Dicloxacillin D 631 GB: Daranide (Merck Sharp & 1: Antidrasi (SmithKline Glaumid (SIFI) Dohme); wfm Beecham) J: Daranide (Merck-Banyu) Fenamide (Farmigea) USA: Daranide (Merck) Dicloxacillin ATC: JOlCFOl Use: antibiotic RN: 31 16-76-5 MF: C,9Hl,CIZN30sS MW: 470.33 EINECS: 221 -488-3 CN: [2S-(2a,5a,6~)]-6-[[[3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7- oxo-4-thia-l-azabicyclo[3.2.0]heptane-2-carboxylic acid monosodium salt monohydrate RN: 13412-64-1 MF: C,,H16C12N,Na0,S . H20 MW: 5 10.33 LD,,: 875 mglkg (M, i.v.); 4560 mglkg (M, p.0.); 520 mgkg (R, i.v.); 3579 mglkg (R, p.0.); >3 glkg (dog, p.o.1 ~CI C12. CHCI, NoOCH, H2N-OH CI CHO h~drox~l- CI N. CI methyl amine 2,6-dichloro- benzaldehyde 6-aminopeni- cillonic acid 0 H 4 'OH ocetoacetote 3-(2.6-dichloro- phenyl)-5-methyl- isoxozole-4- carbaxylic acid Reference (s): NoOH + US 3 239 507 (Beecham; 8.3.1966; GB-prior. 17.10.1962). COOH CI H H Dicloxocillin GB 978 299 (Beecham; appl. 17.10.1962; addition to GB 905 778 from 14.3.1961). BE 657 504 (Bayer; appl. 23.12.1964; D-prior. 24.1 2.1963). Formulation(s): cps. 500 mg (as sodium salt) Trade Narne(s): D: Dichlor-Stapenor (Bayer) F: Cefaplus (Labif-comb.; Diclocil (Bristol); wfm wfm I: Diclo (Firma) 632 D Dicvcloverine Diclocil (Bristol); wfrn Diclocillin (Aristochimica); wfrn Diclocillin (Lagap); wfrn Diclocta (Lusofarmaco)- comb.; wfm Dicloeta (Lusofarmaco)- comb.; wfrn Diclomax (Pulitzer); wfrn Dicloxapen (Magis); wfm Diflor (Coli); wfm Etadipen (Chimas)-comb.; wfrn Novapen (IBP); wfrn Versaclox (Bristo1)-comb.; wfrn numerous combination preparations J: Clocil (Bristre-Banyu) Combipenix (Toyo Jozo)- comb. Diclex (Meiji) Staphcillin (Banyu) USA: Dycill (Beecham); wfm Dynapen (Bristol); wfm Pathocil (Wyeth); wfm Veracillin (Ayerst); wfm Dic ycloverine (Dicyclomine) ATC: A03AA07 Use: antispasmodic, anticholinergic RN: 77-19-0 MF: C,,H,,NO, MW: 309.49 EINECS: 201-009-4 CN: [I,]'-bicyclohexyl]-1-carboxylic acid 2-(diethy1amino)ethyl ester hydrochloride RN: 67-92-5 MF: C,,H,,NO, . HCI MW: 345.96 EINECS: 200-671-1 LD,,: 3 1.5 mg/kg (M, i.v.); 625 mg/kg (M, p.0.); 1290 mgkg (R, p.0.) benzyl cyanide 1.5-dibromo- 1 -cyano- 1 - pentane phenylcyclo- hexone ethyl 1 -phenyl- cyclohexane-1 - carboxylate (I) I Dicycloverine 1. NaNH 0-CH, 1. sodium amide 2. cyclohexyl cyano- bromide 1 -cyana- ethyl bicyclo- cyclohexane bicyclohexyl hexyl-1 -corb- oxylote (Ill) Rcrfcrrence(s): US 2 474 796 (Merrell Comp.; 1949; prior. 