Ojima I. (ed.) Fluorine in Medicinal Chemistry and Chemical Biology
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594 Fluorine in Medicinal Chemistry and Chemical Biology
Active
ingredient/
trade name
Chemical name Structure
Fluocinolone
Acetonide/
Neo - synalar
Synalar
Synotic
Synsac
(6 α ,11 β ,16 α ) - 6,9 -
difl uoro - 11,21 - dihydroxy - 16,17[(1 -
methylethylidene)bis(oxy)] - pregna -
1,4 - diene - 3,20 - dione
O
H
OH
H
H
O
O
F
F H
H
O
OH
Fluoxetine
Hydrochloride/
Reconcile
N - methyl - 3 - phenyl - 3 - [4 - (trifl uo
romethyl)phenoxy]propan - 1 - amine
hydrochloride
F
F
O
HN
F
H Cl
Fluprostenol
Sodium/
Equimate
sodium ( E ) - 7 - [(1 S ,3 S ,5 R ) - 3,5 -
dihydroxy - 2 - [( E ,3 S ) - 3 - hydroxy - 4 -
[3 - (trifl uoromethyl)phenoxy]but - 1 -
enyl]cyclopentyl]hept - 5 - enoate,
O
F
F
F
OH
HO
O
O
HO
Na
sodium ( Z ) - 7 - [(1 R ,2 R ,3 R ,5 S ) - 3,5 -
dihydroxy - 2 - [( E ,3 R ) - 3 - hydroxy - 4 -
[3 - (trifl uoromethyl)phenoxy]but - 1 -
enyl]cyclopentyl]hept - 5 - enoate
O
F
F
F
OH
HO
O
O
HO
Na
Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 595
Formula Pharmaceutical
action
Dosage form
(species)
CAS No. Approval date /
drug sponsor
C
24
H
30
F
2
O
6
Anti -
infl ammatory
Glucocorticoid
Antipruritic
Vasoconstrictive
agent
Topical liquid
and cream
(Dog, Cat)
67 - 73 - 2
Prior to 1982/
Medicis
Dermatologics,
Inc.
Fort Dodge Animal
Health, Division
of Wyeth
C
17
H
19
ClF
3
NO
Serotonin uptake
inhibitors
Antidepressive
agents
Oral tablet
(Dog)
59333 - 67 - 4
Jan. 2007/
Elanco Animal
Health, A
Division of Eli
Lilly & Co.
C
23
H
28
F
3
NaO
6
Luteolytic agents
Estrus
synchronization
agent
Injectable
(Horse)
55028 - 71 - 2
Prior to 1982/
Bayer Healthcare
LLC, Animal
Health Division
596 Fluorine in Medicinal Chemistry and Chemical Biology
Active
ingredient/
trade name
Chemical name Structure
Flurogestone
Acetate/
Synchro - Mate
[(8 S ,9 S ,10 S ,11 S ,13 S ,14 S ,17 R ) - 17 -
acetyl - 9 - fl uoro - 11 - hydroxy - 13,14 -
dimethyl - 3 - oxo - 1,2,6,7,8,10,11,12,
15,16 - decahydrocyclopenta[ a ]
phenanthren - 17 - yl] acetate
O
O
F
H
HO
H
O
O
Halothane/
Fluothane
2 - bromo - 2 - chloro - 1,1,1 - trifl uoroethane
F
F
F
Br
Cl
Isofl upredone
Acetate/
Predef
Neo - Predef
[2 - [(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,17 R ) - 9 -
fl uoro - 11,17 - dihydroxy - 10,13 -
dimethyl - 3 - oxo - 6,7,8,11,12,14,15,16 -
octahydrocyclopenta[ a ]phenanthren -
17 - yl] - 2 - oxoethyl] acetate
O
O
O
O
OH
H
F
H
OH
Isofl urane/
Aerrane
IsoFlo
2 - chloro - 2 - (difl uoromethoxy) -
1,1,1 - trifl uoroethane
O
F
F
F
Cl
F
F
Lufenuron/
Program
Sentinel
Capstar
N - [[2,5 - dichloro - 4 - (1,1,2,3,3,3 -
hexafl uoropropoxy)phenyl]
carbamoyl] - 2,6 - difl uorobenzamide
HN
HN
O
F
F
F
F
F
F
Cl
Cl
F
F
O
O
Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 597
Formula Pharmaceutical
action
Dosage form
(species)
CAS No. Approval date /
drug sponsor
C
23
H
31
FO
5
Estrus
synchronization
agent
Vaginal
sponge
(Sheep)
2529 - 45 - 5
Prior to 1982/
G.D. Searle LLC,
Pharmacia Corp
C
2
HBrClF
3
Anesthetic
Inhalation
Liquid
(Dog, Cat)
151 - 67 - 7
Prior to 1982/
Fort Dodge Animal
Health, Division
of Wyeth
Halocarbon
Laboratories,
Div. of
Halocarbon
Products Corp.
