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IB CHEMISTRY 2017 EXAM > Topic 12; Medicinal Chemistry > Flashcards

Topic 12; Medicinal Chemistry Flashcards

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1
Q

Drug

A

a chemical that affects how the body works (both positive and adverse)
- affects physiological, sensory and emotions of a human

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2
Q

Medicine

A

a substance that improves health (beneficial drug); brings around a therapeutic effect

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3
Q

therapeutic effect

A

beneficial effect of a medicinal treatment

- intended physiological effect

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4
Q

placebo effect

A

when patients gain therapeutic effect from their belief that they have been given a useful drug even when they have not

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5
Q

placebo

A

drugs containing no active ingredient which ‘fool’ the body into healing

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6
Q

drug administration

A

the manner in which drugs are delivered to a patients body

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7
Q

subcutaneous

A

directly under skin surface into fat

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8
Q

intraveneous

A

directly into blood stream

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9
Q

intramuscular

A

directly into muscle

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10
Q

side effect

A

unintended physiological effect that ranges from drug to drug and person to person

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11
Q

dosing regime

A

the amount of a drug used for each dose and frequency of administration relative to patients state

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12
Q

therapeutic window

A

range of doses between minimum amount of drug that produces desired effect that the medically unacceptable adverse effect

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13
Q

tolerance

A

reduced response to the drug due to repeated dosage; therefore larger quantities of drug needed for effect

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14
Q

lead compounds

A

compounds with biological activity that are made and tested

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15
Q

analogues

A

chemically related compounds that are made and tested

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16
Q

effective dose

A

required dose to bring about an effect in 50% of the patients

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17
Q

lethal dose

A

dose required to kill 50% of patients
LD/ED= therapeutic index
TD; toxic dose used for humans

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18
Q

bioavailability

A

fraction of administred drug that reaches the target molecule in the body

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19
Q

analgesic

A

pain killer; can be strong or weak

target at source or pain receptors in brain

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20
Q

antibiotic

A

chemically produced by a microrganism to have action against another microorganism (bacteria)

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21
Q

antacid

A

a weak base that regulates stomach acidity

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22
Q

virus

A
  • live in a host cell
  • rapidly mutate and reproduce
  • don’t have metabolism like a bacteria does
  • antibiotics dont effect it
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23
Q

HIV

A
  • retrovirus; turns RNA into DNA
  • releases RNA into a cell to create viral DNA to then produce viral particles
  • destroys helper T cells
  • mutates rapidly
  • lies dormant in host cell
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24
Q

body immune response

A
  • produces antibodies to attack virus

- build immunity

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25
Q

types of treatments against a virus

A
  • prophylatic

- antiviral

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26
Q

prophylatic

A
  • (preventative measure) stimulate body to prepare specific antibodies to gain immunity (VACCINE)
  • limit of this is that viruses can mutate
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27
Q

antiviral

A

interferce with viral life cycle and prevent release of new viral particles from the host cell

e. g. - alter cells DNA to prevent virus’s multiplication
- block enzyme activity within host cells to stop virus’s mutliplication

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28
Q

example of a preventative anti-viral

A

Amantadine; changes cell membrane to prevent virus’s entry into host cell

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29
Q

Flu virus proteins

A
  • hemmaglutinin

- neuraminidase

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30
Q

hemaglutinin (H)

A

glycoprotein that enables a virus to attach with hose cell before entering

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31
Q

neuraminidase (N)

A

enzyme that catalyzes a cleavage reaction that allows a vrisus to release viral particles from the host cell to spread infection
- snips sialic acids form glycoproteins on host cell sufrace membrane

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32
Q

Tamiflu

A 
(oseltamivir)
- taken orally
- inhibits neuraminidase action
- taken within first 48 hours of symptoms
- some resistance reported
nausea and vomitting as side effects
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33
Q

Relenza

A 
(zanamivir)
- taken by inhalation
- inhibits neuraminidase action
- taken within first 48 hours of symptoms
- no resistance reported
possibly asthma as side effect
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34
Q

aids

A

acquirred immune defiency syndrome

  • pandemic
  • when the white blood cell count becomes too low
  • HIV becomes aids
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35
Q

how is aids/hiv transmitted?

A
  • sexually from person to person
  • sharing of needles
  • blood transfusions
  • mother to child
36
Q

why is HIV hard to combat?

A
  1. virus is dormant in cells
  2. virus destroys helper t cells (attacks own immune system)
  3. virus tends to mutate rapidly so a lot of variation exists
37
Q

how do we combat HIV?

