CHAPTER 23

HISTAMINE AND ANTIHISTAMINE AGENTS

First-Generation Antihistamine Classes

AGENT DESCRIPTION TYPE CHEMICAL OTHER CLASSIFICATION STRUCTURAL MoA EFFECTS/PHARMAC OTHER INFO.
NAME NAME FORMULA OLOGICAL USE
Diphenhydra Is an oily, lipid- AMINOAL 2- Benadryl Antihistamic. In the usual dose
mine soluble free base KYL (diphenylmeth It is also used in range of 25 to 400
Hydrochloride available as the ETHERS oxy)-N,N- OTC sleep-aid mg,
, Tannate, and bitter-tasting (ETHANOL dimethylethan products. It is diphenhydramine is
Citrate hydrochloride salt, AMINES) amine administered not a highly active
which is a stable, hydrochloride either orally or H1- antihistamine.
white crystalline parenterally in the Conversion to a
powder soluble in treatment of quaternary
water (1:1), alcohol urticaria, seasonal ammonium salt
(1:2) and rhinitis (hay does not alter the
chloroform (1:2) fever), and some antihistaminic
dermatoses. The action greatly but
most common does increase the
side effect is anticholinergic
drowsiness, and action
the concurrent
use of alcohol and
other CNS
depressants
should be
avoided.
Dimenhydrina Is a white AMINOAL 8- Dramami Dimenhydrinate is
te crystalline, KYL chlorotheophyl ne recommended for
odorless powder ETHERS line 2- nausea of motion
that is highly (ETHANOL (diphenylmeth sickness and for
soluble in water AMINES) oxy)-N,N- hyperemesis
and freely soluble dimethylethyla gravidarum (nausea
in alcohol and mine of pregnancy).
chloroform.
Bromodiphen Is a white to pale AMINOAL 2-[(4- Ambodry Relative to
hydramine buff crystalline KYL bromophenyl)- l diphenhydramine,
Hydrochloride powder that is ETHERS phenylmethoxy Hydrochl bromodiphenhydra
freely soluble in (ETHANOL ]-N, N- oride mine is more lipid
water and in AMINES) dimethylethan soluble and was
alcohol. amine twice as effective in
hydrochloride protecting against
the lethal effects of
histamine aerosols.
Doxylamine Is a white to AMINOAL 2-[-[2- Decapryn Indicated for the Doxylamine
Succinate creamy-white KYL (dimethylamin Succinate rhinitis symptoms, succinate is
powder with a ETHERS o)ethoxy]-- but is also used as comparable in
characteristic odor. (ETHANOL methylbenzyl]p a nighttime potency to
It is soluble in AMINES) yridine sedative. diphenhydramine.
water (1:1), alcohol bisuccinate Concurrent use of
(1:2), and alcohol and other
chloroform (1:2). A CNS depressants
1% solution has a should be
pH of about 5. avoided.
Carbinoxamin Is a white AMINOAL (d, l)-2-[p- Clistin Carbinoxamine is a
e Maleate crystalline powder KYL chloro--[2- potent
that is very soluble ETHERS (dimethylamin antihistaminic and is
in water and freely (ETHANOL o)ethoxy]benzy available as the
soluble in alcohol AMINES) l]pyridine racemic mixture.
and in chloroform. bimaleate The more active
The pH of a 1% levo isomer of
solution is between carbinoxamine has
4.6 and 5.1. the (S) absolute
configuration30 and
can be
superimposed on
the more active
dextro isomer (S
configuration) of
chlorpheniramine.
Clemastine Has two chiral AMINOAL R,R-2[2[1-(4- Dextroro Used for its This member of the
Fumarate centers, each of KYL chlorophenyl)- tatory central ethanolamine series
which has the (R) ETHERS 1- clemastin cholinergic- is characterized by a
absolute (ETHANOL phenylethoxy]e e blocking activity. long duration of
configuration. A AMINES) thyl]-1- Tavist action, with an
comparison of the methylpyrrolidi activity that reaches
activities of the ne hydrogen a maximum in 5 to 7
enantiomers furnarate (1:1) hours and persists
indicates that the for 10 to 12 hours. It
asymmetric center is well absorbed
close to the when administered
terminal side chain orally, and it is
nitrogen is of lesser excreted primarily in
importance to the urine.
antihistaminic
activity.
