Ojima I. (ed.) Fluorine in Medicinal Chemistry and Chemical Biology

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 583

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

34

H

36

F

3

NO

13

Antineoplastic agent

Intravescial

solution

56124 - 62 - 0

Sept. 1998/

Indevus Pharms

C

16

H

14

F

3

N

5

O Antifungal agent

Oral suspension

and tablet

Injectable

137234 - 62 - 9

May 2002/

Pﬁ zer

Section 2. Fluorine - containing Drugs

for Veterinary Use Approved by FDA

in the United States

Fluorine in Medicinal Chemistry and Chemical Biology Edited by Iwao Ojima

586 Fluorine in Medicinal Chemistry and Chemical Biology

Active

ingredient/

trade name

Chemical name Structure

Azaperone/

Stresnil

1 - (4 - ﬂ uorophenyl) - 4 - (4 - pyridin - 2 -

ylpiperazin - 1 - yl)butan - 1 - one

N

O

F

Betamethasone

Acetate/

Betavet

Soluspan

Gentocin

Duraﬁ lm

[2 - [(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 S ,17 R ) -

9 - ﬂ uoro - 11,17 - dihydroxy - 10,13,16 -

trimethyl - 3 - oxo - 6,7,8,11,12,14,15,16 -

octahydrocyclopenta[ a ]phenanthren -

17 - yl] - 2 - oxoethyl] acetate

O

HO

H

O

OH

F

Betamethasone

Dipropionate/

Betasone

[(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 S ,17 R ) - 9 -

ﬂ uoro - 11 - hydroxy - 10,13,16 -

trimethyl - 3 - oxo - 17 - (2 -

propanoyloxyacetyl) - 6,7,8,11,

12,14,15,16 - octahydrocyclopenta[ a ]

phenanthren - 17 - yl] propanoate

O

HO

H

O

F

O

Betamethasone

Sodium

Phosphate/

Betavet

Soluspan

Betasone

[2 - [(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 S ,17 R ) - 9 -

ﬂ uoro - 11,17 - dihydroxy - 10,13,16 -

trimethyl - 3 - oxo - 6,7,8,11,12,14,15,

16 - octahydrocyclopenta[ a ]

phenanthren - 17 - yl] - 2 - oxoethyl]

phosphate

O

HO

H

O

P

O

OH

F

O

Na

Betamethasone

Valerate/

Gentocin Otic

Topagen

Otomax

Gentavet

Betagen

Tri - Otic

Vetro - Max

GBC

(1) pregna - 1,4 - diene - 3,20 - dione, 9 -

ﬂ uoro - 11,21 - dihydroxy - 16 - methyl -

17 - [(1 - oxopentyl)oxy] - , (11 β , 16 β ) - ;

(2) 9 - ﬂ uoro - 11 β ,17,21 - trihydroxy -

16 β - methylpregna - 1,4 - diene - 3,20 -

dione 17 valerate

O

HO

H

OH

O

F

O

Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 587

Formula Pharmaceutical

action

Dosage form

(species)

CAS No. Approval date /

drug sponsor

C

19

H

22

FN

3

O

Sedative

Tranquilizer

Injectable

(Swine)

1649 - 18 - 9

Oct. 1983/

Schering - Plough

Animal Health

Corp.

C

24

H

31

FO

6

Bronchodilator

agent

Glucocorticoid

Injectable

(Horse)

Ophthalmic

drops

(Dog)

987 - 24 - 6

Prior to 1989/

Schering - Plough

Animal Health

Corp.

C

28

H

37

FO

7

Anti - inﬂ ammatory

agent

Glucocorticoid

Injectable

(Horse, Dog)

5593 - 20 - 4

Prior to 1989/

Schering - Plough

Animal Health

Corp.

C

22

H

28

FNa

2

O

8

P Glucocorticoid

Injectable

(Horse, Dog)

151 - 73 - 5

Prior to 1989/

Schering - Plough

Animal Health

Corp.

C

27

H

37

FO

6

Glucocorticoid

Topical spray,

liquid, and

ointment

(Dog, Cat)

2152 - 44 - 5

Prior to 1989 /

Schering - Plough

Animal Health

Corporation

Med - Pharmex, Inc.

Altana, Inc.

