Clocortolone
C
51
1
+
B~-CI
NoNH2
ti
CI
ornide
3-chloro-l0,1 1 -di-
1
-brorno-3-
hydro-5H-dibenz- chloropropane
[bblazepine
DMF
,
+
HN*3
+
NH2
piperidine-4-
corboxamide
(cf, piparnperone
synthesis)
Reference(s):
DOS
1 905 765 (Yoshitomi; appl. 6.2.1969; J-prior. 7.2.1968).
US
3
668 210 (Yoshitomi; 6.6.1972; J-prior. 7.2.1968).

Formulation(s):
tabl. 10 mg, 25 mg (as hydrochloride)
Trade Nurne(s)c
J:
Clofekton (Yoshitomi-
Takeda; 1974)
Clocortolone
ATC: D07AB21
IJse:
glucocorticoid
RN:
4828-27-7 MF: C2,H2,C1FO4 MW: 41 0.9 1 EINECS: 225-406-7
CN:
(6a,l
I
P,l6a)-9-chloro-6-fluoro-
1
I
,2 1 -dihydroxy-
16-methylpregna-1,4-diene-3,20-dione
pivalate
RN: 34097- 16-0
MF:
C2,H,,C1F05 MW: 495.03 EINECS: 25 1-826-5
caproate
RN: 4891-71-8 MF: C2,H,,ClF05 MW: 509.06 EINECS: 225-513-9
&I:3
+,
CD4,
dioxane

b
N-chloro-
0
'.
succinirnide
F
3.20-dioxa-6a-fluoro-21-
Clocortolone
hydraxy-16a-methyl-
1,4,9(1 1)-pregnatriene
512
C
Clodantoin
pivalic onhydride
I
F
Clocortolone pivolote
I
0 0
pyridine
Clocortolone
f
H3C
coproic anhydride
Reference(s):
F
Clocortolone caproote
~i-a~~l. 6 4 12 708 (Schering AG; appl. 2.1 1.1964; D-prior. 9.1 1.1963).
FR
6 752 M (Schering AG; appl. 9.1 1.1966; D-prior. 9.1 1.1965).

synthesis
qf
starting compound:
DOS
1
913 042 (Schering AG; appl. 11.3.1969).
alternative syrzthesis:
DOS 2 01 1 559 (Schering AG; appl. 7.3.1970).
Forrnulation(s):
cream 1 mglg
Trade Name(s):
D: Crino-Kaban (Asche; as Kabanimat (Asche; as
pivalate-comb.) pivalate and capronate)
Kaban (Asche; as
pivalate
Procto Kaban (Asche; as
and capronate-comb.)
capronate)-comb.
I:
Cilder (Cilag;
as
pivalate);
wfm
USA: Cloderm
(Penedem;
as
pivalate)
Clodantoin
(Chlordantoin)
ATC: GOlAXOl

Use: fungicide
RN: 5588-20-5 MF: CI,HI,CI3N,O2S
MW:
347.69 EINECS: 226-995-3
LDS,,:
>I165 mglkg
(R,
p.0.)
CN:
5-(1-ethylpentyl)-3-[(trichloromethyl)thio]-2,4-imidazolidinedione
H3c2.3fyo
+
CI
\
S-CC13
+
N-
Na+
0
Reference(s):
US 2 553 770 (Standard Oil; 1951; prior. 1949).
H3cqyo
N,
0
S-CCI,
5-(1
-ethylpentyl)- trichlorornethyl-
Clodontoin
hydontoin sodium solt sulfenyl chloride
Clodronate disodium

C
5
13
Formuiation(s):
cream; gel; powder
Trade Name(s):
GB:
Sporostacin (Ortho); wfm USA: Sporostacin (Ortho)-comb.;
J:
Gynelan (Eisai)-comb. wfm
Clodronate disodium
ATC: ~05~~02
(Clodronic acid disodium salt)
Use: calcium metabolism regulator
RN: 22560-50-5 MF: CH2CI,Na,0,P, MW: 288.86 EINECS: 245-078-9
CN:
(dichloromethylene)bis(phosphonic
acid) disodium salt
free
acid
RN: 10596-23-3 MF: CH,C120,P2 MW: 244.89 EINECS: 234-212-1
H C
0,
,0
CH3
3Y
P
Y
H3C
0hr

+
CH3 CH,
A
H3C CH3
H~c (
~CH~
CH3 H3C
dibromo-
triisopropyl
tetraisopropyl
methane
phosphite
rnethylenediphosphonote
(1)
1.
Na
1.
HCI
1
1.
sadium
I
Clodronote
disodiurn
Reference(s):
DOS 1 467 655 (Procter
&
Gamble; appl. 17.3.1964; USA-prior. 18.3.1963).
DOS 1 793 768 (Procter
&