Diphenylpyrali Is a white or AMINOAL 4- Hispril, It is a potent
ne slightly offwhite KYL (diphenylmeth Diafen antihistaminic, and
Hydrochloride crystalline powder ETHERS oxy)-1- the usual dose is 2
that is soluble in (ETHANOL methylpiperidi mg 3 or 4 times
water or alcohol. AMINES) ne daily.
hydrochloride
Tripelennamin Is available as a ETHYLENE 2-[benzyl[2- Pyribenz For oral
e Citrate monocitrate salt, DIAMINES dimethylamino amine administration in liq.
which is a white )- Citrate dose forms, the
crystalline powder ethyl]amino]py citrate salt is less
freely soluble in ridine citrate bitter and thus more
water and in (1:1), PBZ palatable than the
alcohol. hydrochloride.
Because of the
difference in
molecular weight,
the doses of the 2
salts must be
equated 30 mg of
the citrate salt is
equivalent to 20 mg
of the hydrochloride
salt.
Tripelennamin Is a white ETHYLENE It appears to be as The first
e crystalline powder DIAMINES effective as ethylenediamine
Hydrochloride that darkens slowly diphenhydramine developed in the
on exposure to and may have the United States and is
light. The salt is advantage of well absorbed when
soluble in water fewer and less given orally.
(1:0.77) and in severe side
alcohol (1:6). It has reactions.
a pKa of about 9, Drowsiness may
and a 0.1% solution occur, however,
has a pH of about and may impair
5.5. the ability to
perform tasks
requiring
alertness.
Pyrilamine Is available as the ETHYLENE 2-[4- The salt is soluble in
Maleate acid maleate salt DIAMINES methoxybenzyl water and freely
(1:1), which is a [2- soluble in alcohol. A
white crystalline dimethylamino 10% solution has a
powder with a faint )ethyl]- pH of approxi.5. At a
odor and a bitter, amino]pyridine pH of 7.5 or above,
saline taste. the free base begins
to precipitate.
Methapyrilen Is available as the ETHYLENE 2-[[2- Histadyl A study of the solid-
e bitter-tasting, DIAMINES (dimethylamin state conformation
Hydrochloride white crystalline o)-ethyl]-2- of methapyrilene
powder that is thienylarnino] hydrochloride
soluble in water pyridine showed that the
(1:0.5), in alcohol monohydrochl trans-conformation
(1:5), and in oride is preferred for the
chloroform (1:3). two
Its solutions have a ethylenediamine
pH of about 5.5. nitrogen atoms. The
FDA declared
methapyrilene a
potential carcinogen
in 1979, and all
products containing
it have been
recalled.
Thonzylamine Is a white ETHYLENE 2-[[2- It is similar in
Hydrochloride crystalline powder DIAMINES (dimethylamin activity to
soluble in water o)-ethyl](p- tripelennamine but
(1:1), in alcohol methoxybenzyl is claimed to be less
(1:6), and in )amino]pyrimid toxic. The usual
chloroform (1:4). A ine dose is 50 mg taken
2% aqueous hydrochloride up to 4 times daily.
solution has a pH It is available in
of 5.5. certain combination
products.
Antazoline is a bitter, white to ETHYLENE 2- In addition to its Antazoline is less
Phosphate off-white DIAMINES [(Nbenzylanilin use as an active than most of
crystalline powder o)methyl]-2- antihistamine, the other
that is soluble in imidazoline antazoline has antihistaminic drugs,
water. It has a pKa dihydrogen more than twice but it is
of 10.0, and a 2% phosphate the local characterized by the
solution has a pH anesthetic lack of local
of about 4.5. potency of irritation. The more
procaine and also soluble phosphate
exhibits salt is applied
anticholinergic topically to the eye
actions. in a 0.5% solution.
The less soluble
hydrochloride is
given orally.
Cyclizine Occurs as a light- PIPERAZIN 1- Marezine It is used primarily The injection should
Hydrochloride sensitive, white ES (diphenylmeth in the prophylaxis be stored in a cold
crystalline powder (CYCLIZIN yl)-4- and treatment of place, because if it is
with a bitter taste. ES) methylpiperazi motion sickness. stored at room
It is slightly soluble ne The lactate salt temperature for
in water (1:115), in monohydrochl (Cyclizine Lactate several months, a
alcohol (1:115), oride Injection, United slight yellow tint
and in chloroform States may develop. This
(1:75) Pharmacopoeia does not indicate a
[USP]) is used for loss in biologic
intramuscular (IM) potency
injection because
of the limited
water solubility of
the hydrochloride.
