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Chemistry > Option D > Flashcards

Option D Flashcards

1
Q

What do medicines and drugs do?

A

Alter incoming sensory sensations

Alter a person’s mood or emotions

Alter the physiological state of the body including COORDINATION and CONSCIOUSNESS

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2
Q

Define a drug and describe the difference between a pharmaceutical drug and recreational drugs

A

A substance that causes a physiological change in the body. A pharmaceutical drug is taken for medical reasons whereas recreational drugs are taken for leisure purposes e.g: cannabis, ecstasy, alcohol

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3
Q

What is a therapeutic effect

A

The beneficial effect of a medicine

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4
Q

Describe the oral way of taking medication

A

Medicines are taken by mouth e.g: tablets, capsules, pills

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5
Q

Describe inhalation

A

Vapour breathed in by smoking, e.g: asthma medication, neubilisers

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6
Q

Skin patches

A

Absorbed through the skin into the blood e.g: hormone patches

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7
Q

Suppositories

A

Rectum, e.g: laxatives for constipation

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8
Q

Eye or eye drops

A

treatment for eye or ear infections

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9
Q

Injection (parenteral)

A

Injected into the muscle, blood or under the skin

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10
Q

Describe intramuscular injection

A

Drug is injected directly into the muscle

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11
Q

Intravenous?

A

Drug injected into bloodstream - 100% bioavailability as directly in bloodstream

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12
Q

Subcutaneous?

A

Drug is injected directly under the skin

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13
Q

Describe the layers of the skin

Every Doctor Sells Medicine

A

Epidermis
Dermis
Subcutaneous tissue
Muscle

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14
Q

Which drug administration method has the fastest effect?

A

Intravenous

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15
Q

What is bioavailability?

A

The fraction of the administered dosage of a drug that enters the bloodstream, thereby accessing the site of action

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16
Q

What factors affecting bioavailability:

A

Method of admin
Polarity (solubility) of the drug
Types of functional groups present in the drug

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17
Q

Describe the bioavailability of an oral drug

A

They are often broken down during administration during digestion before reaching the bloodstream. An oral dose of a drug must be 4 times higher than dosage that is given intravenously

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18
Q

How does the polarity of a drug affect its solubility?

A

Very hydrophillic drugs are soluble in aqueous body but are poorly absorbed due to their inability to cross cell membranes which are composed of lipids.

Very hydrophobic drugs are not soluble in body fluids

For a drug to be readily absorbed, it must be mostly HYDROPHOBIC but also have some solubility in aqueous solutions.

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19
Q

What are the 2 major properties that contribute towards water solubility of a functional group?

A

Ability to ionize

Ability to form hydrogen bonds

E.g: COOH, NH2

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20
Q

Examples of non-polar functional groups

A

Phenyl group

Hydrocarbon chain (alkyl group)

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21
Q

Describe aspirin solubility

A

Largely non-polar molecule and so has low solubility in WATER due to presence of phenyl group

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22
Q

How to increase aspirin solubility

A

React it with aqueous NaoH, forming an ionic salt

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23
Q

How can drugs be chemically modified to increase their bioavailability?

A

Drugs containing an ACIDIC or BASIC functional group can be chemically modified to form an ionic salt

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24
Q

What is the therapeutic window

A

Measure of the relative margin of the safety of a drug. The wider the therapeutic window, the safer the drug.

A wide therapeutic window means that there is a wide margin between doses that are effective and doses that are toxic

A narrow therapeutic window means only a small increase in the effective doses may produce toxic effects

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25
Q

What is the therapeutic index

A

Ratio between lethal dose and effective dose

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26
Q

Formula for Therapeutic index in humans

A

TI = median toxic dose/ median effective dose

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27
Q

Main stages of drug development

A

Drug is synthesized in the laboratory
tested on animals
tested on humans - half given real drug, other half given placebo

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28
Q

Placebo effect

A

When the body is fooled into healing itself naturally

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29
Q

What are the factors that must be determined during drug testing

A

Risk: benefit ration - balance between risks and benefits
Unwanted side effects
Drug tolerance - when patient needs to take larger doses to gain original effect

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30
Q

BRIEF:

How is aspirin produced? (acetylsalicylic acid) and state the 2 catalysts that can be used

Ethanoic acid is excess and sali is LIMITING

A

Reacting salicylic acid with ethanoic anhydride to produce ASPIRIN and ETHANOIC ACID

Catalyst: CONCENTRATED sulfuric acid or H3Po4

Salicylic acid turns into aspirin via ESTERIFICATION - a condensation reaction

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31
Q

Mr of Aspirin

A

C9 H8 O4

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32
Q

Detailed steps of aspirin production

A
  • Concentrated sulfuric acid is added to the reaction mixture of salicyclic acid and ethanoic anhydride which is warmed gently. This is the catalyst.
  • The product is cooled to form crystals which are then suction filtered and washed with cold water
  • Aspirin has very low solubility in cold water so this removes the soluble acids but not the aspirin
  • Aspirin purified in a process called re-crystallisation
  • This involves dissolving the impure crystals in a small volume of hot ethanol

