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

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 543

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

8

H

10

FN

3

O

3

S

Antiviral agent

Anti - HIV

Reverse transcriptase

inhibitor

Oral capsule,

tablet, solution

143491 - 57 - 0

July 2003/

Gilead

C

3

H

2

ClF

5

O Anesthetic Inhalation 13838 - 16 - 9

Aug. 1972/

Baxter Hlthcare

Corp.

Abbott

∆

Minrad

C

15

H

17

FN

4

O

3

Anti - infective agent Oral tablet 74011 - 58 - 8

Dec. 1991/

Sanoﬁ Aventis US

C

20

H

21

FN

2

O

⋅ C

2

H

2

O

4

Serotonin uptake

inhibitor

Antidepressant

Oral tablet,

capsule, and

solution

219861 - 08 - 2

Aug. 2002/

Forest Labs

IVAX Pharms

Alphapharm

C

24

H

21

F

2

NO

3

Antilipemic Oral tablet 163222 - 33 - 1

Oct. 2002/

MSP Singapore

C

17

H

20

F

6

N

2

O

3

.

C

2

H

4

O

2

Anti - arrhythmia agent Oral tablet 54143 - 56 - 5

Oct. 1985/

Graceway

Alphapharm

Barr

Ranbaxy

Roxane

Sandoz

C

9

H

11

FN

2

O

5

Antineoplastic

Antiviral

Injectable 50 - 91 - 9

Dec. 1970/

Hospira

Bedford

Abraxis Pharm

544 Fluorine in Medicinal Chemistry and Chemical Biology

Active ingredient/

trade name

Chemical name Structure

Fluconazole/

Diﬂ ucan

2,4 - diﬂ uoro - α , α

1

- bis( 1H -

1,2,4 - triazol - 1 - ylmethyl)

N

OH

N

F

N

Flucytosine/

Ancobon

5 - ﬂ uorocytosine

N

H

N

O

NH

2

F

Fludarabine Phosphate/

Fludara

9 H - purin - 6 - amine, 2 - ﬂ uoro - 9 -

(5 - 0 - phosphono - β -

D -

arabinofuranosyl)

(2 - ﬂ uoro - ara - AMP)

N

F

NH

2

O

OH

O

P

HO

O

OH

Fludeoxyglucose F - 18

(2 S ,3 R ,4 S ,5 S ,6 R ) - 3 - ﬂ uoro -

6 - (hydroxymethyl)oxane -

2,4,5 - triol

O

18

F

H

OH

H

OH

CH

2

OH

H

OH

Fludrocortisone Acetate/

Flornef

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

9 - ﬂ uoro - 11,17 - dihydroxy -

10,13 - dimethyl - 3 - oxo -

1,2,6,7,8,11,12,

14,15,16 -

decahydrocyclopenta[a]

phenanthren - 17 - yl] - 2 - oxo -

ethyl] acetate

O

F

HO

H

OH

O

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 545

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

13

H

12

F

2

N

6

O Antifungal agents

Oral tablet and

suspension

Injectable

86386 - 73 - 4

Jan. 1990/Pﬁ zer

IVAX Pharms

Ranbaxy

Roxane

Taro Pharm Inds

Abraxis Pharm

Apotex

Baxter Hlthcare

Bedford

Hikma

Farmaceutica

Hospira

Teva Parenteral

Dr Reddys Lab

Inc.

