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Intro to D&D Final > Med Chem - Acne > Flashcards

Med Chem - Acne Flashcards

1
Q

why is acne more common at puberty?

A

there is an increase in androgens, which causes oil/sebum production

this can clog pores and form a comedone – causes acne

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2
Q

name 2 things that androgens do that causes acne

A

increased sebum production
skin thickening

both can clog pores and cause acne

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3
Q

briefly explain the pathology of acne

A

dead cells and sebum accumulate in the hair follicle, causing a clog

this is a great place for the commensal bacteria - cutibacterium acnes to feed on the sebum and proliferate

the acne in the skin invokes an inflammatory response as well

the result is filled with pus and reddened

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4
Q

excessive ____ + ____ + ____ = acne

A

cell build up
oil
bacteria

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5
Q

is cutibacterium acnes gram positive or negative?

A

positive

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6
Q

name 3 treatment goals for acne

A

-decrease inflammation

-decrease sebum production and c. acnes proliferation

-correct the abnormalities of follicular maturation

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7
Q

name 5 classes of drugs used for acne treatment

A

systemic antibiotics
retinoids
azelaic acid
benzoyl peroxide
salicylic acid

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8
Q

name 4 retinoids used in acne

A

tretinoin
adapalene
isotretinoin
trifarotene

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9
Q

name 4 systemic antibiotics used in acne

A

tetracycline
doxycycline
minocycline
sarecycline

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10
Q

name the 3 dosage forms in which salicylic acid is available

A

cream
lotion
gel

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11
Q

explain how salicylic acid works to treat acne

A

it’s a keratolytic agent with anti-inflammatory action

reduces acne by exfoliating the skin and keeping pores clear

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12
Q

what kind of acne severity is salicylic acid indicated for

A

mild acne

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13
Q

true or false

salicylic acid does not have anti inflammatory action

A

FALSE - it does

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14
Q

benzoyl peroxide is applied topically in concentrations up to…..

A

10%

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15
Q

how does benzoyl peroxide have antimicrobial actions?

A

has an oxidizing effect due to the production of benzoate free radicals

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16
Q

what is azelaic acid indicated for?

A

mild-moderate inflammatory acne vulgaris

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17
Q

true or false

azelaic acid is naturally occurring

A

TRUE

naturally occurring acid found in whole grain cereals and animal products

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18
Q

how does azelaic acid work in acne

A

inhibits the growth of cutibacterum acnes

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19
Q

chemical name azelaic acid

A

nonanedioic acid

“non” - 9 carbons
“di” - 2 COOH groups

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20
Q

what are the 2 types of retinoid receptors

what are the subtypes?

A

RARs - retinoic acid receptors

RXRs - Retinoid X receptors

all have a,B,Y subtypes

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21
Q

what kind of receptors are RARs and RXRs

A

nuclear receptors

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22
Q

RARs and RXRs are activated by what?

A

natural (endogenous) or synthetic retinoid agonists

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23
Q

true or false

RARs and RXRs are GPCRs involved with the modulation of gene transcription

A

FALSE

they are nuclear receptors involved with the modulation of gene transcription

24
Q

what is the dominant RAR subtype present in the skin?

A

GAMMA (Y)

25
Q

explain how RARs and RXRs function

A

RARs dimerize with RXRs to form HETERODIMER. this heterodimer goes to the nucleus where it recognizes RARE DNA sequence in the promoter region of target genes

involved with regulation of cell growth, differentiation, and apoptosis

HOWEVER, while RARs MUST form a HETERODIMER with RXR, RXR can function as a homodimer as well as a heterodimer

26
Q

true or false

in order to be functional, RARs must form a HETERODIMER with RXR

A

true

27
Q

what does the “RARE” DNA sequence stand for

A

retinoic acid response element

28
Q

as mentioned, RARY is the most predominant subtype of retinoic acid receptors in the skin

what is the significance of this?