Water is then added and the solution is then cooled, then chilled

acetylsalicylic acid then crystallises and the unreacted acetylsalicylic acid remains dissolved in solution

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33
Q

How can the purity of aspirin be determined

A

Infrared spectrum - 2 peaks: OH group and C=O in ester and carboxylic

Melting point - pure aspirin has a melting point between 128 and 140 degrees. Impurities lower the melting point and cause it to melt over a much wider temperature range

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34
Q

Describe the difference between the IR spectrum of acetylsalicylic acid and salicylic acid

A

Prescence of a peak corresponds to PHENOL in salicyclic which is absent in aspirin

Abscence of a C=O group corresponding to esters in salicyclic acid. Instead there is only one bond which corresponds to C=O group in carboxylic acids

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35
Q

Describe the 3 functional groups in aspirin

A

Phenol group
Carboxyl group
Ester

Although it has a polar carboxylic group, sol is limited due to non-polar phenol group.

Sodium acetylsalicylate

When water added to ^, dissociates to form Na+ ions and acetylsalicylate ions

Ionic salts are more soluble in water as they form stronger ion-dipole interactions with water

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36
Q

How does converting aspirin to an ionic salt change its bioavailability

A

Increases SOLUBILITY but does NOT increase bioavailability.

This is because the acetylsalicylate ion is converted back to the unionised form in the acidic environment of the stomach

So COO- functional group changed back to COOH

Bioavailability can be increased by injecting it intravenuously

37
Q

Describe uses of aspirin

A

Aspirin is a mild-analgesic (painkiller) - blocks sensation of pain at source
Aspirin works by blocking the action of enzymes that produce prostaglandins which are involved in transmitting impulses to the brain as well as causing fever and swelling. Aspirin prevents prostaglandins to be produced, eliminating pain

Aspirin is also used as an anti-coagulant. Prevent blood from clotting. Prevents heart attack and strokes. Aspirin also has anti-inflammatory properties, taken for arthritis and rheumatism.

38
Q

Side effects of aspirin

A

Bleeding of the lining of the stomach. This is increased by drinking alcohol at the same time as taking aspirin which is known as the synergistic effect.

39
Q

What is a synergistic effect

A

When 2 drugs increase each others effectiveness when taken together

40
Q

What is penicillin

A

A group of antibiotics used to treat a range of bacterial infections. Derived from Penicillium Fungi and can be taken ORALLY or via INJECTION

41
Q

How was penicillin discovered

A

Flemming was working with bacteria cultures. He noticed that a fungus had contaminated some of his cultures and left a clear region where no bacterial colonies were growing.

He concluded that something in the fungus was inhibiting the growth of the bacteria.

42
Q

Describe the structure of penicillin

A

Beta-lactam ring - partly responsible for anti-biotic properties

3 carbon atoms, 1 nitrogen atom - nitrogen and 2 carbons are sp3 hybridised - 109.5

Carbon in carbonyl group is sp2 hybridised

The bond angles are usually reduced to 90 degrees which strains the bonds

Due to the strain, the beta-lactam ring breaks easily

43
Q

How do beta-lactam antibiotics work

A

BLA work by interfering with cell wall formation in bacteria by inhibiting the enzymes responsible for creating cross-links in the cell wall.

When the beta-lactam ring comes into contact with the bacteria, the ring opens and binds irreversibly to the enzyme responsible for catalysing cross-links in the bacterial cell walls.

Water enters cell, increasing the osmotic pressure inside the cell, causing the cell to burst

44
Q

How to make penicillin more resistance to penicillinase enzyme

A

Modify side chains in penicillin to make them more resistant to the P enzyme, which could deactivate the original form of penicillin (penicillin G).

Side chains can also be modified to increase resistance to break down by stomach acid

45
Q

What are morphine and codeine

A

Opiates - strong analgesics

Opiates are natural analgesics that are derived from opium which is found in Poppy seeds.

Opiate analgesis work by temporarily bonding to receptor sites in the brain, preventing the transmission of pain impulses without depressing the CNS

46
Q

When are strong analgesics used?

A

Relieve pain caused by injury, heart attack or cancer. They have side effects

47
Q

Discuss the advantages of strong analgesis

A
  • provide relief for acute or temporary pain
  • Wide therapeutic window
  • relieve anxiety
  • faster distribution of drug due to intravenous admin
48
Q

Discuss the disadvantages of strong analgesis

A
  • euphoria
  • lack of self-control
  • indulge in dangerous behaviour
  • Regular usage can lead to addiction
  • build up tolerance - overdose chances
49
Q

What is the blood-brain barrier?

