25 mg as hydrochloride Histapyrrodine I Trade Names: D: Calcistin Boehringer Calcistin Hestia-comb.. Hydrochlorothiazide H 1019 Trade Names: D: Docidrazin Rhein-Pharma; Zenecabcomb
Trang 1Hexobendine H 101 1
Reference(s):
DRP 595 175 (I G Farben; 193 1)
DRP 590 175 (I G Farben; 1932)
Formulation(s): amp 0.5g15 g (10 %) (as sodium salt)
Trade Name(s):
D: Dormopan (Bayropharm)- F: Dormopan (Bayer- J: Cyclopan (Teikoku
Evipan (Bayer); wfm Noctivane (Vaillant- Oltopan (Dainippon) Stodinox (Lorem)-comb.; Defresne); wfm Ouropan Soda (Shionogi) wfm GB: Evidorm (Winthrop); wfm USA: Sombulex (Riker); wfm
Use: coronary vasodilator RN: 54-03-5 MF: C,oHuN,O1o MW: 592.69 EINECS: 200-189-1
LD,,,: 34 mgkg (R, i.v.)
CN: 3,4,5-trimethoxybenzoic acid 1,2-ethanediylbis[(methylimino)-3,l-propanediyl] ester
dihydrochloride
RN: 50-62-4 MF: C,oHuN,O,o 2HCl MW: 665.61 EINECS: 200-054-7
LD,,: 35.2 mgkg (M, i.v.); 682 m g k g (M, p.0.);
52 mgkg (R, i.v.); 2550 m g k g (R, p.0.)
methyl N.N'-dimethyl-
acrylote ethylenediornine
Trang 21012 H Hexocyclium metilsulfate
Reference(s):
DE 1 217 397 (Lentia; appl 26.3.1962)
I1 +
H3C-0
0
3.4,5-trimethoxy-
benzoyl chloride'
N,N-bis-(3-hydroxypropy1)-1,2-ethylenediamine from 1,2-dichloroethane and 3-aminopropanol:
DAS 2 042 320 (Lentia; appl 26.8.1970)
I
0
0'CH3
Hexobendine
Formulation(s): amp 10 mg; tabl 30 mg, 60 mg
Trade Name(s):
D: Card-Instenon (Byk Reoxyl (Byk Gulden); wfm Ustimon (Merck- Gulden)-comb.; wfm F: Hityl (Biosedra)-comb.; Cltvenot); wfm
Use: antispasmodic, anticholinergic RN: 115-63-9 MF: C,,H,,N,O CH,O,S MW: 428.59 EINECS: 204-097-2
LD,,,: 8900 pg/kg (M, 1.v.)
CN: 4-(2-cyclohexyl-2-hydroxy-2-phenylethyl) 1,l-dimethylpiperazinium methyl sulfate (salt)
2-bromo- 1 -methyl- 4-methyl- 1 -(2-0x0-
ocetophenane piperozine 2-phenylethy1)piperozine
(1) dimethyl sulfote 1 Hexacycliurn mctilsulfote
Reference(s):
US 2 907 765 (Abbott; 6.10.1959; prior 10.9.1956)
Forrnulation(s): drops; f c tabl 25 mg
Trang 3Hexoprenaline H 101 3
Trade Name(s):
D: Traline retard (Abbott); F: Traline (Abbott); wfm USA: Tral (Abhott); wfm
Use: bronchodilator RN: 3215-70-1 MF: C22H32N20, MW: 420.51
CN: 4,4'-[1,6-hexanediylbis[imino(l-hydroxy-2,1-ethanediyl)]]bis[1,2-benzenediol]
dihydrochloride
RN: 4323-43-7 MF: C,,H,,N,O, 2HCI MW: 493.43 EINECS: 224-354-2
LD,: 88 m g k g (M, i.v.); 2036 mglkg (M, p.0.);
58 mglkg (R, i.v.); 10 glkg (R, p.0.)