Buclizine Is a white to PIPERAZIN e, l- (p- Bucladin- This drug has been
Hydrochloride slightly yellow ES tertbutylbenzyl S discontinued in the
crystalline powder (CYCLIZIN )-4-(p-chloro-- United States.
that is insoluble in ES) phenylbenzyl)p
water. The highly iperazine
lipid-soluble dihydrochlorid
buclizine has CNS e
depressant,
antiemetic, and
antihistaminic
properties.
Chlorcyclizine Is a light-sensitive, PIPERAZIN 1-(p-chloro-- Chlorcydizine is Disubstitution or
Hydrochloride white crystalline ES phenylbenzyl)- indicated for the substitution of
powder that is (CYCLIZIN 4- symptomatic halogen in the 2- or
soluble in water ES) methylpiperazi relief of urticaria, 3-position of the
(1:2), in alcohol ne hay fever, and benzhydryl rings
(1:11), and in monohydrochi certain other results in a much
chloroform (1:4). A oride conditions. less potent
1% solution has a compound.
pH between 4.8
and 5.5.
Meclizine Is a tasteless, white PIPERAZIN 1-(p-chloro-- Bonine, Although it is a Dosage forms:
Hydrochloride or slightly yellowish ES phenylbenzyl)- Antivert moderately Tablets (12, 5, 25, 50
crystalline powder (CYCLIZIN 4-(m- potent mg) and capsules
that is practically ES) methylbenzyl)p antihistaminic, (25 mg) Usual adult
insoluble in water iperazine meclizine is used dose: • Motion
(1:1,000). It differs dihydrochlorid primarily as an sickness: 25- to 50-
from chlorcyclizine e monohydrate antinauseant in mg meclizine HCl
in having an N-m- the prevention should be taken 1
methylbenzyl and treatment of hour prior • Vertigo:
group in place of motion sickness 25 to 100 mg daily
the N-methyl and in the in divided doses.
group. treatment of
nausea and
vomiting
associated with
vertigo.
Pheniramine Is a white PROPYLA 2-[-[2- Trimeton This drug is the least
Maleate crystalline powder, MINES dimethylamino , Inhiston potent member of
with a faint (MONOA ethyl]benzyl]- the series and is
aminelike odor, MINOPRO pyridine marketed as the
which is soluble in PYL OR bimaleate racemate. The usual
water (1:5) and ALKYLAMI adult dose is 20 to
very soluble in NE 40 mg 3 times daily.
alcohol. DERIVATI It is available in
VES) certain combination
products.
Chlorphenira Is a white PROPYLA ()2-[p-chloro-- Chlor- It has a pKa of 9.2,
mine Maleate crystalline powder MINES [2- Trimeton and an aqueous
that is soluble in (MONOA dimethylamino solution has a pH
water (1:3.4), in MINOPRO )ethyl]benzyl]p between 4 and 5.
alcohol (1:10), and PYL OR yridine Chlorination of
in chloroform ALKYLAMI bimaleate pheniramine in the
(1:10). NE para position of the
DERIVATI phenyl ring
VES) increases potency
10-fold with no
appreciable change
in toxicity.
Dexchlorpheni Is the PROPYLA Dexchlor In vitro and in vivo
ramine dextrorotatory MINES phenira studies of the
Maleate enantiomer of (MONOA mine, enantiomers it
chlorpheniramine. MINOPRO Polarami showed that the
PYL OR ne antihistaminic
ALKYLAMI activity exists
NE predominantly in
DERIVATI the dextro isomer.
VES) the dextro isomer
has the (S)
configuration, which
is superimposable
on the (S)
configuration of the
more active
levorotatory
enantiomer of
carbinoxamine.