A

A layer of tightly packed cells that protect brain by restricting passage of substances from B.strwam to brain

BBB - composed of Lipids - non-polar + hydrophobic

BBB is not easily crossed by polar molecules

For a drug to penetrate BBB, it must be non-polar and lipid soluble.

50
Q

What do the analgesic properties of opiates depend on?

A

Their ability to move from the blood, where aqueous solubility is important, to the brain where lipid solubility is important to cross the blood-brain barrier

51
Q

What are opiate receptors

A

Once in the brain, opiates attach to opioid receptors which reduce the perception of pain. Opiates produce nausea, drowsiness and can also depress respiration

52
Q

Compare the structures of morphine, coedine and diamorphine (heroin)

A

C=C present in all - alkenyl
Phenol in all
Tertiary amine group
Ether group

Coedine - 1 OH group
Morphine - 2 OH

Coedine - 2 ether groups
Morph and DI - 1 ether group

Dia - 2 ester
Morph + coedine = 0 ester

53
Q

Describe why morphine is a polar molecule

A

2 OH groups make it a polar molecule. But it is less soluble in lipids

54
Q

Describe synthesis of diamorphine from morphine

A

Esterification

Both OH groups are converted into ester groups

Morphine is reacted with either ethanoic acid or ethanoic anhydride to produce diamorphine and WATER

2 hydroxyl groups replaced by 2 ester groups, making DIA less polar and more lipid soluble

This can now cross BBB more rapidly and in higher concentrations than morphine

so diamorphine is more potent but effects do not last as long as diamorphine

55
Q

Describe synthesis of codeine

A

Codeine produced from morphine in a methylation reaction

An OH group is converted to methoxy ( OHCH3 ) group

Codeine becomes less polar than morphine and cross BBB

But reaction also reduces codeine’s ability to bond to opioid receptors, making it a weaker analgesic than morphine

56
Q

Describe use of antacids

A

Antacids reduce excess stomach acid. Stomach contains HCL to kill pathogens.

Antacids work by neutralising excess HCL - they are weak bases
Strong bases cannot be used as antacids

57
Q

Equation for sodium bicarbonate and HCL?

A

NAHCO3 + HCL -> NaCl + CO2 + H2O

58
Q

What are alginates

A

Alginates produce a neutralising layer which prevents acid in the stomach rising into the oesophagus (heart-burn)

59
Q

If asked to compare effectiveness of different bases on HCL:

A

Write out BALANCED chemical equation

Work out moles of base from masses given

Calculate with moles of HCL using the ratio

Whichever base reacts with the greatest number of moles of HCL, that is the most effective base

60
Q

What do stomach acid inhibitors do?

A

Stomach acid inhibitors inhibit the production of stomach acid

PPIs and H2 receptor antagonists are both stomach acid inhibitors

PPIs inhibit proton pumps in stomach

H2 blockers block the histamine receptors in acid-producing cells in the stomach, reducing the amount of acid produced by the cells in the lining of the stomach

61
Q

How does histamine work

A

Histamine stimulates stomach acid secretions by interacting at H2 receptors in the stomach lining.

H2 blockers compete with histamine for binding with H2 receptors

They block the interaction of histamine with H2 receptors, preventing the release of stomach acid

62
Q

Describe an example of a PPI

A

Omeprazole

63
Q

Describe an example of a H2 blocker

A

Ranitidine

64
Q

How to calculate the pH of a buffer solution

A

pH = PKa + LOG (A-/HA)

HA = initial concentration of weak acid
A- = initial concentration of the salt
65
Q

What are the 2 assumptions of the Henderson Hasselbalch equator for pH of buffer

A

A weak acid partially dissociates - equilibrium lies to the left. Initial concentration of weak acid is equal to the equilibrium concentration of the weak acid because dissociation is so small.

Salt we use completely dissociates in solution. Initial conc = equilbirum conc of anion

66
Q

difference between bacteria and viruses

A

Viruses = protein coat and nucleic acids
Not considered living organisms as they do not carry out metabolic processes and derive their energy from host cell

UNLIKE viruses, bacteria are self-reproducing units
many organelles
carry out metabolic processes

Bacteria are much larger than viruses

67
Q

Why are viruses harder to cure

A

Viruses lack a structure whereas bacteria have a cell wall and so antibiotics can cure bacterial infections by disruption of cell wall production

Viruses mutate quickly so adapt to drugs

Bacteria are more complex and can be targeted in more ways whereas viruses lack sub-units that can be targeted by anti-bacterials.

Viruses must be targeted on a genetic level whereas bacteria can be killed by simple chemical agents.

68
Q

How do anti-virals work?

