
CAS Name: 3-(3-Ethylhexahydro-1-methyl-1H-azepin-3-yl)phenol
Additional Names: 1-methyl-3-ethyl-3-(m-hydroxyphenyl)hexahydro-1H-azepine
Percent Composition: C 77.21%, H 9.93%, N 6.00%, O 6.8...
Literature References: Mixed opioid agonist-antagonist. Prepn of the hydrobromide: J. F. Cavalla, A. C. White, DE 1941534 corresp to US 3729465 (1970, 1973 both to Wyeth); of the free base: eidem, US 4197241 (1980 to Wyeth). Properties: P. G. Goode, A. C. White, Br. J. Pharmacol. 43, 462 (1971). HPLC determn in plasma: T. Frost, Analyst 106, 999 (1981). Pharmacokinetics in man: G. Davies, Eur. J. Clin. Pharmacol. 23, 535 (1982). Human pharmacology and abuse potential: R. E. Johnson, D. R. Jasinski, Clin. Pharmacol. Ther. 41, 426 (1987). Clinical studies: R. K. Price, A. N. Latham, Curr. Med. Res. Opin. 8, 54 (1982); C. E. Parker, A. F. Langrick, J. Int. Med. Res. 10, 408 (1982). Symposium on clinical studies: Postgrad. Med. J. 59, Suppl. 1, 1-94 (1983). Review of pharmacology and clinical efficacy: B. Holmes, A. Ward, Drugs 30, 285-312 (1985).
CAS Name: Avermectin B1
Additional Names: 5-O-demethylavermectin A1a and 5-O-demethyl-25-de(1-methylpropyl)-25-(1-methylethyl)avermectin A1a (4:1); avermectin B1a/bTrademarks: Agri-Mek (Syngent...
Literature References: Mixture of avermectins, q.v., containing at least 80% of avermectin B1a (C48H72O14) and not more than 20% of avermectin B1b (C47H70O14). Isoln from Streptomyces avermitilis: G. Albers-Schönberg et al., DE 2717040; eidem, US 4310519 (1977, 1982 both to Merck Co.). Separation of components: T. W. Miller et al., Antimicrob. Agents Chemother. 15, 368 (1979); by semi-preparative HPLC: C. C. Ku et al., J. Liq. Chromatogr. 7, 2905 (1984). Structure determn: G. Albers-Schönberg et al., J. Am. Chem. Soc. 103, 4216 (1981). Absolute configuration: J. P. Springer et al., ibid. 4221. Partial synthesis of B1a: K. C. Nicolaou et al., ibid. 106, 4189 (1984). Total synthesis: S. Hanessian et al., ibid. 108, 2776 (1986). Anthelmintic activity: L. S. Blair, W. C. Campbell, J. Parasitol. 64, 1032 (1978); J. R. Egerton et al., Antimicrob. Agents Chemother. 15, 372 (1979); K. S. Todd et al., Am. J. Vet. Res. 45, 976 (1984). Pesticidal activity: I. Putter et al., Experientia 37, 963 (1981); R. A. Dybas, A. St. J. Green, Proc. Br. Crop Prot. Conf. - Pests Dis. 1984, 947. Control of red imported fire ants: J. A. Greenblatt et al., J. Agric. Entomol. 3, 233 (1986). Interaction with GABA receptors: S. S. Pong et al., J. Neurochem. 34, 351 (1980); T. N. Mellin et al., Neuropharmacology 22, 89 (1983). Receptor binding studies: S. S. Pong, C. C. Wang, ibid. 19, 311 (1980); G. Drexler, W. Sieghart, Eur. J. Pharmacol. 99, 269 (1984). Fate in soil and plants: D. L. Bull et al., J. Agric. Food Chem. 32, 94 (1984); H. A. Moye et al., ibid. 35, 859 (1987); M. S. Maynard et al., ibid. 37, 178, 184 (1989). Review: J. R. Babu, ACS Symp. Ser. 380, 91-108 (1988). Reviews of modes of action: C. C. Wang, S. S. Pong, Prog. Clin. Biol. Res. 97, 373-395 (1982); D. J. Wright, Biochem. Soc. Trans. 15, 65-67 (1987); of insecticidal activities and use: L. Strong, T. A. Brown, Bull. Entomol. Res. 77, 357-389 (1987). Book: Ivermectin and Abamectin, W. C. Campbell, Ed. (Springer-Verlag, New York, 1989) 363 pp.
