Hydrocortisonc H 102 1 Trade Name(s): D: Dicodid (Knoll) USA: Hycotuss (Endo)-comb. numerous combination 1: Dicodid (Knoll); wfm Tussend (Monarch)-comb. preparations Hydrocortisone ATC: AOlAC03; A07EA02; D07AA02; COSAAO I ; DO7XAO 1 ; H02AB09; S01BA02; S01CB03; S02BA01 Use: glucocorticoid, anti-inflammatory RN: 50-23-7 MF: C,,H,,O, MW: 362.47 EINECS: 200-020-1 LD,,:' >500 mglkg (M, s.c.); 150 mgkg (R, i.p.); 449 mg/kg (R, s.c.) CN: (1 1 P)-11,17,21-trihydroxypregn-4-ene-3,20-dione 1. Hz. Pd-C 2. HCOOH. 1- & & @ * No, 11 OHC-0 ' OHC-0 Br~r 1. 1 H3C OK 2. 3 3 , Tos-OH HJC 0 CH, ____, AI[OCH(CH,),I, microbiologicol hydroxylation 2. KOH [Curvularia lunola] lil * Reichstein's substance S Hydrocortisane 1022 H Hydrocortisone cortisone 21 -acetate semicorbazide hydrochloride KBH4 IV - potassium boro- hydride 0 3.3:20.20-bis(ethy1enedioxy)- 11p,17,21 -trihydroxy-5-pregnene (from cortisone) rnicrobiologicol hydroxylation CH3 [Rhiiopua arrhims Archer (ATCC-1 1 145) or Rhizopus nigricans] , dH3 HO,,,, H H 0 0 I Hydrocortisone I progesterone 1 1 a-hydroxy- progesterone (V) 0 Cr03, CH3COOH v diethyl oxalate Hydrocortisone H 1023 1. H20, H+ FH3 2 j 3 . pyridine , H~o,. 050, H3C 0 CH3 + morpholine hydrocortisone 21 ocetate (IX) Reference(s): a US 2 649 401 (Upjohn; 1953; appl. 1950). US 2 658 023 (Pfizer; 1953; appl. 1952). US 2 794 816 (Upjohn; 1957 appl. 1954). synthesis of cortexolon: Julian, PL.: J. Am. Chem. Soc. (JACSAT) 72, 5145 (1950). Sondheimer, F. et al.: J. Am. Chem. Soc. (JACSAT) 78, 816 (1956). The Merck Index, 289 1 (Rahway 1976). b Oliveto, E. et al.: J. Am. Chem. Soc. (JACSAT) 78, 1736 (' c US 2 666 069 (American Cyanamid; 1954; appl. 195 1). synthesis of starting inaterial: US 2 622 081 (American Cyanamid; 1952; appl. 1951). US 2700 666 (American Cyanamid; 1955; appl. 1953). d Hogg, J.A. et al.: J. Am. Chcm. Soc. (JACSAT) 77,4436 ( US 2 769 823 (Upjohn; 1956; appl. 1954). alternative syntheses: US 2 541 104 (Merck & Co.; 195 1; appl. 1947). GB 800 797 (Pfizer; appl. 1956; USA-prior. 1955). US 4 041 055 (Upjohn; 9.8.1977; appl. 17.1 1.1975). DOS 2 803 660 (Schering AG; appl. 25.1.1978). DOS 2 803 661 (Schering AG; appl. 25.1.1978). review: Fieser, L.F.; Fieser, M.: Steroide, 7 10,737 (Weinheim 1961) Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 13.52. pharmaceurical fortnulation: DOS 2 606 516 (Dermal; appl. 18.2.1976; GB-prior. 19.2.1975). Formulation(s): cream 0.5 %; lotion 0.5 %: ointment 1 76, 2.5 %; tabl. 10 mg 1024 H Hydrocortisone acetate Trade Name(s1: D: Dermallerg-ratiopharm (ratiopharm) Dcrm Posterisan (Kade) Ficortril (Pfizer; as acetate) Hydrocort (Pharmagalen) Hydrocortison Hoechst (Hoechst) H ydroderm (Karrcr) Hydrogalen (Pharmagalen) Munitren H (Rohugen) Sanatison (Parke Davis) generics and several combination preparations F: Daktacort (Janssen-Ci1ag)- comb. Hydracort (Galderma) numerous gcnerics and combination preparations GB: Cobadex (Cox)-comb. Corlan (Evans) Efcortelan (Glaxo Wellcome) Eurax Hydrocortisone (Novartis Consumer)- comb. Hydrocortistab (Knoll) Hydrocortisyl (Hoechst) Hydrocortone (Merck Sharp & Dohme) several combination preparations 1: Algicortis (Vaillant) Daktacort crema (Janssen)- comb. Dermocortal (Purophanna) Molidex (C1intec)-comb. Nasomixin (Pierrel)-comb. Sintotrat (Edrnond) Vasosterone (Angelhi)- comb. several combination preparations J: Cortril (Taito Plizer) Solu-cortef (Sumitomo Chern.) USA: Cortenema (Solvay) Hydrocortone (Merck Sharp & Dohme) Hy tone (Dermik) Protocort (Monarch) several combination preparations Hydrocortisone acetate ATC: A07EA02; D07AA02 Use: glucocorticoid RN: 50-03-3 MF: C,,H,,O, MW: 404.50 EINECS: 200-004-4 LD,,,: 2300 mgkg (M, i.p.); 45.05 mdkg (M, s.c.) CN: (I 1 ~)-21-(acetyloxy)-11,17-dihydroxypregn-4-ene-3,2O-dione hydrocortisone (9. v.) ocetic onhydride Hydrocortisone acetate Rqference(s): US 2 183 589 (Roche-Organon; 1939; CH-prior. 1936). alterilative syntheses: US 2 541 104 (Merck & Co.; 1% 1 ; appl. 1947). US 2 769 823 (Upjohn; 1956; appl. 1954). Formulation(s): cream 3.3 mg; ointment (0.5 %, I %, 2 %); suppos. 3.3 mg Trade Name(s): D: Colifoam (Trommsdorff) Cortisol Thilo (Thilo) Ebcnol (Strathrnann) F: Ficortril Augensalbe (Pfizer) H ydrocortison-POS (Ursapharm) Litraderm (Desitin) numerous combination preparations and generics Colofoam (Norgine Pharma) Hydrocortisone Rousscl GB: Susp. Inj. (Roussel) Onctose hydrocortisone (Monot)-comb. Proctocort (Boehringer Ing.1 numerous combination preparations and generics Actinac (Hoechst)-comb. Anugesic HC (Parke Davis)-comb. Anus01 HC (Parke Davis)- comb. Hydrocortisone 17-butyratc H 1025 Colifoam (Stafford-Miller) Cortison-Chernicetina Xyloproct (Byk Gulden)- Fucidin H (Leo)-comb. (Carlo Erbai-comb. comb. Neo-cortef (Dominion)- Emorril (Po1i)-comb. J: Dortizon Oint. (Kobayashi comb. Idrocet (Lusofarmaco)- Kako) Proctofoam (Stafford- comb. Hydrocortisone (Banyu) Miller)-comb. Idrocortisone Roussel Hydrocortone (Merck- Xyloproct (Astra)-comb. (Roussel) Banyu) numcrous combination Idroneomicil (Poli)-comb. KC Oint. (Hokuriku) preparations Lenirit (Bonomelli Farm.) Manosil (Surnitomo I: Antiacne Samil (Sarni1)- Mictasone (Zoja)-comb. Kagaku) comb. Proctosedyl (Rousse1)- Otozon Babe (Nakano) Antiemorroidale comb. Scheroson F (Nihon Milanfarma (Milanfarma)- Reumacort (Teofarmai- Schering) comb. comb. USA: Anusol-HC (Parke Davis) Argisone (Teofarrna)-comb. Urecortyn (Roussel) Cortifoam (Schwarz) Cortidro (Salus Research) Vasosterone antib. Pramosone (Femdale) Cortinal (Teofarma)-comb. (Angelhi)-comb. numerous combination preparations and gcncric Hydrocortisone 17-butyrate ATC: D07A~02 Use: glucocorticoid