sulfate
RN: 30117-45-4 MF: C22H,2N,0,.xH2S0, MW: unspecified EINECS: 250-057-2
NWdibenzyl- 2-chloro-3',4'-
hexameihylene- dihydroxy-
diomine ocetophenone
Reference(s):
DE 1 215 729 (Lentia; appl 14.6.1963)
US 3 329 709 (Osterr Stickstoffwerke; 4.7.1967; A-prior 11.6.1963)
Formulation(s): aerosol 5.7 mg (as sulfate); amp 0.005 mg, 0.025 mg; tabl 0.5 mg (as sulfate)
Trade Name(s):
D: Etoscol (Byk Gulden); wfm I: Tocolysan (Byk Gulden; as J: Leanal (Yoshitomi; as
Hexylcaine
RN: 532-77-4 MF: C,6H,3N0, MW: 261.37
CN: I-(cyclohexylamino)-2-propanol benzoate (ester)
ATC: NOlB Use: local anesthetic
hydrochloride
RN: 532-76-3 MF: C,,H2,N02 HCI MW: 297.83 EINECS: 208-544-2
LD,,: 23 mglkg (M, i.v.); 1080 mglkg (M, p.0.)
Trang 4Reference(s):
US 2 486 374 (Sharp & Dohme; 1949; prior 1944)
Cope, A et al.: J Am Chem Soc (JACSAT) 66,1453 (1944)
Formulation(s): amp 1 %, 2 %; sol (as hydrochloride)
Trade Name(s):
USA: Cyclaine (Merck Sharp &
Dohme); wfrn
chloride 2-proponol hydrochloride
Use: anthelmintic, antiseptic RN: 136-77-6 MF: C,,H,,O, MW: 194.27 EINECS: 205-257-4
LD,,,: 1040 m g k g (M, p.0.);
550 mglkg (R, p.0.)
CN: 4-hexyl- l,3-benzenediol
resorcinol hexonoic acid
Reference(s):
DRP 488 419 (Sharp & Dohme; appl 1923; USA-prior 1923)
DRP489 117 (Sharp & Dohme; appl 1925; USA-prior 1925)
Dohme, A.R.L et al.: J Am Chem Soc (JACSAT) 48, 1688 (1926)
Twiss, D.: J Am Chem Soc (JACSAT) 48,2206 (1926)
Formulation(s): cream 20 mg; drg 2.4 mg; ointment 4.3 mg
Trade Name(s):
D: Hexamon (Beiersdorf- Mycatox (Bremer-Efeka)-
Jodo-Muc (Merz & Co.); GB: Kamillosan (Norgine)-
CH3
Hexylresorcinol
I: Oxana (Biologici Italia); wfrn
Use: antihistaminic, antiallergic RN: 493-80-1 MF: C,,H,,N, MW: 280.42 EINECS: 207-781-9
CN: N-phenyl-N-(phenylmethy1)- 1-pyrrolidineethanamine
Trang 5L-Histidine H 1015
monohydrochloride
RN: 61 13-17-3 MF: CI9H2,N2 HC1 MW: 31 6.88 EINECS: 228-079-9
N-(%chloroethyl)- N-benzyl-
pyrrolidine aniline
hydrochloride
Reference(s):
U S 2 623 880 (H Hopff et al.; 1952; D-prior 1948)
GB 659 730 (BASF; appl 1949; D-prior 1948)
Fonnulation(s): tabl 25 mg (as hydrochloride)
Histapyrrodine
I
Trade Name(s):
D: Calcistin (Boehringer Calcistin (Hestia)-comb
Mannh.)-comb with with calcium lactate; wfm
calcium lactate; w h F: CrBme domistan vit F
(Servier); wfm
Domistan (Servier); wfm I: Calcistin (Roehringer Biochemia)-comb.; wfm
ATC M01 Use: essential proteinogen amino acid (for mfusion solutions), dletary
supplement RN: 71-00-1 MF: C,H,N,O, MW: 155.16 EINECS: 200-745-3
LD,,,: >2 glkg (M, i.v.); > I 5 g k g (M, p.0.);
>2 g/kg (R, i.v.); >I5 g k g (R, p.0.)
