numerous generics I: Estraderm Ciba-Geigy Progynon Schering J: Ovahormon Pasta Teikoku Zoki Alora Procter & Gamble Climara Berlex Estraderm Novartis Estring Pharmacia & Upjohn Estro-Plus
Trang 1Estradiol benzoate E 781 Vagifem (Novo Nordisk;
RhBne-Poulenc Rorer)
F: Estrofem (Novo Nordisk)
Oestrogel (Besins-
Iscovesco)
Prkmarin (Wyeth-Ayerst)-
comb
Trisequens (Novo
Nordisk)-comb
Estradiol benzoate
(Oestradiolbenzoat)
GB: Cycloprogynova (ASTA USA:
Medica) Hormonin (Shire) Trisequens (Nova)-comb
numerous generics I: Estraderm (Ciba-Geigy) Progynon (Schering) J: Ovahormon Pasta (Teikoku Zoki)
Alora (Procter & Gamble) Climara (Berlex)
Estraderm (Novartis) Estring (Pharmacia &
Upjohn) Estro-Plus (Rocky Mtn.)- comb
FemPatch (Parke Davis) Vivelle (Novartis)
ATC: G03CA Use: estrogen
RN: 50-50-0 MF: C25H2,0, MW: 376.50 EINECS: 200-043-7
eatmdiol
(9 v.)
benzoyl
Referencefs):
a US 2 054 271 (Schering Corp.; 1933; D-prior 1932)
GB 485 388 (Lab Franq de ChimiothCrapie; appl 1936)
b DRP 641 994 (Schering AG; appl 1932)
alternative synthesis:
US 2 225 419 (Schering Corp.; 1940; D-prior 1937)
US 2 156 599 (Ciba; 1939; CH-prior 1936)
Formulation(s): amp 2 mglml, 10 mglml, 50 mg12 ml; sol 5 mg1100 ml
Trade Namefs):
D: Alpicort F (Wo1ff)-comb
Jephagynon (Wo1ff)-comb
Ney Normin (vit0rgan)-
comb
Syngynon (Jenapharm)
I? Benzo-Gynoestryl
(Roussel)
Dermestril (Sanofi
Winthrop)
Estraderm (Novartis)
Estreva (ThCramex)
Estrofem (Specia)
Menorest (Specia)
Oesclim (Fournier)
GB: Benztrone (Paines &
Byrne); wfm I: Benztrone (Amsa) Duo-Ormogyn (Amsa)- comb
Menovis (Parke Davis)- comb
Progynon (Schering) J: Estradin Susp (Santen- Yamanouchi)
Femihormon (Tokyo Hosei) Follikelmon (Kyorin) Ovahormon Benzoat Susp
(Teikoku Zoki)
Pelanin Inj (Mochida) Profollior B (Schering) Progynon B (Nihon Schering)
USA: Gynetone Inj (Schering)- comb.; wfm
Testradiol (Consolidated Midland)-comb.; wfm Testradiol (Truxton)-comb.; wfm
Trimonal (Vitacine)-comb.; wfm
numerous generics; wfm
Trang 2782 E Estradiol cypionate
Estradiol cypionate
(Oestradiol- 17-cyclopentylpropionat)
ATC: G03C Use: estrogen RN: 313-06-4 MF: C,,H,,O, MW: 396.57 EINECS: 206-237-8
LD,,: >I glkg (M, i.p.)
CN: (17P)-estra- 1,3,5(IO)-triene-3,17-diol 17-cyclopentanepropanoate
eslrodiol 3-benzoate 3-cyclopentyl-
(9 v.1 propionic acid
estrodiol
(9 v.1 3-cyc~opentyl-
propionyl chloride
Reference(s):
a FR 1 215 503 (Lab Rolland; appl 1955)
h US 2 61 1 773 (Upjohn; 1952; prior 195 1)
For-mulation(s): amp 10 mg (1 mglml), 25 mg (5 mglml), 50 mg (5 mglml)
Trade Nume(s):
D: Femovirin Amp (Albert- I: Cicloestradiolo (Farmigea); Neoginon Depositum
F: Oestradiol-retard Rolland Estradiolo Depositum
Trang 3F
E s t r a d i d valerate E 783 J: Depo-Estradiol (Upjohn- USA: Depo-Estradiol (Upjohn);
Use: estrogen RN: 979-32-8 MF: C&& MW: 356.51 EINECS: 213-559-2
LD,,: 1224 mglkg (M, p.0.)