Bromphenira Differs from PROPYLA ()2-[p-bromo-- Dimetan Its actions and It has a half-life of
mine Maleate chlorpheniramine MINES [2- e uses are like those 25 hours, which is
and Tannate by the substitution (MONOA (dimethylamin of almost twice that of
of a bromine atom MINOPRO o) chlorpheniramine. chlorpheniramine.
for the chlorine PYL OR ethyl]benzyl]py
atom. ALKYLAMI ridine
NE bimaleate
DERIVATI
VES)
Dexbromphen Like the chlorine PROPYLA
iramine derivative, the MINES
Maleate antihistaminic (MONOA
activity of MINOPRO
brompheniramine PYL OR
exists ALKYLAMI
predominantly in NE
the dextro isomer, DERIVATI
dexbromphenirami VES)
ne maleate (D-
isomer), and is of
comparable
potency.
Pyrrobutamin Is a white PROPYLA (E)-1-[4-(4- Pyronil Clinical studies
e Phosphate crystalline powder MINES chlorophenyl)- indicate that it is
that is soluble to (MONOA 3-phenyl-2- long acting, with a
the extent of 10% MINOPRO butenyl]pyrroli comparatively slow
in warm water. PYL OR dine onset of action. The
Pyrrobutamine was ALKYLAMI diphosphate weak antihistaminic
investigated NE properties of several
originally as the DERIVATI analogs point to the
hydrochloride salt, VES) importance of
but the having a planar
diphosphate was ArCCH-CH2N unit
absorbed more and a pyrrolidino
readily and group as the side
completely. chain tertiary amine.

Triprolidine Is a white PROPYLA (E)-2-[3-(1- Actidil The antihistaminic

Hydrochloride crystalline powder MINES pyrrolidinyl)-1- activity is confined
with a slight, but (MONOA p- mainly to the
unpleasant, odor. It MINOPRO tolylpropenyl]p geometric isomer in
is soluble in water PYL OR yridine which the
and in alcohol, and ALKYLAMI monohydrochl pyrrolidinomethyl
its solutions are NE oride group is trans to the
alkaline to litmus. DERIVATI monohydrate 2-pyridyl group.
VES)
Phenindamine Occurs as a PROPYLA 2,3,4,9- It is most stable in
Tartrate creamy-white MINES tetrahydro-2- the pH range of 3.5
powder, usually (MONOA methyl-9- to 5.0 and is
with a faint odor MINOPRO phenyl-1H- unstable in solutions
and sparingly PYL OR indeno[2, 1-c] of pH 7 or higher.
soluble in water ALKYLAMI pyridine Oxidizing substances
(1:40). A 2% NE bitartrate or heat may cause
aqueous solution DERIVATI isomerization to an
has a pH of about VES) inactive form.
3.5.
Dimethindene Is a white to off- PHENOTHI ()2- [1-[2-[2- Forhistal The principal side
Maleate white crystalline AZINES dimethylamino Maleate effect is some
powder that has a )ethyl]-inden- sedation or
characteristic odor 3- drowsiness. The
and is sparingly yl]ethyl]pyridin antihistaminic
soluble in water. e bimaleate activity resides
This potent (1:1) mainly in the
antihistaminic levorotatory isomer.
agent may be
considered a
derivative of the
unsaturated
propylamines.
Promethazine Occurs as a white PHENOTHI ()10-[2- Phenerga Dosage forms:
Hydrochloride to faint yellow AZINES (dimethylamin n Tablets (12.5, 25,
crystalline powder o)- and 50 mg), oral
that is very soluble propyl]phenot syrup (6.25 mg/5
in water, in hot hiazine mL), rectal
absolute alcohol, monohydrochl suppositories (12.5,
and in chloroform. oride 25, and 50 mg),
Its aqueous injection (25 and 50
 solutions are mg/mL) Usual adult
slightly acid to dose: • Allergy: 25
litmus. mg taken before
retiring; however,
12.5 mg may be
taken before meals
or on retiring, if
necessary.
Trimeprazine Occurs as a white PHENOTHI ()10- [3- Temaril Clinical studies have
Tartrate to off-white AZINES (dimethylamin shown it has a
crystalline powder o)-2- pronounced
that is freely methylpropyl] antipruritic action
soluble in water phenothiazine that may be
and soluble in tartrate unrelated to its
alcohol. Its histamine-
antihistaminic antagonizing
action is reported properties.
to be from 1.5 to 5
times that of
promethazine.