A
  • using antiretroviral drugs (ARV’s)
  • don’t cure it, but supress/treat its effects
  • target the binding and fusion of the virus and its reverse transcription from rna to dna
  • also target integreation of viral DNA into host chromosome and release of new particles from host cell surface
38
Q

aspirin

A

a mild analgeisc; prevents stimulation of nerve endings at site of pain and inhibit the release of new prostagladins at site of injury

  • antipyretic
  • relieves infmallatory reponse
  • anticoagulant (reduces ability of blood to clot)
39
Q

aspirin reaction

A

esterification reaction

saliclylic acid + ethanoic anhydride to produce aspirin and ethanoic acid

40
Q

problems with aspirin use

A
  • syngergy

- increases effects of stomach ulcers

41
Q

synthesis of aspirin

A
  • esterification reaction of salicylic acid and ethanoic anhydride
  • concentrated sulfuric or phosphoric acid added to reactants
  • mixture is warmed gently
  • aspirin product is isolated and purified from mixture
42
Q

how is aspiring purified?

A
  1. prooduct is cooled to allow chrystals to form, then suction filtered and washed with chilld water
  2. recrystalization occurs; disolving of impure chrystals with hot ethanol
  3. mixture is let cool; aspirin crystallizes out of solution and then separated by filtration
  4. purity of product determined by melting point determinition
43
Q

modification of aspirin

A
  • aspirin isn’t very soluble (large non polar molecule)
    bioavailability is increased by increasing solubility
  • aspirin is reacted with an alkali (such as NaOH and NaHCO3) so it forms an ionic salt
44
Q

penicillin

A

antibiotic; targets bacterial cell wall building enzyme

- alexander fleming + chain-florey

45
Q

who was penicllin discovered and produced

A
  • alex fleming noticed had cultures had grown mold in his bacterial cultures that killed the bacteria
  • ernst chain and howard florey extracted and purified i and conducted animal and human trials on it
46
Q

penicillin action

A
  • has a beta lactam ring with reduced bong angles (to 90 degrees) which makes it unstable
  • it inhibits bacterial enzyme TRANSPEPTIDASE that contructs the cell wall (ring binds and inhibits it)
  • this makes the cell wall of the bacteria unstable
    = osmosis causes it to burst and die
47
Q

disadvantage of peniciilin G

A

broken down by stomach acid; has to be intravenously injected
- R groups are played with to change this

48
Q

antibiotic resistance

A
  • beta lactamase/penicillinase inhibit the beta lactam ring action by opening up the ring and make it inactive
  • this is due to mutation and overuse of antibiotics
49
Q

response to antibiotic resistance

A
  • modified side chains (r groups) to prevent penicillinase enzyme binding
  • control and restriction of antibiotic use by legilisation (make them prescription only drugs)
  • doctors encouraged to not over prescribe and educate patients on use
  • educate patients to finish term
  • reduce use in animal produce
50
Q

antacid

A
  • a weak base that neutralizes stomach acid

e. g. Calcium Carbonate, Aluminium hydroide, magnesium hydroxide

51
Q

excess acid production?

A
  • causes heart burn and damage to the stomach lining

- creates good envrionment for helicobateria pylori to cause peptic ulcers

52
Q

proton pump inhibitors

A

inhibit proton pumps from release acid into stomach lumen

e.g. osomeprazole (nexium)

53
Q

How does the proton pump work?

A
  • in the last step of gastric acid secretion, the parietal cells in the gastric glands pump hydrogen ions accros their membranes and into the lumen of the stomach
  • for each hydrogen ion pumped into the lumen, a potassium ion is pumped in opposition direction so there is no charge build up
  • the movement of ions requires ATP and happens in the use of the gastric proton pump
54
Q

H2 Receptor antagonists

A

block histamine-h2 interaction by competitive inhibition

55
Q

histamine

A

in stomach; stimulates the secretion of stomach acid by interacting at receptors known as H2 in the parietal cells in the gastric gland
- target for antacid action

56
Q

example of a H2 receptor antagonist

A
  • rantitidine (zantac)
57
Q

acidic buffer solution

A

pH= pKa + log10[salt]/[acid]

58
Q

opiate

A

strong analgesic that kills pain by preventing pain impulse transmission in brain rather than at source
- known as narcostics (cause changes in behaviour and mood)

59
Q

what are strong analgesics derived from?

A

opium found in poppy seeds

60
Q

where do our analgesic properties arise from?