Gamble; appl. 17.3.1964; USA-prior. 18.3.1963).
US 3 404 178 (Procter
&
Gamble; 1.10.1968; appl. l8.3.l963,7.lO.l965).
US
3
422 021 (Procter
&
Gamble; 14.1.1969; appl. 18.3.1963).
Quimby, O.F. et al.:
J.
Org. Chem. (JOCEAH) 32,4111 (1967).
alternative synthesis:
McKenna, C.E. et al.: Phosphorus sulfur 37, 1 (1998)
Formulation(s):
amp. 300 mg/5 ml, 300 mg/lO ml; cps. 400 mg;
f.
c. tabl. 520 mg, 800 mg
Trade Name(s):
D: Bonefos (Astra; medac) F: Clastoban (Rorer; Roger
I:
Clasteon (Gentili)
Ostac (Roche; 1988) Bellon) Difosfonal (SPA)
Cytos (Roche) Ossiten (Roche)
514
C
Clofedanol
Clofedanol
(Chlophedianol)
ATC: R05DB10

Use: antibssive
RN: 791-35-5 MF: C,,H,CINO MW: 289.81 EINECS: 212-340-9
LDSo: 70 mgkg (M,
i.v.);
300 mgfkg
(M,
p.0.)
CN:
2-chloro-a-[2-(dimethylamino)ethyl]-a-phenylbenzenemethanol
hydrochloride
RN: 51
1-
13-7 MF: C,,H,CINO
.
HCI MW: 326.27 EINECS: 208-124-9
LD,,,: 42 mgkg (M, i.v.); 284 mglkg
(M,
p.0.);
53 mgkg
(R,
i.v.); 350 mgkg (R, p.0.);
84 mglkg (dog, p.0.)
2-chloro- acela-
benzophenone nitrile
I
Clofedonol
I
2'-chlaro-
poraform-
dimethyl- 2'-chloro-3-

acetophenane
aldehyde
amine dimethylomino-
propiophenone
(IL)
phenylmagnesium
bromide
Refermce(s):
DE
1
080 568 (Bayer; appl. 8.1.1958).
DE
1
083 277 (Bayer; appl. 19.3.1958).
US 3 031 377 (Bayer; 24.4.1962: appl. 26.11.1957).
fort nu la ti on(^):
syrup 25 mg, 30
mg;
tabl. 12.5 mg (as
hydrochloride)
Clofexamide
C
515
Trade Namefs):
D:
Dicton (Do1orgiet)-comb.; Pectolitan (Kettelhack-
I:
Soltux (Corv1)-comb.
wfm Riker); wfm
J:

Coldrln (N~ppon Shinyaku)
F: Tussipltgyl (Bayer); wfm USA: Ulo (Riker); wfrn
Clofexamide
ATC: N06B
Use: psychoanaleptic
1
RN: 1223-36-5 MF: C,,H2,ClN202 MW: 284.79 EINECS: 214-951-6
I
CN:
2-(4-chlorophenoxy)-N-[2-(diethylamino)ethyl]acetamide
4-chlorophenoxy- N,N-diethyl- Clofexarnide
ocetyl chloride ethylenediarnine
Referencefs):
GB
942 761 (Centre National de la Recherche Scientifique; appl. 8.4.1960; F-prior. 15.4.1959, 30.7.1959).
Fonnulation(s):
tabl. 50 mg, 400 mg
Trade Namefs):
F:
Clofexan
B
la
noramidopyrine (Anpharl-
comb.; wfm
Clofezone
ATC: M01 AAO5; M02AA03
Use: anti-inflammatory, antirheumatic
RN: 17449-96-6 MF: CI,H,oN20,
.
C14H2,C1N202 MW: 593.17 EINECS: 241-466-7

LD,,:
1700 mgkg (M, p.0.);
1950 mgkg
(R,
p.0.)
CN:
2-(4-chlorophenoxy)-N-[2-(diethylamino)ethyl]acetamide
compd. with 4-butyl- l,2-diphenyl-3,s-
pyrazolidinedione (1: 1)
dihydrate
RN: 60104-29-2 MF: C,,H20N202. C14H21ClN202. 2H20 MW: 629.20
clofexornide phenylbutozone
516
C
Clofibrate
I
Clofezone
Reference(s):
US
3 491 190 (P. Rumpf,
J E.,
G.
Thuillier; 20.1.1970; F-prior. 8.9.1965).
Fbrmulation(s):
cps. 200 mg, 400 mg; ointment 5 gI100 g; suppos. 400 mg
Trade Name(s):
D:
Perclusone (Mack, Illert.); F: Perclusone (Serb)-comb.
J:
Panas (Grelan)