Methdilazine Is a light-tan PHENOTHI 10-[(1-methyl- Tacaryl Methdilazine, as Some local
crystalline powder AZINES 3- the free base, is anesthesia of the
that has a pyrrolidinyl)me used in chewable buccal mucosa may
characteristic odor thyl]phenothia tablets because its be experienced if
and is practically zine low solubility in the tablet is chewed
insoluble in water. water contributes and not swallowed
to its promptly.
tastelessness.
Methdilazine Also occurs as a PHENOTHI Tacaryl The activity is like
Hydrochloride lighttan crystalline AZINES Hydrochlo that of
powder with a ride methdilazine, and
slight characteristic it is administered
odor. The salt is orally for its
freely soluble in antipruritic effect.
water and in
alcohol, however.
Cyproheptadi is slightly soluble in DIBENZOC 4-(5H-dibenzo- Periactin Cyproheptadine Sedation is the most
ne water and sparingly YCLOHEPT [a,d]- possesses both prominent side
Hydrochloride soluble in alcohol. ENES AND cyclohepten-5- antihistamine and effect, and this is
 DIBENZOC ylidine)-1- antiserotonin usually brief,
YCLOHEPT methylpiperidi activity and is disappearing after 3
ANES ne used as an or 4 days of
hydrochloride antipruritic agent. treatment.
sesquihydrate It is indicated for
the treatment of
hypersensitivity
reactions,
perennial, and
seasonal allergic
rhinitis;
vasomotor
rhinitis; allergic
conjunctivitis,
uncomplicated
allergic skin
manifestations of
urticaria and
angioedema;
amelioration of
allergic reactions
to blood or
plasma; and cold
urticaria. It is also
used off-label for
nightmares
associated with
posttraumatic
stress disorder
(PTSD),
prevention of
migraine,
suppression of
vascular
headaches, and
appetite
stimulation.
Azatadine Is a potent, long- DIBENZOC 6,11- Optimine
Maleate. acting YCLOHEPT dihydro11-(l-
antihistaminic with ENES AND methyl-4-
 antiserotonin DIBENZOC piperidylidene)
activity. In early YCLOHEPT -5H-benzo-
testing, azatadine ANES [5,6]cyclo
exhibited more hepta(1,2-
than three times b]pyridine
the potency of maleate (1:2)
chiorpheniramine
in the isolated
guinea pig ileum
screen and more
than seven times
the oral potency of
chlorpheniramine
in protection of
guinea pigs against
a double lethal
dose of
intravenously
administered
histamine

Second-Generation Antihistamines
AGENT DESCRIPTION TYP CHEMICAL NAME OTHER CLASSIFICATIO STRUCTURA Mo EFFECTS/PHARMACOLOGIC OTHER INFO.
E NAME N L FORMULA A AL USE
Fexofenadin piperinyl]butyl-,- ()-4-[1-hydroxy-4-[4- Allegr This
e dimethylbenzeneace (hydroxyldiphenylmethy a compound
Hydrochlorid tic acid (Allegra), l)-1-piperinyl]butyl-,- is marketed
e occurs as a white to dimethylbenzeneacetic as a
off-white crystalline acid racemate
powder that is freely and exists
soluble in methanol as a
and ethanol, slightly zwitterion
soluble in chloroform in aqueous
and water, and media at
insoluble in hexane. physiologic
al pH.
Loratadine Is a white to off- 4-(8-chloro-5, 6-dihydro- Is structurally
white powder 11Hbenzo[5,6]- related to the
insoluble in cyclohepta[1,2-b]pyridin-l 1- antihistamines
water but very ylidene-1-carboxylic acid azatadine and
soluble in ethyl ester cyproheptadine,
acetone, and to some
alcohols, and tricyclic
chloroform. antidepressants.
