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Flashcards on untitled 2, created by lola_smily on 22/06/2015.
lola_smily
Flashcards by lola_smily, updated more than 1 year ago
lola_smily
Created by lola_smily almost 9 years ago
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Question Answer
Acetylcholine -muscarinic receptor agonist
Metacholine - muscarinic receptor agonist - modification of the ethylene bridge - S(+) equipotent to ACH - beta methyl substitution => more selective to Muscarininc receptor - more resistant to AChE => slow hydrolysis
Carbachol -muscarinic receptor agonist - modification of the acetoxy group - converting ester to carbamate - similar ACh potency, same profile -hydrolysis by AChE
Bethanechol - muscarinic receptor agonist - beta methyl substitution - potent and selective Muscarinic agonist -S(+) more potent
choline ethyl ether - muscarinic receptor agonist - exception to the classical SAR of muscarinic activity
alkyl amino ketones - muscarinic receptor agonist - exception to the classical SAR of muscarinic activity
L(+)- Muscarine Chloride
epimuscarine
pilocarpine - alkaloid, produced from Pilocarpus jaborandi - Potent muscarinic agonist - chemically unstable => ring opening
pilocarpic acid - inactive - product of hydrolysis of pilocarpine
isopilocarpine - epimerization of pilocarpine - inactive product
Physostigmine -indirectly acting parasympathomimetics - reversible AChE - 3ary alkaloid obtained from the Calabar Bean, Physostigma venosum - exhibits high affinity to AChE of 10^-9 to carbachol of 10^-4 -used to treat glaucoma and over dose of anticholinergic -light sensitive -undergoes hydrolysis in aqueous solutions
eseroline inactive degradation product of physostigmmine in aqueous solutions
rubreserine -inactive degradation product of physostigmmine in aqueous solutions - red color
neostigmine -indirectly acting parasympathomimetics - reversible AChE synthetic ionized -indicated for Myastenia Gravis
pyridostigmine -indirectly acting parasympathomimetics - reversible AChE synthetic ionized -indicated for Myastenia Gravis
donepezil hydrochloride -indirectly acting parasympathomimetics - reversible AChE - lack hepatotoxicity - used for Alzheimer's disease
tacrine indirectly acting parasympathomimetics - reversible AChE - cause hepatotoxicity - used for Alzheimer's disease
rivastigmine indirectly acting parasympathomimetics - reversible AChE - lack hepatotoxicity - used for Alzheimer's disease
Edrophonium -used for diagnostic purposes - improve Myastenia Gravis -worsen cholinergic chrisis
Malathion irreversible AChEi organophosphate thio group
parathion irreversible AChEi organophosphate thio group low Anti-AChE activity
sarin irreversible AChEi organophosphate
paraoxon irreversible AChEi organophosphate oxo group high Anti-AChE activity
echothiophate iodide irreversible AChEi organophosphate ionized => clnical application for glaucoma
oxime reactivation of AChE
Pralidoxime chloride (2 -PAM) reactivation of AChE
obidoxime reactivation of AChE
diacetylmonoxime reactivation of AChE
atropine parasympatholytics muscarine receptor antagonist alkaloid obtained from atropa belladonna atropine also found in datura stramonium
scopolamine parasympatholytics muscarine receptor antagonist alkaloid obtained from atropa belladonna aslo found in Hyascyamus niger
glycopyrrolate -antiholinergic -amino alcohol ester -ionized, exert effect locally in GI
propantheline antiholinergic -amino alcohol ester -ionized, exert effect locally in GI
clinidium antiholinergic -amino alcohol ester -ionized, exert effect locally in GI
ipratronium antiholinergic -amino alcohol ester -ionized, exert effect locally in GI
flavoxate antiholinergic -amino alcohol ester -ionized, exert effect locally in GI
oxyphencyclimine anticholinergic amino alcohol ester 3ary amine, used for Parkinson treatment systemic, can cross BBB
procyclidine anticholinergic amino alcohol 3ary amine, systemic effect
trihexyphenidyl anticholinergic amino alcohol 3ary amine, systemic effect
benztropine anticholinergic amino ethers
orphenadrine anticholinergic amino ether antihistaminic anticholinergic> antihistaminic
