Success Stories of Enolate Form of Drugs
Keywords:
Stereochemistry, Keto-enol form, Tautomerism, geometric form
Abstract
Stereochemistry of clinical agents play a key role in their success to become drugs. Tautomerism is a structural isomerism, playing a key role in the orientation of organic compounds and also found significant in distinctive base pairing in nucleic acids. Keto-enol form usually occurs and found prominently among different types of tautomers. The enolform ionizes in the physiological solution into enolate and alter the biological activity. So, how this enolate form brings modification in pharmacokinetics and pharmacodynamics of a drug is very important and quite interesting to know. As this form is ionic in nature so it increases the interaction with the concerning receptors, enzymes, ion channels or functional proteins. In this review we cover and compile success, role and the significance of the enolate form of clinical agents which succeed to become drugs
References
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33.Gershwin M, Smith NT: Mode of action of hydralazine on guinea pig atria. Archives internationales de pharmacodynamie et de thérapie 1967, 170 (1): 108.
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35.Knox WE, Pitt BM: Enzymic catalysis of the keto-enoltautomerization of phenylpyruvic acids. Journal of Biological Chemistry 1957, 225 (2): 675-688.
36.Reece PA: Hydralazine and related compounds: chemistry, metabolism, and mode of action. Medicinal research reviews 1981, 1 (1): 73-96.
37.Negi A, Ramarao P, Kumar R: Recent Advancements in Small Molecule Inhibitors of Insulinlike Growth Factor-1 Receptor (IGF-1R) Tyrosine Kinase as Anticancer agents. Mini reviews in medicinal chemistry 2013, 13 (5): 653-681.
38.Guardado-Mendoza R, Prioletta A, Jiménez-Ceja LM, Sosale A, Folli F: The role of nateglinide and repaglinide, derivatives of meglitinide, in the treatment of type 2 diabetes mellitus. 2013.
39.Fuhlendorff J, Rorsman P, Kofod H, Brand CL, Rolin B, MacKay P, Shymko R, Carr RD: Stimulation of insulin release by repaglinide and glibenclamide involves both common and distinct processes. Diabetes 1998, 47 (3): 345.
40.Mortimer R, Cannell G, Addison R, Johnson L, Roberts M, Bernus I: Methimazole and propylthiouracil equally cross the perfused human term placental lobule. Journal of Clinical Endocrinology & Metabolism 1997, 82 (9): 3099-3102.
41.Atkinson H, Begg E, Darlow B: Drugs in human milk. Clinical pharmacokinetics 1988, 14 (4): 217-240.
2.Elguero J, Marzin C, Katritzky AR, Linda P: The tautomerism of heterocycles. Academic Press New York: 1976.
3.Shukla MK, Leszczynski J: Tautomerism in nucleic acid bases and base pairs: a brief overview. Wiley Interdisciplinary Reviews: Computational Molecular Science 2013.
4.Culbertson J: Factors affecting the rate of hydrolysis of ketimines. Journal of the American Chemical Society 1951, 73 (10): 4818-4823.
5.Ball P, Nicholls C: Azo-hydrazonetautomerism of hydroxyazo compounds—a review. Dyes and Pigments 1982, 3 (1): 5-26.
6.Negi A, Bhushan S, Gupta P, Garg P, Kumar R: Cystathionine-Lyase-Like Protein with Pyridoxal Binding Domain Characterized in Leishmania major by Comparative Sequence Analysis and Homology Modelling. 2013.
7.Metzler DE: Tautomerism in pyridoxal phosphate and in enzymatic catalysis. Advances in Enzymology and Related Areas of Molecular Biology 1979, 50: 1-40.
8.Allen G, Dwek RA: An NMR study of keto-enoltautomerism in β-diketones. Journal of Chemical Society B 1966: 161-163.
9.Iglesias E: Tautomerization of 2-acetylcyclohexanone. 1. Characterization of keto-enol/enolateequilibria and reaction rates in water. Journal of Organic Chemistry 2003, 68 (7): 2680-2688.
10.Cederstav AK, Novak BM: Investigations into the chemistry of thermodynamically unstable species. The direct polymerization of vinyl alcohol, the enolic tautomer of acetaldehyde. Journal of the American Chemical Society 1994, 116 (9): 4073-4074.
11.Rogawski MA, Löscher W: The neurobiology of antiepileptic drugs. Nature Reviews Neuroscience 2004, 5 (7): 553-564.
12.Stewart IC, Bergman RG, Toste FD: Phosphine-catalyzed hydration and hydroalkoxylation of activated olefins: use of a strong nucleophile to generate a strong base. Journal of the American Chemical Society 2003, 125 (29): 8696-8697.
13.Hardman JG, Limbird LE: Goodman & Gilman's the pharmacological basis of therapeutics. McGraw-Hill New York: 1996.
