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Intro to D&D Final > Med chem - glaucoma part 1 > Flashcards

Med chem - glaucoma part 1 Flashcards

1
Q

explain what glaucoma is

A

elevated IOP that eventually leads to irreversible damage to the optic nerve and permanent loss of vision (blind)

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2
Q

IOP is also referred to as….

A

ocular hypertension

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3
Q

what are the 2 main types of glaucoma

A

open angle and closed angle

open angle more common

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4
Q

increased IOP is a result of what?

A

A buildup of aqueous hemor

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5
Q

what is aqueous humor and is it produced in the front of rear of the eye

A

clear

front of the eye

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6
Q

true or false

aqueous humor is continuously produced

A

true

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7
Q

name 2 drainage systems where aqueous humor normally exits the eye

A

trabecular meshwork

uveoscleral pathway

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8
Q

name 7 classes of drugs used for treating glaucoma

A

muscarinic agonists/AChE inhibitors

sympathomimetic amines

CAIs (carbonic anhydrase inhibitors)

Beta blockers

a2 adrenergic agonists

prostaglandin F analogs

ROCK inhibitor (Rho kinase)

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9
Q

name 2 muscarinic agonists used for treatment of glaucoma
(direct acting - not cholinomimetics)

A

carbachol
pilocarpine

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10
Q

name a AChE inhibitor used for treating glaucoma
(indirect cholinomimetic)

A

physostigmine

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11
Q

name 2 sympathomimetic amines used for treatment of glaucoma

A

epinephrine and dipivefrin

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12
Q

who do CAIS (carbonic anhydrase inhibitors) work in the treatment of glaucoma

A

they reduce the production of aqueous humor in the eye

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13
Q

name 4 CAIs used in treatment of glaucoma

A

acetazolamide
methazolamide
brinzolamide
dorzolamide

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14
Q

how do beta blockers work in glaucoma treatment

A

slow the production of aqueous humor in the eye to reduce intraocular pressure

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15
Q

name 3 beta blockers used in glaucoma

A

betaxolol
timolol
levobunalol

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16
Q

how do alpha2 adrenergic agonists work in glaucoma

A

reduce aqueous humor production and increase drainage

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17
Q

name 2 alpha 2 adrenergic agonists used in glaucoma

A

brimonidine
apraclonidine

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18
Q

how do prostaglandin F agonists work in glaucoma treatment

A

they increase the outflow of aqueous humor from the eye

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19
Q

name 6 prostaglandin F agonists used in glaucoma treatment

A

bimatoprost
travaprost
latanoprost
unoprostone
tafluprost
latanoprostene bunod

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20
Q

how do Rho kinase (ROCK) inhibitors work in treating glaucoma

A

increases aqueous humor drainage

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21
Q

give an example of a ROCK inhibitor

A

netarsudil

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22
Q

true or false

carbonyls and ester groups are essential for ACH activity

A

FALSE

bc ketones and ethers are also potent (muscarine)

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23
Q

give 3 reasons why acetylcholine is not a good drug

A

-not specific - will activate all kinds of cholinergic receptors in the body with no selectivity

-quaternary ammonium group is not good bc it won’t permeate across membrane - very polar

-has an ester, which is extremely susceptible to hydrolysis

therefore, to produce direct muscarinic agonists, we need to alter the structure

24
Q

explain the structure of carbachol just by looking at the name

what is the reasoning behind this

A

carbamic acid + choline

carbamic acid avoids ester hydrolysis, which is an issue with pure acetylcholine

25
Q

difference between acetylcholine structure cv carbachol

A

only difference is acetylcholine has terminal CH3 and carbachol has terminal NH2

purpose is to avoid ester hydrolysis

26
Q

how do pilocarpine and carbachol work in glaucoma

A

increase the outflow of aqueous humor via the trabecular pathway

27
Q

when carbachol was discovered, the only difference was bioisoteric replacement of….

A

CH3 in ACh with NH2 (amino) in carbachol

28
Q

true or false

pilocarpine is NOT structurally derived from acetylcholine, but carbachol is

A

TRUE

29
Q

TRUE OR FALSE

pilocarpine is a natural product

A

true

derived from plant pilocarpus jaborandi

30
Q

explain the mechanism of AChE (without any drug)

A

the nucleophile – AChE-Ser-OH

the lone pair on OH attacks the CARBONYL on acetylcholine, forming a highly unstable tetrahedral intermediate, and effectively kicking out the leaving group

this forms
AChE-Ser-O bound to acetate + choline

the Acetylcholinesterase-acetate complex undergoes hydrolysis in MILLISECONDS – and the enzyme is back in its active form

