Physicochemical

Question 1

interdisciplinary science at the intersection of organic chemistry, biochemistry (biochemistry), computational chemistry, pharmacology, molecular biology and physical chemistry

Answer 1

Medicinal Chemistry

Question 2

Involved with the identification, design, synthesis and development of new drugs that are safe and suitable for therapeutic use in humans and pets

Answer 2

Medicinal Chemistry

Question 3

Study of marketed drugs, their biological and their quantitative structure-activity relationships (QSARs)

Answer 3

Medicinal Chemistry

Question 4

Studies how chemical structure influences biologic activity

Answer 4

Medicinal Chemistry

Question 5

Studies How the molecular and physicochemical properties of the molecule influences the drug’s pharmacokinetics (ADME) and pharmacodynamics (what the drug does to the body).

Answer 5

Medicinal Chemistry

Question 6

how functional groups present within the molecule influence its acid-base properties, water solubility, partition coefficient, crystal structure, stereochemistry, and ability to interact with biologic systems, such as enzyme active sites and receptor sites

Answer 6

Physicochemical

Question 7

relationship of how structural features of the molecule contribute to, or take away from, the desired pharmacologic properties

Answer 7

Structure-activity relationships (SARs)

Question 8

influences the biologic activity of chemical entities and that alterations in structure produce changes in biologic action.

Answer 8

Molecular structure

Question 9

“one chemical group gives one biological action”

Answer 9

Postulate

Question 10

developed the concept of drug receptors

Answer 10

Ehrlich (Paul Ehrlich)

Question 11

Interaction of the chemical with the cell surface “side chains” produces a what

Answer 11

Toxic effect

Question 12

Selectivity permitted eradication of disease states without significant harm coming to the organism being treated.

Answer 12

Selective Toxicity (albert)

Question 13

The underlying principle of medicinal chemistry

Answer 13

Structure-Activity Relationships

Question 14

T or F. Similar molecules exert similar biologic action in a qualitative sense

Answer 14

T. SAR

Question 15

groups within a specific structure are important for its pharmacologic activity and how these groups can be modified to produce more potent, mode selective, and safer compounds

Answer 15

Functional Groups

Question 16

Example of drugs with structural similarity:

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PABA and sulfanilamide

Question 17

How can drug molecules exhibit their pharmacologic activity?

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By interacting with a biologic target , typically a receptor, enzyme, nucleic acid, or excitable membranes or other biopolymer

Question 18

The relative fit of each drug molecule with its target is a function of a number of what

Answer 18

Physicochemical properties

Question 19

What are the three physicochemical qproperties

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1.Acid-base chemistry and related ionization
2. Functional group shape and size
3. Three dimensional-spatial orientation

Question 20

are natural polymers produced by the cells of living organisms.

Answer 20

Biopolymers

Question 21

consist of monomeric units that are covalently bonded to form larger molecules.

Answer 21

Biopolymers

Question 22

Most appropriate to explain and predict acid-base behavior

Answer 22

Bronsted-Lowry acid-base theory

Question 23

When an acid gives up a proton to a base, it is converted to its what

Answer 23

Conjugate base

Question 23

any substance capable of yielding a proton (H+)
- Based on BLABT

Answer 23

Acid

Question 24

any substance capable of accepting a proton - according to BLABT

Answer 24

Base

Question 25

When a base accepts a proton, it is converted to its whatt

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Conjugate acid

Question 26

T or F. When a basic functional group is converted to the corresponding conjugate acid, it too become unionized.

Answer 26

F. Ionized

Question 27

Functional groups that cannot give up or accept a proton are considered to be ___ with respect to their acid-base properties.

