Medicinal Chemistry IB SL Chemistry

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60 Terms

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Drug

Something that causes a physiological change in the body

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Medicine

Something used to treat or prevent diseases

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Medicine and Drugs must do one of the following…

  • alter incoming sensory sensations
  • alter a person’s mood or emotions
  • alter the physiological state of the body, including consciousness and coordination
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Therapeutic effect

beneficial effect of a medicine

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What are the 3 parenteral methods of administration?

  • intramuscular - into muscle
  • subcutaneous - directly under the skin
  • intravenous - bloodstream(most rapid effect)
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bioavailability

fraction of administered dosage of a drug that enters the bloodstream and have an active effect

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What factors affect bioavailability?

  • method of drug administration
  • polarity of drug
  • type of function groups in drug
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True or False? Intravenous administration has a bioavailability of 100%

True

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True or False? Oral doses need to be 3 times stronger than an intravenous dose

False. They must be 4 times stronger

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What are the best type of molecules to be administered, in terms of solubility

One that is largely hydrophobic but still has some solubility

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Which functional groups are able to form hydrogen bonds easily?

  • carboxyl
  • hydroxyl
  • amine
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Which functional groups enhance lipid solubility(non-polar)?

Ones that lack the ability to ionize or form hydrogen bonds

  • phenyl group(benzene ring)
  • hydrocarbon chain
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How is the solubility of aspirin increased?

It reacts with NaOH

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True or False? Ionic salts increase solubility

True

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Therapeutic window

Measure of safety of a drug. A wide window means a wide margin between toxic and safe doses

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Therapeutic Index(TI) for humans

TI = TD(50)/ED(50)

  • TD(50) - median toxic dose
  • ED(50) - median effective dose
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What are the main stages of drug development?

  • drug is synthesized
  • Drug is tested on animals to find lethal dose
  • Drug is tested on humans in a double blind experiment
  • Unwanted side effects and tolerance must be determined
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How can you test the purity of aspirin?

Can be determined by melting points and IR spectrum

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True or False? More impurities means higher a melting point

False. More impurities means a lower melting point

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Analgesic

painkiller

  • aspirin
  • ibuprofen
  • paracetamol
  • morphine
  • codeine
  • dimorphine
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How does aspirin block the sensation of pain?

It blocks the action of enzymes that produce prostaglandins, which are involved in the transmission of pain impulses to the brain

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Anticogulant

prevents blood from clotting

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What are 5 common methods of drug administration?

  • oral
    • polar, water-soluble
  • intravenous
    • unstable or poorly soluble
  • transdermal(skin patch or ointment)
    • non-polar, lipid-soluble
  • rectal
    • unstable in gastric acid
  • inhalation
    • volatile
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Antibiotics

Drugs that kill or inhibit the growth of bacteria

  • penicillin
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What is a beta-lactam ring?

A box shaped structure found in penicillin consists of three carbons and a nitrogen to make the base. One of the carbons in double bonded to an oxygen

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What doe beta-lactam antibiotics do?

They interfere with cell wall formation in bacteria by inhibiting the enzymes responsible for creating cross-links in the cell wall

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Antibiotic resistance

Bacteria that resists the effects of an antibiotic

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What are the causes of antibiotic resistance?

  • overprescription of antibiotics for basic illnesses
  • patients don’t complete their course of antibiotics
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How are antibiotics released into the environment?

  • antibiotics are given to healthy farm animals
  • Improper disposal by hospitals or companies
  • excreted by human urine
  • pharmaceutical waste
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Opiates

Natural analgesics derived from opium. Bind to opioid receptors in the brain and block transmissions of pain impulses.

  • morphine
  • codine
  • dimorphine
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What are the advantages and disadvantages of strong analgesics/opiates?