CN: L-histidine
monohydrochloride monohydrate
RN: 5934-29-2 MF: C,H,N,O, HC1 H,O MW: 209.63
LD,,: >1.677 glkg (M, i.p.)
Isolation from hydrolysates of blood meal by ion-exchange chromatography
Reference(s):
Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed., Vol A2, 70
Vickery, M.B.: J Biol Chem (JRCHA3) 143.77 (1942)
Formulation(s): sol 0.25 gI100 ml (as hydrochloride)
Trang 61016 H Homatropine
Trade Name(s):
D: Histinorm (A.S.); wfm USA: NephrAmine (R & D)
Homatropine
(Omatropina)
ATC: SOlFA05 Use: anticholinergic, antispasmodic, mydriatic
RN: 87-00-3 MF: C,,H,,NO, MW: 275.35 EINECS: 201-716-8
CN: a-hydroxybenzeneacetic acid endo-(f)-8-methy1-8-azabicyclo[3.2.1]oct-3-y1 ester
hydrobromide
RN: 51-56-9 MF: C1,H,,NO, HBr MW: 356.26 EINECS: 200-105-3
LD,,,: 107 mglkg (M, i.v.)
- co2 OHC) + H3C-NH2 +
O H C
C O O H
oldehyde omine corboxylic dicorboxylic
Hz, Ran,-Ni H ' % 9 OH
H~C' = (f )-rnondelic ocid
H
tropine
Reference(s):
DRP 95 853 (E Tauber; appl 1896)
Homatropine
Ladenburg, A,: Justus Liebigs Ann Chem (JLACBF) 217,75 (1883)
Chemnitius, F.: J Prakt Chem (JPCEAO) 117, 142 (1927)
tropinone synthesis:
Robinson, R.: J Chem Soc (JCSOA9) 111,762 (1917); 111, 876 (1917)
Schopf, C.: Angew Chem (ANCEAD) 50,779 (1937)
racernate resolution:
Werner, G.; Miltenberger, K.: Justus Liebigs Ann Chem (JLACBF) 631, 163 (1960)
Formulation(s): eye drops 1 %; eye ointment 1 % (as hydrobromide)
Trade Name(s):
D: Homatropin POS 1 % I: Omatr Br (Formulario J: Homatropine Augentropfen (Ursapharm) Naz.; Tariff Nazionale) hydrobromide (Torii) GB: Minims Homatropine Omatropina Lux coll
Hydrobromide (Chauvin) (Allergan)
Trang 7Homatropine methylbromide H 1017
(Methylhornatropine bromide)
ATC: A07AA54 Use: anticholinergic, antispasmodic RN: 80-49-9 MF: C,7H24BrN03 MW; 370.29 EINECS: 201-284-0
LD,,: 1400 m g k g (M, p.0.);
12 m g k g (R, i.v.); 1200 mglkg (R, p.0.)
CN: endo-3-[(hydroxyphenylacetyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2 ]]octane bromide
Reference(s):
Cahen, R.L.; Tvede, K.: J Pharmacol Exp Ther (JPETAB) 105, 166 (1952)
homatropine methyl
Formulalion(s): eye drops I %, 2 %, 5 %; syrup 1.5 mg/5 ml, 5 mg15 ml; tabl 1.5 mg, 5 mg
Hornatropine methylbromide
Trade Name(s):
F: Entercine (Robapharm)- Ulfon (Lafon)-comb.; wfm I: Novatropina (ASTA
Supadol (Lederlej-comb.; comb.; wfm USA: Hycodan (Endo)
Surparine (Licardy)-comb.; Vagantyl (Robapharm)-
(9 v.) bromide
Use: neuroleptic, psychosedative RN: 3833-99-6 MF: C2,H,,F3N,0S MW: 451 S 6
CN: hexahydro-4-[3-[2-(trifluoromethy1)- 10H-phenothiazin-10-yllpropyll-I H-1,4-diazepine-l -ethanol
dihydrocldoride
RN: 1256-01-5 MF: C23H2nF3N30S 2HCl MW: 524.48 EINECS: 21 5-017-0
LD,,,: 73.5 mglkg (M, i.v.); 790 mglkg (M, p.0.);
102 mglkg (R, i.v.); 880 m g k g (R, p.0.)