CN: (17P)-estra- 1,3,5(IO)-triene-3,17-diol 17-pentanoate
17P-estradiol valeric anhydride
(4 v.1
estrodiol divalerate (I) I &tradioI valerate
Reference(s):
US 2 205 627 (Ciba; 1940; CH-prior 1936)
US 2 233 025 (Ciba; 1941; CH-prior 1936)
use as antidepressant:
DOS 2 758 549 (Schering AG; appl 23.12.1977)
Formulafion(s): amp 5 mglml, 10 mglml; drg 1 mg, 2 mg; drops 2 mg10.5 ml; f c tabl 2 mg; tabl 2 mg, 4 mg
Trade Name(s):
Gynokadin (Kade)
Merimono (Novartis
Pharma) -
Progynon Depot (Schering)
Progynova (Schering)
numerous combination
preparations
Climkne (Schering)-comb
Divina (1nnothCra)-comb
Progynova (Schering)
Cyclo-Progynova (ASTA
Medica)-comb
Progynova (Schering)
Gravibinan (Schering)-
comb
Gynodian Depot
(Schering)-comb
Progynon Depot (Schering)
Progynova (Schering) J: Pelanin Depot (Mochida) Progynon Depot (Nihon Schering)
USA: Ardefem (Burgin-Arden);
wfm Atladiol (Atlas); wfm Delestrogen (Squibb); wfm Depogen (Hyrex); wfm Depogen (Sig); wfm Dioval (Keene); wfm Ditate DS (Savage); wfm Dura-Estate (Ries); wfm Dura-Estradiol (Myers- Carter); wfm
Dura-Estradiol (Ruckstuhl); wfm Duratrad (Ascher); wfm
Estate (Savage); wfm Estral-L (Pasadena Res.); wfm
Estraval (Kay); wfm Estravel-P.A (Tutag); wfm Feminate (Western Res.); wfm
Femogen L.A (Fellows); wfm
Repo-Estra (Central); wfm Repo-Estro Med (Medics); wfm
Reposo E (Canfield); wfrn Retestrin (Rocky Mtn.); wfm
Span-Est (Scrip); wfm Testaval (Legere); wfm Valergen (Hyrex); wfm
Trang 47 8 4 E Estradiol undecylate
numerous combination
preparations; wfm
Estradiol undecylate
(Oestradiolundecanoat)
ATC: G03CA Use: estrogen RN: 3571-53-7 MF: C2,H,03 MW: 440.67 EINECS: 222-677-3
CN: (1 7p)-estra- 1 ,3,S(IO)-triene-3,l'i'-diol 17-undecanoate
176-estrodiol undeconoyl estrodiol diundeconoote (1)
US 2 990 414 (Syntex; 27.1.1 961; appl 18.3.1948; MEX-prior 26.3.1957)
Fornzulation(s): amp 100 rnglml
Trade Name(s):
F: Oestradiol-Retard J : Depogin (Shionogi)
ThCramex (Thkramex) USA: Delestrec (Squibb); wfm
Use: antineoplastic RN: 489 1- 15-0 MF: C2,H,2C12N0,P MW: 520.39 EINECS: 225-5 12-3
RN: 52205-73-9 MF: C2,H&I,NNa,O6P MW: 564.35
0
ethy1)arnine
Trang 51 Estriol E 785
Reference(s):
GB 1 016 959 (Leo; appl 9.4.1963; valid from 24.3.1964)
US 3 299 104 (Leo; 17.1.1967; GB-prior 9.4.1963)
GB 1 523 035 (Leo; appl 10.3.1976; valid from 8.3.1977)
complex compounds with alcohols (for purification):
US 4 115 414 (Leo; 19.9.1978; GB-prior 10.3.1976)
DE2710 293 (Leo; appl 9.3.1977; GB-prior 10.3.1976)
Formulation(s): cps 151.8 mg, 303.6 rng (as disodiurn salt); vial 621 rng (as meglumine salt)
Trade Name(s):
D: Cellmustin (cell pharm) F: Estracyt (Pharmacia & J: Estracyt (Nippon Shinyaku) Estracyt (Pharmacia & Upjohn) USA: Erncyt (Pharmacia &
Upjohn) GB: Estracyt (Pharmacia & Upjohn; as sodium salt)
Prostamustin (Azupharma) I: Estracyt (Farmitalia)
Use: estrogen RN: 50-27-1 MF: C,,HUO3 MW: 288.39 EINECS: 200-022-2
LD,,: >2 g k g (R, p.0.)