wfm I: Perclusone (Marxer); wfm
Clofibrate
ATC: COlABOl
Use: cholesterol depressant,
antihyperlipidemic,
antiarteriosclerotic
RN: 637-07-0 MF:
CI2Hl5C1O3
MW:
242.70 EINECS: 21 1-277-4
CN:
2-(4-ch1orophenoxy)-2-methylpropanoic
acid ethyl ester
4-chloro- acetone chloro- 2-(4-chloro- Clofibrate
phenol
f
orrn phenoxy)-2-
methylpropanoic
acid
Reference(s):
Julia, M. et al.: Bull. Soc. Chim. Fr. (BSCFAS) 1956,777.
US 3 262 850 (ICI; 26.7.1966; GB-prior. 20.6.1958).
Formulation(s):
cps. 250 mg, 500 mg
Trade Name(s):
D:
Regelan N 500 (Zeneca)
F: Lipavlon (Zeneca)
GB: Atromid S (Zeneca)
I:

Sinteroid (Crinos)
J:
Amotril (Sumitomo)
Apoterin A (Seiko)
Artehard (Nissin)
Ateculon (Nippon
C hemiphar)
Ateles (Tokyo Hosei)
Atemarol (Kowa Yakuhin)
Athebrate (Kakenyaku)
Atherolate (Fuji
Zoki)
Atheromide (Ono)
Atmol (Taisho)
Atosterine (Kanto)
Auparton (Samva)
Binograc
(Zeria)
Bresit (Toyo Jozo)
Cholenal (Yamanouchi)
Cholestol (Toho)
Cholesrun (Hokuriku)
Clarol (Toy ama)
Clobrate (Chugai)
Clobren
(Morishita)
Clofbate (Mohan)
Climinon (Meiji)
Deliva (Nippon Kayaku)
Hyclorate (Funay)

Hy pocerol (Fuso)
Clofoctol
C
517
t?
Liprinal (Bany u)
Scrobin (Nlkken) USA: Atromid S (Wyeth-Ayerst)
t
4
:
Clofoctol
ATC: JOl XXO3; R07A
Use: antibacterial (in respiratory
infections)
RN: 37693-01-9 MF:
C21H26C120 MW: 365.34 EINECS: 253-632-6
LD,: >4000 mglkg (R, p.0.)
CN:
2-[(2,4-dichlorophenyl)methyl]-4-(1,1,3,3-tetramethylbutyl)phenol
CH3
4-(1,1,3,3-tetra- 2.4-dichloro
rnethylbuty1)- benzyl
phenol chloride
Clofoctol
I
CH3
Reference(s):
FR
1602455 (I. R.
C.

E.
B. A,; appl. 21.8.1968; GB-prior. 31.8.1967).
US 3 830 852 (I. R. C. E. B. A.; 20.8.1974; F-prior. 18.8.1970).
DOS 2
140 765 (I. R. C. E. B. A.; appl. 13.8.1971; F-prior. 18.8.1970).
preparation of
4-(1,1,3,3-tetramethylbutyI)phenol:
US 2 726 270 (Dow Chem.; 195 1).
DE 842 073 (Reichhold Chem. Inc.; 1950).
US 2 732
448
(California Research Corp.; 1953).
US 2 572 019 (DuPont de Nemours
&
Co.; 1950).
further patents are described before 1950.
Formulation(s):
suppos. 100 mg, 200 mg, 750 mg
Tmde Name(s):
F:
Octofene (DCbat; 1978) I: Gramplus (Chiesi) Octofene (Roussel; 1985)
Clometacin
ATC: NO2
Use: anti-inflammatory, analgesic
RN: 25803-14-9
MF:
C19H,6CIN04 MW: 357.79 EINECS: 247-271-3
LD,,: 1 g/kg (M, p.0.)
CN:
3-(4-chlorobenzoyl)-6-methoxy-2-methyl-1H-indole-l-acetic

acid
4-rnethoxy-2- nitroethone
nitrobenzaldehyde
518
C
Clomethiazole
6-methoxy-2-
N.N-dirnethyl-4-
methylindole
(I)
chlorobenzornide
1.
NaH,
DMF
1.
KOH,
CH30H
rCOOH
2.
HCI
acetate
Clornetacin
Reference(s):
DE 1 901 167 (Roussel-Uclaf; appl. 10.1.1969; F-prior. 11.1.1968, 10.4.1968, 10.9.1968, 11.9.1968, 10.12.1968).
Formulatinn(s):
tabl. 150 mg
Trade Name(s):
F:
.
DupCran (Cassenne); wfm