CAS Name: Omega-3 polyunsaturated fatty acids ethyl esters
Trademarks: Omacor (Pronova)
Literature References: Mixture of ethyl esters of long-chain omega-3 fatty acids extracted from fish oil, primarily docosahexaenoic and eicosapentaenoic acids, q.q.v. Purification from crude fish oil: H. Breivik et al., US 5656667 (1997 to Norsk Hydro). Clinical effect on lipid profile in hyperlipidemia: L. Calabresi et al., Atherosclerosis 148, 387 (2000); in combination with simvastatin: P. N. Durrington et al., Heart 85, 544 (2001). Clinical trial to prevent sudden death following myocardial infarction: A. Macchia et al., Eur. J. Heart Fail. 7, 904 (2005).
Additional Names: Sugar cane wax alcohols
Trademarks: Ateromixol (Dalmer); Lipex (Elea); Mercol (Exakta); Phytocor (Pharma Dynamics); PPG (Bago)
Literature References: Mixture of higher (C24 to C34) primary aliphatic alcohols purified from wax of sugar cane, Saccharum officinarum L., Gramineae. Composed of octacosanol (60-70%), triacontanol (10-15%), dotriacontanol (5-10%), hexacosanol (3-8%), heptacosanol, nonacosanol, tetratriacontanol, and tetracosanol. Prepn: L. Granja et al., WO 9407830; eidem, US 5856316 (1994, 1999 both to Dalmar). Clinical pharmacology: I. Gouni-Berthold, H. K. Berthold, Am. Heart J. 143, 356 (2002). Antiplatelet effects: M. L. Arruzazabala et al., Clin. Exp. Pharmacol. Physiol. 29, 891 (2002). Review of clinical studies: M. Janikula, Altern. Med. Rev. 7, 203-217 (2002); and comparison with plant sterols and stanols: J. T. Chen et al., Pharmacotherapy 25, 171-183 (2005).
Trademarks: Interceptor (Novartis)
Literature References: Mixture of milbemycin oximes containing ~80% milbemycin A4 5-oxime (C32H45NO7) and 20% milbemycin A3 5-oxime (C31H43NO7). Prepn: J. Ide et al., EP 110667; eidem, US 4547520 (1984, 1985 both to Sankyo). Anthelmintic activity in experimentally induced infections in dogs: D. D. Bowman et al., Am. J. Vet. Res. 49, 1986 (1988); D. D. Bowman et al., ibid. 52, 64 (1991); in cats: B. L. Blagburn et al., The OVMA Newsletter (February, 1990), 1; in naturally acquired infections in dogs: D. D. Bowman et al., Am. J. Vet. Res. 51, 487 (1990). Physical data and toxicity: Ciba-Geigy Material Data Safety Sheet.
Additional Names: (4''R)-5-O-demethyl-4''-deoxy-4''-(methylamino)avermectin A1a and (4''R)-5-O-demethyl-25-de(1-methylpropyl)-4''-deoxy-4''-(methylamino)-25-(1-methylethyl)avermectin A1a (9:1)
Literature References: Mixture of semi-synthetic avermectins, q.v., consisting (9:1) of 4¢¢-epi-(methylamino)-4¢¢-deoxyavermectin B1a, (C49H75NO13) and 4¢¢-epi-(methylamino)-4¢¢-deoxyavermectin B1b, (C48H73NO13). Prepn: H. Mrozik, US 4874749 (1989 to Merck Co.); and insecticidal activity: H. Mrozik et al., Experientia 45, 315 (1989). Synthesis: R. J. Cvetovich et al., J. Org. Chem. 59, 7704 (1994). Avian toxicity studies: A. C. Chukwudebe et al., Environ. Toxicol. Chem. 17, 1118 (1998). Review: M. H. Fisher, ACS Symp. Ser. 524, 169-182 (1993); H. Mrozik, ibid. 551, 54-73 (1994).
CAS Name: (4''R)-4''-(Acetylamino)-4''-deoxyavermectin B1Trademarks: Eprinex (Merck Co.)
Literature References: Mixture of semisynthetic avermectins, q.v.; containing 90% or more of component B1a and 10% or less of component B1b. Prepn: H. H. Mrozik, US 4427663 (1984 to Merck Co.). Synthesis: R. J. Cvetovich et al., J. Org. Chem. 59, 7704 (1994) and biological activity: T. K. Jones et al., J. Agric. Food Chem. 42, 1786 (1994). Mechanism of action study: J. P. Arena et al., J. Parasitol. 81, 286 (1995).
