Podcast
Questions and Answers
Which topic will be covered in lecture 3?
Which topic will be covered in lecture 3?
- Androgens and anabolics (correct)
- Estrogens and progestins
- Estrogens
- Adrenocorticoids
What is a key learning objective from today's lecture?
What is a key learning objective from today's lecture?
- Oral bioavailability of steroids
- Steroid hormone structure and nomenclature (correct)
- Dissociated ligands
- Steroid-based medications
Which compound is specifically used for oral contraception?
Which compound is specifically used for oral contraception?
- Hydrocortisone
- 17b-estradiol
- 17a-ethinylestradiol (correct)
- Cortisol
What is a focus area for drugs targeting the estrogen receptor?
What is a focus area for drugs targeting the estrogen receptor?
Which steroid hormone is related to specificity and potency optimization through medicinal chemistry?
Which steroid hormone is related to specificity and potency optimization through medicinal chemistry?
What is a characteristic used to optimize the action of hydrocortisone (cortisol)?
What is a characteristic used to optimize the action of hydrocortisone (cortisol)?
Which lecture will delve into the medicinal chemistry of adrenocorticoids?
Which lecture will delve into the medicinal chemistry of adrenocorticoids?
What is the parent compound of steroids?
What is the parent compound of steroids?
Which of the following is not a type of steroids?
Which of the following is not a type of steroids?
What is the correct numbering of the fundamental saturated tetracyclic hydrocarbon skeleton?
What is the correct numbering of the fundamental saturated tetracyclic hydrocarbon skeleton?
What is the stereochemistry of cholestane?
What is the stereochemistry of cholestane?
What is the configuration of androsterone?
What is the configuration of androsterone?
What is the principal bile salt?
What is the principal bile salt?
What is the stereochemistry of etiocholanolone?
What is the stereochemistry of etiocholanolone?
Who first isolated androsterone?
Who first isolated androsterone?
What is the metabolic activity of cis-trans-trans etiocholanolone in urine?
What is the metabolic activity of cis-trans-trans etiocholanolone in urine?
Which of the following statements about digitoxin is correct?
Which of the following statements about digitoxin is correct?
Which statement about batrachotoxin is incorrect?
Which statement about batrachotoxin is incorrect?
Which statement about rocuronium's structure is correct?
Which statement about rocuronium's structure is correct?
Which of the following is a characteristic of the basic steroid structure?
Which of the following is a characteristic of the basic steroid structure?
What is the metabolic activity of androsterone?
What is the metabolic activity of androsterone?
Which statement about etiocholanolone is correct?
Which statement about etiocholanolone is correct?
Which of the following is a characteristic of 17a-estradiol?
Which of the following is a characteristic of 17a-estradiol?
Which enzyme catalyzes the aromatization of androgens into estrogens?
Which enzyme catalyzes the aromatization of androgens into estrogens?
What is the role of aromatase inhibitors in cancer treatment?
What is the role of aromatase inhibitors in cancer treatment?
Which steroid compound has the systematic name 10-fluoro-11β,17,21-trihydroxy-16a methylpregna-1,4-diene-3,20-dione?
Which steroid compound has the systematic name 10-fluoro-11β,17,21-trihydroxy-16a methylpregna-1,4-diene-3,20-dione?
Which steroid hormone has the 17b-hydroxyandrost-4-en-3-one structure?
Which steroid hormone has the 17b-hydroxyandrost-4-en-3-one structure?
Which steroid hormone is correctly named 'estradiol'?
Which steroid hormone is correctly named 'estradiol'?
Which steroid hormone has the structure 11β,17α,21-Trihydroxypregn-4-ene-3,20-dione?
Which steroid hormone has the structure 11β,17α,21-Trihydroxypregn-4-ene-3,20-dione?
Which steroid hormone has the structure 3b-hydroxyandrost-5-en-17-one?
Which steroid hormone has the structure 3b-hydroxyandrost-5-en-17-one?
Which steroid hormone has the structure 17b-hydroxyandrost-4-en-3-one?
Which steroid hormone has the structure 17b-hydroxyandrost-4-en-3-one?
Which steroid hormone has the structure estra-1,3,5-triene-3,17b-diol?
Which steroid hormone has the structure estra-1,3,5-triene-3,17b-diol?
Which steroid hormone has the structure 4-pregnene-3,20-dione?
Which steroid hormone has the structure 4-pregnene-3,20-dione?
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Study Notes
Steroid Medicinal Chemistry
- The next 4 lectures will cover general introduction to steroid medicinal chemistry, medicinal chemistry of estrogens, progestins, androgens, and adrenocorticoids.
Steroid Hormone Structure and Nomenclature
- Cyclopentanoperhydrophenanthrene is the parent compound of steroids.
- The basic steroid structure is a plane with a bottom (a) surface and a top (b) surface.
- Substituents oriented towards the bottom surface obtain the prefix ‘a‘ and substituents oriented towards the top surface obtain the prefix ‘b ‘.
Steroid Stereochemistry
- Configurational isomers: cis and trans
- Decaline stereochemistry: cis-decalin (bicyclo[4.4.0]decane) and trans-decalin
- Tetracyclic system: three ring fusions, 23 (=8) isomers
- Cholic acid is a cis-trans-trans isomer, a principal bile salt.
Estrogens
- 17β-estradiol is an endogenous estrogen.
- 17α-ethinylestradiol is a synthetic estrogen.
- Estrogen receptor targeting drugs: oral contraception, breast cancer chemoprevention and chemotherapy, infertility, hormone replacement therapy, and osteoporosis.
Aromatase
- Aromatase is an enzyme that catalyzes a key step in estrogen biosynthesis.
- Aromatase converts androgens into estrogens during steroidogenesis.
- Aromatase inhibitors are cancer therapeutics that suppress estrogen biosynthesis.
Medicinal Chemistry of Steroids
- Hydrocortisone (cortisol) is a potent steroid with high specificity and dissociated ligands.
- Optimization of steroid drugs through medicinal chemistry: potency, specificity, duration of action, oral bioavailability, and toxicity.
Exam Questions
- Identify synthetic agents: 17α-ethinylestradiol, 17β-estradiol, and others.
- Identify the incorrect statement about Batrachotoxin: a potent cardiotoxic and neurotoxic natural product.
- Identify the specific connectivity between rings A&B, B&C, and C&D in Rocuronium: a neuromuscular blocking agent.
- Identify the systematic name of the synthetic glucocorticoid dexamethasone.
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