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Med Chem Cardio > Test 2: Lipid Med Chem > Flashcards

Test 2: Lipid Med Chem Flashcards

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1
Q

What is the rate-limiting step of cholesterol biosynthesis?

A

The conversion of HMG CoA to Mevalonic Acid

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2
Q

What kind of reaction does Acetyl CoA under go to get HMG-CoA

A. Reduction

B. Oxidation

C. Condensation

D. Hydrolysis

A

C. Condensation

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3
Q

Statins resemble which structure in cholesterol biosynthesis?

A. Acetyl CoA

B. HMG-CoA

C. Mevalonic Acid

D. 3,4-dihydroxy acid Intermediate

A

D. 3,4-dihydroxy acid intermediate

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4
Q

Which of the following groups make up Acetyl CoA? (Select All) A. Pantothenic Acid B. Pyrazine C. ADP with 3’ Phosphate D. Thioester

A

A, C, D

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5
Q

What is true about the OH groups at the 3 and 5 position?

A. Gives molecule its inhibitory effects

B. Gives molecule its prodrug characteristics

C. Gives molecule agonist activity

D. Can be switched with methyl groups

A

A.

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6
Q

HMGRIs (statins) perform which of the following functions? (select all)

A. Decrease Liver Cholesterol Biosynthesis

B. Increase LDL receptors

C. Increase LDL clerance from the body

D. Increase LDL precursors

E. Decrease LDL precursors

A

A, B, C, E

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7
Q

What is the SAR of the COOH at the 1 position?

A. Free carboxylic acid signifies the Statin is a prodrug

B. Cyclic formation between the COOH at the 1 position and OH at the 5 position creates a Lactam

C. Cyclic formation between the COOH at the 1 position and the OH at the 5 position creates an active drug

D. Cyclic formation between the COOH at the 1 position and the OH at the 5 position creates a Prodrug.

A

D

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8
Q

Which of the following is true about the carbons at positions 6-7?

A. Always contain a single bond between carbons 6-7

B. May contain a double bond between carbons 6-7

C. Carbons 6-7 are essential for optimal activity

D. Resembles fluvastatin when containing a double bond between the 6-7 carbon.

E. Carbons 6-7 can be absent from some Statins

A

B, C, D

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9
Q

Which of the following Statins contain a Ring A SAR? (Select All)

A. Lovastatin

B. Simvastatin

C. Fluvastatin

D. Atorvastatin

E. Pravastatin

F. Rosuvastatin

G. Pitavastatin

A

A, B, E

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10
Q

What type of reaction needs to occur to make this prodrug an active metabolite?

A. Condensation reaction

B. Reduction reaction

C. Hydrolysis reaction

D. Esterification

A

C

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11
Q

Which of the following is true about this structure (Select All)

A. A hydrogen at the R2 position is associated with increased potency

B. Cyclohexene rings are not essential for activity

C. Replacing Cyclohexene rings are associated with a 10,000 fold decrease in activity

D. Cyclohexene rings are Essential for activity

E. Atorvastatin contains this Ring System

F. Simvastatin contains a methyl at the R2 position of this ring system. Making it more potent.

A

C, D, F

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12
Q

All of the following statements are true about this Ring B system except:

A. This ring system can be found in Atorvastatin

B. The R group can contain Aryl Groups, Hydrocarbon chains, amides and SO2NH2

C. The W, X, Y positions can contain Nitrogens, Carbons and Sulfurs

D. N=1 on the ring signifies it is a six-member ring

E. N=0 on the ring signifies it is a five-member ring

A

C. Cannot contain sulfurs in those positions

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13
Q

The functional group highlighted in red indicates that:

A. The drug is active

B. The drug is a prodrug

C. The functional group is a lactam

D. The functional group is a lactone

E. Both B and D

A

E

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14
Q

Which of the following Statins is metabolized by CYP2C9 enzymes? (Select All)

A. Rosuvastatin

B. Atorvastatin

C. Fluvastatin

D. Pitavastatin

E. Simvastatin

A

A, C

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15
Q

Which of the following statements is true about statins?

A. Lipophilic statins are able to pass through the GI membrane without the need of an OATP1B1 transporter

B. Hydrophilic statins must utilize an OATP1B1 Transporter in order to pass through the GI membrane.

C. All statins are substrates of OATP1B1 transporters

D. Gemfibrozil increases chances of Rhabdomyolysis by the blocking of OATP1B1 transporters.

E. All of the above

A

E

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16
Q

The functional group circled in this picture is a:

A. Part of a Ring A functionality

B. A Pyrrole functional group

C. A 6-member heteroaromatic ring

D. A 5-member heteroaromatic ring

E. B and D

A

E

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17
Q

Which of the following is true about this drug: (Select all)

A. This drug structure can be identified as Atorvastatin

B. The free carboxylic acid makes this a prodrug.

C. This drug is a substrate for OATP1B1 transport

D. This drug contains a Pyrrole functional group.

E. This drug represents a Ring A system

F. This drug is acidic

A

A, C, D, F

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18
Q

Which of the following statements are true about Atorvastatin?