C
23
H
29
FO
6
Anti - infl ammatory
Injectable
Topical
ointment
(Dog, Cat,
Horse,
Cattle,
Swine)
338 - 98 - 7
Prior to 1982/
Pharmacia &
Upjohn Co.
C
3
H
2
ClF
5
O Anesthetic
Inhalation
(Dog, Horse)
26675 - 46 - 7
Jan. 1986/
Abbott
Laboratories
Halocarbon
Laboratories,
Div. of
Halocarbon
Products Corp.
Marsam
Pharmaceuticals,
LLC
Minrad, Inc.
C
17
H
8
Cl
2
F
8
N
2
O
3
Ectoparasiticide
Oral tablet
Injectable
(Dog, Cat)
103055 - 07 - 8
Nov. 1994/
Novartis Animal
Health US, Inc.
598 Fluorine in Medicinal Chemistry and Chemical Biology
Active
ingredient/
trade name
Chemical name Structure
Marbofl oxacin/
Zeniquin
9 - fl uoro - 2,3 - dihydro - 3 - methyl - 10 - (4 -
methyl - piperazino) - 7 - oxo - 7H -
pyrido[1,2,3 - ij][1,2,4]benzoxadiazine -
6 - carboxylic acid
N
O
N
F
N
OH
N
O
O
Methoxyfl urane/
Metofane
2,2 - dichloro - 1,1 - difl uoro - 1 -
methoxyethane
O
Cl
Cl
F
F
Orbifl oxacin/
Orbax
1 - cyclopropyl - 7 - [(3 R ,5 S ) - 3,5 -
dimethylpiperazin - 1 - yl] - 5,6,8 -
trifl uoro - 4 - oxoquinoline - 3 - carboxylic
acid
N
O
OH
O
F
F
N
HN
F
Ponazuril/
Marquis
1 - methyl - 3 - [3 - methyl - 4 - [4 -
(trifl uoromethylsulfonyl)phenoxy]
phenyl] - 1,3,5 - triazinane - 2,4,6 - trione
N
N
NH
OO
O
O
S
O
CF
3
O
Romifi dine
Hydrochloride/
Sedivet
N - (2 - bromo - 6 - fl uorophenyl) - 4,5 -
dihydro - 1 H - imidazol - 2 - amine
hydrochloride
F
N
HN
HN
Br
• HCl
Sarafl oxacin
Hydrochloride/
SaraFlox
∆
6 - fl uoro - 1 - (4 - fl uorophenyl) - 4 - oxo - 7 -
piperazin - 1 - ylquinoline - 3 - carboxylic
acid hydrochloride
• HCl
N
F
O
FN
HN
HO
O
Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 599
Formula Pharmaceutical
action
Dosage form
(species)
CAS No. Approval date /
drug sponsor
C
17
H
19
FN
4
O
4
Antibacterial agent
Oral tablet
(Cat)
115550 - 35 - 1
June 1999/
Pfi zer, Inc.
C
3
H
4
Cl
2
F
2
O Anesthetic
Inhalation
(Dog, Cat,
Horse,
Swine,
Sheep,
Psittacines)
76 - 38 - 0
Prior to 1982/
Schering - Plough
Animal Health
Corp.
C
19
H
20
F
3
N
3
O
3
Antibacterial agent
Oral tablet
(Dog, Cat)
113617 - 63
April 1997/
Schering - Plough
Animal Health
Corp.
C
18
H
14
F
3
N
3
O
6
S
Antiprotozoal to
Sarcocystis
neurona .
Paste
(Horse)
69004 - 04 - 2
July 2001/
Bayer Healthcare
LLC, Animal
Health Division
C
9
H
9
BrFN
3
· HCl
Adrenergic
alpha - agonist
Anesthetic
Intravenous
(Horse)
65896 - 14 - 2
June 2004/
Boehringer
Ingelheim
Vetmedica, Inc.
