Abstract
In the previous handbook of this series on this topic (Casy 1978), attention was drawn to the fact that most compounds known at that time which effectively antagonized histamine at H1-receptor sites could be described by the general structure (1)
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Aceves J, Mariseal S, Morrison KE, Young JM (1985) The binding of doxepin to histamine H1-receptors in guinea-pig and rat brain. Br J Pharmacol 84:417–424
Adam K, Oswald I (1986) No effects on sleep of a histamine H1receptor antagonist: temelastine. Br J Clin Pharmacol 22:718–720
Anonymous (1988) New antihistamine for Allen and Hanburys. Pharm J 241:15
Awouters F, Niemegeers CJE, Janssen PAJ (1983) Pharmacology of the specific H1- antagonist astemizole. Arzneimittelforschling 33:381–388
Barlow JLR, Beitman RE, Tsai TH (1982) Terfenadine safety and tolerance in controlled clinical trials. Arzneimittleforschling 32(2): 1215–1217
Barlow RB, Franks FM, Pearson JDM (1972) The relation between biological activity and the degree of resolution of optical isomers. J Pharm Pharmacol 24:753–761
Barough V, Dall H, Patel D, Hite G (1971) Stereochemical aspects of antihistamine action: 4. Absolute configuration of carbinoxamine antipodes. J Med Chem 14:834–836
Biehl B (1979) Effects of azatadine maleate on subjective appraisal and psychomotor functions relevant to driving performance. Curr Med Res Opin 6:62–69
Blakemore RC, Ganellin CR, Garbarg M, Gros C, Ife RJ, Körner M, Ruat M, Schwartz J-C, Tertiuk W, Theoald CJ (1987) Iodobolpyramine and other iodinated derivatives as ligands for detecting histamine Η1 receptors. Eur J Med Chem 22:91–100
Borehard U, Hafner D, Heise R (1985) Η1-antagonistic actions of (+) and (-)- dimethindene (Abstr 42). Naunyn Schmiedebergs Arch Pharmacol [Suppl 1] 330: R9
Bourquin JP, Schwarb G, Waldvogel E (1973) 4-(4-Piperdylidene)-4H-benzo [4,5]cyclohepta[l,2-b] thiophen-10(9H)-ones. Ger Offen 2 302 970 2 Aug. Chem Abstr 79:105, 090p
Branch SK, Casy AF, Hussain R, Upton C (1988) The structure of phenindamine base and salts in the solute state. J Pharm Pharmacol 40:83–84
Branch SK, Casy AF (1989) Applications of modern high-field NMR spectroscopy in medicinal chemistry. Prog Med Chem 26:355–436
Brittain RT, D’Arcy PF, Hunt JH (1959) Resolution of chlorpheniramine and the pharmacological properties of its isomers. Nature (Lond) 183:734–735
Britton MG, Empey DW, John GC, McDonnell KA, Hughes DTD (1978) Histamine challenge and anterior nasal rhinometry: their use in the assessment of pseudoephedrine and triprolidine as nasal decongestants in subjects with hay fever. Br J Clin Pharmacol 6:51–58
Brogden RN, Heel RC, Speight TM, Avery GS (1978) Mianserin: a review of its pharmacological properties and therapeutic efficacy in depressive illness. Drugs 16:273–301
Brown EA, Griffiths R, Harvey CA, Owen DAA (1986) Pharmacological studies with SK and F 93944 (temelastine), a novel histamine Η1-receptor antagonist with negligible ability to penetrate the central nervous system. Br J Pharmacol 87: 569–578
Buckle DR, Rockwell CJM, Smith H, Spicer BA (1986) Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy) [l]benzopyrano [2,3-d ]-l,2,3-triazol-9(lH)-ones with combined Η1-antihistamine and mast cell stabilizing properties. J Med Chem 29: 2262–2267