pirenzepine - selective M1 receptor antagonist - they are competitive antagonists -have antispasmodic effects -produce mydriasis -antisecretory: -decrease gastric secretions -decrease saliva secretions -decrease bronchial secretions
telenzepine selective M1 receptor antagonist - they are competitive antagonists -have antispasmodic effects -produce mydriasis -antisecretory: -decrease gastric secretions -decrease saliva secretions -decrease bronchial secretions
hexamethonium - ganglionic blocking agent - bisquaternary ammonium -MOA: they block autonomic ganglia => inhibit ganglionic transmission - main therapeutic indication: antihypertensive
trimethophan ganglionic blocking agent - sulfonium -MOA: they block autonomic ganglia => inhibit ganglionic transmission - main therapeutic indication: antihypertensive
pentolinium ganglionic blocking agent - bisquaternary ammonium -MOA: they block autonomic ganglia => inhibit ganglionic transmission - main therapeutic indication: antihypertensive
mecamylamine ganglionic blocking agent - secondary amines -MOA: they block autonomic ganglia => inhibit ganglionic transmission - main therapeutic indication: antihypertensive
pempidine ganglionic blocking agent - tertiary amine -MOA: they block autonomic ganglia => inhibit ganglionic transmission - main therapeutic indication: antihypertensive
succinylcholine chloride - depolarizing NMJ blocker - produce a 2 phase block phase 1: stimulation phase 2: depression block by receptor desensitization - therapeutic use : muscle relaxation - reversal of effects of depolarizing : give antagonist to sensitize the receptor
tubocurarine - non depolarizing NMJ blocker - cc: benzylisoquinoline - they are competitive receptor antagonist - all are ionized - lack CNS side effect - therapeutic use: muscle relaxation - reversal of effects of non depolarizing: AChI
atracurium besylate - non depolarizing NMJ blocker - cc: benzylisoquinoline - they are competitive receptor antagonist - all are ionized - Exception: CNS side effects - therapeutic use: muscle relaxation - reversal of effects of non depolarizing: AChI
mivacurium chloride non depolarizing NMJ blocker - cc: benzylisoquinoline - they are competitive receptor antagonist - all are ionized - lack CNS side effect - therapeutic use: muscle relaxation - reversal of effects of non depolarizing: AChI
doxacurium chloride non depolarizing NMJ blocker - cc: benzylisoquinoline - they are competitive receptor antagonist - all are ionized - lack CNS side effect - therapeutic use: muscle relaxation - reversal of effects of non depolarizing: AChI
L-Tyrosine
L-Dopa
Dopamine
Norepinephrine - released NE : binding to receptor postsynaptic and presynaotic uptake 1( recycling NE) uptake 2 ( degradation, metabolism ) - receptor selectivity: alpha 1, 2, beta 1
epinephrine - increasing the size of R1 ( CH3) increase beta and decrease alpha adrenergic activity - receptor activity: Beta 2 > alpha 1,2, beta 1
Isoproterenol increasing the size of R1 (isopropyl) increase beta and decrease alpha adrenergic activity - receptor activity: Beta 2, Beta 1
Colterol - increase the size of R1 to t-butyl group increase selectivity to beta 2 agonistic activity -cc: phenylethanolamines -receptor selectivity :beta 2 > beta 1 beta 2 agonist
ritodrine -increasing the size of R1 => increase selectivity to beta 2 agonistic activity - at least one hydroxyl group is required to form hydrogen bonding with receptor
Ethylnorepinephrine substation on Carbon 2, R2: ethyl increase beta activity chiral center at C2 -receptor activity: beta > alpha
alpha- methylnorepinephrine (1R, 2S) 1R, 2S isomer : maximum direct activity 1R, 2R isomer: indirect activity receptor activity: alpha 2 > alpha 1
terbutaline 3', 5'- dihydroxy substitution: orally active no COMT metabolism receptor activity: beta 2> beta 1
albuterol 3' hydroxymethyl,4'hydroxy substitution non cathechol => orally active receptor activity: beta 2 > beta 1
Phenylephrine 3' hydroxyl substitution => alpha 1 activity
Metaraminol 3' hydroxyl substitution => alpha 1 activity
Methoxamine 2',5' -dimethoxy substitution => alpha 1 activity