isopropenyl 3-rnethoxyestra-1,3.5(10).16-tetra- acetate en-1 7-01 acetate (I)
I - perbenzoic acid
olonote
16a.17~-epoxy-3-rnethoxy- Estriol estro-1,3.5(10)-trien-17-01
acetate
Reference(s):
Gallagher, T.F.: J Am Chem Soc (JACSAT) 76, 2943 (1954)
Trang 6a
7 8 6 E Estriol succinate
alternative syntheses:
Butenandt, A.; Schaffler, E.L.: Z Naturforsch (ZNTFA2) 1, 82 (1946)
Huffmann, M.N et al.: Science (Washington, D.C.) (SCIEAS) 100,312 (1944)
Huffmann, M.N.; Lott, M.H.: J Am Chem Soc (JACSAT) 69, 1835 (1947)
US 1 967 351 (Pres and Board of Trustees of St Louis; 1934; appl 1930)
The Merck Index 12th Ed., 63 1 (Rahway 1996)
Formulnrion(s): cream 0.5 mg/g; drg 1 mg; f c tabl 2 mg; ovula 0.03 mg, 0.5 mg; tabl I mg, 2 mg
Trade Name(s):
D: Cordes (Ichthyol)
Estiol (Jenapharm)
Gynasan (Bastian-Werk)-
comb
Oekolp (Kade)
Ortho-Gynest (Janssen-
Cilag)
Ovestin (Organon)
Ovo-Vinces 200 (Wolff)
Synapause (Nourypharma)
Xapro (Jenapharm)
numerous combination
preparations
F: Gydrelle (Iprad) Physiogine (Organon) Trophicrkme (Sanofi J:
Winthrop) Trophigil (Sanofi Winthrop)-comb
GB: Hormonin (Shire)-comb
Ortho-Gynest (Janssen- USA:
Cilag) Ovestin (Organon) Trisequens (Novo Nordisk)-comb
I: Colpogyn (Angelini)
Ortho Gynest Depot (Cilag) Ovestin (Organon Italia) Climatol (Santen) Estriel (Mochida) Molin (Teikoku Zoki) Ovapause (Organon) Season (Teikoku Zoki) Estro Plus Tab (Rocky Mtn.)-comb.; wfm Hormonin (Camrick)- comb.; wfm
Use: estrogen RN: 514-68-1 MF: C2,H3,0, MW: 488.53 EINECS: 208-185-1
CN: (1 6 a , 17P)-estra- 1,3,5(10)-triene-3,16,17-trio1 16,17-bis(hydrogen butanedioate)
disodium salt
RN: 113-22-4 MF: C,,H,,,Na,O, MW: 532.50
Rejerence(s):
GB 879 014 (Organon; appl 26.5.1960; NL-prior 29.5.1959)
estriol succinic
Formulation(s): tabl 2 mg, 4 mg (as disodium salt); vial 20 mg (as disodium salt)
Estriol succinate
Trade Natne(s):
D: Orgastyptin (Organon Synapause (Nourypharma); F: Synapause (Organon); wfm
(4 v.) anhydride
Trang 7Estrone E 787
Estrone
(Oestron)
ATC: G03CA07; G03CC04 Use: estrogen
RN: 53-16-7 MF: Cl,HzzOz MW: 270.37 EINECS: 200-164-5
CN: 3-hydroxyestra-1,3,5(10)-trien-17-one
oxide
androatenolone
3.17-dioxo-1.4- ondrostadiene (n)
$17-dioxo-1.4.6-
ondrostatnene
(from 3,17-dioxo-
1,4-androstadiene)
3-ocetoxy-19-hydroxycholesterol
(from cholesterol)
microarganism
CSD-I 0
H , C ~ S O , H
lithium, biphenyl
ethylene
glycol
Reference(s):
a,b Ehrhart, Ruschig, 111, 3 15