Buckle RB, Outred DJ, Smith H, Spicer BA (1984) N-benzylpiperazino derivatives of 3-nitro-4-hydroxycoumarin with Η1 antihistamine and mast cell stabilizing properties. J Med Chem 27:1452–1457
Bye CE, Dewsburg D, Peck AW (1974) Effects on the human central nervous system of two isomers of ephedrine and triprolidine and their interaction. Br J Clin Pharmacol 1:71–78
Bye CE, Claridge R, Peck AW, Plowman F (1977) Evidence for tolerance to the central nervous effects of the histamine antagonist triprolidine in man. Eur J Clin Pharmacol 12:181–186
Calcutt CR, Ganellin CR, Jackson B, Leigh BK, Owen DAA, Smith IR (1987) Evidence for low brain penetration by the Η1-receptor antagonist temelastine. Eur J Pharmacol 133:65–74
Carr AA, Meyer DR (1982) Synthesis of terfenadine. Arzneimittelforschung 32(2): 1157–1159
Casy AF (1978) Chemistry of anti-Η1 histamine antagonists. In: Roche e Silva MR (ed) Histamine II and anti-histaminics. Springer, Berlin Heidelberg New York, pp 176–214 (Handbuch der experimentellen Pharmakologie, vol 18/2)
Casy AF, Mercer AD (1988) Application of cyclodextrins to chiral analysis by 1H NMR spectroscopy. Magn Reson Chem 26:765–774
Chang RSL, Tran VT, Snyder SH (979) Heterogeneity of histamine Η1-receptors: species variations in [3H]mepyramine binding of brain membranes. J Neurochem 32:1653–1663
Church MK, Gradidge CF (1980a) Inhibition of histamine release from human lung in vitro by antihistamines and related drugs. Br J Pharmacol 69:663–667
Church MK, Gradidge CF (1980b) Oxatomide: inhibition and stimulation of histamine release from human lung and leucocytes in vitro. Agents Action 10:4–7
Clarke CH, Nicholson AN (1978) Performance studies with antihistamines. Br J Clin Pharmacol 6:31–35
Cohen AF, Hamilton MJ, Liao SHT, Findlay JWA, Peck AW (1985) Pharmacodynamics and pharmacokinetics of BW 825C: a new antihistamine. Eur J Clin Pharmacol 28:197–204
Connell JT, Williams OW, Allens, Cato A, Perkins JG (1982) A double-blind controlled evaluation of Actifed and its individual constituents in allergic rhinitis. J Int Med Res 10:341–347
DeAngelis RL, Kearney MF, Welch RM (1977) Determination of triprolidine in human plasma by quantitative TLC. J Pharm Sci 66:841–843
Ebnöther A, Weber H-P (1976) Synthese und absolute Konfiguration von Clemastin und seiner Isomeren. Helv Chim Acta 59:2462–2468
Empey DW, Bye C, Hodder M, Hughes DTD (1975) A double-blind crossover trial of pseudoephedrine and triprolidine alone and in combination, for the treatment of allergenic rhinitis. Ann Allergy 34:41–46
Findlay JWA, Butz RF, Coker GG, DeAngelis RL, Welch RM (1984a) Triprolidine radioimmunoassay: disposition in animals and man. J Pharm Sci 73:1339–1343
Findlay JWA, Butz RF, Sailstad JM, Warren JT, Welch RM (1984b) Pseudoephedrine and triprolidine in plasma and breast milk of nursing mothers. Br J Clin Pharmacol 18:901–906
Fleish JH, Rinkema LE, Haisch KD, Whitesitt CA (1987) Pharmacologic analysis of LY188695 (KB-2413), l-(2-ethoxyethyl)-2-(4-methyl-l-homopiperzinyl)-benz-imidazole difumarate, a potent histamine, receptor antagonist. Agents Actions 20:40–49
Fouda HG, Hobbs DC, Stambaugh JE (1979) Sensitive assay for determination of hydroxyzine in plasma and its human pharmacokinetics. J Pharm Sci 68:1456–1458
