Med Chem Exam 1

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mineralcorticoids and glucocorticoids

classes of corticosteroids

cholesterol

precursor to all steroids

ACTH

rate limitor in biosynthesis of steroids

low ACTH

Addison's disease

high ACTH

Cushing's disease

A and D

rings that differ between androgens and corticosteroids

cis

plant A/B formation

cis/trans

mammilian A/B formation

trans

plant B/C formation

trans

mammilian B/C formation

cis

plant C/D formation

trans

mammilian C/D formation

acetate

biosynthesizes estrogens through cholesterol

exogenous hormones

administered to mimic biological effects of the lost (or reduced) hormone

1,3,5 (10) - triene system in the A ring

estrogen SAR

esterfication and adding C-17 alkyls

modifications of estradiol that increases the duration of action

estrone

metabolite of estradiol

estrone

equine estrogen

Clomiphen

postcoital contraceptive

Tamoxifen

breast cancer treatment

4-ene-3-one in ring A and C-21 CH3

progestin SAR

progesterone

secreted during the follicular phase of the menstral cycle

progesterone

amounts increase in development of uterine lining in preparation of pregnanacy

C-17

position where most oral contraceptives have modifications

reduction of C-20 and C-3 ketones and the 4,5 double bond

metabolism of progesterone

medroxyprogesterone

designed to reduce the rate of metabolism seen in progesterone

4-ene-3-one in ring A and C-17 OH

androgen SAR

C-17 hydroxyl oxidation to ketone

metabolism of testosterone

methyltestosterone

leads to hepatic disturbances and jaundice

jaundice

excess bilirubin in the blood

methyltestosterone

1/2 as active as testosterone

nandrolone deconate

popular anobolic steroid of abuse

phenoproprionate and deconate

available esters of nandrolone

mineralcorticoids and glucocorticoids

useful and managing inflammation

phospholipase A2

removes the fatty acid from the phospholipid membrane

corticosteroids

inhibit the removal of the fatty acid from the phospholipid

PGI2 and PGE2

prostaglandins most responsible for inflammation

4-ene-3-one in ring A, C-11 oxygen, C-17 hydroxy

steroidal anti-inflammatory SAR

cortisone, hydrocortisone

natural corticosteroids

COX2

induced in inflammation

aniline

has powerful antipyretic effects

acetanilid and phenacetin

toxic anilides

acetaminophen

analgetic effects are great, however, has poor anti-inflammatory effects

glucuronide and sulfate conjugates

metabolites of acetaminophen

salicin

active constituent in Willow bark

aspirin

acetylsalicylic acid

carboxylic acid adjacent to a hydroxy group on a benzene ring

salicylate SAR

aspirin

prepared by treating salicylic acid with acetic anyhydride

inhibition of COX

salicylate MOA

salsalate

ester of two salicylic acid molecules

COX

oxidizes arachidonic acid

optimal separtion of carboxyl group by one methylene unit

arylalkanoic acid SAR

ibuprofen

first in the class of arylalkanoic acids

oxidative o-demetylation

metabolism of naproxen

ketoprofen

good for compounding into a gel to use topically at the site of pain and inflammation

indomethacin

gold standard arylalkanoic acid

sulfone

inactive functional group of sulindac

sulfoxide

parent functional group of sulindac

sulfide

active functional group of sulindac

diclofenac

arylalkanoic acid with similarities to salicylic acid

4-hydroxydiclofenac

principle metabolite of diclofenac

ketorolac

arylalkanoic acid not used as an anti-inflammatory but as an analgesic

ketorolac

has analgesic action compared to small doses of morphine, but does not act on opiod receptors

etodolac

arylalkanoic acid with uricosuric properties

4-hydroxy-1,2-benzothiazine

oxicam SAR

C-4 OH

where the acidity of non-selective oxicams comes from

meloxicam

preferential inhibitor of COX2

selective COX2 inhibitors

interfere with the the balance of prostacyclin and thromboxane

platelet aggregation

occurs when COX2 is selectively blocked

ARG120

amino acid where the acid part of arachidonic acid anchors in the COX active site

