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MEDICINAL ORGANIC CHEMISTRY > MEDICINAL CHEMISTRY > Flashcards

MEDICINAL CHEMISTRY Flashcards

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1
Q

A chemistry-based discipline, involving the aspects of biological, medical, and pharmaceutical science.

A

Medicinal Chemistry

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2
Q

Medicinal chemistry encompasses ____, ____, ____, and ____.

A

Identification, Discovery, Development, Synthesis

IDDS

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3
Q

Main driving force/highlight for medicinal chemistry

A

Random Screening

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4
Q

One of the first groups of drugs that was discovered thru medicinal chemistry

A

Nitrofurans

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5
Q

Metronidazole (Flagyl) is indicated as an ____.

A

Anti-protozoal/Anti-fungal

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6
Q

Chemical compound that is used to treat, mitigate, diagnose, and prevent diseases both in humans and animals.

A

Drugs

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7
Q

Compounds that interact with a biological system to produce a biological response - beneficial or toxic.

A

Drugs

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8
Q

Chemical compound that has a pharmacologic or biological activity whose chemical structure is used as a starting point for chemical modification in order to improve potency, selectivity, or pharmacokinetics parameters.

A

Lead Compound

“Prototype”

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9
Q

Lead compounds thar underwent modifications.

A

Analogues

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10
Q

Innovative or new drugs for previously unmet medical needs

A

Novel Drugs

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11
Q

Drugs for rare medical conditions

A

Orphan Drugs

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12
Q

Ideal drug that is free from side effects

A

Goal Drug

Non-existent

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13
Q

Compound that undergoes biotransformation prior to exhibiting its pharmacological effects

A

Prodrug

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14
Q

2 Broad categories of prodrugs

A
  1. Carrier-linked prodrug
  2. Bio-precursors
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15
Q

Consist of the attachment of a carrier group to the active drug to alter its physicochemical properties and the subsequent enzymatic or non-enzymatic mechanisms to release the active drug moiety

Ex: Macromolecules

A

Carrier-linked prodrug

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16
Q

Compounds that already contain the embryo of the active species within their structure.

A

Bio-precursors

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17
Q

IDENTIFY THE PRODRUG CATEGORY.

Inactive prontosil reduction to sulphanilamide (anti-bacterial)

A

Bio-precursor

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18
Q

IDENTIFY THE PRODRUG CATEGORY.

Inactive cyclophosphamide oxidation to phosphoramide mustard (antineoplastic)

A

Bio-precursor

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19
Q

Mechanism of action of phosphoramide mustard

A

Alkylation

Cross-linking of DNA that leads to death of cancer cells

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20
Q

2 Other terms for double prodrug

A

Pro-Prodrug or Cascade Latentiated Prodrugs

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21
Q

Carried out by enzymatic conversion to prodrug is possible before the “pro-drug” release the active ingredient

A

Double Prodrug, Pro-Prodrug, or Cascade Latentiated Prodrugs

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22
Q

Prodrugs that use macromolecules as carriers

A

Macromolecular Prodrugs

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23
Q

Carrier acts as transporter of the active drug to a specific targeted site

A

Site-Specific Prodrugs

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24
Q

Example of a site-specific prodrug liberated in the colon

A

Sulfazalazine

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25
Q

Consists of two synergistic drugs chemically linked together, in order to improve the drug delivery properties of one or both drugs

A

Co-drug/Mutual Prodrug

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26
Q

EXAMPLES OF CO-DRUG/MUTUAL PRODRUG

Sulfasalazine

A

Sulfapyridine + 5-aminosalicylic acid

For enterocolitis

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27
Q

EXAMPLES OF CO-DRUG/MUTUAL PRODRUG

Benorylate

A

Paracetamol + Aspirin

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28
Q

EXAMPLES OF CO-DRUG/MUTUAL PRODRUG

Sultamicillin

A

Ampicillin + Sulbactam

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29
Q

EXAMPLES OF PRODRUGS

Metabolized into Meprobamate

A

Carisoprodol

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30
Q

EXAMPLES OF PRODRUGS

Bioactivated by esterase (hydrolysis of the ethyl ester) to the active Enalaprilat

A

Enalapril

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31
Q

EXAMPLES OF PRODRUGS

Bioactivated by esterase (valacyclovir hydrolase enzyme) to the active form Acyclovir

A

Valaciclovir

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32
Q

EXAMPLES OF PRODRUGS

Bioactivated by Peripheral DOPA decarboxylase to the active form Dopamine

A

Levodopa

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33
Q

EXAMPLES OF PRODRUGS

IV prodrug of chloramphenicol, because pure chloramphenicol is poorly soluble in water (2.5mg/mL) or palmitate ester to make a suspension (1.95mg/mL)

A

Chloramphenicol Succinate

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34
Q

EXAMPLES OF PRODRUGS

Deacetylated by esterase to the active form 6-monoacetylmorphine and morphine

A

Heroin

aka Diacetyl Morphine

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35
Q

EXAMPLES OF PRODRUGS

Designed to prolong the drug activity of its active metabolite 6-mercaptopurine

A

Azathioprine

36
Q

EXAMPLES OF PRODRUGS

Designed to mask the toxic side effects of the active metabolite 4-hydroxy–cyclophosphamide and Phosphoramide Mustard.

A

Cyclophosphamide

37
Q

EXAMPLES OF PRODRUGS

Designed to increase the chemical stability of the active metabolite Ampicillin.

A

Hetacillin

Failed prodrug

38
Q

Phenomenon when a patient receives a placebo treatment will have a perceived or actual improvement of medical condition.