A. Has significant interactions with drugs that affect CYP3A4, PgP and OATP1B1

B. Is an Acidic Lipophilic Molecule

C. Can be given to patients with renal dysfunction

D. Has a long half life

E. All of the above

A

E

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19
Q

What type of ineraction is Aspartate having with the OH group on Atorvastatin?

A. Ionic Interaction

B. Ion-Dipole Interaction

C. Covalent Bond

D. Hydrogen Bond

A

B. OH groups are dipoles and the Asp group is charged (ionic) so it is an ion-dipole interaction

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20
Q

What type of interaction is Serine having with the OH group on Atorvastatin?

A. Ionic Bond

B. Ion-Dipole Bond

C. Covalent Bond

D. Hydrogen Bond

A

D

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21
Q

What type of interaction is happening between the Lysine of enzyme and the COO- of Atorvastatin?

A. Ionic bond

B. Covalent bond

C. Hydrogen bond

D. Ion-dipole bond

A

A

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22
Q

What kind of interaction is the Lysine of the enzyme having with the OH group of Atorvastatin?

A. Ionic bond

B. Ion-Dipole bond

C. Covalent bond

D. Hydrogen bond

A

B.

23
Q

What type of interaction is the Serine of the enzyme having with the NH of Atorvastatin?

A. Hydrogen Bond

B. Ionic Bond

C. Covalent Bond

D. Ion-Dipole bond

A

A

24
Q

What type of interaction is the Arginine from the enzyme having with the Flourine from Atorvastatin?

A. Ionic bond

B. Covalent bond

C. Hydrogen bond

D. Ion-Dipole bond

A

D. Halogen groups such as fluorine act as dipoles as well.

25
Q

Which amino acid from the enzyme HMG CoA is interacting with the OH from Atorvastatin?

A. Lysine

B. Arginine

C. Serine

D. Aspartate

A

C

26
Q

Which amino acid is forming the Ion-Dipole bond with the OH group on Atorvastatin?

A. Serine

B. Lysine

C. Arginine

E. Aspartate

A

E

27
Q

Which amino acid is forming the Ionic bond with the COO- group of Atorvastatin?

A. Serine

B. Lysine

C. Arginine

D. Aspartate

A

B

28
Q

Which amino acid is forming the Ion-Dipole bond with the OH group on Atorvastatin?

A. Serine

B. Arginine

C. Lysine

D. Aspartate

A

C

29
Q

Which amino acid is forming the hydrogen bond with the NH group on Atorvastatin?

A. Lysine

B. Aspartate

C. Arginine

D. Serine

A

D. Serine

30
Q

Which amino acid is forming the Ion-Dipole bond with the Flourine group in Atorvastatin?

A. Arginine

B. Aspartate

C. Serine

D. Lysine

A

A

31
Q

What types of interactions can the 3 phenyl (aryl) rings and the isopropyl group make with the enzyme?

A. Ionic Interactions

B. Hydrophobic interactions

C. Covalent interactions

D. Dipole-Dipole interactions

E. Ion-DIpole interactions

A

B

32
Q

Which of the following is true about this reaction? (select all that apply)

A. It is CYP3A4-mediated reaction

B. It is CYP2C9-mediated reaction

C. It is forming an equipotent metabolite with a longer half-life

D. It is being hydroxylated in the Ortho and Para position

E. The active metabolite formed signifies that Atorvastatin is a prodrug

A

A, C, D.

Not E because Atorvastatin is already active and only forms an equipotent metabolite when metabolized.

33
Q

What is the name of the functional group present in fluvastatin?

A. Pyrrole

B. AminoBenzene

C. Indole

D. Furan

A

C

34
Q

Which statements about this drug are correct? (Select all)

A. The drug is Lipophilic and Acidic

B. Not a substrate of OATP1B1

C. Metabolized by CYP3A4

D. Has shortest elimination half-life of the statins (1 hour)

E. Metabolized by CYP2C9

F. Metabolites of fluvastatin are inactive

A

A, D, E, F

35
Q

Which statement(s) are true about Rosuvastatin

A. Has a long Half-life

B. Metabolized by CYP2C9

C. Contains a 6-member Pyrimidine Core and contains sulfonamide group

D. Produces a less potent Active N-Desmethyl metabolite when metabolized

E. All of the above

A

E

36
Q

Which group in Rosuvastatin will undergo N-Demethylation to form teh N-Desmethyl metabolite?

A. Carboxylic acid (Brown)

B. Fluorine group (Blue)

C. Pyrimidine group (Red)

D. Sulfonamide Nitrogen (Purple)

A

D

37
Q

Which of the following statements is true?

