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Intro to D&D Midterm > med chem part 7 > Flashcards

med chem part 7 Flashcards

1
Q

what is capsaicin

A

in cayenne peppers (0.02%)

another name for cayenne pepper = capsicum

as an analgesic effect in RA patients

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2
Q

how is capsaicin used as an analgesic in RA patients

A

topical application reduces neuropeptide SUBSTANCE P from local sensory (C-type) nerve fibers

reduces transmission of pain to the CNS by inhibiting nociceptor

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3
Q

____ is an extremely pungent phenol

A

capsaicin

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4
Q

Osteoarthritis is characterized by the erosion of….

A

articular cartilage

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5
Q

the conventional treatment of RA consists of what 3 classes of drugs

A

NSAIDS
corticosteroids
SYSADOA (Symptomatic slow acting drugs for osteoarthritis)

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6
Q

what are osteophytes

A

bony spurs on the edge of bone that grow in osteoarthritis patients

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7
Q

what is an important component that maintains cartilage strength

A

prostaglandins

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8
Q

name 2 osteoarthritis treatments that work by increasing the production of prostaglandins

A

glucosamine sulfate
chondroitin sulfate

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9
Q

what is hyaluronate sodium used to treat

A

osteoarthritis

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10
Q

what is the structural distinction between chondroitin sulfate and hylauronate sodium

A

it is a glycosaminoglycan, but NON-SULFATED

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11
Q

name some MOAs of hyaluronate sodium that make it useful to treat osteoarthritis

A

increases flow of joint fluid

inhibits hyaluronate degredation

reduce joint pain and improve function

normalize endogenous hyaluronate synthesis

restores elasticity of synovial fluid

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12
Q

what is atopic dermatitis?

it is predominantly mediated by what?

A

chronic inflammatory skin disease

primarily mediated by helper T cells

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13
Q

what is another name for atopic dermatitis

A

eczema

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14
Q

explain what the skin looks like in a patient with atopic dermatitis

A

dry with red scaly patches and very itchy

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15
Q

what is a virulence factor for atopic dermatitis

A

staph aureus

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16
Q

what is treatment for atopic dermatitis aimed at?

A

limiting itchiness, inflammation, further skin thickening

remove the scaly lesions, prevent/control skin infection

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17
Q

in AD, there is increased ________ production

A

cytokine

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18
Q

the increased cytokine production in AD causes what 3 things to happen?
what do all these 3 things ultimately lead to?

A

loss of skin barrier

itch-scratch cycle

increased chance of skin infection

ultimately leads to skin lesions

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19
Q

explain the pathogenesis of atopic dermatitis

A

allergens get into the skin due to mechanical injury

dendritic cells recognize the allergen as foreign and present to helper T cells

they then activate B cells (who came to site of infection by chemokines and cytokines), who produce IGE antibodies to the allergen, resulting in allergic dermal and epidermal inflammation

the impaired barrier opnes the door for antimicrobial peptides and staph aureues

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20
Q

what is first line treatment for pruritis (itching) in atopic dermatitis

A

1st generation antihistamine

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21
Q

what is the treatment to treat INFLAMMATION in atopic dermatitis

A

systemic and topical corticosteroids

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22
Q

name 4 classes of drugs used in atopic dermatitis that are used to prevent flare ups and help the skin repair

A

TCIs (topical calcineurin inhibitors)

Topical PDE4 inhibitor

IL-4 receptor a targeted monoclonal antibody

JAK inhibitors

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23
Q

as mentioned, TCIS (topical calcineurin inhibitors) are used to prevent flare ups and help the skin repair

name 2 of them

A

tacrolimus
pimecrolimus

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24
Q

as mentioned, topical PDE4 inhibitors can be used to prevent flare ups and help the skin repair

give an example

A

crisaborole

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25
Q

as mentioned, there is an IL-4 receptor monocolonal antibody that can be used to prevent flare ups and help the skin repair

what is the name

A

dupilumab

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26
Q

name 3 JAK inhibitors used to prevent flare ups and help the skin repair in AD

A

Abrocitinib
Upadacitinib
Baricitinib

27
Q

name the 5 minium requirements for glucocorticoid receptor binding

A

double bond between carbons 4 and 5

ketone at 3

beta hydroxy at 11

alpha hydroxy at 17

hydroxy at 21

28
Q

what is the LEAST potent topical steroid

A

hydrocortisone

29
Q

is mineralocorticoid activity desirable?

A

NO - lot of unwanted side effects like sodium and water retention

30
Q

what is the name for a 21 carbon steroid?

name a 21 carbon steroid

A

pregnane

hydrocortisone

31
Q

what are the rings in a steroid

A

3 6-membered rings and 1 5-membered ring

32
Q

____ isomers project above the plane of the steroid nucleus

A

BETA

33
Q

Name 4 changes that can be done to hydrocortisone to change the activity, and the results of each

A
  1. adding = at C1 increases gluco. activity and decreases mineral. activity and inc metabolic stability
  2. adding hydroxyl at C16 increaes GC activity, and decreased MC activity
    ISSUE - too hydrophilic and wont penetrate skin well (triamcinolone) change to methyl to fix this (dexamethasone and betamethasone)
  3. Halogen (Cl or F) at C6 inc metabolic stability, dec MC inc GC
  4. Halogen at C9 inc Metabolic stability, dec mc inc gc
34
Q

hydrocortisone is class ____ corticosteroid

A

7, meaning its not very potent

35
Q

adding a halogen at C21 does what?