IVA Animal Health

First Priority

588 Fluorine in Medicinal Chemistry and Chemical Biology

Active

ingredient/

trade name

Chemical name Structure

Danoﬂ oxacin

Mesylate/

A180

1 - cyclopropyl - 6 - ﬂ uoro - 7 - [(1 S ,4 S ) - 3 -

methyl - 3,6 - diazabicyclo[2.2.1]

heptan - 6 - yl] - 4 - oxoquinoline - 3 -

carboxylic acid; methanesulfonic

acid

N

HO

F

N

O

H

O

S

O

OH

Deracoxib/

Dermaxx

4 - [3 - (diﬂ uoromethyl) - 5 - (3 - ﬂ uoro - 4 -

methoxyphenyl)pyrazol - 1 - yl]

benzenesulfonamide

N

F

O

F

S

NH

2

O

Dexamethasone

Sodium

Phosphate/

Dex - A - Vet

Dexium - SP

[2 - [(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 R ,17 R ) -

9 - ﬂ uoro - 11,17 - dihydroxy - 10,13,16 -

trimethyl - 3 - oxo - 6,7,8,11,12,14,15,16 -

octahydrocyclopenta[ a ]phenanthren -

17 - yl] - 2 - oxoethyl] phosphate

O

HO

H

F

H

HO

O

P

O

Na

Dexamethasone/

Azium

Naquasone

Tresaderm

Dexium

Dexameth - A - Vet

Pet Derm

Zonometh

Dexachel

Dexium

9 - ﬂ uoro - 11 β ,17,21 -

trihydroxy - 16 α - methylpregna - 1,4 -

diene - 3,20 - dione

(8 S ,9 R ,10 S ,11 S ,

13 S ,14 S ,16 R ,17 R ) - 9 - ﬂ uoro - 11,17 -

dihydroxy - 17 - (2 - hydroxyacetyl) -

10,13,16 - trimethyl - 6,7,8,11,12,14,

15,16 - octahydrocyclopenta[ a ]

phenanthren - 3 - one

O

HO

H

F

H

HO

OH

O

Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 589

Formula Pharmaceutical

action

Dosage form

(species)

CAS No. Approval date /

drug sponsor

C

20

H

24

FN

3

O

6

S Anti - bacterial agent

Injectable

(Cattle)

119478 - 55 - 6

Sept. 2002/

Pﬁ zer, Inc.

C

17

H

14

F

3

N

3

O

3

S

Anti -

inﬂ ammatory

Analgesic

Oral tablet

(Dog)

169590 - 41 - 4

Aug. 2002/

Novartis Animal

Health US, Inc.

C

22

H

28

FNaO

8

P

Anti -

inﬂ ammatory

Glucocorticoid

Injectable

(Dog, Horse)

1869 - 92 - 7

April 2004/

Cross Vetpharm

Group Ltd.

Watson

Laboratories,

Inc.

IVX Animal Health

C

22

H

29

FO

5

Anti - inﬂ ammatory

Antiemetics

Antineoplastic

agent

Hormonal

Glucocorticoid

Oral Tablet

and liquid

Injectable

Bolus

Topical liquid

(Dog, Cat,

Cattle,

Horse)

50 - 02 - 2

April 1995/

Schering - Plough

Animal Health

Corp.

Merial Ltd.

Cross Vetpharm

Group Ltd.

Pﬁ zer

IVX Animal Health

Sparhawk

Laboratories,

Inc.

590 Fluorine in Medicinal Chemistry and Chemical Biology

Active

ingredient/

trade name

Chemical name Structure

Dexamethasone -

21 -

isonicotinate/

Voren

[2 - [(8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 R ,17 R ) -

9 - ﬂ uoro - 11,17 - dihydroxy - 10,13,16 -

trimethyl - 3 - oxo - 6,7,8,11,12,14,15,16 -

octahydrocyclopenta[ a ]phenanthren -

17 - yl] - 2 - oxoethyl] pyridine - 4 -

carboxylate

O

HO

H

F

H

OH

O

N

O

Diﬂ oxacin

Hydrochloride/

Dicural

6 - ﬂ uoro - 1 - (4 - ﬂ uorophenyl) - 7 - (4 -

methylpiperazin - 1 - yl) - 4 -

oxoquinoline - 3 - carboxylic acid

hydrochloride

N

HO

F

N

O

HCl

O

N

F

Dirlotapide/

Slentrol

1 - methyl - N - [(1 S ) - 2 - (methyl -

(phenylmethyl)amino) - 2 - oxo - 1 -

phenylethyl] - 5 - [[2 - [4 -

(triﬂ uoromethyl)phenyl]benzoyl]

amino]indole - 2 - carboxamide

F

3

C

NH

O

N

OHN

N

O

Droperidol/

Innovar - Vet

3 - [1 - [4 - (4 - ﬂ uorophenyl) - 4 - oxobutyl] -

3,6 - dihydro - 2 H - pyridin - 4 - yl] -

1 H - benzimidazol - 2 - one

N

H

N

O

N

O

F

Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 591

Formula Pharmaceutical

action

Dosage form

(species)

CAS No. Approval date /

drug sponsor

C

28

H

32

FNO

6

Anti - inﬂ ammatory

Anti - allergic

Glucocorticoid

Injectable

(Dog, Cat,

Horse)

2265 - 64 - 7

Prior to 1989/

Boehringer

Ingelheim

Vetmedica, Inc.