A

Alter the cell’s genetic material so the virus cannot use it to multiply

Prevent viruses from multiplying by blocking enzyme activity within the host cell

69
Q

How do anti-virals work?

A

Alter the cell’s genetic material so the virus cannot use it to multiply

Prevent viruses from multiplying by blocking enzyme activity within the host cell

Bind to cellular receptors targeted by viruses

Prevent or hinder the release of viruses from cells

70
Q

Describe Oseltamivir and Zanamivir

A

Both used as antivirals to prevent the spread of the flu virus

Zanamivir is taken in by inhalation due to its low bioavailability when taken orally.

Oseltamivir can be taken orally as its bioav not changed by inhalation

71
Q

Compare structures of oseltamivir

A

O:

Alkenyl
Carboxamide
amine
ester
ether

Z:

Alkenyl 
carboxamide
amine
ether
carboxyl
hydroxyl - 3

Zanamivir is more soluble in polar solvents than O

72
Q

What happens to the ester group in oseltamivir in human body

A

Ester group is hydrolysed to a carboxyl group. Both Oseltamivir and Zanamivir work by inhibiting the enzyme, neuraminidase by binding to its active site

73
Q

What is neuraminidase

A

An enzyme found on the surface of the influenza virus that enables the virus to be released from the host cell

By inhibiting this enzyme, virus does not leave host and infect other cells

74
Q

What the difficulties of treating HIV:

A

HIV destroys T-cells, cells that protect body from infection

HIV mutates rapidly

HIV uses host cells to replicate

Drugs used to treat HIV may also harm the host cell

75
Q

What is radioactive waste

A

Can be classified as low level, intermediate, or high level waste

High level waste gives off large amounts of ionizing radiation for a long time - long half life

76
Q

Examples of low level waste and disposal method

A

Shoes
Protective clothing
gowns

Stored in shielded containers until the isotopes have decayed and then disposed as non-radioactive waste

77
Q

Examples of intermediate waste and disposal method

A

Co-60, Cs-137

Stored in shielded containers in underground repositories

78
Q

What are the 3 ways in which antibiotics are released

A

Antibiotics given to animals to prevent livestock diseases

Improper disposal of antibiotic medicines by hospitals and households

Antibiotics excreted by humans in urine

79
Q

Dangers of antibiotic waste

A

AB in agricultural waste like manure and water run off can end up in soil and groundwater

Antibiotics in urine and pharmaceutical waste enter the sewage system at low concentrations

Sewage treatment plants are rarely equipped to remove antibiotics to remove antibiotics from waste water and can ultimately end up in the drinking water supply

80
Q

Preferred solvents for reaction media?

A 
Water
Propan-1-ol
Ethyl ethanoate
methanol
ethanol
81
Q

Useable solvents for reaction media

A 
Cyclohexane
octane
ethanoic acid
Ethane nitrile
Methyl benzene
82
Q

Undesirable solvents?

A 
Pentane
Dichloromethane
Dichloroethane
Carbon tetrachloride
Trichloromethane
83
Q

Discussion of environmental issues related to left-over solvents.

A

Many undesirable solvents are volatile organic compounds

VOCs can cause nose and throat discomfort, nausea and fatigue

Form low level ozone and smog

84
Q

What is green chemistry

A
  • Prevent waste
  • Maximise atom economy
  • Design less hazardous chemical syntheses
  • Design safer chemicals and products
  • Increase energy efficiency
  • Use safer solvents and reaction conditions
85
Q

Explain how green chemistry was used to develop the precursor for Tamiflu (oseltamivir)

A

Synthesis of oseltamivir requires shikimic acid, extracted from the pods of star anise

Problems with synthesis of oseltamivir:

  • complex, ten step process
  • 6-8 months needed
  • 30kg of star anise produces only 1kg of shikimic acid

Using the principles of green chemistry:

  • production of shiki from fermentation of genetically engineered bacteria
  • Extraction of shikimic acid from pine needles
86
Q

What is taxol and where is it obtained from

A

Taxol is an anti-cancer drug used in chemotherapy.

Obtained from the bark of a yew tree

Bark contains very small amount of taxol, so initially supply was limited and the process was non-renewable

A semi-synthetic route was developed in which the precursor of taxol was isolated from the leaves of the European Yew Tree.

This route gives a yield 0.2% higher

But conversion from 10-DAB to taxol is complex and requires a range of solvents and organometallic reagents

87
Q

Is taxol soluble?

A

Low solublility in water

Only 3 hydroxyl groups

To increase its water solubility, taxol is dissolved in alcohol with the addition of polyoxyethylated castor oil

88
Q

What is a chiral auxilliary

A

A chiral auxiliary is an optically active substance that is temporarily incorporated into an organic synthesis so that it can be carried out asymmetrically with the selective formation of a single enantiomer.

Chemistry (7 decks)

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