Oral contraceptive - Anderson

Question 1

name of the oral contraceptive we study

Answer 1

norethindrone

Question 2

what is norethindrone an analogue of

Answer 2

progesterone

Question 3

what structure do steroids usually have

Answer 3

C17 tetracyclical fused ring system

planar

Question 4

examples of other steroids

Answer 4

cholesterol, testosterone and oestrogen

Question 5

how many chiral centres do steroids have

Answer 5

many

Question 6

chemical formula of progesterone

Answer 6

C21H30O2

Question 7

how many stereogenic centres does progesterone have

Answer 7

14

Question 8

how many women worldwide use the pill

Answer 8

100 million

Question 9

how many women age 19-49 take the pill

Answer 9

1/3

Question 10

when was norethindrone first marketed

Answer 10

1961

Question 11

other name for oestrogen

Answer 11

estradiol

Question 12

when is increase and decrease in estradiol

Answer 12

increases first part of cycle

decreases before ovulation

Question 13

what triggers lutenising hormone

Answer 13

drop off of oestrogen

Question 14

which hormones cause ovulation

Answer 14

LH and FSH - lutenising and follicle stimulating hormone

Question 15

how does oral contraceptive work

Answer 15

constant level of hormones mimic pregnancy so LH and FSH not released

Question 16

how does progesterone prevent pregnancy

Answer 16

creates a thick layer of cervical mucus which sperm cannot penetrate
produce a thinner endometrium so eggs cannot implant

Question 17

how successful is oral contraceptive

Answer 17

99.9%

Question 18

steps 1-2 synthesising norethodrone

Answer 18

synthesis of a methyl ether

Question 19

steps 2-3 of synthesising norethodrone

Answer 19

birch reduction
aromatic ring to diene
makes enol ether which is protected form of a ketone

Question 20

steps 3-4 of synthesising norethindrone

Answer 20

oxidation of a secondary alcohol to form a ketone

using PCC under dry conditions

Question 21

steps 4-5 synthesis of norethindrone

Answer 21

addition of a metal-acetylide to a ketone

stereoselective

Question 22

steps 5-6 of synthesis of norethindrone

Answer 22

hydrolysis of the enol ether

Question 23

synthesis of norethindrone steps 6-7

Answer 23

migration of a double bond

Question 24

how was the combined pill invented

Answer 24

residues of menstranol (analogue of estradiol) from previous steps found to be more effective

Question 25

pros of oral contraceptive

Answer 25

99.9% effective
oral administration
improves maternal mortality
protects against some cancers
prevents birth of unwanted children that can cause social issues
on list of essential medicine

Question 26

disadvantages of oral contraception

Answer 26

does not protect against sexually transmitted diseases
must be taken every day within 4-12 hours of specified daily time
higher risk of deep vein thrombosis and embolism
increased risk of some cancers
environmental impact of excretion of synthetic oestrogens