Podcast
Questions and Answers
Which topic will be covered in lecture 3?
Which topic will be covered in lecture 3?
What is a key learning objective from today's lecture?
What is a key learning objective from today's lecture?
Which compound is specifically used for oral contraception?
Which compound is specifically used for oral contraception?
What is a focus area for drugs targeting the estrogen receptor?
What is a focus area for drugs targeting the estrogen receptor?
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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?
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What is a characteristic used to optimize the action of hydrocortisone (cortisol)?
What is a characteristic used to optimize the action of hydrocortisone (cortisol)?
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Which lecture will delve into the medicinal chemistry of adrenocorticoids?
Which lecture will delve into the medicinal chemistry of adrenocorticoids?
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What is the parent compound of steroids?
What is the parent compound of steroids?
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Which of the following is not a type of steroids?
Which of the following is not a type of steroids?
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What is the correct numbering of the fundamental saturated tetracyclic hydrocarbon skeleton?
What is the correct numbering of the fundamental saturated tetracyclic hydrocarbon skeleton?
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What is the stereochemistry of cholestane?
What is the stereochemistry of cholestane?
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What is the configuration of androsterone?
What is the configuration of androsterone?
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What is the principal bile salt?
What is the principal bile salt?
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What is the stereochemistry of etiocholanolone?
What is the stereochemistry of etiocholanolone?
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Who first isolated androsterone?
Who first isolated androsterone?
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What is the metabolic activity of cis-trans-trans etiocholanolone in urine?
What is the metabolic activity of cis-trans-trans etiocholanolone in urine?
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Which of the following statements about digitoxin is correct?
Which of the following statements about digitoxin is correct?
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Which statement about batrachotoxin is incorrect?
Which statement about batrachotoxin is incorrect?
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Which statement about rocuronium's structure is correct?
Which statement about rocuronium's structure is correct?
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Which of the following is a characteristic of the basic steroid structure?
Which of the following is a characteristic of the basic steroid structure?
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What is the metabolic activity of androsterone?
What is the metabolic activity of androsterone?
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Which statement about etiocholanolone is correct?
Which statement about etiocholanolone is correct?
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Which of the following is a characteristic of 17a-estradiol?
Which of the following is a characteristic of 17a-estradiol?
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Which enzyme catalyzes the aromatization of androgens into estrogens?
Which enzyme catalyzes the aromatization of androgens into estrogens?
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What is the role of aromatase inhibitors in cancer treatment?
What is the role of aromatase inhibitors in cancer treatment?
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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?
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Which steroid hormone has the 17b-hydroxyandrost-4-en-3-one structure?
Which steroid hormone has the 17b-hydroxyandrost-4-en-3-one structure?
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Which steroid hormone is correctly named 'estradiol'?
Which steroid hormone is correctly named 'estradiol'?
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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?
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Which steroid hormone has the structure 3b-hydroxyandrost-5-en-17-one?
Which steroid hormone has the structure 3b-hydroxyandrost-5-en-17-one?
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Which steroid hormone has the structure 17b-hydroxyandrost-4-en-3-one?
Which steroid hormone has the structure 17b-hydroxyandrost-4-en-3-one?
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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?
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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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Description
This quiz covers the introduction lecture 1 of Medicinal Chemistry of Steroids in the PCOL 826B course, focusing on pages 1386-1433 in Foye’s Medicinal Chemistry. The lecture includes topics such as steroid hormone structure, nomenclature, stereochemistry, and endogenous estrogens.