    Advantages:
  • provide relief for pain

  • wide therapeutic window

  • improve quality of life

  • reduce anxiety

    \
    Disadvantages:

  • euphoria and lack of self-control

  • regular usage can lead to addiction, dependence, and withdraw

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Blood-brain barrier

Tightly packed cell restricting passage of substances from bloodstream to brain that is largely composed of lipids

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How is dimorphine created from morphine?

morphine + ethanoic acid →dimorphine + water

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algmates

type of antacids that prevents acid from rising in the esophagus

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Proton pump inhibitor

inhibits the secretion of H+ ions into gastric juice. Stomach acid inhibitor that can last up to three days.

  • omeprazole
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H2 Receptor antagonists(H2 blockers)

stomach acid inhibitor that blocks histamine receptors in acid-producing cells in the stomach

  • ranitidine
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Virus

submicroscopic organism that replicates inside living cells of other organisms. Consist of a protein coat and nucleic acid

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Bacteria

small single cell microorganisms that are self reproducing, living, and contain various cell organelles. They are larger than viruses

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Why are viruses harder to target with drugs than bacteria?

  • they lack a cell structure
  • they lack subunits that can be targeted by antivirals
  • they mutate quicker
  • they must be targeted at a genetic level
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True or False? Antibiotics are effective against bacteria but ineffective against viruses

True

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How do antiviral drugs work?

  • alter a cell’s genetic material
  • block enzyme activity
  • bind to cellular receptors targeted by viruses
  • prevent release of viruses
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What are some examples of antiviral drugs for the common flu?

  • oseltamivir(oral)
  • zanamivir(inhalation)
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Why is HIV hard to treat?

  • mutates rapidly

  • has host cells to replicate

  • drugs that treat HIV may harm the host cell

  • high price of anti-viral drugs

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What are Socio-Cultural factors that affect AIDS?

  • condom use
  • ignorance and misinformation
  • stigmas
  • prostitution
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What are the three levels that nuclear waste is classified into?

  • Low-Level waste(LLW)
    • produces weak radiation for a short time
  • Intermediate-Level Waste(ILW)
    • produces strong radiation for a short time
  • High-Level Waste(HLW)
    • produces strong radiation for a long time
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What levels of radiation are typically found in medical settings?

  • Low-Level and Intermediate-Level
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What are examples of low-level waste?

  • gowns
  • protective clothing
  • shoe covers
  • tissues
  • needles
  • mops
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How do you dispose Low-level waste?

Store in shielded containers until the isotopes have decayed, then dispose of as non-radioactive waste

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What are some examples of Intermediate-level waste?

  • sources for radiotherapy
  • Co-60
  • Cs-137
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How do you dispose of Intermediate-level waste?

  • long term storage in shielding containers or concrete chambers, then buried underground
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In green chemistry, what are the preferred solvents in synthesizing drugs?

  • water
  • methanol
  • ethanol
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In green chemistry, what are the undesired solvents in synthesizing drugs?

  • pentane
  • dichloromethane
  • dichloroethane
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True or False? Many undesirable solvents are VOC(volatile organic compounds)

True

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Why are VOCs used as solvents?

They have high volatility

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Chlorinated vs non-chlorinated solvent types

Chlorinated:

  • ozone-depleting
  • accumulates in ground water
  • forms toxins if burned
  • toxic, irritant, and forms greenhouse gases

Non-chlorinated:

  • flammable
  • toxic, irritant, and forms greenhouse gases
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What are some of the Green Chemistry principles?

  • prevent waste
  • design less hazardous chemical synthesis
  • design safer chemicals and products
  • use safer solvents
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How are some bacteria inactivating penicillin?

They produce penicillinase/enzyme that deactivates penicillin

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How has the structure of penicillin been modified to overcome this resistance?

the side chain has been changed to preserve the beta-lactam ring

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How do antacids neutralize stomach acid

weak base + stomach acid(HCl) →XCl + water

  • CaCO3 + 2HCl →CaCl2 + H2O + CO2
  • MgO + 2HCl → MgCl2 + H2O
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What are the advantages of taking ranitidine instead of antacid?

  • ranitidine can treat stomach ulcers
  • ranitidine prevents long term damage
  • ranitidine lasts longer
  • ranitidine doesn’t cause bloating