Structural Biochemistry, Norethindrone

Introduction

Norethindrone (or norethisterone) is a form of female hormone that prevents ovulation (the release of egg from an ovary). This medicine causes changes in a woman's cervical mucus and uterine lining, making it harder for sperm to reach the uterus and therefore harder for conception.

Norethindrone is used for birth control (contraception) to prevent pregnancy. Norethindrone is also used to treat menstrual disorders, endometriosis, or abnormal vaginal bleeding caused by a hormone unbalance.

Side Effect

Immediately contact for medical help if you have any of these signs of an allergic reaction after consuming Norethindrone:

• hives
• difficulty breathing
• swelling of your face, lips, tongue, or throat.

Stop using this medication and call your doctor if you have any of these serious side effects:

• sudden numbness or weakness, especially on one side of the body;
• sudden headache, confusion, pain behind the eyes, problems with vision, speech, or balance;
• pain or swelling in one or both legs;
• migraine headache;
• swelling in your hands or feet, rapid weight gain;
• symptoms of depression (sleep problems, weakness, mood changes);
• severe pelvic pain;
• chest pain or heavy feeling, pain spreading to the arm or shoulder, nausea, sweating, general ill feeling; or
• nausea, stomach pain, low fever, loss of appetite, dark urine, clay-colored stools, jaundice (yellowing of the skin or eyes).
• Less serious side effects may include:
• mild nausea, vomiting, bloating, stomach cramps;
• breast pain, swelling, or tenderness;
• dizziness;
• freckles or darkening of facial skin;
• increased acne or hair growth;
• changes in weight;
• vaginal itching or discharge;
• skin itching or rash;
• changes in your menstrual periods, decreased sex drive; or
• mild headache.

History of Synthesis

In 1951, norethindrone was synthesized by chemists Luis Miramontes, Carl Dijerassi, and George Rosenkranz at Syntex in Mexico City.

Synthesis

The synthesis of 19-nor-17α-ethnyltestosterone:

(Image: Yid at en.wikipedia, CC BY-SA 3.0)

Structure

(Image: Fvasconcellos, Public domain)

Functional groups: ketone, alkene, methyl(2) , alcohol, alkynes

Reference

• http://www.drugs.com/mtm/norethindrone.html
• Djerassi, C.; Miramontes, L.; Rosenkranz, G.; Sondheimer, Franz (1954). "Steroids. LIV. Synthesis of 19-Nor-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone". J. Am. Chem. Soc. 76 (16): 4092–94. doi:10.1021/ja01645a010
• http://commons.wikimedia.org/w/index.php?title=Special%3ASearch&profile=default&search=Norethisterone+&fulltext=Search

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