Clomethiazole
ATC: N05CM02
Use: anticonvulsant, hypnotic, sedative
RN: 533-45-9 MF: C,H,ClNS MW: 161.66 EINECS: 208-565-7
LDo,: 94 mglkg (M, i.v.); 21 10 mglkg (M, p.0.)
CN:
5-(2-chloroethy1)-4-methylthiazole
ethanedisulfonate
(2:l)
RN: 1867-58-9 MF: C,H,ClNS. 1/2C2H606S2 MW: 513.51 EINECS: 217-483-0
LD,,,: 150 mglkg (M, i.v.); 835 mglkg (M, p.0.)
ornrnoniurn
1.3-dichloro-
5-(2-chloroethy1)-
dithiocarbarnate
4-oxopentone
2-rnercapto-4-
rnethylthiazole
Clornethiazole
I2
Reference(s):
CH 200 248 (Roche; 1937).
US 3 031 457 (R. Charonnat, J. Chareton, A. Boune; 24.4.1962; F-prior. 28.9.1955).
alternative syntheses:
Buchman, E.R.: J. Am. Chem. Soc. (JACSAT)
58,
1803 (1936).
Sawa, Y.; Ishida,
T.:
Yakugaku Zasshi (YKKZAJ)

76,
337 (1956).
Fnrmulation(s):
amp. 0.8
%
(as ethanedisulfonate); cps. 192 mg, 300 mg; syrup 320 mgllO ml; tabl. 500
mg
Clometocillin
C
519
+
Tmde Name(s):
D:
Distraneurin (Astra) F: Hemineurine (Dkbat); wfm
GB:
Heminevrin (Astra)
ATC: JO ICE07
Use: antibiotic
RN: 1926-49-4 MF: C17H,,C12N205S MW: 433.3 1 EINECS: 217-657-6
CN:
[2S-(2a,5a,6~)]-6-[[(3,4-dichlorophenyl)methoxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-
azabicyclo[3.2.0]heptane-2-carboxylic
acid
RN: 15433-28-0 MF: C,,H1,Cl2KN20,S MW:
47
1.40
$4-dichloro-a-
msthoxyphenyl-
acetic acid
COOH

I
I
+
0,
NQH3
K2C0,,
acetone.
O°C,
P*
7-6
k~
CH3
HzN
H
6-ominopenl
cillon~c acid
ReJerence(s):
US
3
007
920 (Recherche Industrie Therapeutiqucs; 7.1 1.196 1; GB-prior. 28.10.1960)
Formulation(s):
tabl. 500 mg
Tmde Name(s):
F:
Rixapen (Smith Kline
&
French); wfm
Clomifene
(Clomiphene)

ATC: G03GB02
Use: synthetic gonadotropin stimulant,
antiestrogen
RN: 91 1-45-5 MF: C,H2,C1N0
MW:
405.97 EINECS: 21 3-008-6
LD~
1700 mgkg (M,
p.0.)
CN: 2-[4-(Zchloro-
1,2-diphenylethenyl)phenoxy]-N,N-diethylethanamine
citrate
(Id)
RN: 50-41-9 MF: C2,H2,C1N0
.
C6H80, MW. 598.09 EINECS: 200-035-3
LD,: 1400 mgkg (M, p.0.);
5750 mgkg
(R,
p.0.)
520
C
Clomipramine
w
+
rCH3
NOOH
+
I
-

0b
f-3
benzylrnagnesiurn
OH
of
chloride
4-hydroxy-
2-diethylomino- 4-(2-diethylamino-
benzophenone
ethyl
chloride ethoxy)benzophenone
HCI
+
0
<N-C
0
N-chloro-
succin-
irnide
Reference(s):
US 2 914 563 (Merrell; 24.1 1.1959; prior. 6.8.1957).
medical use:
BE
782 321 (Richardson-Merrell; appl. 19.4.1971).
Forrnulation(s):
cps. 50 mg; tabl. 50 mg (as citrate)
Trade Name(s):
D: Clornhexal (Hexal)
GB:
Clomid (Hoechst)

Dyneric (Henning Berlin) Serophene (Hoechst)
Pergotime (Serono) I:
Clomid (Lepetit)
F:
Clomid (Marion Merrell) Prolifen (Chiesi)
Pergotime (Serono)
J: Clomid (Shionogi)
Clornifene
Orifen (Iwaki)
USA: Clomid (Hoechst
Marion
Roussel; as citrate)
Serophene (Serono)
Clomipramine
ATC: N06AA04
Use: antidepressant
RN: 303-49-1
MF:
C,,H,,ClN, MW:. 314.86 EINECS: 206-144-2
LD,,,: 27 mglkg (M, i.v.); 380 rnglkg (M, p.0.);
6 13 rnglkg (R, p.0.)
CN:
3-chloro-l0,11-dihydro-N,N-dimethyl-5H-dibenz[b~azepine-5-propanamine
monohydrochloride
RN: 17321-77-6 MF: C,,H,,CIN,. HCI MW: 351.32 EINES: 241-344-3
LD,,,: 22 mgkg (M, i.v.); 470 mgkg (M, p.0.);
26 mgkg (R, i.v.); 914 rnglkg (R, p.0.);
32 mgkg (dog, i.v.); 383 mgkg (dog, p.0.)