A

want to have highly selective RARY agonists.
this will lead to less side effects.

also, RARY subtype is not present in the placenta. therefore, a highly selective RARY agonist will not be teratogenic like every other retinoid!!

29
Q

tretinoin is a _____ form of _____

A

oxidized (active) form of vitamin A (retinol)

30
Q

how is tretinoin an oxidized form of vitamin A?

A

it has exact same structure

only difference is that the -CH2OH in vitamin A (retinol) has been oxidized to COOH in tretinoin

31
Q

what is retinol

A

vitamin A

32
Q

explain the receptor selectivity of tretinoin

A

NONSELECTIVE RAR agonist

33
Q

how does tretinoin work in acne

A

unplugs the hair follicles and keeps the pores clear

also, increases speed that surface skin cells are replaced

34
Q

explain in detail the conversion of vitamin A to ATRA, as well as the inactivation of ATRA

include all enzymes and whether the steps are reversible or irreversible

A

retinol <-> retinal by retinol dehydrogenase

retinal -> ATRA (COOH) by retinal dehydrogenase

ATRA inactivated by CYP2D6 into an inactive 4-oxometabolite

35
Q

as mentioned, CYP2D6 mediates the inactivation of ATRACOOH into an INACTIVE 4-oxometabolite

what potential drugs may be used to block the action of CYP2D6, and thus prolong the action of retinoids by preventing their inactivation?

A

RAMBAS
(retinoic acid metabolism blocking agents)

36
Q

where are RAR and RXR receptors located?
what does this mean regarding the drug?

A

in the NUCELUS, bound to RARE regions on DNA

this means the retinoic acid (drug) has to diffuse into the nucleus and bind to RAR to form the heterodimer and modulate gene transcription

37
Q

what effect does retinoic acid binding to RARs have

A

cell differentiation and proliferation

apoptosis

immune modulation

beneficial acne effects

38
Q

chemical name for isotretinoin

A

13-cis-retinoic acid

39
Q

true or false

isotretinoin is a selective RARY agonist

A

FALSE - non selective bc of rotation

it is a result of ATRA isomerization

40
Q

retinoids are also called_______

A

diterpenes

41
Q

why are retinoids also called diterpenes?

A

bc they have 20 carbons

42
Q

true or false

isotretinoin is a 13-cis isomer of ATRA

A

true

43
Q

what is isotretinoin indicated for

A

severe and recalcitrant (stubborn) cases of inflammatory acne

44
Q

how is isotretinoin useful in acne

A

inhibits sebaceous gland function and inhibits follicular keratinization

45
Q

true or false

adapalene is a natural retinoid compound

A

FALSE

it’s a synthetic retinoid-like compound

46
Q

does adapalene have any selectivity? why or why not

A

YES - has selectivity for RARB and RARY subtypes found in the epidermis

this is because the double bonds are locked into the aromatic ring - RIGID. cannot cis-trans isomerize. thus, able to have some selectivity

47
Q

what is a similarity between adapelene and ATRA

A

the distance between the C with the bulky group and COOH is ~TEN CARBONS APART

48
Q

How does adapalene work to reduce the formation of pimples

A

it affects the growth of skin cells, thus reducing formation of pimples bc clogs not as likely

49
Q

name of the bulky group on adapalene

A

adamantyl

50
Q

what is the retinoid that has RARY selectivity

A

trifarotene

51
Q

what group on trifarotene allows it to have RARY selectivity?

A

hydroxyethoxy group

52
Q

explain some benefits of trifatorene over other retinoids

A
  1. RARY selective: safer than others for teratogenity bc RARY is not expressed in placenta. also less side effects bc RARY selective and its predominantly in the skin
  2. has poor systemic absorption than other retinoids because of polar hydroxyethoxy group - less systemic side effects!!
53
Q

what is trifatorene indicated for

A

ages 9 and older for facial and truncal acne

54
Q

trifarotene belongs to ______ class of compounds

explain

A

meta-terphenyl

meaning 3 phenyl rings all meta to each other

55
Q
A

Intro to D&D Final (22 decks)

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