2-trifluoromethyl
phenothiazine
2 I -(3-chloropropyl)- hexahydro- 1,4-diazepine
phenothiazine (1)
Trang 81018 H Hydralazine
Reference(s):
DE 1 160 442 (Degussa; appl 18.2.1960)
US 3 040 043 (Degussa; 19.6.1962; D-prior 18.3.1959)
2-chloro-
Formulation(s): tabl 3 mg (as hydrochloride)
Homofenorine
Trade Name(sj:
D: Pasaden (Homburg); wfm Seda-Ildamen (Homburg)- I: Pasaden (Farmades); wfm
comb.; wfrn
Use: antihypertensive RN: 86-54-4 MF: C,H,N4 MW: 160.18 EINECS: 201-680-3
LD,,,: 52mgkg(M,i.v.); 122mgkg(M,p.o.);
34 m g k g (R, i.v.); 90 mglkg (R, p.0.);
50 m g k g (dog, i.v.); 100 mglkg (dog, p.0.)
CN: l(2H)-phthalazinone hydrazone
monohydrochIoride
RN: 304-20-1 MF: C8H,N4 HC1 MW: 196.64 EINECS: 206-151-0
LD,,,: 84mgkg(M,i.v.); 188mg/kg(M,p.o.);
34 m g k g (R, i.v.)
0 1 Cl, 0
2 H20
hydrazine
0
phtholic phthalide
onhydride
hydrate (I)
phthalozone (11)
Reference(s):
US 2 484 029 (Ciba; 1949; CH-prior 1945)
DE 848 818 (Ciba; CH-prior 1945)
Formulation(s): amp 20 mg; drg 10 rng, 25 mg, 50 mg; tabl 25 mg, 50 mg (as hydrochloride)
Trang 9Hydrochlorothiazide H 1019
Trade Name(s):
D: Docidrazin (Rhein-Pharma;
Zenecabcomb
I~npresso-Puren (Isis
Puren)-comb
pertenso (Fournier
Pharma)-comb
Treloc (Astra1Promed)-
comb
Trepress (Novartis
~harma)-comb
Td-Normin (Zeneca)-
comb
GB: Apresoline (Novartis; as hydrochloride)
I: Apresolin Retard (Novartis;
as hydrochloride)
J: Anaspasmin (Vitacain) Aprelazine (Kaigai) Apresoline (Novartis) Aprezine (Kanto) Basedock D (Sawai) Deselazine (Kobayashi Kako)
Diucholin (Toyama)
Homoton (Horii) Hypatol (Yamanouchi) Hypos (Nippon Shinyaku) Pressfall (Nissin)
Propectin (Maruishi) Solesorin (Hishiyama) USA: Hydralazine Hydrochloride (SoloPak)
Hydra-Zide (Par)
Use: diuretic RN: 58-93-5 MF: C7H8CIN304S2 MW: 297.74 EINECS: 200-403-3
LDso: 590 mgfkg (M, i.v.); 1175 rnglkg (M, p.0.);
990 mglkg (R, i.v.); 2750 mglkg (R, p.0.);
250 mglkg (dog, i.v.)
CN: 6-chloro-3,4-dihydro-2H- l,2,4-benzothiadiazine-7-sulfonamide 1,l-dioxide
4-amino-6-chloro- poraform-
benzene-1,S- aldehyde
disulfarnide
Hydrochlorothiazide
0 0
Hydrochlorothiazide
CI
chlorothiazide formaldehyde
(4 v.)