1946). Tilford, C.H. et al.: J. Am. Chem. Soc. (JACSAT) 69,2903 (1947). Rmularion(s): cps. 10 mg Tmde Name(s): D: Atumin (Merrell); wfm I: Bentyl (Merrell) Mamiesan (Kyowa Spasrno-Rhoival (Tosse)- Merankol (Lepetit)-comb. Yakuhln- hoe^) comb.; wfm J: Bentyl (Shionogi) USA: Bentyl (Hoechst Marion GB; Diarrcst (Galen)-comb. BentylIPhenobarbital Roussel; as hydrochloride) Kolanticon (Hoechst)- (Shionogi)-comb. generics comb. lncron (Seiko Eiyo)-comb. Merbentyl (Florizel) Kolantyl (Shionogi) ATC: Use: J05AF02 anti-AIDS therapeutic, symptomatic oral treatment 2',3'-didsoxy- odonosina Didonosine I Reference(s): US4970 148 (Ajinomoto; 13.1 1.1990; appl. 7.10.1988; J-prior. 24.12.1987,7.10.1987, 13.9.1988). Plunkett, W.; Cohen, S.S.: Cancer Res. (CNREAS) 35, 1547 (1975). alternative synthesis: US 5 01 1 774 (Bristol-Mycrs Squibb; 30.4.1991; appl 28.2.1990; prior. 17.7.1987). Prisbe, E.J.; Martin, J.C.: Synth. Commun. (SYNCAV) 15,401 (1985). Horwitz, J.P. et al.: J. Org. Chem. (JOCEAH) 32, 8 17 (1 967). purification: US 4 962 193 (Ajinomoto; 9.10.1990; appl. 28.1 2.1988; J-prior. 22.12.1987). JP 1 175 991 (Ajinomoto; appl. 29.12.1987). JP 1 165 390 (Ajinomoto; appl. 22.12.1987). medical use for treatment of AIDS: EP 206 497 (Wellcome; appl. 14.5.1986; GB-prior. 15.5.1985, 20.2.1986). EP216 510 (US Department of Health; appl. 21.8.1986; USA-prior. 26.8.1985). US4861 759 (US Department of Health; 29.8.1989; appl. 15.5.1989; prior. 11.8.1987,26.8.1985,4.12.1986). US 5 026 687 (National Institute of Health; 25.6.199 1 ; appl. 3.1.1990). medical use for treatment of hepatitis B virus infections: WO9 014 091 (US Department of Health; appl. 15.5.1990; USA-prior. 15.5.1989,4.12.1986, 11.8.1987). synthesis of dideoxy adenosine: The Merck Index, 3091 (Rahway 1989). Formulation(s): chewable tabl. 10 mg, 25 mg, 50 mg, 100 mg, 150 mg; powder 2 g, 4 g 634 D Dienestrol Trade Name(s): D: Videx (Bristol-Myers GB: Videx (Bristol-Myers USA: Videx (Bristol-Myers Squibb) Squibb) Squibb; 1991) F: Videx (Bristol-Myers J: Videx (Bristol-Myers Squibb) Squibb; 1992) Dienestrol (Dienoestrol) ATC: G03CBOl; G03CC02 Use: estrogen RN: 84-17-3 MF: CIp,H,,O2 MW: 266.34 EINECS: 201-519-7 CN: 4,4'-( 1,2-diethylidene-l,2-ethanediyl)bis[phenol] 4'-hydroxy- propiophenone I. Nu-Hq ______+ 1. sodium omolgome 2. benzoyl chloride (1) 2. KOH. C2H50H I I Dienestrol I Reference(s): GB 566 881 (Boots Pure Drug; appl. 1943). US 2 464 203 (Boots; 1949; GB-prior. 1943). US 2 465 505 (Roche; 1949; CH-prior. 