Genpharm

Glenmark Pharma

Mylan

Pliva

Sandoz

Torpharm

Unique Pharm

Labs

Teva

Taro

C

4

H

4

FN

3

O Antifungal agent Oral capsule 2022 - 85 - 7

Nov. 1971/

Valeant

C

10

H

13

FN

5

O

7

P

Antineoplastic

Antimetabolite

Immunosuppressive

agent

Injectable 75607 - 67 - 9

April 1991/

Bayer Hlthc

Hospira

Teva Parenteral

C

6

H

11

18

FO

5

Diagnostic aid Injectable 105851 - 17 - 0

Aug. 2004/

Weill Medcl Coll

North Shore LIJ

C

23

H

31

FO

6

Mineralocorticoid Oral tablet 514 - 36 - 3

Aug. 1955/

King Pharms

546 Fluorine in Medicinal Chemistry and Chemical Biology

Active ingredient/

trade name

Chemical name Structure

Flumazenil/

Romazicon

ethyl 8 - ﬂ uoro - 5,6 - dihydro - 5 -

methyl - 6 - oxo - 4 H - imidazo

[1,5 - a ](1,4) benzodiazepine -

3 - carboxylate

N

F

CO

2

C

2

H

5

O

Flumethasone Pivalate

∆

/

Locorten

[2 - [(6 S ,9 R ,11 S ,14 S ,16 R ,17 R ) -

6,9 - diﬂ 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] 2,2 -

dimethylpropanoate

F

O

HO

H

F

H

OH

Flunisolide/

Aerospan

Aerobid

Nararel

(6 α ,11 β ,16 α ) - 6 - ﬂ uoro - 11,21 -

dihydroxy - 16,17 - [(1 - methyle

thylidene)bis(oxy)]pregna -

1,4 - diene - 3,20 - dione

O

OH

H

O

OH

F

O

Fluocinolone Acetonide * /

Synalar

Retisert

Derma - Smoothe

FS Shampoo

Tri - Luma

(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

HO

H

F

O

HO

Fluocinonide/

Lidex

6 α ,9 α - diﬂ uoro - 11 β ,21 -

dihydroxy - 16 α ,17 α -

isopropylidenedioxypregna -

1,4 - diene - 3,20 - dione

21 - acetate

O

HO

F

O

Fluorometholone Acetate/

Flarex

Tobrasone

9 - ﬂ uoro - 11 β ,17 - dihydroxy -

6 α - methylpregna - 1,

4 - diene - 3,20 - dione

17 - acetate

O

HO

F

O

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 547

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

15

H

14

FN

3

O

3

Benzodiazepine

antagonist

Injectable 78755 - 81 - 4

Dec. 1991/

Bedford Labs

Abraxis Pharm

Apotex Inc.

Baxter Hlthcare

HLR

Sandoz

Teva Parental

C

27

H

36

F

2

O

6

Anti - inﬂ ammatory

Glucocorticoid

Antipruritic

Topical cream 2002 - 29 - 1

Prior to 1982/

Novartis

C

24

H

31

FO

6

Anti - inﬂ ammatory

Anti - asthmatic

Glucocorticoid

Nasal spray 3385 - 03 - 3

Aug. 1984/

Forest Labs

Roche Palo

Apotex Inc.

IVAX Res LLC

Bausch and Lomb

C

24

H

30

F

2

O

6

Anti - inﬂ ammatory

Anti - asthmatic agent

Glucocorticoid

Topical cream

and solution

Otic drops

Intravitreal

implant

67 - 73 - 2

April 1982/

Fougera

G and W Labs

Medics

Taro

Bausch and Lomb

Hill Dermac

Galderma Labs LP

C

26

H

32

F

2

O

7

Anti - inﬂ ammatory

Antipruritic

Glucocorticoid

Topical cream

and solution

Otic drops

Intravitreal

implant

356 - 12 - 7

April 1984/

Fougera

G and W Labs

Medicis

Taro

Bausch and Lomb

Hill Dermac

Galderma Labs LP

C

24

H

31

FO

5

Glucocorticoid Ophthalmic drops 3801 - 06 - 7

Feb. 1986/

Alcon

548 Fluorine in Medicinal Chemistry and Chemical Biology

Active ingredient/

trade name

Chemical name Structure

Fluorometholone/

FML

Fluor - Op

9 - ﬂ uoro - 11 β , 7 - dihydroxy -

6 α - methylpregna - 1,4 - diene -

3,20 - dione

O

HO

F

OH

O

Fluorouracil/

Fluoroplex

Carac

Efudex

5 - ﬂ uoro - 2,4 (1 H ,3 H ) -

pyrimdinedione

N

H

NH

F

O

Fluoxetine Hydrochloride/

Prozac

Sarafem

Symbax

N - methyl - 3 - phenyl - 3 - [4 - (triﬂ uo

romethyl)phenoxy]propan - 1 -

amine hydrochloride

F

O

HN

F

H Cl

Fluoxymesterone/

Halotestin

9 - ﬂ uoro - 11,17 - dihydroxy -

10,13,17 - trimethyl - 1,2,6,7,8,

11,12,14,15,16 -

decahydrocyclopenta[ a ]

phenanthren - 3 - one

O

F

H

OH

H

HO

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 549

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

22

H

29

FO

4

Anti - inﬂ ammatory

Glucocorticoid

Ophthalmic drops

and ointment

426 - 13 - 1

July 1982/

Allergan

Novartis

C

4

H

3

FN

2

O

2

Antineoplastic

Antimetabolite

Immunosuppressive

agent

Topical solution

and cream

Injectable

51 - 21 - 8

Sept. 1998/

Abraxis Pharm

Allergan Herbert

Sanoﬁ Aventis US

Valeant Pharm Intl

Generamedix

Teva Parenteral

Valeant

Taro

Valeant Pharm

Intl.

C

17

H

18

F

3

NO ⋅ HCl

Antidepressant agent

Serotonin uptake

inhibitor

Oral tablet,

capsule, and

solution

56296 - 78 - 7

Dec. 1987/Barr

Lilly

Alphapharm

Carlsbad

Dr Reddys Lab

Ltd.

IVAX Pharms

Mallinckrodt

Mylan

Par Pharm

Pliva

Ranbaxy

Rxelite

Sandoz

Teva

Actavis Mid

Atlanitc

Hi Tech Pharma

Mallinckrodt

Morton Grove

Novex

Pharm Assoc.

