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65 Cards in this Set

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Mild analgesics
decrease awareness to pain while raising pain threshold.
Antipyretics
eg Tylenol
decrease temp in feverish individual
Anti-inflammatory
in animals and humans
Treat, not cure
Uses of analgesics
relief of:
pain if arthritis
other skeletal muscle conditions
headache
other types of visceral pain
analgesics
prototype drug: ASA
NSAIDS
Salicylates
all are synonymous
Group 1: salicylates
Aspirin
a-acetyl
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
(CH3)3N+CH2CH2OH
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
Counterirritants:
allyl isothiocyanate
stronger-ammonia water
methyl salicylate
turpentine oil
menthol
camphor
capsaicin
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
<4g/24hr
975mg=max dose
HYDROLYSIS
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
Olsalazine
azo linkage
Salicylamide
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.
Pyrazoline
from pyrazole to hydrated N at position 2
Pyrazolidine
hydrated from pyrazoline
5-pyrazolone
oxidized from pyrazoline
3,5-pyrazolidinedione
oxidized from 5-pyrazolone
Pyrazolidinediones
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
5-pyrazolones
antipyrine: 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
-for ear infection, but no longer used due to high blood toxicity
aminopyrine
2,3-dimethyl-4-dimethylamino-1-phenyl-3-pyrazolin-5-one
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
Indomethacin
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:
Indomethacin
for RA & OA
contraindicated w/ ASA
active in sulfide form
ibuprofen
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
Naproxen
S+isomer, so more $$
R.A., gout
not for lactating/pregnant woman
children under 16: AVOID
Tolmetin
R.A.
Zomepirac sodium
R.A.
REMOVED from market
Suprofen
for dysmenorrhea
Ketoprofen [orudis] (+/-)
causes fluid retention
Nabumetone [Relafen]
4-(6-methoxy-2-naphyl-2-BUTANONE)
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
Piroxicam
Tenoxicam
Oxaprozin
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
Piroxicam
OA + RA
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]