Garteiz DA, Hook RH, Walker BJ, Okerholm RA (1982) Pharmakinetics and biotransformation studies of terfenadine in man. Arzneimittelforschung 32(2): 1185–1190
Gengo FM, Gabos C (1987) Antihistamine, drowsiness, and psychomotor impairment: central nervous system effect of cetirizine. Ann Allergy 59:53–57
Gengo FM, Dabrozo J, Yurchak A, Love S, Miller JK (1978) The relative anti-histaminic and psychomotor effects of hydroxyzine and cetirizine. Clin Pharmacol Ther 42:265–272
Gibson JR, Medder KT, McDonnell KA, Bye CE, Hughes DTD (1982) The effect of orally administered triprolidine and pseudoephedrine singly and combined on histamine-induced skin reactions. Eur Clin Pharmacol 22:411–412
Hall H, Ögren S-O (1984) Effects of antidepressant drugs on histamine-H1 receptors in the brain. Life Sci 34:597–605
Hansen EB, Heflich RH, Korfmacher WA, Miller DW, Cerniglia CE (1988) Microbial transformation of the antihistamine drug triprolidine hydrochloride. J Pharm Sci 77:259–264
Heim EB (1968) Erste therapeutische Erfahrungen an ambulanten Patienten mit einem neuen, kaum sedierenden Antihistaminikum. Praxis 57:1191–1195
Heykants J, van Peer A, Woestenborghs R, Jageneau A, van den Bussche G (1986) Dose-proportionality, bioavailability, and steady-state kinetics of astemizole in man. Drug Dev Res 8:71–78
Hill SJ (1987) Histamine receptors in the mammalian central nervous system: biochemical studies. Prog Med chem 23:29–84
Hill SJ, Young JM (1981) Characterization pf [3H]mepyramine binding to the longitudinal muscle of guinea pig small intestine. Mol Pharmacol 19:379–387
Hill SJ, Young JM, Marrian DH (1977) Specific binding of 3H-mepyramine to histamine H1 receptors in intestinal smooth muscle. Nature 270:361–363
Hill SJ, Emson PC, Young JM (1978) The binding of [3H]mepyramine to histamine H1 receptors in guinea-pig brain. J Neurochem 31:997–1004
Hussain RB (1988) Investigation of the structure of phenindamine and its analogues by high-field NMR techniques. Thesis, University of Bath
Hüther KJ, Renftle G, Barraud N, Burke JT, Koch-Wesser J (1977) Inhibitory activity of terfenadine on histamine-induced skine wheals in man. Eur J Clin Pharmacol 12:195–199
Iemura R, Kawashima T, Fukuda T, Itok, Tsukamoto G (1986) Synthesis of 2-(4-substituted-l-piperazinyl)benzimidazoles as Η1-antihistaminic agents. J Med Chem 29:1178–1183
Ison RR, Franks FM, Soh KS (1973) The binding of conformationally restricted antihistamines to histamine receptors. J Pharm Pharmacol 25:887–894
Janssens F, Torremans J, Janssen M, Stokbroekx RA, Luyckx M, Janssen PAJ (1985a) New antihistaminic N-heterocyclic-4-piperidinamines. I. Synthesis and antihistamine activity of N-(4-piperidinyl)-lH-benzimidazol-2-amines. J Med Chem 28: 1925–1933
Janssens F, Torremans J, Janssen M, Stokbroekx RA, Luyckx M, Janssen PAJ (1985b) New antihistaminic-N-heterocyclic-4-piperidinamines. II. Synthesis and antihistaminic activity of l-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-lH-benz-imidazol-2-amines J Med Chem 28:1934–1943
Janssens F, Torremans J, Janssen M, Stokbroekx A, Luyckx M, Janssen PAJ (1985c) New antihistaminic N-heterocyclic 4-piperidinamines. III. Synthesis and antihistaminic activity of N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amines. J Med Chem 28:1943–1947