pirbuterol beta 2 agonist cc: phenylethanolamies
salmeterol beta 2 agonist cc: phenylethanolamines
bitolterol -beta 2 agonist - phenylethanolamine - non catechol : orally active - bi- toluoylester ( more lipophilic) - given by inhalation -hydrolyzed by esterase in the lungs to give colterol - twice the DOA than catechol
Dobutamine (-) dobutamine : alpha agonist + beta 1 agonist (+) dobutamine: alpha antagonist + beta 1 agonist ( 10x) racemic mixture: selective beta 1 activity exception to SAR
dopamine - not strictly adrenergic agonist - DA receptor agonist => dialates renal blood vessels - at higher dose acts on beta 1 receptor - at much higher dose acts on alpha 1 receptor - not orally active
(+,-) ephedrine - mixed acting sympathomimetics - alkaloid from Ephedra species (Ma Huang) - non cathechol : orally active more lipophilic - 1R, 2S: direct + indirect acting -used as nasal decongestant - cc: phenylethanoloamines
pseudoephedrine - 1S, 2R and 1S, 2S : indirectly acting sympathomimetics
amphetamine indirectly acting sympathomimetics dextro> levo non cathechol: orally active no hydrolysis: no 0H, very lipophilic, CNS stimulant
metamphetamine indirectly acting sympathomimetics dextro> levo non cathechol: orally active no hydrolysis: no 0H, very lipophilic, CNS stimulant
propylhexedrine indirectly acting sympathomimetics same as metamphetamine dextro> levo non cathechol: orally active no hydrolysis: no 0H, very lipophilic, POTENT CNS stimulant
xylometazoline - alpha 1 adrenergic agonists - cc: imidazoline derivatives - contain a carbon between C2 of imidazoline and a phenyl ring - contain phenylethylamine moiety ortho methyl: agonistic activity at alpha 1 and alpha 2 receptors - bulky group at para position: increase alpha 1 and decrease alpha 2 activity - mainly used as nasal decongestant
oxymetazoline - alpha 1 adrenergic agonists - cc: imidazoline derivatives contain a carbon between C2 of imidazoline and a phenyl ring - contain phenylethanolamine moiety ortho methyl: agonistic activity at alpha 1 and alpha 2 receptors - bulky group at para position: increase alpha 1 and decrease alpha 2 activity - mainly used as nasal decongestant
tetrahydrozoline alpha 1 adrenergic agonists - cc: imidazoline derivatives contain a carbon between C2 of imidazoline and a phenyl ring - contain phenylethylamine moiety ortho methyl: agonistic activity at alpha 1 and alpha 2 receptors - mainly used as nasal decongestant
naphazoline alpha 1 adrenergic agonists - cc: imidazoline derivatives contain a carbon between C2 of imidazoline and a phenyl ring - contain phenylethylamine moiety ortho methyl: agonistic activity at alpha 1 and alpha 2 receptors - mainly used as nasal decongestant
clonidine - potent alpha 2 adrenergic receptor agonist -cc: imidazoline derivatives - developed as nasal vasoconstrictor - produce marked hypotensive effects, maily centrally mediated throughpostsynaptic alpha2 adrenergic receptor - used as antihypertensive agent - effects on peripheral postsynaptic alpha 2 receptors: vasoconstriction - effects on peripheral presynaptic: negative feedback, decrease NE - pka 8.5, 80% ionized, 20% NI
Apraclonidine alpha 2 adrenergic agonist imidazoline moiety
brimonidine alpha 2 adrenergic agonist imidazoline moiety
guanabenz potent alpha 2 adrenergic agonist non imidazoline, clonidine like same indication as clonidine
guanfacine potent alpha 2 adrenergic agonist non imidazoline, clonidine like same indication as clonidine
alpha -methyldopamine alpha 2\ adrenergic antagonist non imidazoline derivative undergoes bioinactivation
phenoxybenzamine - adrenergic antagonist - irreversible alpha blocker - non selective ( alpha 1 and 2 ) - Beta-haloalkylamine derivative - slow onset of action: because it is a prodrug, must undergoe bioactivation ( alkylated receptor active ) -limited use in pheochromocytoma (cancer of adrenal medulla)
tolazoline - adrenergic receptor antagonist - reversible - non selective ( blocks alpha 1 and 2 ) - similar to xylometazoline BUT no ortho substitution: no alpha agonistic effects - limited use in treatment of symptoms of pheochromocytoma - rapid onset of action