Silarx

Warner Chilcott

C

20

H

29

FO

3

Anabolic agent

Antineoplastic agents

Androgen

Oral tablet 76 - 43 - 7

Prior to 1982/

USL Pharma

Pharmacia and

Upjohn

550 Fluorine in Medicinal Chemistry and Chemical Biology

Active ingredient/

trade name

Chemical name Structure

Fluphenazine Decanoate

4 - [3 - [2 - (triﬂ uoromethyl)10 H -

phenothiazin - 10 - yl]propyl] -

1 - piperazineethanol

decanoate

S

N

CF

3

N

O

H

3

C(H

2

C)

8

O

Fluphenazine Enanthate

∆

/

Prolixin Enanthate

2 - [4 - [3 - [2 - (triﬂ uoromethyl)

phenothiazin - 10 -

yl]propyl]piperazin - 1 -

yl]ethyl heptanoate

S

N

F

N

O

Fluphenazine Hydrochloride

2 - [4 - [3 - [2 - (triﬂ uoromethyl)

phenothiazin - 10 -

yl]propyl]piperazin - 1 -

yl]ethanol dihydrochloride

S

N

CF

3

N

HO

2HCl

Fluprednisolone

∆

/

Alphadrol

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

6 - ﬂ uoro - 11,17 - dihydroxy - 17 -

(2 - hydroxyacetyl) - 10,13 -

dimethyl - 7,8,9,11,12,14,15,

16 - octahydro - 6 H - cyclope

nta[ a ]phenanthren - 3 - one

F

OH

O

H

HO

H

OH

Flurandrenolide/

Cordran

(6 α ,11 β ,16 α ) - 6 - ﬂ uoro - 11,21 -

dihydroxy - 16,17 - [(1 -

methylethylidene)bis(oxy)]

pregn - 4 - ene - 3,20 - dione

O

H

OH

H

O

OH

F

Fluorine-containing Drugs for Human Use Approved by FDA in the United States 551

Formula Pharmaceutical action Dosage form CAS No. Approval date/

drug sponsor

C

32

H

44

F

3

N

3

O

2

S Antipsychotic agent Injectable 5002 - 47 - 1

July 1987/

Abraxis Pharm

Apotex Inc.

Bedford

Teva Parenteral

C

29

H

38

F

3

N

3

O

2

S Antipsychotic agent Injectable 2746 - 81 - 8

March 1967/

Apothecon

C

22

H

28

Cl

2

F

3

N

3

OS Antipsychotic agent Injectable 146 - 56 - 5

June 1960/

Schering

∆

Abraxis Pharm

Pharm Assoc.

Mylan

Par Pharm

Sandoz

C

21

H

27

FO

5

Anti - inﬂ ammatory

agent

Glucocorticoid

Oral tablet 53 - 34 - 9

Prior to 1982/

Pharmacia and

Upjohn

C

24

H

33

FO

6

Anti - inﬂ ammatory

agents

Glucocorticoid

Topical cream

and ointment

1524 - 88 - 5

March 1963/

Oclassen

Watson Labs

552 Fluorine in Medicinal Chemistry and Chemical Biology

Active ingredient/

trade name

Chemical name Structure

Flurazepam Hydrochloride

9 - chloro - 2 - (2 -

diethylaminoethyl) - 6 -

(2 - ﬂ uorophenyl) - 2,5 -

diazabicyclo[5.4.0]undeca -

5,8,10,12 - tetraen - 3 - one

dihydrochloride

N

O

F

Cl

2HCl

Flurbiprofen Sodium/

Ocufen

sodium ( ± ) - 2 - (2 - ﬂ uoro - 4 -

biphenylyl) - propionate

dihydrate

F

O

Na

Flurbiprofen/

Ansaid

[1,1 ′ - biphenyl] - 4 - acetic acid,

2 - ﬂ uoro - alphamethyl - , ( ± ) -

F

O

OH

Flutamide

2 - methyl - N - [4 - nitro - 3 -

(triﬂ uoromethyl)phenyl]

propanamide

N

NH

CF

3

O

Fluticasone Furoate/

Flonase

(6 α ,11 β ,16 α ,17 α ) - 6,9 - diﬂ uoro -

17 - {[(ﬂ uoro - methyl)

thio]carbonyl} - 11 - hydroxy - 1

6 - methyl - 3 - oxoandrosta - 1,4 -

dien - 17 - yl 2 - furancarboxylate

HO

F

O

S

F

O

Fluticasone Propionate/

Advair

Flovent

Cutivate

(6 α ,11 β ,16 α ,17 α ) - 6,9 -

diﬂ uoro - 11 - hydroxy - 16 -

methyl - 3 - oxo - 17 - (1 - oxopropoxy)

androsta - 1,4 - diene - 17 -

carbothioic acid,

S - ﬂ uoromethylester

O

F

OCOC

2

H

5

HO

COSCH

2

F

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

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