Janssens F, Janssen MAC, Awouters F, Niemegeers CJE, van den Bussche G (1986) Chemical development of astemizole-like compounds. Drug Dev Res 8:27–36
Jarrousse MJ, Regnier MT (1951) Separation et activite physiologique des deux isomeres optique du dimethylaminoethoxy-(p-tolylphenyl)methane. Ann Pharm Franc 9:321–325
Kanba S, Richelson E (1984) Histamine Η1 receptors in human brain labeled with [3H]doxepin. Brain Res 304:1
Kandel SI, Steinberg GH, Kandel M, Wells JW, Gornall AG (1980) Separate binding sites for histaminic drug in rat cerebral cortex. Biochem Pharmcol 29:2269–2272
Korner M, Bouthenet M-L, Ganellin CR, Garberg M, Gros C, Ife RJ, Sales N, Schwartz J-C (1986) [125I]Iodobolpyramine, a highly sensitive probe for histamine H1receptors in guinea-pig brain. Eur J Pharmacol 120:151–160
Kulshrestha VK, Gupta PP, Turner P, Wadsworth J (1978) Some clinical pharmacological studies with terfenadine, a new antihistamine drug. Br J Clin Pharmacol 6:25–29
Kuntzman R, Sernatinger E, Tsai I, Klutch A (1968) In: Tedeschi D, Tedeschi R (eds) Importance of fundamental principles in drug evaluation. Raven, New York, p 87
Laduron PM, Janssen PFM, Gommeren W, Leysen JE (1982) In vitro and in vivo binding characteristics of a new long-acting histamine Η1-antagonist, astemizole. Mol Pharmacol 21:294–300
Le Fur G, Malgouris C, Uzan A (1981) Effect of mequitazine, a non sedative antihistamine on brain Ηχ-receptors. Life Sci 29:547–552
Lichtenstein LM, Gillespie E (1975) The effects of the H1 and H2 antihistamines on “allergic” histamine release and its inhibition by histamine. J Pharmacol Exp Ther 192:441–450
Luscombe DK, Nicholls PJ, Spencer PS (1980) Effect of azatadine on human performance. Br J Clin Pract 34:75
Martin U, Römer D (1978) The pharmacological properties of a new orally active antianaphylactic compound: ketotifen, a benzocycloheptathiophene. Arzneimittelforschung 28:1–12
Mattila MJ, Mattila Μ, Konno K (1986) Acute and subacute actions on human performance and interactions with diazepam of temelastine (SK and F93944) and diphenhydramine. Eur J Clin Pharmacol 31:291–298
McCall MK, Nair N, Wong S, Townleg RG, Lang D, Weiss SJ (1985) Double-blind controlled safety and efficacy trial of SK and F93944 (Abstr 256). J Allergy Clin Immunol 168:75
Mercer AD (1989) PhD Thesis University of Bath, UK
Merck Index (1983) Fontazine, 10th edn. Merck, Rahway
Meuldermans W, Hendrickx J, Lauwers W, Hurkmans R, Swysen E, Heykants J (1986) Excretion and biotransformation of astemizole in rats, guinea-pigs, dogs, and man. Drug Dev Res 8:37–51
Michiels M, van Peer A, Woestenborghs R, Heykants J (1986) Pharmacokinetics and tissue distribution of astemizole in the dog. Drug Dev Res 8:53–62
Morley J, Page CP, Mazzoni L, Sanjar S (1986) Effects of ketotifen upon responses to platelet activating factor: a basis for asthma prophylaxis. Ann Allergy 56:335–340
Naspitz CK (1984) User of calcium channel blocking agents in the managment of childhood asthma. J Asthma 21:451–460
Nauta WT, Rekker RF (1978) Structure-activity relationships of H1-receptor antagonists. In: Roche e Silva MR (ed) Histamine II and anti-histaminics. Springer, Berlin Heidelberg New York, pp 215–249 (Handbuch der experimentellen Pharmakologie, vol 18/2)