phentolamine - adrenergic receptor antagonist - reversible - non selective ( blocks alpha 1 and 2 ) - limited use in treatment of symptoms of pheochromocytoma - rapid onset of action
prazosin - selective alpha 1 receptor antagonist reversible - quinazoline derivative -contain 4-amoni-6-7-dimethoxyquinazoline ring connected to piperazine at C2 -lower Blood Pressure
terazosin selective alpha 1 receptor antagonist reversible - quinazoline derivative -contain 4-amoni-6-7-dimethoxyquinazoline ring connected to piperazine at C2 -lower Blood Pressure
doxazosin selective alpha 1 receptor antagonist reversible - quinazoline derivative -contain 4-amoni-6-7-dimethoxyquinazoline ring connected to piperazine at C2 -lower Blood Pressure
tamsulosin selective alpha 1 receptor antagonist reversible high affinity to alpha 1 A subtype present in prostate gland => used to treat BHP ( benign prostatic hyperplasia) - cc: sulfonamide phenylpropylamine
indoramin - reversible selective alpha 1 receptor antagonist and H1 (histamine) and 5receptor antagonistHT (serotonin) - indole derivative
yohimbine - reversible selective alpha 2 blocker - indole alkaloid from Yohimbe bark - increase Blood Pressure AND Heart Rate - very limited use to treat male sexual impotency
practolol - Beta adrenergic receptor antagonist - aryloxypropanolamine with p-acylamino -change of acylamino to ortho or meta => loss of selectivity - inhibited isoproterenol induced tachycardia with minimal effects on isoproterenol induced hypotension -withdrawn from the market due to visual loss
pronethalol - beta adrenergic receptor antagonist non selective -arylethanolamine - no partial agonistic activity - carcinogenic in animals
propranolol -aryloxypropanolamine -beta adrenergic receptor non selective -10X> potent -no partial agonistic activity -not carcinogenic - used in hypertension, agnia pectoris, arrhythmia, migraine
bunolol -non selective beta adrenergic receptor antagonist
carteolol -non selective beta adrenergic receptor antagonist
metipranolol -non selective beta adrenergic receptor antagonist - exception para postion - ester hydrolysis=> short acting
nadolol -non selective beta adrenergic receptor antagonist
penbutolol -non selective beta adrenergic receptor antagonist
pindolol -non selective beta adrenergic receptor antagonist
sotalol -non selective beta adrenergic receptor antagonist - aryl sulfonamide ethanolamine derivative
timolol -non selective beta adrenergic receptor antagonist
acebutolol -selective beta 1 adrenergic receptor antagonist cardio slective
atenolol -selective beta 1 adrenergic receptor antagonist cardio slective
betaxolol - selective beta 1 adrenergic receptor antagonist cardio selective
esmolol - selective beta 1 adrenergic receptor antagonist cardio slective
metoprolol selective beta 1 adrenergic receptor antagonist cardio slective
bisoprolol selective beta 1 adrenergic receptor antagonist cardio slective
labetolol non selective beta blocker and alpha 1 blocker mixed acting
carvedilol non selective beta blocker and alpha 1 blocker mixed acting
metyrosine - drugs affecting NE biosynthesis - tyrosine hydroxylase inhibitor
carbidopa - drugs affecting NE biosynthesis - L-Dopa decarboxylase inhibitor
reserpine -drugs affecting NE storage ( catecholamine depleting agents) - indole alkaloid -isolated from Rauwolfa Serpentina - inhibit catecholamine storage in storage vesicle => depletion of catecholamines
guanadrel - drugs affecting NE release ( adrenergic neuronal blocking agents)
guanethidine - drugs affecting NE release ( adrenergic neuronal blocking agents)
bretylium - drugs affecting NE release ( adrenergic neuronal blocking agents)
ergot alkaloid - produced by calviceps purourea, a fungus that infects grains
ergotamine - ergot alkaloid - produced by calviceps purourea, a fungus that infects grains -mixed agonist/ antagonist - potent smooth muscle contraction - also used for migraine treatment
ergonovine -ergot alkaloid -mixed agonist/ antagonist - potent smooth muscle contraction - also used for migraine treatment - potent inducer of uterine - because of better bioavailability, used to replace ergotmaine