It differs from
azatadine, in that
a neutral
carbamate group
has replaced the
basic tertiary
amino moiety,
and a phenyl ring
has been
substituted with
a chlorine at
Desloratadine is a white to off- 8-chloro-6,11-dihydro11-(4- Clarinex . It is It is the proposed
white powder piperdinylidene)-5H- indicated for active metabolite
that is slightly benzo[5,6]cyclohepta[1,2- the loratadine and
soluble in water, b]pyridine symptomatic has a very similar
but very soluble relief of receptor binding
in ethanol and pruritus and and safety profile
propylene glycol reduction in (Table 23.2).
the number
and size of
hives in
chronic
idiopathic
urticaria
patients 6
months of
age and
older and for
the relief of
the nasal and
nonnasal
symptoms of
 perennial
allergic
rhinitis (in
patients 6
months of
age and
older) and
seasonal
allergic
rhinitis (in
patients 2
years of age
and older)
Cetirizine is a racemic ()-[2-[4-[(4- Zyrtec Cetirizine is Cetirizine is not
compound chlorophenyl)phenylmethyl] indicated for extensively
available as a -1-piperazinyl]ethoxy]acetic the metabolized, and
white crystalline acid temporary more than 60%
powder thatis relief of of a 10-mg oral
water soluble. runny nose, dose is excreted
Cetirizine is the sneezing, in the urine (60%
primary acid itching of the as unchanged
metabolite of nose or drug) and 10% is
hydroxyzine, throat, recovered in the
resulting from and/or itchy, feces (Table
complete watery eyes 23.3). The drug is
oxidation of the caused by highly protein
primary alcohol hay fever or bound (93%) and
moiety. This other upper has a terminal
compound is respiratory half-life of 8.3
zwitterionic and allergies. It hours.
relatively polar also relieves
and thus does itching
not penetrate or caused by
accumulate in hives
the CNS. (urticaria),
but it will not
prevent hives
or an allergic
skin reaction
from
 occurring.
Levocetirizine Is a white, Levocetirizine Xyzal Its
Dihydrochlorid crystalline Dihydrochloride pharmacokinetics
e powder and is and clearance
water soluble. profile are
essentially the
same as the
racemate,
cetirizine
Acrivastine is a fixed- (E, E)-3-[6-[1-(4- Semprex
combination methylphenyl)- 3-(1-
product of the pyrrolidinyl)-1-propenyl-2-
antihistamine pyridinyl]-2-propenoic acid
acrivastine (8
mg) with the
decongestant
pseudoephedrin
e (60 mg).
Acrivastine is an
odorless, white
to pale cream
crystalline
powder that is
soluble in
chloroform and
alcohol and
slightly soluble in
water

INHIBITION OFHISTAMINE RELEASE:MAST CELL STABILIZER

AGENT DESCRIPTION TYP CHEMICAL NAME OTHER CLASSIFICATI STRUCTUR Mo EFFECTS/PHARMACOLOGI OTHER INFO.
E NAME ON AL A CAL USE
FORMULA
Cromolyn Is a hygroscopic, disodium 1,3- bis(2- Intal Nebulized and aerosol . It is available
Sodium white, hydrated carboxychromon-5-yloxy)- cromolyn has been used as a solution
crystalline powder 2-hydroxypropane for prophylactic for a
that is soluble in management of nebulizer, an
water (1:10). It is bronchial asthma and aerosol spray,
 tasteless at first prevention of exercise- a nasal
but leaves a very induced solution, an
slightly bitter bronchospasm.52 ophthalmic
aftertaste. The pK Cromolyn nasal solution solution, and
of cromolyn is 2. is used for the an oral
prevention and concentrate.
treatment of allergic
rhinitis, and oral
concentrate is used to
treat the histaminic
symptoms of
mastocytosis (diarrhea,
flushing, headaches,
vomiting, urticaria,
abdominal pain, nausea,
and itching). Topical
cromolyn (eye drops) is
used to treat allergic
conjunctivitis and
keratitis. In the
treatment of asthma,
cromolyn efficacy is
manifested by
decreased severity of
clinical symptoms
Nedocromil It was available as disodium 9-ethyl-6, 9- Tilade
Sodium an aerosol in a dihydro-4,6-dioxo-10-
metered-dose propyl-4H-pyrano[3, 2-
inhaler for asthma g]quinoline-2,8-
treatment, and dicarboxylate
currently remains
available as
ophthalmic
solution for the
treatment of
itching associated
with allergic
conjunctivitis. The
inhalation
formulation was
 marketed for
maintenance
therapy in the
management of
patients with mild-
to-moderate
bronchial asthma,
but since has been
withdrawn.