Nicholson AN (1979) Effect of the antihistamines brompheniramine maleate and triprolidine hydrochloride on performance in man. Br J Clin Pharmacol 8:321–324
Nicholson AN, Pascoe PA, Turner C, Ganellin CR, Casy AF, Mercer AD (1989) Alertness and performance in man with enantiomers of chlorpheniramine and dimethindene. Proc Brit Pharmacol Soc Leeds July 1989 Abstr C44
Niemegeers CJE, Awouters F, van Nueten JM, de Nollin S, Janssen PAJ (1978) Protection of rats from compound 48/80-induced lethality. A simple test for inhibitors of mast cell-mediated shock. Arch Int Pharmacodyn Ther 234:164–176
Novak L, Protiva M (1959) Mephenhydramine derivatives substituted in the p - and m -position. Collect Czech Chem Commun 24:3966–3977
Okerholm RA, Weiner DL, Hoak RH, Walker BJ, Leeson GA, Biedenbach SA, Cawein MJ, Dusebout TD, Wright GJ, Myers M, Schindler V, Cook CE (1981) Bioavailability of terfenadine in man Biopharm Drug Dispos 2:185–193
Otsuri I, Ishiko J, Sakai M, Shimahara K, Momiyama T (1972) Comparison of pharmacological activities of doxepin hydrochloride and its geometrical isomer. Pharmacometrics (Tokyo) 6:973–982
Peck AW, Fowle ASE, Bye C (1975) A comparison of triprolidine and clemastine on histamine antagonism and performance tests in man: implications for the mechanism of drug induced drowsiness. Eur J Clin Pharmacol 8:455–463
Peroutka SJ, Snyder SH (1981) [3H] Miaserin: differential labeling of serotonin2 and histamine1 receptors in rat brain. J Pharmacol Exp Ther 216:142–148
Rege SR, Sharma SD (1986) Comparative efficacy and safety of azatadine and pheniramine in allergic rhinitis. Curr Ther Res 39:378–382
Remy DC, Rittle KE, Hunt CA, Anderson RS, Engelhardt EL (1977) (+) and (-)- 3-Methoxycyproheptadine. A comparative evaluation of the antiserotonin, anti-histaminic, anticholinergic, and orexigenic properties with cyproheptadine. J Med Chem 20:1681–1684
Richard DM, Brogden RN, Heel KC, Speight TM, Avery GS (1984a) Oxatomide. A review of its pharmacodynamic properties and therapeutic efficacy. Drugs 27: 210–231
Richards DM, Borgden RN, Heel RC, Speight TM, Avery GS (1984b) Astemizole: a review of its pharmacodynamic properties and therapeutic efficacy. Drugs 28: 38–61
Römer D, Weidmann H (1966) Pharmakologishe Studien über das neue Antihista-minicum Tavegil. Med Welt 17:2791–2794
Roszkowski AP, Govier WM (1959) Comparison of racemic carbinoxamine with its optically active isomers. Pharmacologist 1:60
Roth FE, Govier WM (1958) Comparative pharmacology of chlorpheniramine (chlor-trimeton) and its optical isomers. J Pharmacol Exp Ther 124:347–349
Saito T, Fukuda T, Sukamoto T, Yoshidomi M, Morimoto Y, Shimohara K, Ito K (1988) General pharmacology of l-(2-ethoxyethyl)-2-(4-methyl-l-homopiperazinyl) benzimidazole difumarate. Arzneimittelforschung 38:66–69
Schoeffter P, Ghysel-Burton J, Cabanie M, Godfraind T (1987) Competitive and steroselective histamine Η1 antagonist effect of cicletanide and guinea-pig isolated ileum. Eur J Pharmacol 139:235–237
Shafi’ee A, Hite G (1969) The absolute configurations of the pheniramines, methylphenidates and pipradols. J Med Chem 12:266–270