c Sih, Ch et al.: J Am Chem Soc (JACSAT) 87, 2765 (1965)
Trang 8788 E Etacrvnic acid
starting material:
Kalvoda, J et al.: Helv Chim Acta (HCACAV) 46, 1361 (1963)
d Dryden, H.L et al.: J Am Chem Soc (JACSAT) 86,742 (1964)
production of conjugated estrogens:
US 2 565 115 (Squibb; 1951; prior 1948)
US 2 720 483 ( O h Mathieson; 1955; prior 1951)
US 4 154 820 (Akzona; 15.5.1979; prior 26.9.1977, 23.2.1976)
toral syntheses:
EP 37 973 (Hoechst; appl 2.4.1981; D-prior 12.4.1980)
Morand, P.; Lyall, J.: Chem Rev (Washington, D C.) (CHREAY) 68, 85 (1968)
Veliuz, L et al.: Angew Chem (ANCEAD) 72,725 (1960)
Velluz, L et al.: Angew Chem (ANCEAD) 77, 185 (1965)
Smith, 13 et al.: J Chem Soc (JCSOA9)1963,5072
Smith, H et al.: Experientia (EXPEAM) 19, 177 (1963)
Anachenko, S.N.; Torgov, J.V.: Tetrahedron Lett (TELEAY) 1963, 1553; 1964, 171
Blickenstaff, R.T.; Ghosh, A.C.; Wolf, G.C.: Total Synthesis of Steroids (Organic Chemistry Vol 30) p 58-63, 142-145, Academic Press, New York, London 1974
Formulation(s): e g 1.4 mg in comb.; amp 20 mg; drg 0.625 mg, 1.25 mg, 2.5 mg; vial 20 mg
Trade Narne(s):
D: Coniugen (K1inge)-comb.;
wfrn
G T 50 B (Gewo)-comb.;
Menrium (Roche)-comb.; USA:
wfrn
Oestro-Feminal (Mack,
Illert.; as estrogen
conjugate)-comb.; wfm
Ovaribran (Thomae; as
estrogen conjugate)-comb.;
wfrn
Ovowop (Hor-Fer-Vit)-
comb.; wfrn
F: Colpormon (Lipha SantC)
PrCmarin (Wyeth-Lederle)
Synergon (Lipha Sant6)-
comb
GB: Hormonin (Shire)-comb
I: Emopremarin (Wyeth; as
estrogen conjugate)
Premarin (Wyeth; as estrogen conjugate) Prempak (Wyeth)-comb
Estropan (Mochida)-comb
Di-Genik (Savage)-comb.;
wfrn Di-Met (0rganon)-comb.;
wfrn Duogen (Smith, Miller &
Patch)-comb.; wfrn Estro-V (Webcon); wfrn Estrus01 (Smith, Miller &
Patch); wfrn FolleStrol (Blue Line); wfrn Foygen (Foy); wfm Hormestrin (Smith, Miller
& Patch)-comb.; wfrn Mal-0-Fem (Fellows)- comb.; wfm
Menagen (Parke Davis);
wfrn
Menformon (Organon); wfm
Natural Estrogenic Substance (Legere); wfm Nestronaq (Noyes); wfm Ogen (Abbott; as estropipate); wfrn Prinn (Scirp); wfrn Propagon-S (Spanner); wfrn
Spanestrin (Savage)-comb.; wfrn
Theelin (Parke Davis); wfm Wynastron (Wyeth); wfm further combination preparations and generic; wfrn
Etacrynic acid
( ~ t h a c r y n s a u r e ; Acide etacrynique)
ATC: CO3CCO1 Use: diuretic RN: 58-54-8 MF: C,,HI2Cl2O4 MW: 303.14 EINECS: 200-384-1
LD,,,: 176 mglkg (M, i.v.); 600 mglkg (M, p.0.);
1 glkg (R, p.0.)