A. Rosuvastatin and Atorvastatin are administered in the evening or at bedtime

B. CYP3A4 inhibitors may increase levels of Simvastatin, Atorvastatin and Lovastatin

C. Gemfibrozil is associated with increased chances of Rhabdomyolysis when given with Statins

D. CYP2C9 inhibitors will decrease the plasma levels of Rosuvastatin and Fluvastatin

E. B and C

A

E

38
Q

The precursor for steroid hormones and Bile Acids is:

A. Cholesterol

B. Aldosterone

C. Plant Sterols

D. Triglycerides

A

A

39
Q

Which of the following are major bile acids? (select all)

A. Glycholic Acid

B. Cholesterol

C. Cholic Acid

D. Taurocholic Acid

E. Sterols

A

A, C, D

40
Q

Based on the structure of the major bile acid glycocholic acid which statement is true?

A. Represents a very Hydrophilic Molecule

B. Belongs to the class of steroids

C. Cannot pass through membranes easily

D. Cannot utilize enterohepatic ciculation

A

B.

41
Q

Which of the following statements is true about Bile Acid Sequestrants?

A. Causes an increase in bIle acid elimination

B. Increases the hepatic conversion of Cholesterol to bile acid.

C. Decreases fatty acid absorption

D. Bile acid sequestrants do not need good oral absorption

E. All of the above

A

E

42
Q

Bile Acid Sequestrants: (Select all that apply)

A. Usually contain positively charged amines

B. Are known as ion-exchange resins

C. Usually consist of negatively charged ions

D. Usually bind to positively-charged bile-acids

E. Are not orally absorbed across the GI membrane into circulation

F. Form insoluble complexes with bile acids to be excreted in the feces

A

A, B, E, F

43
Q

What type of amine is present in cholestyramine?

A. Primary

B. Secondary

C. Tertiary

D. Quaternary

A

D

44
Q

What is the advantage of cholestyramine having a quaternary amine?

A. Quaternary amines are negatively charged molecules that are dependent on pH

B. Quaternary amines are positively charged molecules that are independent of pH

C. Quaternary amines are positively charged molecules that are dependent on pH

D. Quaternary amines are negatively charged molecules that are indepenent of pH

A

B.

Quarternary amines are independent of pH meaning they will be very effective in binding bile acids since they do not lose their positive charge.

45
Q

Fragment A of colesevelam consists of:

A. Primary amine

B. Secondary amine

C. Alkylated amine with Quarternary ammonium

D. Decylated amine

A

A

46
Q

Fragment B of Colesevelam consists of:

A. Primary amine

B. Pair of secondary amines

C. Alkylated amine attached to a quaternary amonium

D. Decylated Amine

A

B

47
Q

Fragment C of Colesevelam contains:

A. Primary Amine

B. Pair of Secondary Amines

C. Alkylated amine attached to a quaternary ammonium

D. Decylated amine

A

C

48
Q

Fragment D of Colesevelam contains:

A. Primary Amine

B. Pair of Secondary Amines

C. Alkylated amine and Quarternary ammonium

D. Decylated amine

A

D

49
Q

Which of the following are effects of Fibrates?

A. Decrease Cholesterol levels

B. Decrease TG synthesis for VLDL

C. Increase Fatty acid oxidation

D. Increases HDL

E. All of the above

A

E

50
Q

When comparing the the structure of Gemfibrozil and Fenofibrate which statement is incorrect?

A. Gemfibrozil and Fenofibrate both contain phenoxy groups

B. Gemfibrozil does not contain a spacer while Fenofibrate does contain a spacer

C. Both structures have isobutyric acids

D. Fenofibrate contains an ester at the end of it’s group, making it a prodrug.

A

B

Both structures have phenoxy groups (green), isobutyric acid (red) and fenofibrate does have an ester while gemfibrozil does not have one. This makes fenofibrate a prodrug. Gemfibrozil DOES have a spacer (blue) so that statement is incorrect.

51
Q

Which of the following statements is true about Gemfibrozil? (select all)

A. The methyl groups on the aromatic ring can both undergo oxidation to produce hydroxy methyl groups then o-glucuronidation

B. Gemfibrozil is a strong inhibitor of CYP2C8, CYP2C9 and CYP2C19

C. Gemfibrozil cannot undergo O-glucuronidation

D. Is not contraindicated with statins

E. Is primarily eliminated renally

A

A, B, E

52
Q

Which of the following statements is true about Fenofibrate?

A. Ester group in drug makes it a prodrug

B. Chloro group attached to the aromatic ring increases half-life by slowing down hydroxylation of benzene ring. (Aromatic hydroxylation)

C.Is a weaker inhibitor of CYP2C8 and CYP2C9 in comparison to gemfibrozil

D. Can have ester metabolized to form free carboxylic acid that will undergo O-glucuronidation

E. All of the above

A

D

53
Q

Which statement is true regarding Niacin and Nicotinamide? (select all)

A. They both have Pyridine functional groups

B. Once Niacin is converted to Nicotinamide it no longer has antihyperlipdemic effects

C. Niacin is a prodrug that is converted to active nicotinamide

D. Niacin is the active form that decreases synthesis of TGs in the liver, thus lowering VLDL and LDL

A

A, B, D

Remember that for identifying pyradines:

Pyr= double bonds (6 member ring)

idine= one nitrogen

Med Chem Cardio (4 decks)

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