Additional Names: Carrageen; carrageenin
Literature References: Mixture of sulfated polysaccharides extracted from red seaweed (Rhodophyceae). Chief sources are Chondrus crispus (L.) Stackhouse, and Gigartina stellata (G. mammillosa) (Goodenough and Woodward) J. Aghardh, Gigartinaceae, found most abundantly in North Atlantic coastal regions from Norway to North Africa. The name carrageenan is derived from the Irish coastal town of Carragheen. The k and l structural families are identified based on position of sulfate and the presence/absence of anhydrogalactose. Kappa (k) family consists of k,i,m,n carrageenans of which k and i are the most prevalent. Characterized by a repeating unit of 4-sulfate-b-D-galactopyranosyl(1®4)-a-D-galactose linked (1®3). The galactose unit varies: 3,6-anhydro-a-D-galactose for k-form; 3,6-anhydro-a-D-galactose-2-sulfate for i-form. Due to helical tertiary structure which allows for gelling, k-family is of major commercial importance. Lambda (l) family consists of l and x; characterized by a repeating (1®3) linked disaccharide of 2-sulfate-b-D-galactopyranosyl(1®4)-a-D-galactose. The galactose residue is 2,6-sulfated for l form and 2-sulfated for x form. These carrageenans are non-gelling. Conformational study: N. S. Anderson et al., J. Mol. Biol. 45, 85 (1969); and structural analysis: D. A. Rees, E. J. Welsh, Angew. Chem. Int. Ed. 16, 214 (1977); C. Bodeau-Bellion, Physiol. Veg. 21, 785 (1983). Use as phlogistic agent: C. A. Winter et al., Proc. Soc. Exp. Biol. Med. 111, 544 (1962); L. Levy, Life Sci. 8, 601 (1969). IR determn of k, i, and l forms: E. Tojo, J. Prado, Carbohydr. Res. 338, 1309 (2003). Review of effect on inflammation and immunity: H. J. Schwartz in Inadvert. Modif. Immune Resp. FDA-80-1074, 109-114 (1980); S. Nicklin, K. Miller, Food Addit. Contam. 6, 425-436 (1989). Review of toxicology: M. L. Weiner, Agents Actions 32, 46-51 (1991). Review of industrial and non-food uses: R. J. Tye, Carbohydr. Polym. 10, 259-280 (1989). General Reviews: G. H. Therkelsen in Industrial Gums, R. L. Whistler, J. N. BeMiller, Eds. (Academic Press, New York, 3rd ed., 1993) pp 145-180; J. K. Baird, "Gums" in Kirk-Othmer Encyclopedia of Chemical Technology vol. 12 (Wiley-Interscience, New York, 4th ed., 1994) pp 842-862.
Additional Names: Cresylic acid; cresylol; tricresol
Percent Composition: C 77.75%, H 7.46%, O 14.80%
Literature References: Mixture of the three isomeric cresols, in which the m-isomer predominates. Obtained from coal tar: Paulsen, US 2998457 (1962 to Ashland Oil Ref.). Usually contains a few per cent phenol. Prepn by sulfonation of toluene: Englund et al., Ind. Eng. Chem. 45, 189 (1953); by oxidation of toluene: Braunwarth, Winsted, US 2994722 (1961 to Pure Oil). Toxicity study: W. B. Deichmann, S. Witherup, J. Pharmacol. Exp. Ther. 80, 233 (1944). Review of manuf processes: Faith, Keyes Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 285-293; of toxicology and human exposure: Toxicological Profile for Cresols (PB93-110732, 1992) 175 pp.
CAS Name: (aS)-4-(2-Benzothiazolylmethylamino)-a-[(3,4-difluorophenoxy)methyl]-1-piperidineethanolTrademarks: Prosynap (Janssen)
Percent Composition: C 60.95%, H 5.81%, F 8.76%, N 9.69%, O 7.38...
Literature References: Modulates the glutamate-activated nitric oxide synthase (NOS) pathway. Prepn: R. A. Stokbroekx, G. A. J. Grauwels, EP 501552; US 5434168 (1992, 1995 both to Janssen). Mechanism of action study: M. De Ryck et al., J. Pharmacol. Exp. Ther. 279, 748 (1996); A. S. Lesage et al., ibid. 759. Clinical pharmacokinetics: J. De Keyser et al., Clin. Ther. 19, 1340 (1997). Clinical trial in acute ischemic stroke: J. Grotta et al., Stroke 28, 2338 (1997).
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