methylergonovine -ergot alkaloid -mixed agonist/ antagonist - potent smooth muscle contraction - also used for migraine treatment - potent inducer of uterine - because of better bioavailability, used to replace ergotmaine
methylseregide -ergot alkaloid -mixed agonist/ antagonist -mainly used for migraine treatment
morphine - cc: phenantrene - teriary amine group, N-methyl: good agonist Removal of N-methyl: decrease activity increase size of alkyl group: antagonist
phenanthrene
benzoquinone -oxidation od morphine product
codeine - weak mu agonist - potent antitussive agent -partial O-demethylated => morphine
Heroin -3,6-diacetyl derivative of morphine - weak affinity to mu receptor -more lipophilic: penetrates BBB - hydrolyzed in the brain to give: 3-acetylmorphine (3-MAM) 6-acetylmorphine (6-MAM) - 6-MAM has potent mu agonist
oxymorphone - 3-hydroxy-N-methyl derivative 10X as potent as morphine - 14 beta hydroxyl enhances mu agonist activity and decrease antitussive activity
oxycodone -3-hydroxyl-N-methyl derivative same activity as morphine but better oral bioavailability - 14 beta hydroxyl enhances mu agonist activity and decrease antitussive activity
naloxone - N-allyl oxymorphone - pure non selective opioid receptor antagonist
nalorphine - N-allyl substitution for N-methyl 7,8-double bond reduction 6-keto reduction u
morphinan - removal of 4,5 epoxide bridge (modification of E ring)
levorphanol -removal of 4,5 epoxide bridge - 8X more potent mu receptor agonist
butorphanol -removal of 4,5 epoxide bridge - mu antagonist and kappa agonist
dextromethorphan -removal of 4,5 epoxide bridge (+) levorphanol = dextrophan - lacks analgesia - antitussive activity
benzomorphans - lacks the epoxide ring and the C ring - retain opioid activity
cyclazocine - R: N-cyclopropyl methyl - mixed agonist/ antagonist kappa agonist mu antagonist
phenazocine - R: N-ethylphenyl -potent mu agonist about 10X> morphine
pentazocine -R: N-methyl of 2-methyl-2-butene - mixed agonist/antagonist kappa agonistic activity: analgesic mu antagonistic activity -only one marketed in US
metazocine -R: CH3 - mu agonist -metasocine > morphine
meperidine - A and D ring analogs of morphine - cc: phenylpiperidine -first synthesized agent with mu agonist activity of 1/4 of morphine -short DOA (useful in some medical procedure)
MPTP 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine -damages DA neurons => parkinsonism - product of reversed ester of meperidine
fentanyl - cc: anilidopiperidine - 80X> potent than morphine
sufentanil - cc: anilidopiperidine - 10X> potent than fentanyl (fentanyl 80X> morphine)
remifentanyl - cc: anilidopiperidine - 25X> potent than morphine
alfentanil - cc: anilidopiperidine - 20X> potent than morphine
methadone -cc: diphenylheptanone - orally active and long DOA - useful for maintenance therapy of opoids addicts and for pain suppression of terminally ill patients
isomethadone
diphenoxylate -cc: diphenylheptanone - structural modification of methadone -antidiarrheal opioids
loperamide -cc: diphenylheptanone - structural modification of methadone -antidiarrheal opioids
thebaine -oripavine derivative - from papaver bracteatum no activity as opioid agonist
etorphine - oripavine derivative - 1000 X> morphine - severe respiratory depression -low therapeutic index in humans, used for veterinary medicine
buprenorphine -orpavine derivative - 20-50X> morphine - mixed agonist / antagonist -does not produce tolerance and addiction
tramadol - synthetic mu agonist - orally active - possess opioid and non opioid analgesic activity -analgesic not reversed by naloxone -O-dimethyl metabolite is 6X> parent drug -less respiratory depression than morphine
dezocine -mixed agonist / antagonist -only primary amine opoid agent - exact receptor selectivity is not known - equipotent with morphine
nalbuphine - N-cyclobutylmethyl substitution for N-methyl 7,8-double bond reduction 6 keto reduction -mu antagonist and kappa agonist
naltrexone -N-cyclopropyl-methyl oxymorphone - pure non selective opioid antagonist
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