A

because we possess opiod receptors in the brain to which they bind to;

  • the binding blocks the transmission of impulses between brain cells that would signal pain
  • they interfere with the perception of pain without depressing the CNS
61
Q

strong analgesic action

A
  • bind to opion receptors in the brain
  • must pass through blood-brain barrier (hydrophobic, lipid, nonpolar environment) that protects the brain from chemicals
  • has to be both blood and lipid soluble (polar and non polar)
62
Q

codeine

A
  • derived through methylation reaction of morphine
  • 0.5% derived from opium
  • sometimes used in prep with nonnarcostic drug like aspiri in second stage of pain managemanent ladder
  • used in cought medications + short term diarrhoea treatment
  • semi-synthetic drug
63
Q

morphine

A
  • derived from raw opium 10%
  • used in severe pain management
  • can form addiction; must be regulated my medical professional
64
Q

diamorphine (heroine)

A
  • found in opium, usually obtained by esterification reaction of morphine
  • used medically only in few countries
  • rapid acting and strong narcostic
  • produces euphoic effects
  • high addiction and tolerance potential
  • dependence leads to withdrawal symptoms
  • broken down into morphine in brain (pro-drug)
65
Q

pain management ladder

A
  1. use mild analgesics
  2. use weak opioid
  3. use strong opioid
66
Q

side effects of strong analgesics

A
  • constipation
  • suppression of cough reflex
  • constriction of pupil in eye
  • narcotic effects (suppression of brain function like sleep and addiction; dulls pain)
  • illegal + criminal actions and other social problems
  • HIV due to dirty, shared needles
67
Q

solvent waste

A

emission of drug industry
involve incineration during disposal which releases toxins to environment
- solvents are the biggest contributor to the emissions of the pharmaceutical industry
-solvent recycling can cut emissiosn to air, water and soil

68
Q

how is the suitability of solvents determined

A
  1. toxicity to workers
  2. saftey of process
  3. harm to environment
69
Q

preferred solvents

A

water, ethanol, ethyl ethanoate, propanone

70
Q

undesirable solvents

A

methanal
benzne
dichloromethane

71
Q

principles of green chemistry

A
  • use of safer solvents
  • avoid use of auxillaries where possible
  • prevent waste and recyle
72
Q

nucelar waste

A
  • use of nuclear chemistry in diagnosis and treatment of disease
  • assosiated with radioactive waste (can be hazardous to living things and environment)
73
Q

high level waste

A

gives off large amounts of ionizing radiation for a long time; the isotopes have long half lives

74
Q

low level waste

A

gives off small amounts of ionizing radiation for a short time
- the isotopes have short half lives

75
Q

examples of low level waste

A

clothing
protective show covers
paper towels
(implements that have been contaminated with radioactive matieral)

76
Q

how is low level waste disposed of?

A
  • involves first interim storage in sealed containers that are safe and secure and enrivonmentally sound
  • radioactivity decays in hours or days
  • waste can be disposed of by concentional means (compaction, landfill, sewers)
77
Q

high level waste examples

A
  • spent isotopes from medical diagnosis techniques (e.g. MRI’s)
  • toxic and radioactive
78
Q

how is high level waste disposed of

A
  • stored underwater in cooling ponds for a couple o fyears

- transferred to dry stroage and buried deep in the earth

79
Q

how can we reduce nuclear waste?

A
  • extracting enriched uranium from incerinerate ash using supercritical carbon dioxide
  • reduce use of radioactive isoptopes in dianogsis by placing them in fluorscent dye
80
Q

superbug

A

super resistant and strong bacteria that arise from mutations

e. g. methicillin-resistant staplyoccocus aureus (MRSA)
- hospitals often face problems with them

81
Q

how does antibiotic resitante arise

A
  • overuse and extensive use of antbiotics
  • use in humans, animals, sanitation, research and pest control
  • inproper disposal (leaks into water systems and ground supplies)
82
Q

tamiflu

A

antiviral obtained from shikimik acid (from the chinese star anise)
- low yield

83
Q

how has green chemistry enhanced tamiflu

A
  • as it has a low yield from star anise; other sources have bee developmnd
  • production of shikimate from fermentation reactions of genetically engineered bacteria
  • harvesting of shikimate from pine needles
  • extraction o fshikimate from indian sweetgum tree culture suspensions
84
Q

examples of green chemistry success stories

A
  • viagra drug production (modified reaction route to reduce solvent and toxic reagant use)
  • ipuprofen production (6 step to 3 step route)
  • Lyrica analgesic; use water reagant to reduce non-renewable organic compound solvent use
85
Q

what determines the administration of a drug?

A
  • its solubility
  • the functional groups of the drug
  • the situation of the patient

IB CHEMISTRY 2017 EXAM (12 decks)

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