Lodoxamide is a white N-(2-chloro-5-cyano-m- Alomid Lodoxamide is indicated Lodoxamide
Tromethamin crystalline, water- phenylene)dioxamic acid e in the treatment of the is available as
e. soluble powder. ocular disorders a 0.1%
The only including vernal solution, with
significant keratoconjunctivitis, each milliliter
structural vernal conjunctivitis, containing
similarity between and vernal keratitis 1.78 mg of
lodoxamide and lodoxamide
cromolyn and tromethamin
nedocromil is the e equivalent
presence of two to 1 mg of
acidic groups. lodoxamide
Pemirolast is a yellow, water- 9-methyl-3-(1H-tetrazol-5- Alamas Pemirolast is indicated The
Potassium soluble powder. It yl)-4Hpyrido[1, t for the prevention of commercial
Ophthalmic can be considered 2-]pyrimidin-4-one itching of the eye preparation is
Solution. an analog of one potassium. caused by allergic available as a
portion of the conjunctivitis 0.1% sterile
cromolyn ophthalmic
structure in which solution for
the carboxyl group topical
has been replaced administratio
with an isosteric n to the eyes.
tetrazole moiety.
Azelastine is a white ()-4-[(4-chlorophenyl) Optivar The
Hydrochlorid crystalline powder methyl]-2-(hexahydro-l- commercial
e Ophthalmic that is sparingly methyl-1H-azepin-4-yl)-l- preparation is
Solution soluble in water, (2H)- phthalazinone available as a
methanol, and monohydrochloride 0.05% sterile
propylene glycol ophthalmic
and slightly solution for
 soluble in ethanol, topical
octanol, and administratio
glycerine. n to the eyes.
Ketotifen is a fine crystalline 4-(1-methyl-4- Zaditor The solution
fumarate powder. Ketotifen piperidylidene)- contains
is a ketothiophene 4Hbenzo[4,5]cyclohepta[1,2 0.345 mg of
isostere analog of -b]thiophen-10(9H)-one ketotifen
the hydrogen fumarate fumarate,
dibenzocyclohepta which is
ne antihistamines. equivalent to
0.25 mg of
ketotifen. The
solution also
contains the
preservative
benzalkonium
chloride
(0.01%) as
well as
glycerol,
sodium
hydroxide
and/or
hydrochloric
acid (to adjust
pH), and
purified
water. It has a
pH of 4.4 to
5.8 and an
osmolality of
210 to 300
mOsm/kg.
Famotidine, is a white to pale- N-(aminosulfonyl)-3- Pepcid is a
USP yellow crystalline [[[2[(diamnomethylene)ami competitive
compound that is no]-4-thiazolyl]methyl] inhibitor of
very slightly thio]propanimidamide histamine H2-
soluble in water receptors
and practically with a
insoluble in potency
 ethanol. It is a significantly
thiazole bioisotere greater than
of cimetidine that cimetidine. It
contains a inhibits basal
guanidine and nocturnal
substituent that gastric
may mimic the secretion as
imizadole of well as
cimetidine secretion
stimulated by
food and
pentagastrin.
Its current
labeling
indications
are for the
short-term
treatment of
duodenal and
benign gastric
ulcers
Ranitidine, s a white solid, N-[2-[[[5- Zantac Bioavailability
USP which in its (dimethylamino)methyl]-2- of an oral
hydrochloride salt furanyl]methyl]thiol] ethyl]- dose of
form is highly N-methyl-2- nitro-l,1- ranitidine is
soluble in water. It ethenediamine about 50%
is an aminoalkyl and is not
furan derivative significantly
with pKa values of affected by
2.7 (side chain) the presence
and 8.2 of food.66
(dimethylamino). Some
Ranitidine is more antacids may
potent than reduce
cimetidine, but ranitidine
less potent than absorption
famotidine and should
not be taken
within 1 hour
of
 administratio
n of this drug
Nizatidine is an off-white to N-[2-[[[2-(dimethylamino) Axid Nizatidine has
buff crystalline methyl]-4- excellent oral
solid that is thiazolyl]methyl]thio]- bioavailability
soluble in water, ethyl]-N-methyl-2-nitro1,1- (90%). The
alcohol, and ethenediamine effects of
chloroform antacids or
food on its
bioavailability
are not
clinically
significant.66
The
elimination
half-life is 1 to
2 hours. It is
excreted
primarily in
the urine
(90%) and
mostly as
unchanged
drug (60%).