RN: 13609-67-1 MF: C,,H,,O, MW: 432.56 EINECS: 237-093-4 LD,,: >3 glkg (M, p.0.); >3 glkg (R, p.0.) CN: (1 1 P)-11,21 -dihydroxy- 17-(I-oxobutoxy)pregn-4-ene-3,20-dione hydrocortisone N,N-dimethyl- (9. v.) butyromide 1. (H,CO),SO*. NaOCH3 2. CH3COOH 1. dimethyl sulfate Hydrocortisone 17-butyrote I Referencefs): DAS 2 644 556 (Beiersdorf AG; appl. 2.10.1976). alternative syntheses: DAS 2 441 284 (Schering AG; appl. 16.9.1974). JP 52 010 489 (Taisho; appl. 15.7.1975). JP 52 136 157 (Taisho; appl. 14.4.1976). JP 53 015 360 (Taisho; appl. 26.7.1976). DOS 2 055 221 (Lab. Chimico Farma Untico; appl. 10.11.1970). DOS 2 204 366 (Dermal; appl. 27.1.1962). Formulation(si: cream 1 mg/g; emulsion 1 mglg; lotion 1 mglg; ointment 1 mglg Trade Name(s): D: Alfason (Yamanouchi) GB: Locoid (Yamanouchi) Molidex (Clintec)-comb. Laticort (medphano) I: Daktacort crema (Jamsen)- Nasomixin (Pierrel)-comb. E Locoid (Yamanouchi comb. J: Locoid (Torii) Pharma) Locoidon (Brocades) USA: Locoid (Ferndale) 1026 H Hydrocortisone sodium phosphate Hydrocortisone sodium phosphate ATC: S01XA99 Usc: glucocorticoid RN: 6000-74-4 MF: C,,H,,Na20,P MW: 486.41 EINECS: 227-843-9 LD,,,: 746 mglkg (M, i.v.); 3950 mgkg (M, p.0.); 632 mg/kg (R, i.v.); 6100 mgtkg (R, p.0.) CN: ( 1 10)- 1 1,17-dihydroxy-21-(phosphonooxy)pregn-4-ene-3,20-dione disodium salt free acid RN: 3863-59-0 MF: C2,H3,08P MW: 442.45 EINECS: 223-382-2 pyridine ___, \\ ,LH3 Nol, DMF + I hydrocortisone methone (4. v.) sulfonyl chloride Hydrocortisone sodium phosphote Kejerence (s): US 2 936 313 (Glaxo; lO.S.1960; appl. 18. 11.1958; GB-prior. 19.1 1 .l957). US 2 932 657 (Merck & Co.; 12.4.1960; appl. 30:6.1957). alternative syntheses: US 2 870 177 (Merck & Co.; 20.1.1959; appl. 4.8.1954). US 3 068 223 (Merck & Co.; 11.12.1962; appl. 18.1 1.1958; prior. 4.8.1954). DE 1 134 075 (Merck AG; appl. 26.11.1959). Formularion(s); amp. 100 mg; drops 0.335 % Trude Name(s): D: Pantocrinale (Simons)- I: Idracemi coll. (Farmigea) USA: Hydrocortone Phosphate comb. Idracemi eparina Inj. (Merck Sharp & GB: Efcortesol (Glaxo (Farrnigea)-comb. Dohme) Wellcome) J: Gleiton (Sankyo Zoki) Hydroflumethiazide ATC: C03AA02 LJse: diuretic, antihypertensive RN: 135-09-1 MF: C,H,F3N304S, MW: 331.30 EINECS: 205-1 73-8 LD,,,: 750mg/kg(M,i.v.);>10g/kg(M,p.o.) CN: 3,4-dihydro-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sullunamide 1,1 -dioxide Hydromorphone H 1027 3-lrilluaromethyl aniline 4-amino-6-trifluoromethyl- benzene-1.3-disulfomide (I) paraform- Hydroflumethiazide oldehyde Reference(s1: US 3 254 076 (Lovens Kemiske Fabrik; 31.5.1966; GB-prior. 