sodium salt
RN: 6500-81-8 MF: C,,H,,CI,NaO, MW: 325.12
Trang 9Etafenone E 789
1 hutyry chloride 2.3-dichlorophen-
4-butyryl-2,3-dichloro- phenoxyacetic acid (I)
form- dimethyl-
aldehyde amine
I Etocrynic ocid
BE 612 755 (Merck & Co appl 17.1.1962;USA-prior 19.1.1961)
US 3 255 241 (Merck & Co.; 7.6.1966; prior 19.1.1961, 6.12.1961)
alternative synthesis:
DE 1 276 030 (Merck & Co.; appl 18.12.1964; USA-prior 23.12.1963)
Formulation(sJ: tabl 25 rng, 50 mg (as free acid); vial 53.6 mg (as sodium salt)
Trade Name(s):
D: Hydromedin (Merck Sharp GB: Edecrin (Merck Sharp & Reomax (Bioindustria)
F: Edecrine (Merck Sharp & I: Ac Etacr (Formulario Naz.) USA: Edecrin (Merck Sharp &
Dohme)
Use: coronary vasodilator RN: 90-54-0- MF: C2,H2,N02 MW: 325.45 EINECS: 202-002-9
hydrochloride
RN: 2192-21-4 MF: C2,H2,NO2 HCl MW: 361.91 EINECS: 218-587-9
LD,,: 28 mgkg (M, i.v.); 352 mglkg (M, p.0.);
20.8 mgkg (R, i.v.); 71 6 mgkg (R p.0.);
50 mgkg (dog, p.0.)
Trang 10790 E Etamiphylline
2'-hydroxy-3- 2-diethylomino-
phenylpropio- ethyl chloride
phenone
I Etofenone I
R<ference(s):
DAS 1 265 758 (S p A Lab Guidotti; appl 25.5.1960)
Formulation(s): amp 25 mg; drg 75 mg; s r cps 50 mg (as hydrochloride)
Trade Name(s):
D: Baxacor (Helopharm); wfrn
Baxacor (Mack, Illert.);
wfrn
Digi-Baxacor (Mack,
1llert.)-comb.; wfrn
Iso Baxacor (Helopharm)-
comb.; wfrn
Pagano-Cor (Helopharm);
wfrn Seda-Baxacor (Helopharm)-comb.; wfm Seda-Baxacor (Mack
1llert.)-comb.; wfm I: Dialicor (Guidotti) J: Asamedel (Maruko)
Cardilicor (Uji) Corodilan (Meiji) Dialicor (Kissei) Esanthin-S (Kyoritsu Yakuhin)
Etafenarin (Taiyo) Korofenon (Nissin)
Etamiphylline
(Dietamiphylline)
ATC: R03DA06 Use: cardiotonic, diuretic
RN: 314-35-2 MF: C13H2,N,02 MW: 279.34 EINECS: 206-244-6
LD,,,: 1237 m g k g (M, p.0.)
monohydrochloride
RN: 17140-68-0 MF: CI3H2,N,O2, HCI MW: 315.81 EINECS: 241-204-1
LD,,,: 127 mglkg (M, i.v.1
camphersulfonate (1 : 1)
RN: 19326-29-5 MF: C13H?IN50? C10Hlh04S MW: 51 1.64 EINECS: 242-962-6
LD,,,: 604 mglkg (M, s.c.)
1 NoOH
C I ~ N - C H ,
A
O Y 2 2-diethylomino-
Reference(s):
GB 669 070 (A J.-M Moussalli et al.; appl 1949; F-prior 1948)
Klosa, J.: Arch Pharm Ber Dtsch Pharm Ges (APBDAJ) 288160, 301 (1955)
Formulation(s): 75 mg in comb.; suppos 200 mg, 500 mg; tabl 100 mg (as camphersulfonate)