MCQ Quiz: Medicinal Chemistry: Androgens

The medicinal chemistry of androgens provides a classic illustration of how modifying a core chemical structure can lead to profound changes in pharmacokinetic properties and therapeutic use. Understanding the relationship between the steroid nucleus, its functional groups, and its pharmacological activity is a key concept rooted in principles from Medicinal Chemistry I and applied in the Patient Care 5 curriculum. This quiz will test your knowledge on the structure-activity relationships, prodrug strategies, and chemical principles governing androgen and anti-androgen therapies.

1. Androgens like testosterone are classified as steroid hormones because they all share a core structure known as the:

• a. Phenothiazine nucleus
• b. Benzodiazepine ring
• c. Cyclopentanoperhydrophenanthrene nucleus
• d. Purine ring

Answer: c. Cyclopentanoperhydrophenanthrene nucleus

2. The conversion of testosterone to the more potent androgen, dihydrotestosterone (DHT), is what type of chemical reaction?

• a. Oxidation
• b. Reduction of a double bond
• c. Esterification
• d. Aromatization

Answer: b. Reduction of a double bond

3. Which functional group on the testosterone molecule is essential for its binding to the androgen receptor?

• a. The C3-keto group
• b. The C17-hydroxyl group
• c. The C4-C5 double bond
• d. All of the above are important for binding and activity.

Answer: d. All of the above are important for binding and activity.

4. Why is oral administration of native testosterone ineffective?

• a. It is not absorbed from the gut.
• b. It undergoes extensive first-pass metabolism in the liver.
• c. It is too acidic and damages the stomach.
• d. It is too large to be absorbed.

Answer: b. It undergoes extensive first-pass metabolism in the liver.

5. Testosterone cypionate and testosterone enanthate are administered via intramuscular injection. They are examples of what type of chemical modification?

• a. A soft drug
• b. A salt formulation
• c. A prodrug created by esterification
• d. A chiral inversion

Answer: c. A prodrug created by esterification

6. The purpose of adding a long-chain ester to the C17-hydroxyl group of testosterone is to:

• a. Increase its water solubility.
• b. Make the molecule more potent at the receptor.
• c. Increase its lipophilicity, allowing it to be slowly released from an oily depot.
• d. Allow for intravenous administration.

Answer: c. Increase its lipophilicity, allowing it to be slowly released from an oily depot.

7. Finasteride treats benign prostatic hyperplasia (BPH) by inhibiting which enzyme?

• a. Aromatase
• b. 5-alpha reductase
• c. CYP3A4
• d. Xanthine oxidase

Answer: b. 5-alpha reductase

8. From a medicinal chemistry perspective, finasteride is designed to act as a(n):

• a. Competitive agonist at the androgen receptor.
• b. Allosteric modulator of the androgen receptor.
• c. Mechanism-based inhibitor of the 5-alpha reductase enzyme.
• d. Prodrug of testosterone.

Answer: c. Mechanism-based inhibitor of the 5-alpha reductase enzyme.

9. Bicalutamide is a non-steroidal anti-androgen used for prostate cancer. What is its mechanism of action?

• a. It inhibits 5-alpha reductase.
• b. It inhibits the release of GnRH.
• c. It competitively antagonizes the androgen receptor.
• d. It inhibits testosterone synthesis.

Answer: c. It competitively antagonizes the androgen receptor.

10. The aromatase enzyme is responsible for converting testosterone into what other hormone?

• a. Dihydrotestosterone (DHT)
• b. Progesterone
• c. Estradiol
• d. Aldosterone

Answer: c. Estradiol

11. The management of men’s health disorders is a topic within the Patient Care 5 curriculum.

• a. True
• b. False

Answer: a. True

12. The historical practice of adding a methyl group to the C17-alpha position of testosterone (e.g., methyltestosterone) allowed for oral activity but significantly increased the risk of:

• a. Nephrotoxicity
• b. Cardiotoxicity
• c. Hepatotoxicity
• d. Neurotoxicity

Answer: c. Hepatotoxicity

13. Predicting the effects of functional groups on drug properties is a key objective of which foundational course?

• a. PHA5439 Principles of Medicinal Chemistry and Pharmacology I
• b. PHA5161L Professional Practice Skills Lab I
• c. PHA5007 Population Health
• d. PHA5103 Principles of Patient-Centered Care

Answer: a. PHA5439 Principles of Medicinal Chemistry and Pharmacology I

14. Anabolic steroids are synthetic derivatives of testosterone often designed to maximize the anabolic (muscle-building) effects relative to the androgenic (masculinizing) effects. This is an example of modifying:

• a. The drug’s formulation.
• b. The drug’s structure-activity relationship (SAR).
• c. The drug’s route of administration.
• d. The drug’s half-life only.

