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65 Cards in this Set

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Mild analgesics
decrease awareness to pain while raising pain threshold.
eg Tylenol
decrease temp in feverish individual
in animals and humans
Treat, not cure
Uses of analgesics
relief of:
pain if arthritis
other skeletal muscle conditions
other types of visceral pain
prototype drug: ASA
all are synonymous
Group 1: salicylates
spirin-an old name for salicylic or spiric acid
o-hydroxy benzoic acid!!
Know structure :)
Structure and SAR of salicylates
-OH, -COOH ortho to ea other
Derivatives of salicylates to improve toxicity
1) alternate COOH
alternate COOH: salts to make eg Mag salicylate; ester eg phenyl salicylate, methyl salicylate; amide
Derivatives of salicylates to improve toxicity
2) alter the -OH
*ASA was made this way
also salsate
Derivatives of salicylates to improve toxicity
3) alter both OH and COOH
eg aluminum aspirin
Derivatives of salicylates to improve toxicity
4) add more gps to phenyl ring
Derivatives of salicylates to improve toxicity
5) OH-->NH2
"Bioisosteric change"
* (are same size and shape)
salts of salicylic acid
sodium salicylic acid
choline salicylate (arthropan)
magnesium salicylate (Doan's pills)
Triethanolamine salicylate
Sodium salicylate
less GI irritation :)
Choline salicylate
good solubility
Triethanolamine salicylate
topical analgesic
magnesium salicylate (Doan's Pills)
nothing special
Esters of salicylic acid
via carboxylic acid or hydroxy group
Phenyl salicylate (Salol): intestinal disinfectant in diarrhea; also in combo w/ methenamine and atropine alkaloids as urinary tract antiseptic and analgesic.
Methyl Salicylate: external analgesic; Counterirritant
Acetyl Salicylic acid! ("dirty drug")
Salsate (salicyl salicylic acid)
Salicylamide (not true salicylate)
Mesalamine (5-aminosalicylic acid)
Olsalazine (azo linkage)
Diflunisal: 5-(2,4-difluorophnyl) salicylic acid $
Others that are not really esters:
Mesalamine (5-aminosalicylic acid)
Olsalazine (azo linkage)
Diflunisal: 5-(2,4-difluorophnyl) salicylic acid $
External analgesics
Counterirritants: bind skin receptors
Mech of action: cause mild inflammatory rxn when applied topically
allyl isothiocyanate
stronger-ammonia water
methyl salicylate
turpentine oil
Phenyl salicylate (salol)
Intestinal disinfectant in diarrhea
also in combo w/ methenamine and atropine alkaloids as urinary tract antiseptic and analgesic.
Acetyl salicylic acid (aspirin)
325-650 mg/4hr
975mg=max dose
Inhibits prostaglandins --> COX enzymes 1 & mainly 2 (irreversible)
Cox1-->SE's of the stomach
1) lengthen bleeding time; 1 wk prior to surgery
2) gum ulceration after local application
3) avoid in hypoprothrombinemic, VitK deficiency, peptic ulcer, GI bleeding.
4) ! GI irritation and bleeding !
5) 0.3% have aspirin hypersensitivity..asthma-like symptoms, skin rxn, rash, hives.
aspirin toxicity
mean lethal dose adult: ! 20-30g !
child: 150mg/kg
Products to decr GI upset from aspirin:
effervescent, buffered tab, time release product, EC tab.
Salsate (salicyl salicylic acid)
less GI upset
Mesalamine (5-aminosalicylic acid)
enema for ulcerative colitis
azo linkage
not a true salicylate--not an ester
more potent with fewer SE's
Diflunisal (5-(2,4-difluorophnyl) salicylic acid)
$ longer acting.
Pyrazole derivatives: nomenclature
the simple doubly unsaturated compound containing 2 N and 3 C atoms in the ring and with the N atoms neighboring is known as pyrazole.
from pyrazole to hydrated N at position 2
hydrated from pyrazoline
oxidized from pyrazoline
oxidized from 5-pyrazolone
Phenylbutazone [butazolidin]
Oxyphenyl butazone [tandearil]
sulfinpyrazone [anturane]
phenylbutazone [butazolidin]
SE's: blood dyscrasias makes it for short term use, sore throat, mouth lesions, BM suppression: short term use.
For gout--uricosuric effect
Arthritis use
oxyphenyl butazone [tandearil]
removed b/c HEMATOLOGICAL effects
sulfinpyrazone [anturane]
Weak analgesic; potent uricosuric agent; effective in (chronic) gouty arthritis
antipyrine: 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
-for ear infection, but no longer used due to high blood toxicity
has been employed as an antipyretic & analgesic as is antipyrine but is somewhat slower in action. more powerful and its effects last longer.
!Can cause fatal agranulocytosis! (not often used)
Arylacetic acids
a-methyl arylacetic acid or arylpropionic acid: CHIRAL
Not for children
For those who cannot tolerate ASA, in place of phenyl butazone (in long-term therapy).
Drug of choice for acute gouty arthritis
Sulindac is a Non-nitrogenous analog of:
Used for:
for RA & OA
contraindicated w/ ASA
active in sulfide form
for RA
*S(+) isomer is active form of mix
chiral with ibuprofen R=CH3
fenoprofen calcium
highly protein bound
when taking hydrantoins, sulfonamides, & sulfonylureas, USE CAUTION
S+isomer, so more $$
R.A., gout
not for lactating/pregnant woman
children under 16: AVOID
Zomepirac sodium
REMOVED from market
for dysmenorrhea
Ketoprofen [orudis] (+/-)
causes fluid retention
Nabumetone [Relafen]
ketone for RA and OA
Prodrug metabolized to 6-methoxy-2-naphthyl acetic acid
Flurbiprofen [ocufen] (+/-) mix
ophthalmic NSAID for eye surgery
-inhibits miosis
Ketorolac [Torado]
more effective as analgesic than anti-inflammatory
contraindicated w/ ASA or other NSAIDS
Diclofenac (Voltasen)
arylacetic acid AND N-Arylanthranilic acid
Etodolac [iodine]
Just another NSAID
Arylacetic acid conclusions
particular value in patients who can not tolerate aspirin: ASA is 1st choice
Appear to have fewer SE's than usually anti-inflamm dose of ASA
If one agent not effective for a particular agent try another.
Group 4 Once per Day:
Benoxaprofen {oraflex} +/-R&S
Flunoxaprofen (priaxim) S isomer
Tenidap sodium
Benoxaprofen (oraflex)
R isomer caused hepatotox-->removal
For RA and OA
Flunoxaprofen (priaxim) S isomer
For RA and OA
Once a day
modified benoxaprofen
Tenoxicam (Tilcotil)
Canada & UK
Oxaprozin (Daypro-Searle)
For RA
Tenidap sodium (enablex)
has disease modifying profile
also provides symptomatic relief
For RA & OA.
Inhibits COX, interferes w/ 5-lipoxygenase, inhibits production of IL-1, inhibits cytokines.
(long-term use effects led to not be US approved)
Chirality and NSAIDs
Racemates: chiral drugs that exist 2 or more mirror-image forms (enantiomers) are frequently offered as half-and-half enantiomer mixes (racemates)
-single enantiomer agents-one enantiomer.
Group 5: N-Arylanthranilic Acids
Use 7 or less days
mefenamic acid [ponste]
flufenamic acid [arlef]
meclofemanate sodium [meclomen]
diclofenac [voltaren]