1944). c;!ternative synthesis: Hobday, G.I.; Short, W.F.: J. Chem. Soc. (JCSOA9) 1943,609. review: Ehrhart, Ruschig 111, 330. Dodds, E.C. et al.: Proc. R. Soc. London, Ser. B (PRLBA4) 127, 162 (1939). Formulation(s): cream 0.01 %; tabl. 5 mg, 25 mg Trade Narne(s): D: Sanoprostal GB: Orho Dienoestrol (Janssen- Sebohormal (Bruschettini)- (Pharmakochemie)-comb.; Cilag) comb. wfm I: Sebohermal (Bruschettini)- USA: Ortho Dienestrol (Ortho- F: Cycladikne (Bruneau); wfm comb. McNeil Pharmaceutical) Diethylcarbamazine D 635 Diethylcarbamazine ATC: P02CB02 Use: anthelmintic RN: 90-89-1 MF: CloH21N30 MW: 199.30 EINECS: 202-023-3 t LDSO: 240mg/kg(M,i.p.) CN: N,N-diethyl-4-methyl-I-piperazinecarboxam~de RN: 1642-54-2 MF: C,oH2,N30 . C6H807 MW: 39 1.42 EINECS: 216-696-6 LD,: 180 mag (M, i.v.); 660 mglkg (M, pa); 1400 mg/kg (R, p.0.) piperozine S 2467 895 (American Cyanamid; 1949; prior. 1946). Formularion(s): tabl. 50 mg D: Hetrazan (Lederle); wfm GB: Banocide (Wellcome); wfm USA: Hetrazan (Lcdcrle); wfm F: Notbine (Specia); wfnl J: Hetrazan (Lederle) ATC: G03CB02; G03CC05; L02AAO1 Use: formerly in estrogenic hormone therapy, listed as a known carcinogen RN; 56-53-1 MF: C,,H,,O, MW: 268.36 EINECS: 200-2784 LDSO: 300 mgkg (M, i.v.); >3 glkg (M, p.0.); >3 g/kg (R, p.o.1 CN: (0-4,4'-(1,2-diethyl-1,2-ethenediyl)bis[phenol] I. NoNH?. NH3, - 80 OC anethole Diethylstilbestrol 636 D Diethylstilbestrol deoxyanisoin ethyl iodide KOH, 220 OC 11 -b 1. No-Hg HCL ether H~~ 1. sodium + / HO HO ' CH3 4'-hydroxy- propiaphenone No, amyl olcohol H~~ HCI TI 111 * Diethylstilbestrol HO HO CH3 Reference(s): a US 2 392 852 (Lilly; 1946; prior. 1941). US 2 402 054 (Lilly; 1946; prior. 1941). b Dodds, E.C.: Nature (London) (NATUAS) 141,247 (1938). c US 2 421 401 (Hoffmann-La Roche; 1947; S-prior. 1943). DRP 715 542 (Schering AG; appl. 1939). alternative syntheses: Ullmanns Encykl. Tech. Chem., 3. AuB., Vol. 8, 327. GB 526 927 (Richter Gedcon; appl. 1939; H-prior. 1938). BE 665 818 (Miles Lab.; appl. 23.6.1965; USA-prior. 24.6.1964). review: Solmssen, U.V.: Chem. Rev. (Washington, D. C.) (CHREAY) 37,481 (1945). Ehrhart, Ruschig, 111,327. Formulation(s): tabl. 1 mg, 5 mg Trade Name(s): D: Cyren A (Bayer); wfm Stilboestrol and Lactid USA: Diethylstilbestrol (Lilly); F: Distilbkne (Gerda) Acid (Norgine)-comb.; wfm GB: Menopax Cream wfm Tylosterone (Lil1y)-comb.; (Nicholas); wfm wfm Diethylstilbestrol dipropionate D 637 Diethylstilbestrol dipropionate ATC: GO~CB @iethylstilboestrol-dipropionat; Diathylstilboestrol- Use: estrogen dipropionat) RN: 13C-80-3 MF: C24H2804 MW: 380.48 EINECS: 204-995-4 CN: (4-4,4'-(1,2-diethyl-l,2-ethenediyl)bis[phcnol] dipropanoate pyridine wH + H~c~~~cH~ 0 0 -, HO