13.8.1958). Holdrege, C.T. et al.: J. Am. Chem. Soc. (JACSAT) 81,4807 (1959). Formulation(s): tabl. 25 mg, 50 mg Trade Name(s): F: Eusod (Leo)-comb.; wfm Hydrenox (Knoll) Robezon (Mitsu) Leodrine (Leo); wfm I: Diuritens (Biotrading) Rontyl (Leo-Sankyo) Plurine (Leo)-comb, with comb.; wfm USA: Diucardin (Wyeth-Ayerst) KC]; wfm Rivosil (Benvegna); wfm GB: Aldactide 50 (Sear1e)- J: Di-Ademil (Squibb-Showa) comb. Enjit (Meiji) Hydromorphone ATC: N02AA03 Use: analgesic RN: 466-99-9 MF: C,,HI,NO, MW: 285.34 EINECS: 207-383-5 LD,: 104 mglkg (M, i.v.) CN: (5cl)-4,5-epoxy-3-hydroxy-I7-methylmorphinan-6-one monohydrochloride RN: 71-68-1 MF: C,,H,,NO, . HCI MW: 321.80 CINECS: 200-762-6 LD,: 55 mglkg (M, i.v.) Pd or Pt. A isornerizotion morphine I Hydromorphone Reference(s): Ehrhart, Ruschig I, 120. DRP 365 683 (Knoll; 1922). DRP 607 93 1 (Knoll; 1935). DRP 617 238 (Knoll; 1935). DRP 623 821 (Knoll; 1935). 1028 H Hydroxocobalamin Forrnulation(s): amp. 1 mglml, 2 mglml, 10 mglml, 50 mgl5 ml; tabl. 2 mg, 4 mg, 8 mg; vial 500 mg15 ml (as hydrochloride) Trade Narne(s): D: Dilaudid (Knoll; as GB: Palladone (Napp; as hydrochloride) hydrochloride) Dilaudid-Atropin (Knoll; as USA: Dilaudid (Knoll; as hydrochloride)-comb. hydrochloride) generics Hydroxocobalamin ATC: ~03~~33 (Aquocobalamin; Hydroxycobalamin; Vitamin BIZa) Use: antipernicious vitamin (depot form: acetate) RN: 13422-5 1-0 MF: C,2H,,CoNl,0,5P MW: 1346.38 EINECS: 236-533-2 LD,,: >50 mglkg (M, i.v.) CN: cobinamide dihydroxide dihydrogen phosphate (ester) mono(inner salt) 3'-ester with 5,6-dimethyl-1-a-D- ribofuranosyl- 1 H-benzimidazole hydrate RN: 13422-52- 1 MF: C,2H,,CoNl,0,5P~ H20 MW: 1364.39 EINECS: 236-534-8 acetate RN: 22465-48- 1 MF: C,H,lCoN,301,P MW: 1388.41 EINECS: 245-019-7 LD,,,: 2 glkg (M, i.v.) cyanocobalamin I Hydroxocobalarnin Reference(s): US 2 738 301 (Merck & Co.; 1956; appl. 1950). US 2 738 302 (Merck & Co.; 1956; appl. 1950). Hydroxycarbamide H 1029 stabilized solutions: FR 1336 671 (Merck & Co.; appl. 28.2.1962; USA-prior. 13.3.1961). Formulation(s): amp. 0.5 mgll ml; cps. 460 mg; vial 5 mg, 10 mg (as hydrochloride) Trade Name(s): D: Aquo-Cy tobion (Merck) Lophakomp-B 12 Depot (Lomapharm) Novidroxin (Fatol; as acetate) numerous comhination preparations F: Arginotri-B (Bouchara)- comb. DodCcavit (L'Arguenon; as acetate) Hydroxo 5000 (Lipha SantC Division Aron-MCdica) Inadrox (Logeais; as acetate)-comb. Nbparyl B I2 (CIBA Vision Ophthalmics; as acetate)-comb. Tcrncurine H 5000 (Bristol- Myers Squibb; Labs. Al1ard)-comb. Vibalgan (Doms-Adrian; as acetate)-comb. generic and numerous combination preparations GB: Cobalin-H (Link) Neo-Cytamen (Evans) numerous combination preparations I: Idroxoc (Formulario Naz.) Idroxoc (Biologici Italia) Neocytamen (Teofarma) numerous combination preparations J: Anemisol (Tobishi) Aquo B'av (Nippon Zoki) Bistin (Yamanouchi) B-Red S (Kyorin) B-Valet BIZ (Tokyo Tanabe) Cobalamin H (Otsuka) Colsamine (Kanto) USA: Dasvit H (Tanabe) Docelan (Nippon Roussel- Chugai) Dolevern (Seiko) Fresmin-S (Takeda; as . acetate) Funacomin-F (Funai) Hicobala (Mitaka) Hicobalan (Maruko) Hydocobamin (Hishiyama) Hydocomin (Sanwa) Hydroxomin (Tokyo Hosei) Laseramin (Choseido) Masblon H (Fuso) Nichicoba (Nichiiko) OH-B,, (Morishita) Rasedon (Sawai) Red-B (Kowa) Redisol H (Merck-Banyu) Runova (Squibb-Sankyo) Solco H (Tobishi) Tsuerumin S (Mohan) Twelvmin (Mohan) Vigolatin (Kowa) Bevitamel (Westlake)- comb. Chromagen (Savage)- comb. Mega-B (Arco)-comb. numerous combination preparations Hydrox ycarbamide (Hydroxyurea) ATC: LOIXX05 Use: antineoplastic RN: 127-07-1 MF: CH4N202 MW: 76.06 EINECS: 204-821-7 LD,,,: 2350 mgkg (M, i.v.); 7330 mglkg (M, p.0.); 4730 mgkg (R, i.v.); 5760 mgkg (R, p.0.); >I g/kg (dog, i.v.); >2 glkg (dog, p.0.) CN: hydroxyurea Amberlite IRA-41 0 NaOCN + H2N-OH *HC - sodium hydroxylamine cyanote hydrochlaride Hydroxycarbamide u Rejerence(s): US 2 705 727 (Du Pont; 1955; prior. 1952). 1030 H Hydroxychloroquine Trade Name(s): D: Litalir (Bristol-Myers GB: Hydrea (Bristol-Myers USA: Hydrea (Bristol-Myers Squibb) Squibb) Squibb) Syrea (medac) I: Onco-Carbide (Astra- F: HydrCa (Bristol-Myers Simes) Squibb) I: Hydrea (Bristol) Hydroxychloroquine ATC: POIBA02 Use: antirheumatic, antimalarial RN: 1 18-42-3 MF: C,,H,,ClN,O MW: 335.88 EINECS: 204-249-8 LD,,,: 1240 mglkg (M, pa) CN: 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol sulfate (1:l) RN: 747-36-4 MF: C,,H,,ClN,O . H,SO, MW: 433.96 EINECS: 212-019-3 phosphate (1:2) RN: 6168-85-0 MF: C,,H,,ClN,O . 2H,P04 MW: 531.87 NH3, Hz, Raney-Ni I + CH3 5-chloro- 2-ethylamino- 2-oentanone ethanol H2NwN"d)H CH3 bH3 CI (1) 4,7-dichloro- Hydroxychloroquine quidhe Refermce(s): US 2 546 658 (Sterling Drug; 195 1 ; prior. 1949). Formulation(s): drg. 200 mg (as hydrochloride) Trade Name(s): D: Quensyl (Sanofi Winthrop) I: Plaquenil (Maggioni- F: PlaquCnil (Sanofi Winthrop) Rhyurnapirine S:Q (Nichiiko) Toremonil (Iwaki) winthrop) J: Eroquin (Shionogi) GB: Plaquenil (Sanofi Plaquenil (Yamanouchi) USA: Plaquenil (Sanofi Winthrop) Winthrop; as sulfate) Hydroxyethyl salicylate (Glycol salicylate) ATC: M02AC Use: anti-inflammatory, analgesic RN: 87-28-5 MF: C9H,,,0, MW: 182.18 EINECS: 201-737-2 CN: 2-hydroxybenzoic acid 2-hydroxyethyl ester . RN: 13 5-0 9-1 MF: C,H,F3N304S, MW: 331.30 EINECS: 20 5-1 7 3-8 LD,,,: 750mg/kg(M,i.v.);>10g/kg(M,p.o.) CN: 3,4-dihydro- 6-( trifluoromethyl )-2 H-1,2,4-benzothiadiazine-7-sullunamide 1,1 -dioxide. 432.56 EINECS: 23 7-0 9 3-4 LD,,: >3 glkg (M, p.0.); >3 glkg (R, p.0.) CN: (1 1 P )-1 1,21 -dihydroxy- 1 7-( I-oxobutoxy)pregn-4-ene-3,20-dione hydrocortisone N,N-dimethyl- (9. v.) butyromide. glucocorticoid RN: 5 0-0 3-3 MF: C,,H,,O, MW: 404.50 EINECS: 20 0-0 0 4-4 LD,,,: 2300 mgkg (M, i.p.); 45.05 mdkg (M, s.c.) CN: (I 1 ~ )-2 1-( acetyloxy )-1 1,17-dihydroxypregn-4-ene-3,2O-dione hydrocortisone