C
20
H
17
F
2
N
3
O
3
⋅
HCl
Antibacterial agent
Oral Powder
Injection
(Embryonated
broiler eggs,
Chicken,
Turkey)
91296 - 87 - 6
Aug. 1995/
Abbott
Laboratories
600 Fluorine in Medicinal Chemistry and Chemical Biology
Active
ingredient/
trade name
Chemical name Structure
Sevofl urane/
SevoFlo
1,1,1,3,3,3 - hexafl uoro - 2 -
(fl uoromethoxy)
propane
CF
3
F
3
C
O
F
Ticarbodine/
Tribodine
∆
2,6 - dimethyl - N - [3 - (trifl uoromethyl)
phenyl]piperidine - 1 -
carbothioamide
N
S
HN
F
3
C
Triamcinolone
Acetonide/
Vetalog
Panolog
Neo - Aristovet
∆
Derma - Vet
Panavet
Animax
Derma 4
Derm - Otic
∆
Genesis
Medalon
Animax
pregna - 1,4 - diene - 3,20 - dione,
9 - fl uoro - 11,21 - dihydroxy - 16,17 -
[(1 - methylethylidene)bis(oxy)] - ,
(11.beta.,16.alpha.) -
O
O
O
HO
H
F
H
O
HO
Triamcinolone/
Aristova
∆
9 - fl uoro - 11,16,17 - trihydroxy - 17 - (2 -
hydroxyacetyl) - 10,13 - dimethyl -
6,7,8,9,10,11,12,13,14,15,16,17 -
dodecahydrocyclopenta[ a ]
phenanthren - 3 - one
OH
OH
O
HO
H
F
H
O
HO
Trifl uomeprazine
Maleate/
Nortran
∆
N,N , β - trimethyl - 2 - (trifl uoromethyl) -
10 H - phenothiazine - 10 - propiamine
maleate
S
N
CF
3
N
OH
O
OHO
Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 601
Formula Pharmaceutical
action
Dosage form
(species)
CAS No. Approval date /
drug sponsor
C
4
H
3
F
7
O Anesthetic
Liquid
inhalant
(Dog)
28523 - 86 - 6
Nov. 1999/
Abbott
Laboratories
C
15
H
19
F
3
N
2
S Anthelmintic
Oral tablet
(Dog)
31932 - 09 - 9
Prior to 1982/
Elanco Animal
Health, A
Division of Eli
Lilly & Co.
C
24
H
31
FO
6
Anti - infl ammatory
agent
Glucocorticoid
Immunosuppressive
agent
Injectable
Ointment
Oral tablet
and
suspension
Topical spray
(Dog, Cat,
Horse)
76 - 25 - 5
Prior to 1982/
Fort Dodge Animal
Health, Division
of Wyeth
Holdings Corp.
Bayer Healthcare
LLC, Animal
Health Division
Boehringer
Ingelheim
Vetmedica, Inc.
Med - Pharmex, Inc.
Altana, Inc.
Pfi zer, Inc.
Biocraft
Laboratories,
Inc.
RMS Laboratories,
Inc.
C
21
H
27
FO
6
Anti - infl ammatory
agent
Glucocorticoid
Oral tablet
Injectable
124 - 94 - 7
Prior to 1982/
Bayer Healthcare
LLC, Animal
Health Division
C
19
H
21
F
3
N
2
S ⋅
C
4
H
4
O
4
Tranquilizer Oral tablet 71609 - 19 - 3
Prior to 1982/
Norden
Laboratories,
Inc.
602 Fluorine in Medicinal Chemistry and Chemical Biology
Active
ingredient/
trade name
Chemical name Structure
Trifl upromazine
Hydrochloride/
Vetame
N,N - dimethyl - 3 - [2 - (trifl uoromethyl)phe
nothiazin - 10 - yl]propan - 1 - amine
hydrochloride
S
N
CF
3
N
• HCl
Zolazepam
Hydrochloride/
Telazol
4 - (2 - fl uorophenyl) - 1,3,8 - trimethyl - 6H -
pyrazolo[4,5 - f ][1,4]diazepin - 7 - one
hydrochloride
N
N
N
N
O
F
• HCl
∆
Withdrawn.
Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 603
Formula Pharmaceutical
action
Dosage form
(species)
CAS No. Approval date /
drug sponsor
C
18
H
20
ClF
3
N
2
S
Antianxiety
Tranquilizer
Antiemetic
Injectable
Oral tablet
(Dog, Cat
Horse)
1098 - 60 - 8
Prior to 1982/
Fort Dodge Animal
Health, Division
of Wyeth
Holdings Corp.
C
15
H
16
ClFN
4
O Anesthetic
Injectable
(Dog, Cat)
33754 - 49 - 3
April 1982/
Fort Dodge Animal
Health, Division
of Wyeth