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“neutral” (or “nonelectrolytes”)

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Acids and Conjugate Base Phenol (9-11)

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Phenolate

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Sulfonamide (9-10)

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Sulfonamidate

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Imide (9-10)

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Imidate

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Alkylthiol (10-11)

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Thiolate

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Thiophenol (9-10)

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Thiophenolate

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N-Arylsulfonamide (6-7)

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N-Arylsulfonamidate

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Sulfonimide (5-6)

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Sulfonimidate

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Alkylcarboxylic acid (5-6)

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Alkylcarboxylate

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Arylcarboxylic acid (4-5)

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Arycarboxylate

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Sulfonic acid (0-1)

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Sulfonate

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Common basic functional groups and conjugate acid Arylamine

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Arylammonium

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Aromatic amine (5-6)

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Aromatic ammonium

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Imine (3-4)

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Iminium

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Alkylamines

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Alkylammonium

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Amidine

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Amidinium

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Guanidine

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Guanidinium

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Neutrals

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Alkyl Alcohol Ether Ester Sulfonic acid ester Amide Diarylamine Nitrile Quaternary ammonium Amine oxide Ketone and aldehyde Thioether Sulfoxide sulfone

Question 45

A molecule can contain multiple functional groups with acid-base properties and, therefore, can possess both acidic and basic character. T or F

Answer 45

T

Question 46

Examples of molecule containing multiple functional groups with acid-base proteins

Answer 46

Ciprofloxacin, (a fluoroquinolone antibacterial agent)

Question 47

are weakly basic - Do not contribute significantly to the acid-base properties

Answer 47

Arylamines

Question 48

- Accept a proton

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Secondary alkylamine

Question 49

- Donate a proton

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Carboxylic acid

Question 50

Can act as an acid and base

Answer 50

Amphoteric

Question 51

one can predict whether a molecule is going to be predominantly ionized or un-ionized at a given pH by knowing what

Answer 51

acidity/basicity of a functional group

Question 52

T or F Ionized (or charged) drugs are not absorbed as efficiently as un-ionized drugs are

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True

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Principle for this: a weak acid will be absorbed primarily in the acidic environment; whereas, a drug that is a weak base will be absorbed in the alkaline environment (small intestines)

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Like dissolves like

Question 54

greatly affects the routes of administration as well as absorption, distribution and elimination

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Water

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Potential for hydrogen bond formation Ionization of one or more functional groups

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Water solubility of a molecule

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Acceptance of a hydrogen bond

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increases the hydrophilic (water-loving) nature of the molecule

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groups that cannot form hydrogen bonds do not enhance hydrophilicity

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contribute to the hydrophobic (water-fearing) nature of the molecule

Question 58

Another type of interaction that plays an important role in determining water solubility, which occurs between either a cation and the partially negative charged atom found in a permanent dipole

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Ion-dipole interaction

Question 59

Ion dipole interaction occurs between either a what and a what

Answer 59

cation and a partially negative charged atom found in a permanent dipole

Question 60

approach in predicting the water solubility of molecules based on the carbon-solubilizing potential of several functional groups.

Answer 60

Empiric approach

Question 61

If the solubilizing potential of the functional group exceeds the total number of carbon atoms present, then the molecule is considered to be what

Answer 61

water soluble

Question 62

Opioid analgesic that contains three functional groups that contribute to water solubility

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Anileridine

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If Solubilizing potential is less than the total number of carbons,

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insoluble in water

Question 64

Molecules that contain the same number and kinds of atoms The same arrangement of bonds, but different three-dimensional shape arrangement of atoms in space

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Stereoisomers

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2 types of stereoisomers

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Enantiomers and Diastereomers

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Pairs of molecules for which three-dimensional arrangement of atoms represents non-superimposable mirror images.

Answer 66

Enantiomers

Question 67

All of other stereoisomeric compounds that are not enantiomers Compounds that contain double bonds (geometric isomers) and ring systems Exhibit different physicochemical properties, including, but not limited to, melting point, boiling point, solubility, and chromatographic behavior

Answer 67

Diastereomers

Question 68

Empiric approach to predicting the water solubility of molecules based on the _______________ of several functional groups.

Answer 68

carbon-solubilizing potential

Question 69

% solubility of water solubility

Answer 69

1%

Question 70

There drugs are not absorbed as efficiently as un-ionized drugs are.

Answer 70

Ionized or charged drugs

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T or F weak acid will be absorbed primarily in the acidic environment; whereas, a drug that is a weak base will be absorbed in the alkaline environment (small intestines)

Answer 71

T

Question 72

Example of an alkaline environment

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Small intestines

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ph of stomach

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1 - 3.5

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pH of Colon

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5.6 -7

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completely donate (dissociate) or accept a proton in aqueous solution

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Strong acids and bases

Question 76

Act as an acid or a base, depending on the prevailing pH of the solution.

Answer 76

AMPHOTERIC