A

Placebo Effect

39
Q

Region of the molecule containing the essential organic functional groups that directly interact with the receptor active site, therefore, confers the biologic activity of interest

Must remain intact upon modification

A

Pharmacophore

40
Q

Chemical reaction that occur in the body to maintain life and supply of energy

A

Metabolism

41
Q

This allows organisms to grow and reproduce, maintain their structures, and respond to their environments.

A

Metabolism

42
Q

2 Categories of metabolism

A
  1. Catabolism
  2. Anabolism
43
Q

Type of metabolism that breaks down organic matter

A

Catabolism

Hydrolysis (Addition Reaction)

44
Q

Type of metabolism that uses energy to build up or contrast components of cells such as proteins and nucleic acids

A

Anabolism

Dehydration synthesis

45
Q

The basic premise of drug metabolism is to convert ____ drugs to ____ metabolites to be excreted.

Lipophilic or Hydrophilic

A

Lipophilic to Hydrophilic

46
Q

3 characteristics of drugs to be excreted

A
  1. Hydrophilic/Water-soluble
  2. Ionized
  3. Polar
47
Q

The main site for drug metabolism

A

Liver

High concentration of enzymes (CYP450) and it is a highly perfused organ

48
Q

Metabolism converts inactive drug to active form in a process called ____.

A

Biotransformation/Bioactivation

49
Q

Two general types of local anesthetic agents

A

Amides and Esters

50
Q

Local anesthetic agents undergo ____ to terminate drug action.

A

Bio-inactivation

51
Q

Disulfiram (Antabuse) is used for ____.

A

Alcohol Withdrawal

52
Q

Termination of drug action for disulfiram

A

Detoxification

53
Q

Termination of drug action for paracetamol metabolism

A

Elimination

54
Q

Bioactivation: MPTP to MPP+

A

Toxification

55
Q

Bioactivation: Imipramine to Desipramine

A

Active Metabolites

56
Q

Reactions involved in the phase 1 of drug metabolism

A
  1. Reduction
  2. Hydrolysis
  3. Oxidation
57
Q

Reaction involved in the phase 2 of drug metabolism

A

Conjugation

58
Q

Phase 1 of drug metabolism is also known as ____.

A

Functionalization Reaction

59
Q

Aspirin is likely to transform into an ____ at room temperature.

Ester or Amide

A

Ester

60
Q

PHASES OF DRUG METABOLISM

Main function is to provide functional groups (OH, COOD, SH, NH2)

A

Phase 1

61
Q

PHASES OF DRUG METABOLISM

Most common Phase 1 reaction

A

Oxidation

62
Q

PHASES OF DRUG METABOLISM

Usually results to loss of pharmacological activity

A

Phase 1

63
Q

PHASES OF DRUG METABOLISM

Non-synthetic reaction

A

Phase 1

64
Q

PHASES OF DRUG METABOLISM

Sometimes maybe equally or more active than parent

A

Phase 1

65
Q

PHASES OF DRUG METABOLISM

Condensation Reaction

A

Phase 2

66
Q

PHASES OF DRUG METABOLISM

Main goal is to attach small, polar, and ionizable endogenous substrates/compounds to the “handles”

A

Phase 2

67
Q

PHASE 2 REACTIONS

Enzyme involved in methylation

A

Methyl transferase (COMT)

68
Q

PHASE 2 REACTIONS

Enzymes involved in acetylation

A
  1. S-Adenosyl Methionine
  2. N-acetyltransferase (NAT)
69
Q

PHASE 2 REACTIONS

Terminate or attenuate activities

A

Methylation and Acetylation

70
Q

PHASE 2 REACTIONS

Protects the body against reactive compounds or metabolites

A

Glutathione (GSH)

71
Q

PHASE 2 REACTIONS

Most common Phase 2 reaction

A

Glucuronidation

72
Q

PHASE 2 REACTIONS

Enzyme for glucuronidation

A

Glucuronosyl Acyltransferase (GluCAT)

73
Q

PHASE 2 REACTIONS

Essential in order to have sufficient supply of glucuronides

A

D-glucuronic acid

74
Q

PHASE 2 REACTIONS

Examples of drugs that may undergo glucuronidation

A
  • Morphine
  • Paracetamol
  • Chloramphenicol
75
Q

PHASE 2 REACTIONS

Newborns are capable of this reaction but it is easily saturated

A

Sulfation

76
Q

PHASE 2 REACTIONS

Enzyme involved in sulfation

A

Sulfonyl Transferase

77
Q

PHASE 2 REACTIONS

Substrates for acetylation

A
  • Hydralazine
  • Isoniazid
  • Procainamide

HIP

78
Q

PHASE 2 REACTIONS

This drug undergoes phase 2 first before phase 1

A

Isoniazid

79
Q

Grapefruit is an example of an enzyme ____.

Inhibitor or Inducer

A

Inhibitor

Prolongs the effect of drug

80
Q

Grapefruit contains ____ that is responsible for the inhibitory effects when taken with drugs.

A

Furanocoumarins (Bioflavonoids)

81
Q

Rifampicin acts as an enzyme ____ when taken with paracetamol and oral contraceptive pills.

Inhibitor or Inducer

A

Inducer

More enzymes = Faster metabolism = Less effect

82
Q

FACTORS THAT AFFECT METABOLISM

Older people have ____ metabolism.

Faster or Slower

A

Slower

83
Q

FACTORS THAT AFFECT METABOLISM

Fast acetylators are prone to experience ____ with the use of isoniazid.

A

Peripheral Neuropathy

84
Q

FACTORS THAT AFFECT METABOLISM

Peripheral neuropathy with the use of isoniazid is managed by taking _____.

A

Vitamin B6 Pyridoxine

85
Q

FACTORS THAT AFFECT METABOLISM

Slow acetylators are prone to experience ____ with the use of isoniazid.

A

Hepatotoxicity

MEDICINAL ORGANIC CHEMISTRY (17 decks)

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