Omeprazole. is a white to off- 5-methoxy-2-(((4- methoxy- Losec Omeprazole
white crystalline 3, 5-dimethyl-2- is an
powder with very pyridinyl)methyl) sulfinyl)- amphoteric
slight solubility in 1Hbenzimidazole compound
water. (pyridine N,
pKa 4.06;
benzimidazol
e N-H, pKa
0.79), and
consistent
with the
proposed
mechanism of
action of the
substituted
benzimidazol
 es, is acid
labile. Hence,
the
omeprazole
product is
formulated as
delayed-
release
capsules
containing
enteric-
coated
granules
Esomeprazol Is the S- S-bis(5-rnethoxy-2-[(S)-[(4- Nexiu The S-isomer
e Magnesium enantiomer of methoxy-3,5-dimethyl2- m of
omeprazole. The pyridinyl)methyl]sulfinyl]- omeprazole
benzimidazole 1H-benzimidazole-l-yl) has slightly
PPIs contain a magnesium trihydrate greater PPI
chiral sulfur atom activity, and
that form an its intrinsic
enantiomeric pair clearance is
that is stable and approximatel
insoluble under y three times
standard lower than
conditions. that of R-
omeprazole
(15 vs. 43
L/min).
Lansoprazole Is a white to 2-[[[3-methyl-4-(2,2,2- Prevaci Lansoprazole
brownish white, trifluoroethoxy)-2- d is a weak
odorless pyridyl]methyl]sulfinyl]-1H- base (pyridine
crystalline powder benzimidazole N, pKa 3.83.)
that is practically and a weak
insoluble in water acid
(benzimidazol
e N-H, pK
0.62). Like
other PPIs,
lansoprazole
is essentially
 a prodrug
that, in the
acidic
biophase of
the parietal
cell, forms an
active
metabolite
that
irreversibly
interacts with
the target
ATPase of the
pump.
Pantoprazole is a white to off- 5-(difluoromethoxy)-2- The
Sodium white crystalline [[3,4-dimethoxy-2-pyridinyl) benzimidazol
powder that is methyl]sulfinyl]-1H- e of this drug
freely soluble in benzimidazole has a weakly
water, very sesquihydrate basic nitrogen
slightly soluble in (pyridine N,
phosphate buffer pKa 3.83) and
at pH 7.4, and an
practically benzimidazol
insoluble in n- e proton (pKa
hexane. 0.11),
facilitating
formulation
as a sodium
salt. The
stability of
compound in
aqueous
solution is pH
dependent;
the rate of
degradation
increases
with
decreasing
Ph.
Rabeprazole is a white to 2[[[4-(3- methoxypropoxy)- Aciphe Rabeprazole
Sodium slightly yellowish 3-methyl-2- x is a weak
white solid. It is pyridinyl]methyl]sulfinyl]- base (pyridine
very soluble in 1H-benzimidazole sodium N, pKa 4.53)
water and salt and a weak
methanol, freely acid
soluble in ethanol, (benzimidazol
chloroform, and e N-H, pKa
ethyl acetate, and 0.62),
insoluble in ether faciliting
and hexane. sodium salt
formation.
Sucralfate is the aluminum 3,4,5,6-tetra- Carafat Sucralfate is
hydroxide (polyhydroxyaluminum)--D- e minimally
complex of the glucopyranosyl sulfate- absorbed
octasulfate ester 2,3,4,5-tetra- from the GI
of sucrose. It is (polyhydroxyaluminum)--D- tract by
practically fructofuranoside sulfate design, and
insoluble in water thus exerts its
and soluble in antiulcer
strong acids and effect
bases. It has a pKa through local
value between rather than
0.43 and 1.19. systemic
action
Misoprostol is a semisynthetic ()-methyl 11, 16-dihydroxy- Misoprostol
derivative of PGE1 16-methyl-9-oxoprost-13E- exhibits both
that derives some en-1-oate, antisecretory
pharmacological and
selectivity as well cytoprotectan
as enhanced t effects
biostability from characteristic
its 16-methyl, 16- of the natural
hydroxy prostaglandin
substitutions. s and has a
therapeuticall
y acceptable
biodis
position
profile