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Medical Chemistry II - Exam 3 Questions with Solutions | MEDC 603, Exams of Health sciences

Material Type: Exam; Class: MEDICINAL CHEMISTRY II; Subject: Medicinal Chemistry; University: Virginia Commonwealth University; Term: Fall 2005;

Typology: Exams

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SCHOOL OF PHARMACY
VIRGINIA COMMONWEALTH UNIVERSITY
MEDC 603
Examination III Fall 2005
Dr. Desai’s Part
Name ______KEY_________________________ Pledge ____________________________
(Signature)
This section has 10 questions. Please select a letter that best matches the answer.
1. Circle the systematic name of the following steroid. (3 pts)
A: 6-methyl-9β-fluoro-11β-hydroxy-19-nor-pregn-4,6-diene-3,20-dione
B: 6-methyl-9α-fluoro-11β-hydroxy-pregn-4,6-diene-3,20-dione
C: 6-methyl-9α-fluoro-11β-hydroxy-19-nor-pregn-4,6-diene-3,20-dione
D: 6-methyl-9α-fluoro-11β-hydroxy-19-nor-androst-4,6-diene-3,20-dione
2. Draw the structure of the following steroid showing its stereochemistry and substitution pattern.
6,16β-dimethyl-estr-1,3,5,6-tetraene-3,17β-diol (3 pts)
3. A key step, targeted by statins, in cholesterol biosynthesis is (4 pts)
A: synthesis of acetyl-Coenzyme A
B: synthesis of mevalonate
C: synthesis of 3-hydroxy-3-methyl-glutaryl Coenzyme A
D: none of the above
4. Inhibition of bile re-absorption from the GI tract is the primary mechanism of (4 pts)
A: mevastatin
B: metformin
C: nicotinic acid
D: colestipol
5. Circle molecule(s) from below that are expected to possess anti-estrogenic activity (antagonist).
Please note: -2 points for every wrong answer circled. (4 pts)
OH
CH3
OH
CH3
OH
CH3
OH
OCH3
OH
OH
OH
H
CH
3
O
O
CH
3
F
OH
CH3OH
OH
CH3
CH3
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SCHOOL OF PHARMACY

VIRGINIA COMMONWEALTH UNIVERSITY

MEDC 603

Examination III Fall 2005 Dr. Desai’s Part

Name ______KEY_________________________ Pledge ____________________________ (Signature) This section has 10 questions. Please select a letter that best matches the answer.

  1. Circle the systematic name of the following steroid. ( 3 pts) A : 6-methyl-9β-fluoro-11β-hydroxy-19-nor-pregn-4,6-diene-3,20-dione B : 6-methyl-9α-fluoro-11β-hydroxy-pregn-4,6-diene-3,20-dione C : 6-methyl-9α-fluoro-11β-hydroxy-19-nor-pregn-4,6-diene-3,20-dione D : 6-methyl-9α-fluoro-11β-hydroxy-19-nor-androst-4,6-diene-3,20-dione
  2. Draw the structure of the following steroid showing its stereochemistry and substitution pattern. 6,16 β -dimethyl-estr-1,3,5,6-tetraene-3,17 β -diol ( 3 pts)
  3. A key step, targeted by statins, in cholesterol biosynthesis is ( 4 pts) A : synthesis of acetyl-Coenzyme A B : synthesis of mevalonate C : synthesis of 3-hydroxy-3-methyl-glutaryl Coenzyme A D : none of the above
  4. Inhibition of bile re-absorption from the GI tract is the primary mechanism of ( 4 pts) A : mevastatin B : metformin C : nicotinic acid D : colestipol
  5. Circle molecule(s) from below that are expected to possess anti-estrogenic activity (antagonist). Please note: -2 points for every wrong answer circled. ( 4 pts) CH 3 OH

HO

CH (^3)

HO

H 3 C

HO

O H^3 C

HO

OH HO

H

CH 3

O

O

CH 3

F

HO

CH 3 OH

HO CH 3

CH 3

  1. Lipoprotein particles are ( 3 pts) A : aggregates of lipoproteins, triglycerides, cholesterol and cholesteryl esters B : the main target of all cholesterol reducing therapies C : synthesized and metabolized in the liver D : all of the above
  2. The mechanism of steroid hormone action requires ( 3 pts) A : the dimerization of the steroid – receptor complex B : the internalization of hormone response element C : the dimerization of hormone response element. D : none of the above
  3. Circle orally active steroidal hormone(s) from the following synthetic compounds. Please note: -2 points for every wrong answer circled. ( 6 pts)
  4. Identify the primary biologic activity of the following drugs from the choices below. You may skip a letter or use a letter more than once. ( 24 points)

CH (^3)

O

OH CCH 3

N

CH 3 H 3 C

Cl

OCH 2 CH 2 N(CH 2 CH 3 ) (^2)

O

CH (^3)

CH 3 OH CH

N

N O

F

F

OH

OH

S N

O O

H

N

O

H

N

H 3 C

CH (^3)

CH (^3)

O

O OH HO OH

F

CH (^3)

_____________ ______________ _________________

_____________ ______________ _________________

C/G G^ E

I J^ A

A: anti-hyperlipidemic B: androgen agonist C: androgen antagonist D: estrogen agonist E: estrogen antagonist F: progestational G: progesterone antagonist

H: mineralocorticoid I: anti—inflammatory J: oralhypoglycemic K: None of the above

CH (^3)

CH 3 OH

O

CH CH 3

O

CH (^3)

H 3 C O

CH 3

HO

O

CH 3

OH

O

CH (^3) CH 3

HO

H

CH 3

O

O O CH OH

HO