C

21

H

20

ClF

2

N

3

O

3

Antibacterial agent

Oral tablet

(Dog) 91296 - 86 - 5

Nov. 1997/

Fort Dodge Animal

Health, Division

of Wyeth

C

40

H

33

F

3

N

4

O

3

Anti - obesity agent

Oral liquid

(Dog)

481658 - 94 - 0

Dec. 2006/

Pﬁ zer, Inc.

C

22

H

22

FN

3

O

2

Anesthetic

Tranquilizer

Injectable

(Dog)

548 - 73 - 2

Prior to 1982/

Schering - Plough

Animal Health

Corp.

592 Fluorine in Medicinal Chemistry and Chemical Biology

Active

ingredient/

trade name

Chemical name Structure

Enroﬂ oxacin/

Baytril

1 - cyclopropyl - 7 - (4 - ethylpiperazin - 1 -

yl) - 6 - ﬂ uoro - 4 - oxoquinoline - 3 -

carboxylic acid

N

HO

F

N

O

N

Florfenicol/

Nuﬂ or

Aquaﬂ or

2,2 - dichloro - N - [(1 R ,2 S ) - 3 - ﬂ uoro - 1 -

hydroxy - 1 - (4 - methylsulfonylphenyl)

propan - 2 - yl]acetamide

S

FHO

HN

Cl Cl

O

OO

Flumethasone

Acetate/

Fluosmin

[(6 S ,9 R ,11 S ,14 S ,16 R ,17 R ) - 6,9 -

diﬂ uoro - 11 - hydroxy - 17 - (2 -

hydroxyacetyl) - 10,13,16 - trimethyl -

3 - oxo - 6,7,8,11,12,14,15,16 -

octahydrocyclopenta[ a ]phenanthren -

17 - yl] acetate

F

OH

O

HO

F

O

H

O

Flumethasone/

Flucort

Anaprime

Fluosmin

Anaprime

Toptic

∆

(6 S ,8 S ,9 R ,10 S ,11 S ,13 S ,14 S ,16 R ,17 R ) -

6,9 - diﬂ uoro - 11,17 - dihydroxy - 17 -

(2 - hydroxyacetyl) - 10,13,16 - trimethyl -

6,7,8,11,12,14,15,16 -

octahydrocyclopenta[ a ]

phenanthren - 3 - one

F

OH

O

HO

F

OH

H

Flunixin

Meglumine/

Banamine

Flunazine

(2 R ,3 R ,4 R ,5 S ) - 6 - methylaminohexane -

1,2,3,4,5 - pentol; 2 - [[2 - methyl - 3 -

(triﬂ uoromethyl)phenyl]amino]

pyridine - 3 - carboxylic acid

F

HN

N

OH

O

H

N

OH

Fluorine-containing Drugs for Veterinary Use Approved by FDA in the United States 593

Formula Pharmaceutical

action

Dosage form

(species)

CAS No. Approval date /

drug sponsor

C

19

H

22

FN

3

O

3

Antibacterial agent

Oral tablet

Topical liquid

Injectable

(Dog, Cat,

Cattle)

93106 - 60 - 6

Dec. 1988/

Mobay

Corporation

Bayer Healthcare

LLC, Animal

Health Division

C

12

H

14

Cl

2

FNO

4

S Antibacterial agent

Injectable

Oral tablet

(Cattle, Swine)

73231 - 34 - 2

May 1996/

Schering - Plough

Animal Health

Corp.

C

24

H

30

F

2

O

6

Glucocorticoid

Injectable

(Dog)

2823 - 42 - 9

Prior to 1982/

Fort Dodge Animal

Health, Division

of Wyeth

C

22

H

28

F

2

O

5

Anti -

inﬂ ammatory

Glucocorticoid

Injectable

Oral tablet

Liquid

(Ophthalmic)

(Dog, Cat, Horse)

2135 - 17 - 3

Prior to 1982/

Fort Dodge Animal

Health, Division

of Wyeth

Elanco Animal

Health, A

Division of Eli

Lilly & Co.

∆

C

21

H

28

F

3

N

3

O

7

Anti -

inﬂ ammatory

Analgesic

Antipyretic

Injectable

Oral granules

and paste

(Cattle, Horse)

42461 - 84 - 7

May 1998/

Schering - Plough

Animal Health

Corp.

Agri Laboratories,

Ltd,

Fort Dodge Animal

Health, Division

of Wyeth

IVX Animal Health

Norbrook

Laboratories Ltd.

Ojima I. (ed.) Fluorine in Medicinal Chemistry and Chemical Biology

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