ILE523

amino acid with a branch that blocks the pocket in the COX active site

ILE523 in COX1 and VAL523 in COX2

difference in COX1 and COX2 active site amino acids

ARG513

amino acid in the COX2 active site that selective COX2 inhibitors anchor to

ARG120

amino acid in the COX active site that most NSAIDs anchor to

thromboxane

induces platelet aggregation

prostacyclin

reduces platelet aggregation

capsaicin

topical analgesic

capsaicin

depletes substance P from local sensory C-type nerve fibers

tramadol

alternative analgesic

tramadol

represents a fragment of codeine

tramadol

weak m-opiod receptor agonist

heart attack or stroke

reason for 1/2 of diabetes-related deaths

urea with N-1 sulfonyl group and N-3 aliphatic group

sulfonylurea SAR

aryl group on N-3

modification that leads to toxic compounds in sulfonylureas

sulfonylureas and meglitinides

oral hypoglycemics that require functioning B-cells

acetohexamide

only hypoglycemic that possesses uricosuric properties

another aromatic ring system added

major difference between first and second generation sulfonylurea chemical structures

biguinides

increase glucose uptake into fat and muscle cells

thiazolidinediones

increase insulin sensitivity of muslce, fat, and liver cells

thiazolidinediones

activate PPAR-y that regulates transcription of insulin-responsive genes which control glucose and lipid metabolism

thiazolidinediones

restricted to patients currently receiving treatment because they can cause or exacerbate heart failure

meglitinides

regulate K+ efflux by closing K+ channels in B-cells

GLP-1

protein that stimulates insulin release in a glucose dependent manner

GLP-1

stimulates insulin production in response to high blood glucose

exenatide (Byetta)

injectable form of the GLP-1 protein

liraglutide (Victoza)

injectable form of a GLP-1 derivative that also inhibits DPP-4

DPP-4

the enzyme that degrades GLP-1

linagliptin (Victoza)

doesn't require dose adjustment for declining liver and kidney function

histamine

activates secretion of HCL into stomach

HCL

secreted by parietal cells

denatures dietary protein and activates pepsinogen to pepsin

actions of HCL

increases cAMP

effect of histamine on the parietal cell

acetylcholine

causes an increase in calcium levels in the parietal cells

proton pump

another name for the H+/K+ ATPase

cimetidine

first H2 antagonist

proton pump inhibitors

block H+/K+ ATPase

sulfenic acid

intermediate metabolite of PPI's

sulfenamide

final metabolite of PPI's

pepsin

involved in protein digestion

pepsin

may hydrolyze proteins of the mucosal lining

sulfated polysaccharides

inhibit pepsin-mediated hydrolysis of proteins

sucralfate

forms a viscous substance that is insoluable in water and adheres to peptic ulcer craters

misoprostol

acts like a natural prostaglandin in the gastric mucosa

metoclopramide

accelarates gastric emptying to reduce reflux

clarithromycin, metronidazole, amoxicillin

treatments for Helicobacter pylori

H1 blockers

classic antihistamines

L-histadine

where histamine is synthesized from

mast cells

store and release histamine

H1

receptors involved in allergic response

mast cells and basophils

primary location for H1 receptors

first

generation of antihistmaines that cause significant sedation

alkylamines

most potent and least sedating class of first generation antihistamines

doxylamine

ethanolamine that is marketed as a sleep agent

clemastine

most potent ethanolamine with the least sedation in its particular class

piperazines

first generation antihistamines with a slower onset of action and longer duration

meclizine

marketed as an anti-nauseant or anti-dizziness drug

phenothiazines

antihistamines with anti-nausea properties

promethazine

really good antiemetic as a suppository

terfenadine

first second generation antihistamine introduced to the market

cetrizine

derived from hydroxyzine

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