Answer: b. The drug’s structure-activity relationship (SAR).

15. The “-steride” suffix in finasteride and dutasteride indicates that these drugs are:

• a. Androgen receptor blockers
• b. 5-alpha reductase inhibitors
• c. Steroidal hormones
• d. Aromatase inhibitors

Answer: b. 5-alpha reductase inhibitors

16. The “Hormonal Agents” lecture in the oncology module covers anti-androgens.

• a. True
• b. False

Answer: a. True

17. What structural feature of testosterone allows it to be a substrate for the aromatase enzyme?

• a. The C17-hydroxyl group.
• b. The C19-methyl group.
• c. The A-ring, which can be converted to an aromatic (phenolic) ring.
• d. The ester linkage.

Answer: c. The A-ring, which can be converted to an aromatic (phenolic) ring.

18. Dutasteride differs from finasteride in that it:

• a. Is more selective for the type 2 isoenzyme of 5-alpha reductase.
• b. Is a non-competitive inhibitor.
• c. Inhibits both type 1 and type 2 isoenzymes of 5-alpha reductase.
• d. Is less potent.

Answer: c. Inhibits both type 1 and type 2 isoenzymes of 5-alpha reductase.

19. From a medicinal chemistry perspective, testosterone is considered a(n):

• a. Prodrug
• b. Active hormone
• c. Antagonist
• d. Peptide

Answer: b. Active hormone

20. An active learning session on urological disorders, where these agents are used, is part of the Patient Care 5 course.

• a. True
• b. False

Answer: a. True

21. The “pharmacophore” for androgen receptor binding requires which key features on the steroid nucleus?

• a. An ionized carboxyl group.
• b. A 3-keto group and a 17-beta-hydroxyl group.
• c. A large peptide chain.
• d. A furan ring.

Answer: b. A 3-keto group and a 17-beta-hydroxyl group.

22. Which of the following is NOT a steroid?

• a. Testosterone
• b. Estradiol
• c. Cortisol
• d. Liraglutide

Answer: d. Liraglutide

23. The principles of drug biotransformation are covered in the Medicinal Chemistry curriculum.

• a. True
• b. False

Answer: a. True

24. An active learning session on men’s health is part of which course?

• a. PHA5787C Patient Care 5
• b. PHA5163L Professional Skills Lab 3
• c. PHA5781 Patient Care I
• d. PHA5782C Patient Care 2

Answer: a. PHA5787C Patient Care 5

25. Non-steroidal anti-androgens like bicalutamide were designed to:

• a. Have the same structure as testosterone.
• b. Mimic the shape of testosterone to bind to the androgen receptor without having a steroid structure.
• c. Inhibit testosterone synthesis.
• d. Be more potent than DHT.

Answer: b. Mimic the shape of testosterone to bind to the androgen receptor without having a steroid structure.

26. The lipophilicity of testosterone is the reason it is formulated in what for IM injections?

• a. An aqueous solution
• b. A saline solution
• c. An oily vehicle (e.g., sesame oil, cottonseed oil)
• d. An alcohol-based solution

Answer: c. An oily vehicle (e.g., sesame oil, cottonseed oil)

27. The term structure-activity relationship (SAR) refers to how:

• a. The structure of a drug influences its activity.
• b. The cost of a drug relates to its activity.
• c. The name of a drug relates to its activity.
• d. The dosage form relates to its activity.

Answer: a. The structure of a drug influences its activity.

28. An active learning session on urological disorders is part of which course module?

• a. Module 8: Urological Disorders
• b. Module 1: Diabetes Mellitus
• c. Module 3: Women’s Health
• d. Module 6: Geriatrics

Answer: a. Module 8: Urological Disorders

29. The androgen receptor is what type of receptor?

• a. A cell surface G-protein coupled receptor.
• b. A ligand-gated ion channel.
• c. An intracellular nuclear hormone receptor.
• d. A receptor tyrosine kinase.

Answer: c. An intracellular nuclear hormone receptor.

30. The “Management of Testosterone Deficiency” is a lecture within the Patient Care 5 curriculum.

• a. True
• b. False

Answer: a. True

31. The removal of the C19-methyl group from testosterone (to form 19-nortestosterone derivatives like nandrolone) generally results in:

• a. A decrease in all activity.
• b. An increase in the anabolic-to-androgenic activity ratio.
• c. An increase in androgenic activity only.
• d. A complete loss of function.

Answer: b. An increase in the anabolic-to-androgenic activity ratio.