A

increased GC activity

36
Q

esterification at C17 or C21 hydroxyl does what?

A

MAKES IT A PRODRUG

more lipophilic so more easily absorbed into the skin

however, it will be cleaved upon hydrolysis and the original OH will be exposed at the site of action. GC activity is maintained

37
Q

as mentioned, esterifying the C17 hydroxyl can increase potency

how can the duration of action be maintained for longer? what is the name of this drug?

A

the esterified C17 can be easily hydrolyzed by esterases

however, replacing C21 OH with Cl can prolong the action of this ester by increasing metabolic stability

an example of this is clobetasol propionate

38
Q

which is a stronger glucocorticoid and why - hydrocortisone or cortisone

A

HYDROCORTISONE

cortisone has a keto group at position 11 rather than an alcohol

an alcohol at that position is essential for Glucocorticoid activity

39
Q

true or false

cortisone and hydrocortisone are biochemically interchangeable

A

true

40
Q

all cyclohexane rings of a steroid are in what conformation

A

chair

41
Q

through which enzyme can cortisone and hydrocortisone be interconverted

A

11 beta hydroxy steroid dehydrogenase

42
Q

TRUE OR FALSE

more water soluble steroids are preferred for dermatological applications

A

FALSE - more lipid
is absorbed better

43
Q

differentiate between triamcinolone vs triamcinolone acetonide vs fluocinolone acetonide
(in terms of structure)

A

triamcinolone acetonide is the same as triamcinolone but with an acetonide between C16 and C17

fluocinolone acetonide is the same as triamcinolone acetonide but with an alpha fluorine at position 6

44
Q

what is amcinonide and which steroid is it derived from

A

21-acetate with additional cyclopentane ring

derived from triamcinoline

45
Q

true or false

amcinomide is a prodrug

A

TRUE

must undergo hydrolysis to 21-OH

46
Q

just by looking at the name, how can you differentiate between dexamethasone and dexamethoasone acetate

A

they’re the same, dex acetate just has 21-acetate

47
Q

just by looking at the name, how can you differentiate between dexamethasone and desoximetasone

A

same, desoxy just has 17a OH group taken off

48
Q

how can you differentiate between betamethasone and betamethasone dipropionate

A

2 positions on betamethasone were esterified with propionic acid (17 and 21)

49
Q

differentiate between betamethasone dipropionate and beclomethasone dipropionate

A

same, beCLO just has a chlorine added at 9 alpha

50
Q

what is the purpose of adding a halogen at carbon 21? name 2 steroids that have this

A

increases the metabolic stability of the ester at 17 position

clobetasol propionate and halobetasol propionate

51
Q

explain the structure of clobetasol propionate by looking at the name

A

chlorine group (at 21)
1 propionate ester (carbon 17)

purpose of chlorine 21 is to increase metabolic stability of the ester at 17

52
Q

by looking at the name, explain the structure of halobetasol propionate

A

1 propionate ester (17)
chlorine at 21 (increased ester stability)
fluorine at 6a

53
Q

which is more lipophilic and why - acetic acid esters or propionic acid esters

A

propionic because they have 3 carbons instead of 2

54
Q

why is amcinonide more potent than triamcinolone

A

polar groups are hidden by acetonide/cyclopentane

enhances the skin permeability.

undergoes hydrolysis to expose OH’s again

55
Q

why is fluocinolone acetonide more potent than triamcinolone acetonide

A

has a fluorine at position 6 to increase glucocorticoid activity

56
Q

why is clobetasol propionate more potent than betamethasone dipropionate

A

has chlorine at position 21 to enhance the metabolic stability of the C17 ester

chlorine also adds lipophilicity and glucocorticoid activity

57
Q

name 3 MOAS of corticosteroids

A

inhibits PLA2 VIA LIPOCORTIN

down regulate inflammatory cytokines like IL-1, IL-6, and TNFa (genomic)

produce anti inflammatory proteins in cytosol (nongenomic)

58
Q

which MOA of corticosteroids happens faster - nongenomic activation or genomic activation?

A

nongenomic — does not have to cross nucleus and bind – happens in cytoplasm

59
Q

explain the genomic mechanism of corticosteroids

A

steroid is highly lipophilic and easily crosses the cell membrane

in the cytoplasm, it binds to glucocorticoid receptor with the help of heat shock proteins (chaperones).

this complex is transported to the nucleus where it dimerizes and binds to a sequence on DNA, mRNA is produced, and antiinflammatory proteins are transcribed such as Lipocortin (PLA2 inhibitor)

also suppresses the transcription of genes responsible for inflammation. cytokines not produced as much

60
Q

what is the kind of DNA sequence that glucocorticoid-glucocorticoid receptor bind to?

A

palindromic sequence

61
Q

true or false

glucocorticoids cannot permeate through the membrane

A

false - they can

lipophilic

62
Q

true or false

steroids are more potent anti inflammatories than NSAIDS

A

TRUE

block synthesis of both PGS and leukotrienes

63
Q
A

Intro to D&D Midterm (29 decks)

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