Silbaugh SA, Stengel PW, Rinkema LE (1987) Pulmonary aerosal actions of LY188695 (KB 2413), a new potent Η1-receptor antagonist. Agents Actions 21:83–88
Snyder SH (1983) Neurotransmitter receptor binding and drug discovery. J Med Chem 26:1667–1672
Speight TM, Avery GS (1972) Pizotifen (BC-105) A review of its pharmacological properties and its therapeutic efficacy in vascular headaches. Drugs 3:159–203
Sterk GJ, Koper J, Vandergoot H, Timmerman H (1987) Studies on histaminergic compounds VIII. A new series of compounds showing H1-antagonistic and H2- agonistic properties; synthesis, in vitro pharmacology and structure-activity relationships. Eur J Med Chem 22:491–498
Stokbroekx RA, Luychx MGM, Willems JJM, Janssen M, Bracke JOMM, Joosen RLP, van Wauwe JP (1986) Levocabastine (R50547): the prototype of a chemical series of compounds with specific Η1-antihistamine activity. Drug Dev Res 8:87–93
Taylor JE, Richelson E (1982) High-affinity binding of [3H]doxepin to histamine Η1-receptors in rat brain: possible identification of a subclass of histamine Η1-receptors. Eur J Pharmacol 78:279–285
Tham R, Norlander B, Hägermark Ö, Fransso L (1978) Gas chromatograpy of clemastine. Arzneimittelforschung 28:1017–1020
Tran TT, Lebovitz R, Toll L, Snyder SH (1981) [3H]Doxepin Interactions with histamine Η1-receptors and other sites in guinea pig and rat brain homogenates. Eur J Pharmacol 70:501–509
Vandenberk J, Kennis LEJ, van der Aa MJMC, van Heertum AHMT (Janssen Pharmaceutica) (1978) Piperazine and piperidine derivatives. Ger Offen 2 714 437 20 Oct 1977. Chem Abstr 88:50920n
Van der Burg WJ, Bonta IL, Delobelle J, Ramon C, Vargaftig B (1970) A novel type of substituted piperazine with high antiserotonin potency. J Med Chem 13:35–39
Van Nueten Jm, Janssen PAJ (1973) Comparative study of the effects of flunarizine and cinnarizine on smooth muscles and cardiac tissues. Arch Int Pharmacodyn Ther 204:37–55
Walsh DA, Franzyshen SK, Yanni, JM (1989) Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-l-[3-(aryloxy)propyl]piperidines and structurally related compounds. J Med Chem 32:105–118
Wiech NL, Martin JS (1982) Absence of an effect of terfenadine on guinea pig brain histamine Η1-receptors in vivo determined by receptor binding techniques. Arzneimittelforschung 32(2):1167–1170
Williams BO, Liao SHT, Lai AA, Arnold JD, Perkin JG, Blum MR, Findlay JWA (1984) Bioavailability of pseudoephedrine and triprolidine from combination and single-ingredient products. Clin Pharm 3:638–643
Woestenborghs RI, Geuens 1, Michiels M, Hendriks R, Heykants J (1986) Radioimmunoassay procedures for astemizole and metabolites in plasma. Drug Dev Res 8:63–69
Woodward JK, Munro NL (1982) Terfenadine, the first non-sedating antihistamine. Arzneim Forsch 32:1154–1156
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1991 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Casy, A.F. (1991). Antagonists of H1 Receptors of Histamine: Recent Developments. In: Uvnäs, B. (eds) Histamine and Histamine Antagonists. Handbook of Experimental Pharmacology, vol 97. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75840-9_26
Download citation
DOI: https://doi.org/10.1007/978-3-642-75840-9_26
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-75842-3
Online ISBN: 978-3-642-75840-9
eBook Packages: Springer Book Archive