Reference(s):
a US 3 163 645 (Ciba; 29.12.1964; appl 25.9.1964; prior 9.4.1958)
Stevens, G de et al.: Experientia (EXPEAM) 14,463 (1958)
b US 3 164 588 (Merck & Co.; 5.1.1965; GB-prior 19.6.1959)
alternative syntheses:
U S 3 025 292 (Merck & Co.; 13.3.1962; prior 26.11.1958)
purification:
U S 3 043 840 (Merck & Co 10.7.1962; appl 14.10.1359)
Formulatioiz(s): tabl 12.5 mg, 25 mg, 50 mg, 100 mg
Trang 101020 H Hydrocodone
Trade Name(s):
D: Disalunil (Berlin-Chemie)
diu melusin (Schwarz)-
comb
Esidrix (Novartis Pharma)
HCT-ISIS (Isis Puren)
numerous generics and
combination preparations
F: Acuilix (ParKe Davis)-
comb
Briazide (Pierre Fable)-
comb
Esidrex (Novartis)
Moducren (Merck Sharp &
Dohme-Chibret)-comb
Moduretic (Du Pont
Pharma)-comb
Prestole (SmithKline
Beecham)-comb
Zestoretic (Zeneca)-comb
numerous generics and
combination preparations
GB: Hydrosaluric (Merck Sharp
& Dohme)
numerous combination preparations
I: Accuretic (Parke Davis)- comb
Acediur (Guidotti)-comb
Aceplus (Bristol-Myers Squibb)-comb
Acequide (Recordati)- comb
Acesistem (Sigma-Tau)- comb
Aldactazide (SPA)-comb
Condiuren (Neopharmed)- comb
Esidrex (Novartis) lndroclor (Formulario
Naz.) Medozide (Malexi)-comb
Moduretic (Merck Sharp &
Dohme)-comb
Prinzide (Du Pont)-comb
Quinazide (Malesci)-comb
Raunova Plus (SmithKline Beecham)-comb
Selozide (Astra)-comb Spiridazide (SIT)-comb Vasoretic (Merck Sharp & Dohme)-comb
Zestoretic (Zeneca)-comb combination preparations J: Chloth~a (Iwaki) Dichlotride (Merck-Banyu) Esidrex (Novartis-Takeda) Maschitt (Showa Shinyaku) Mikorten (Zensei) Newtolide (Towa) Pantemon (Tatsumi) USA: Hydrochlorothiazide (Lederle)
HydroDIURIL (Merck Sharp & Dohme) Hydropres (Merck Sharp &
Dohme)-comb
Oretic (Abbott) Timolide (Merck Sharp & Dohme)-comb
generic and combination preparations
Use: antitussive, narcotic analgesic RN: 125-29-1 MF: C,*H,,NO, MW: 299.37 EINECS: 204-733-9
LD,,,: 8.57 mglkg (M, s.c.);
CN: (5a)-4,5-epoxy-3-methoxy-l7-methylmorphinan-6-one
bitartrate hydrate
RN: 34195-34-1 MF: C,,H,,NO, C4H60c 5/2H20 MW: 988.99
LD,,,: 375 mglkg (R, p.0.)
hydrochloride
RN: 25968-91-6 MF: C,,H21N0, HCl MW: 335.83 EINECS: 247-382-7
Pd or Pt, A
isomerizotion
CH3
Reference(s):
Ehrhart, Ruschig I , 1 19-120
DRP 607 93 1 (Knoll; 1935)
DRP 6 17 238 (Knoll; 1935)
DRP 623 821 (Knoll; 1935)
codeine
Formulation(s): amp 15 mglml (as hydrochloride); syrup 5 mg/5 ml, 100 mg15 ml; tabl 5 mg, 10 mg (as
bitartrate hydrate)
Hydrocodone