31
Q

true or false

physostigmine is not a natural product

A

false - it is an alkaloid obtained from seeds of physostigma venenosum

32
Q

what amino acids are contained in AChE enzyme that are critical for binding acetylcholine

A

histadine
aspartate/glutamate
serine

33
Q

true or false

physostigmine is considered an INDIRECT cholinomimetic

A

TRUE

indirectly increases acetylcholine by inhibiting acetylcholine esterase

34
Q

true or false

physostigmine is an irreversible inhibitor of AChE

A

false

reversible - even tho covalent bond, still hydrolyzed back to active enzyme in minutes

35
Q

explain how physostigmine works to inhibit acetylcholine esterase

A

instead of the OH on AChE attacking acetylcholine, it attacks the carbonyl on phystostigmine instead

a COVALENT BOND is formed to the carbonyl component of the drug

this undergoes hydrolysis back to the active enzyme in MINUTES rather than milliseconds. keeps the enzyme bound and inactive for a longer period of time, causing acetylcholine to not degrade as quickly

the enzyme is CARBAMOYLATED instead of just ACETYLATED, as in the case if no drug was present

this causes more contraction of the ciliary muscle and thus increased outflow of aqueous humor through schlemm’s canal

36
Q

physostigmine is indicated for what type of glaucoma?
how does it work?

A

open angle glaucoma

contracts ciliary muscle, causing increased aqueous humor output into schlemm’s canal

37
Q

which are better acetylcholine esterase inhibitors and why –

aryl carbamates or alkyl carbamates

A

ARYL CARBAMATES

they have a better leaving group due to resonance on aromatic ring

phenoxide better leaving group than alkoxide

38
Q

name 2 sympathomimetic amines for glaucoma

A

epinephrine
dipivefrin

39
Q

name 2 ways that sympathomimetic amines help to treat glaucoma

A

-reduce aq humor formation

-decrease resistance to outflow of aq humor

40
Q

explain the relationship between epinephrine and dipivefrin

A

dipivefrine is the PRODRUG for epinephrine

it has 2 pivalic acids which are hydrolyzed by corneal esterase to produce Oh’s instead – structure of epinephrine

dipivefrine is well absorbed through the cornea and epinephrine is poorly absorbed bc of the polar OH groups

41
Q

there are 4 carbonic anhydrase inhiibtors

break them down into which are given topically and which are given orally

A

oral - acetazolamide and methazolamide

topical - dorzolamide and brinzolamide

42
Q

how do carbonic anhydrase inhibitors work?

A

the carbonic anhydrase enzyme is involved in the formation of aqueous humor

thus, by inhibiting it, the rate of aqueous humor formation is reduced in the hopes that intraocular pressure will decrease

43
Q

what component must potential drugs have in order to inhibit carbonic anhydrase enzyme

A

a sulfonamide group - aryl or heteroaryl

44
Q

explain the MECHANISM in which carbonic anhydrase inhibitors reduce intraocular pressure

A

within the eye, CO2 + H2O is converted to carbonic acid (H2CO3) by carbonic anhydrase. this then dissociates into bicarbonate ions (HCO3-) and H+

these bicarbonate ions in the eye are hyperosmotic compared to the plasma, thus water from capillaries is attracted to the area and intraocular pressure increases

by inhibiting carbonic anhydrase, we’re limiting the number of bicarbonate ions produced, and thus less water is attracted and intraocular pressure decreases. reduced aqueous humor formation

45
Q

the aqueous humor is rich in ___ and ___ ions

A

sodium and bicarbonate

46
Q

formula for carbonic acid

A

H2CO3

47
Q

where is the carbonic anhydrase enzyme located

A

in the cornea

48
Q

“pharmacophore” for carbonic anhydrase inhibitors

A

aryl or heteroaryl sulfonamide group

49
Q

explain mechanism in which dorzolamide and other CAIS inhibit Carbonic anhydrase

A

the sulfonamide is CRTICIAL for inhibition

chelates with zinc and hydrogen bonds with threonine 199 on the enzyme

INHIBITS CATALYTIC ACTIVITY OF CARBONIC ANHYDRASE ENZYME

50
Q

Name the beta blockers for glaucoma

which are b1 selective and which are nonselective?

A

b1 selective – betaxolol

nonselective - timolol, levobunolol

51
Q

mechanism in which beta blockers help with glaucoma

A

lower IOP by reducing production of aqueous humor

52
Q

pharmacophore for beta blockers for glaucoma

A

aryloxylpropanolamine

53
Q

name 2 alpha2 adrenergic agonists

A

brimonidine
apraclonidine

54
Q

mechanism of alpha2 adrenergic agonists in glaucoma

A

reduce production of aqueous humor AND enhance outflow via uveoscleral pathway

55
Q
A

Intro to D&D Final (21 decks)

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