiol was developed in the 1930s and was
introduced for medical use in 1943. The medication is started being used in birth control pills
in the 1960s. Today, ethinyl estradiol can be found in almost all combined forms of birth control
pills making it one of the most widely used estrogen. Other than that, ethinyl estradiol is also
used as menopausal hormone therapy, hypogonadism treatment and osteoporosis
prevention. The structural formula for this compound is as follows:

ETHINYL ESTRADIOL

C20H24O2
The Function of Ethinyl Estradiol in Birth Control Pills.

Female ovaries create a natural hormone called estrogen that flow within the human body. in
common female reproductive cycles, estrogen is involved in a vital role. Estradiol is a naturally
occurring form of estrogen that helps the female reproductive organs to mature. Estradiol also
helps prepare the uterus wall for the implantation of a fertilized egg. To prevent pregnancy
after sex, ethinyl estradiol is most frequently used as contraception (birth control) also
available in combination with a progestin in birth control pills.

Menstrual cycle or period pains in a female can be regulated by ethinyl estradiol. This
is because ethinyl estradiol can help to prevent ovulation. A steady amount of both estrogen
and progestin is been supplied daily by the birth control pills. The ovulation process will be
ceased with the help of daily contribution of the hormone. To get pregnant, a female must
have an egg so that the sperm from male can fertilize it. When there is no ovulation, there is
no egg produced by the ovary causing the sperm to become unable to fertilize the egg and
preventing pregnancy.

The ovulation process halted because of the birth control pills that contain ethinyl
estradiol and progestin prevents the signal that will trigger the two key hormones that are
involved in ovulation which are the follicle-stimulating hormone (FSH) and luteinizing hormone
(LH) that are part of the gonadotropins that are secreted by the anterior pituitary.

The rise in estradiol levels will be prevented because of the depleting level of the FSH
inhibiting the follicular development. LH surge will also be prevented because the lack of
estrogen positive feedback and rise of progestogen negative feedback on LH. The inhibition
of follicular development and the lack of an LH surge will prevent ovulation.

The semisynthetic estrogen was initially included for a better cycle control (reduce the
incidence or breakthrough bleeding), but it was also found to inhibit the follicular development
and prevent ovulation. The negative feedback on anterior pituitary massively decreases the
secretion of FSH, which inhibit follicular development and thus preventing ovulation.
 Normally, during the first and second days of menstrual cycle, the hypothalamus in the
brain will identify when the estrogen levels are low. When the hypothalamus received the
signal, it will next releases gonadotropin-releasing hormone (GnRH). This hormone is used to
signalize the pituitary gland in another part of the brain to make FSH and LH.

Because the pituitary gland never gotten the signal, it will does not produce the FSH,
and without the secretion of FSH, there is no signal to trigger the growth and development of
egg in the ovaries. Ovulation only happens when there is LH surge. Without LH surge, the egg
will not be released by the ovary and thus making no ovulation happening.

Ethinyl estradiol in birth control pills basically keeps the user in the same phase of
menstrual cycle on continuous basis by skipping the release of GnHR from the hypothalamus
and stopping ovulation from taking place by making the ovary relatively inactive because of
the lack of LH surge.

In addition, despite ethinyl estradiol being able to stop ovulation, it also has been found
to lower the risk of ovarian cancer as well as endometrial cancer. Plus, because estrogen have
ability to block bone resorption, ethinyl estradiol can also help to increase bone mineral density
making the bone stronger and prevent osteoporosis.

Ethinyl estradiol is also broken down fast in the body. For the birth control pills to
works, the pills need to be taken at the exact same time each day. If not, there is chance for
the estrogen to be metabolized too quickly and the pills effectiveness will be lessened.

The amount of synthetic estrogen like ethinyl estradiol is been greatly cut down over
the years. The amount of synthetic estrogen found in the latest birth control pills are much
safer for its consumers. During the time when first birth control pills were created, there was
not even a trace of ethinyl estradiol. Instead, mestranol was used back then. Mestranol is a
type of estrogen that will be converted in the body to produce ethinyl estradiol. Back then the
very first birth control pills brand contained 105 mcg of estrogen.
 Today, the combination amount of birth control pills today contains between 20 mcg
(low dose pills) to 30 or 35 mcg of ethinyl estradiol. There are also high dose pills that contains
50 mcg of ethinyl estradiol and one low dose pills, Lo Loestrin Fe, that only contain 10 mcg of
ethinyl estradiol.

Birth control pills that contains ethinyl estradiol can pose risks for some women. Blood
clots and venous thromboembolism may be linked to high estrogen exposure to some women.
Smoking can also increase the risk of blood clotting and venous thromboembolism. In order
to prevent the side effect from consuming birth control pills that contain ethinyl estradiol, it is
important to discuss with medical professional and honestly describe one lifestyle, habit and
medical history so that birth control pills that contain ethinyl estradiol can be consume safely
and work effectively.
Conclusion.

The use of ethinyl estradiol in birth control pills bring many benefits to its consumers. For
example, menstrual cycle can be regulated. There are variety of menstrual issues that women
faced like irregular or heavy bleeding. With the birth control pills, women can make period
lighter and more consistent in their timing. Anemia risk can also be reduced with birth control
pills. Heavy bleeding during period can cause some women to experience anemia which is
when the body do not have enough red blood cell to carries oxygen to rest of the body that
can cause fatigue.

Next, with the usage of ethinyl estradiol in birth control pills, period can become less
painful. About 30% of women that consume ethinyl estradiol birth control pills said that by
consuming the pills, their period will be less painful. This is because ovulation causes uterus
to experience painful contraction that leads to period cramps. Another benefit is that it can
reduce risk of uterine cancer. Women that consume birth control pills are 50% less likely to
get uterine cancer and ovarian cancer can also be reduced.

Menstrual migraine can also be relived by the intake of birth control pills that contain
ethinyl estradiol. Menstrual migraine is intense type of headache that caused from hormonal
changes. Some expert conclude that menstrual migraine may be caused by the drop of
estrogen and progesterone just before period start.

The only downside for birth control pills that contain ethinyl estradiol is it not for women
that are smoking and are over the age of 35 years old. This is because by taking birth control
pills that contain ethinyl estradiol with this condition will lead to blood clotting and venous
thromboembolism that can endangered the consumer life.
References

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estradiol.
Stacey, D. (2019). Does Birth Control Stop Ovulation? Retrieved from
https://www.verywellhealth.com/does-birth-control-stop-ovulation-906740.
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