32. From a chemical perspective, testosterone is a(n) ________ hormone.

• a. hydrophilic
• b. lipophilic
• c. amphipathic
• d. charged

Answer: b. lipophilic

33. Predicting how functional groups interact with receptors is a key objective in which course?

• a. PHA5439 Principles of Medicinal Chemistry and Pharmacology I
• b. PHA5161L Professional Practice Skills Lab I
• c. PHA5007 Population Health
• d. PHA5103 Principles of Patient-Centered Care

Answer: a. PHA5439 Principles of Medicinal Chemistry and Pharmacology I

34. The “trans” fusion of the rings in the steroid nucleus gives the molecule what overall shape?

• a. A flexible, linear shape.
• b. A bent, L-shape.
• c. A rigid, planar-like shape.
• d. A spherical shape.

Answer: c. A rigid, planar-like shape.

35. A pharmacist’s understanding of medicinal chemistry helps them to:

• a. Predict potential drug interactions based on structure.
• b. Explain the mechanism of action of a drug.
• c. Understand why different formulations exist.
• d. All of the above.

Answer: d. All of the above.

36. The nitroaromatic group in flutamide (an older anti-androgen) is a key part of its:

• a. Efficacy
• b. Antagonist properties
• c. Potential for hepatotoxicity
• d. Water solubility

Answer: c. Potential for hepatotoxicity

37. The chemical difference between testosterone and estradiol is primarily:

• a. The number of carbon atoms.
• b. The A-ring of estradiol is aromatic (a phenol), while testosterone’s is not.
• c. The type of functional group at C17.
• d. Estradiol is much larger.

Answer: b. The A-ring of estradiol is aromatic (a phenol), while testosterone’s is not.

38. The lecture “Management of BPH” is part of which course?

• a. PHA5787C Patient Care 5
• b. PHA5163L Professional Skills Lab 3
• c. PHA5781 Patient Care I
• d. PHA5782C Patient Care 2

Answer: a. PHA5787C Patient Care 5

39. A patient is using a transdermal testosterone patch. The drug delivery system must be designed to allow the lipophilic drug to partition out of the patch and into the:

• a. Intramuscular tissue
• b. Stratum corneum of the skin
• c. Bloodstream directly
• d. Stomach

Answer: b. Stratum corneum of the skin

40. An active learning session covering men’s health is part of which course?

• a. PHA5787C Patient Care 5
• b. PHA5163L Professional Skills Lab 3
• c. PHA5781 Patient Care I
• d. PHA5782C Patient Care 2

Answer: a. PHA5787C Patient Care 5

41. The binding of DHT to the androgen receptor is generally ____ than the binding of testosterone.

• a. weaker
• b. stronger and more stable
• c. identical
• d. slower

Answer: b. stronger and more stable

42. Which functional group is common to both testosterone and estradiol?

• a. A C3-keto group
• b. A C17-hydroxyl group
• c. An aromatic A-ring
• d. A C19-methyl group

Answer: b. A C17-hydroxyl group

43. A key skill for a pharmacist is to recognize drug classes based on:

• a. The color of the tablet.
• b. The cost of the medication.
• c. Common suffixes in the drug name (e.g., “-steride”).
• d. The marketing campaign.

Answer: c. Common suffixes in the drug name (e.g., “-steride”).

44. The development of non-steroidal molecules that can fit into the steroid receptor pocket is an example of:

• a. Rational drug design.
• b. A failed clinical trial.
• c. A prodrug strategy.
• d. An accident.

Answer: a. Rational drug design.

45. Which of the following is NOT an androgen?

• a. Testosterone
• b. Dihydrotestosterone
• c. Androstenedione
• d. Progesterone

Answer: d. Progesterone

46. The study of how a drug’s structure influences its ADME properties is a central theme of medicinal chemistry.

• a. True
• b. False

Answer: a. True

47. The “Hormonal Agents” lecture for oncology is part of the Patient Care 2 curriculum.

• a. True
• b. False

Answer: a. True

48. An active learning session on men’s health is part of which course module?

• a. Module 8: Urological Disorders
• b. Module 1: Diabetes Mellitus
• c. Module 4: Medication Safety
• d. Module 6: Geriatrics

Answer: a. Module 8: Urological Disorders

49. The overall goal of designing androgen therapies is to:

• a. Create the most potent molecule possible, regardless of side effects.
• b. Create molecules with desirable pharmacokinetic profiles and receptor interactions to treat specific medical conditions.
• c. Make drugs that are difficult to synthesize.
• d. Only create oral formulations.

Answer: b. Create molecules with desirable pharmacokinetic profiles and receptor interactions to treat specific medical conditions.

50. The ultimate reason to learn the medicinal chemistry of androgens is to:

• a. Understand the “why” behind their pharmacology, which leads to safer and more effective use in patients.
• b. Be able to draw testosterone from memory.
• c. Pass the medicinal chemistry exam.
• d. Appreciate the complexity of steroid synthesis.

Answer: a. Understand the “why” behind their pharmacology, which leads to safer and more effective use in patients.