CH3 Reference (s): Dodds, E.C. et al.: Proc. K. Soc. London, Ser. B (PRLBA4) 127, 140 (1939). H3cJ0 diethylstilbestrol pmpianic anhydride Formulation(s): amp. Diethylstilbeetroi dipropionate Trade Name(s): D: Klimax "Taeschner" USA: Dibestil (Breon); wfm (Taeschner); wfm Diethylstilbestrol disulfate ATC: G03CB @iethylstilboestroldisulfat; Diiithylstilboestroldisulfat) Use: estrogen RN: 316-23-4 MF: C18H2008S2 MW: 428.48 EINECS: 206-257-7 CN: (E)-4,4'-(1,2-diethyl-l,2-ethenediyl)bis[phenol]bis(hydrogen sulfate) wH Cl-S03H, quinoline, HO CH3 diethylstilbestrol KOH 1 + Diethylstilbestrol disulfate (1) Diethylstilbestrol disulfate dipotassiurn salt Reference(s): US 2 234 31 1 (Ciba; 1941; CH-prior. 1938). Formulation(s): ointment 638 D Difenidol Trade Name(s): 1: ldroestril (Maggioni); wfm Pappy (Kanto) J: Estiol (Hokuriku) Stilbestohormon (Tokyo Hosei) Difenidol (Diphenidol) ATC: A04; DO4 Use: anti-emetic, antihistaminic RN: 972-02-1 MF: C2,H,,N0 MW: 309.45 EINECS: 213-540-9 LD,,,: 32 mglkg (M, i.v.); 450 mglkg (M, p.0.); 815 mglkg (R, p.0.) CN: a,a-diphenyl-1-piperidinebutanol hydrochloride RN: 3254-89-5 MF: C,,H,,NO . HCl MW: 345.91 EINECS: 221-850-0 LD,,: 37mg/kg(M,i.v.);400mg/kg(M,p.o.); 29 mglkg (R, i.v.); 5 15 mglkg (R, p.0.) pamoate (2:l) RN: 26363-46-2 MF: C,,H2,N0 1/2C,,H1,0, MW: 1007.28 Rqference(s): US 2 41 1 664 (Ciba; 1946; CH-prior. 1941). Formulation(s): tabl. 25 mg, 50 mg Trade Name(s): J: Ansumin (SS Seiyaku) Antiul (Tokyo Hosei) Cephadol (Nippon S.) Cerachidol (Ono) Cerrosa (Toyo Pharmar) Degidole (Nihon Yakuhin) Gipsydol (Nihon Yakuhin) Maniol (Morishita) Mecalmin (Yoshitomi- Takeda) So ___* benzophenone Difenidol Meniedolin (Toyo Shinyaku) Meranom (Hokuriku) Midnighton (Takata) Pineroro (Maruko) Promodor (Torii) Satanolon (Tatsumi) Sofalead (Nikken) Solnomin (Zensei) Tatimil (Mohan) Verterge (Nippon Chemiphar) Wansar (Hoei) Yophadol (Yoshindol Horita) USA: Vontrol (Smith Kline French); wfm Difenoxin ATC: A07DA04 Use: antidiarrheal, antiperistaltic RN: 28782-42-5 MF: C2,H,,N20, MW: 424.54 CN: 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylic acid monohydrochloride RN: 35607-36-4 MF: C,8H2xN202 . HCI MW: 461.01 EINECS: 252-640-7 LD,,,: 149 mglkg (R, p.0.) Diflorasone diacetate D Reference(s): DAS 1 953 342 (Janssen; appl. 23.10.1969; USA-pnor. 4.11.1968). US 3 646 207 (Janssen; 29.2.1972; appl. 4.1 1.1968). rmulation(s): tabl. 0.5 mg D: Lyspafena (Cilag-Chemie)- I: Motofen (Ci1ag)-comb.; USA: Motofen (Carnrick; as wfm hydrochloride) Diorasone diacetate ATC: DO~AC~O Use: topical