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Med Chem Exam 1

STUDY
PLAY
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