glucocorticoid RN: 33564-31-7 MF: C26H32F20, MW: 494.53 EINECS: 251-575-1 LD5,: >3 g/kg (M, p.0.); >3 g/kg (R, p.o.1 CN: (6a,ll~,16~)-17,21-bis(acetyloxy)-6,9-d1fluoro-11-hydroxy-16-methy1pregna-1,4-diene-3,20-dione ditlorasone RN: 2557-49-5 MF: C22H2,F20, MW: 410.46 EINECS: 219-875-7 1 (F3C-CO),O. CH3COOH, H3C H 1. trifluoroocetic anhydride 0 ', 2. N-brornoocetornide F 3. potossiurn ocetote 21 -ocetoxy-3,20-d~oxo- 6a-fluoro- 17-hydroxy - 16p-methyl-4,9(1 1)- prsgnadiene 1. H2F2. THF "IJ~~ . dioxone CI CI I b 1. hydrogen fluoride 2. 2,3-dichloro-5,6- dicyano-l,4-benzoquinone Diflorosone diocetote ! 640 D Diflucortolone valerate 6a,9a-difluoro-3,20- trimethyl dioxo- 168-methyl- orthoocetote 1 lp,l7,2l -trihydroxy- 1,4-pregnodiene 2. 1 1 , pyridine H3C 0 CH3 Rejerence(s): DE 2 308 73 1 (Upjohn; appl. 22.2.1973; USA-prior. 9.3.1972). US 3 980 778 (Upjohn; 14.9.1976; appl. 20.5.1975; prior. 25.10.1973,20.12.1972,9.3.1972). NL 7 303 262 (Upjohn; appl. 8.3.1973; USA-prior. 9.3.1972, 20.12.1972). starting material: US 3 557 158 (Upjohn; 19.1.1971; prior. 22.1.1962, 18.3.1959.4.8.1958). . Formdation(s): cream 0.05 %; ointment 0.05 % Trade Name(s): D: Florone (Galderma; 1982) S terodelta crema Dlflal (Yamanouchi; 1985) I: Dermaflor (Brocchieri) (Gibipharma) USA: Florone (Decmik; 1978) Sterodelta (Metapharma) J: Diacort (Upjohn- Maxiflor (Allergan; 1981) Sumitomo; 1985) Difiucortolone valerate ATC: D07AC06 Use: glucocorticoid RN: 59198-70-8 MF: C2,H,,F20s . MW: 478.58 EINECS: 261-655-8 LD,,,: 450 mg/kg (M, i.p.); >4 g/kg (M, p.0.); 180 mgkg (M, s.c.); 98 mgkg (R, i.p.); 3.1 g/kg (R, p.0.); 13 mgkg (R, s.c.) CN: (6a, 1 1 P,16a)-6,9-difluoro- 1 1-hydroxy- 16-methyl-21-[(1-oxopentyl)oxy]pregna-1,4-diene-3,20-dione diflucortolone RN: 2607-06-9 MF: C22H2RF204 MW: 394.46 EINECS: 220-022-6 H3C-S02CI, pyridine, DMF F F 21 -0cetoxy-3.20-dioxo-6a- fluoro- 118-hydroxy-16a- methyl-4-pregnene (cf. fluocoriolone synthesis) . [2S-(2a,5a,6~) ]-6 -[ [[ 3-( 2,6-dichlorophenyl )-5 -methyl-4-isoxazolyl]carbonyl]amino ]-3 ,3-dimethyl- 7- oxo-4-thia-l-azabicyclo[3.2.0]heptane-2-carboxylic acid monosodium salt monohydrate RN: 1341 2-6 4-1 MF: C,,H16C12N,Na0,S. 1 1 P,16a )-6 ,9-difluoro- 1 1-hydroxy- 16-methyl-2 1-[ (1-oxopentyl)oxy]pregna-1,4-diene-3,20-dione diflucortolone RN: 260 7-0 6-9 MF: C22H2RF204 MW: 394.46 EINECS: 22 0-0 2 2-6 H3C-S02CI, pyridine,. 25 1-5 7 5-1 LD5,: >3 g/kg (M, p.0.); >3 g/kg (R, p.o.1 CN: (6a,ll~,16~ )-1 7,21-bis(acetyloxy )-6 ,9-d1fluoro-11-hydroxy-16-methy1pregna-1,4-diene-3,20-dione ditlorasone RN: 255 7-4 9-5