14.Bauer LA, Blouin RA: Age and phenytoin kinetics in adult epileptics. Clinical Pharmacology & Therapeutics 1982, 31 (3): 301-304.
15.Leff R, Fischer L, Roberts R: Phenytoin metabolism in infants following intravenous and oral administration. Developmental pharmacology and therapeutics 1986, 9 (4): 217.
16.Richens A, Dunlop A: Serum-phenytoin levels in management of epilepsy. The Lancet 1975, 306 (7928): 247-248.
17.Block JH, Beale JM: Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Lippincott Williams & Wilkins: 2004.
18.Tabern D, Shelberg E: Physico-chemical properties and hypnotic action of substituted barbituric acids. Journal of the American Chemical Society 1933, 55 (1): 328-332.
19.Vree T, Muskens A, RossumJv: Some physico?chemical properties of amphetamine and related drugs. Journal of Pharmacy and Pharmacology 1969, 21 (11): 774-775.
20.Martin W, Sloan J, Sapira J, Jasinski D: Physiologic, subjective, and behavioral effects of amphetamine, methamphetamine, ephedrine, phenmetrazine, and methylphenidate in man. Clinical pharmacology and therapeutics 1970, 12 (2): 245-258.
21.Perrone R, Carbonara G, Tortorella V: Chemical Studies on Drug Metabolism: Oxidation with Ruthenium Tetroxide of Some Medicinal Alicyclic N?Methylamines. Archiv der Pharmazie 1984, 317 (1): 21-27.
22.Nohl H, Stolze K: The effects of xenobiotics on erythrocytes. General Pharmacology: The Vascular System 1998, 31 (3): 343-347.
23.GEORGE P, Lyster R In A Survey of the Evidence for and against a Crevice Configuration for the Heme in Hemoglobin, Conference on Hemoglobin. Nat. Acad. Sei., National Research Council, Washington, DC, Publication, 1958; p 33.
24.L'allemain G, Franchi A, Cragoe E, Pouyssegur J: Blockade of the Na+/H+ antiport abolishes growth factor-induced DNA synthesis in fibroblasts. Structure-activity relationships in the amiloride series. Journal of Biological Chemistry 1984, 259 (7): 4313.
25.Kleyman TR, Cragoe EJ: Amiloride and its analogs as tools in the study of ion transport. Journal of Membrane Biology 1988, 105 (1): 1-21.
26.Russ T, Ried W, Ullrich F, Mutschler E: Preparation and diuretic properties of novel amiloride analogues. Archiv der Pharmazie 1992, 325 (12): 761-767.
27.McKeage K, Siddiqui MAA: Amlodipine/Atorvastatin Fixed-Dose Combination. American journal of cardiovascular drugs 2008, 8 (1): 51-67.
28.Aragoncillo P, Maeso R, Vázquez-Pérez S, Navarro-Cid J, Ruilope LM, Díaz C, Hernández G, Lahera V, Cachofeiro V: The protective role of atorvastatin on function, structure and ultrastructure in the aorta of dyslipidemic rabbits. VirchowsArchiv 2000, 437 (5): 545-554.
29.Schwartz GG, Olsson AG, Ezekowitz MD, Ganz P, Oliver MF, Waters D, Zeiher A, Chaitman BR, Leslie S, Stern T: Effects of atorvastatin on early recurrent ischemic events in acute coronary syndromes. JAMA: the journal of the American Medical Association 2001, 285 (13): 1711-1718.
30.Heel R, Brogden R, Speight T, Avery G: Disopyramide: a review of its pharmacological properties and therapeutic use in treating cardiac arrhythmias. Drugs 1978, 15 (5): 331-368.
31.Koch-Weser J: Disopyramide. New England Journal of Medicine 1979, 300 (17): 957-962.
32.Yeh BK, Sung PK, Scherlag BJ: Effects of disopyramide on electrophysiological and mechanical properties of the heart. Journal of pharmaceutical sciences 1973, 62 (12): 1924-1929.
33.Gershwin M, Smith NT: Mode of action of hydralazine on guinea pig atria. Archives internationales de pharmacodynamie et de thérapie 1967, 170 (1): 108.
34.Facchini V, Timbrell JA: Further evidence for an acetylator phenotype difference in the metabolism of hydralazine in man. British journal of clinical pharmacology 1981, 11 (4): 345-351.
35.Knox WE, Pitt BM: Enzymic catalysis of the keto-enoltautomerization of phenylpyruvic acids. Journal of Biological Chemistry 1957, 225 (2): 675-688.
36.Reece PA: Hydralazine and related compounds: chemistry, metabolism, and mode of action. Medicinal research reviews 1981, 1 (1): 73-96.
37.Negi A, Ramarao P, Kumar R: Recent Advancements in Small Molecule Inhibitors of Insulinlike Growth Factor-1 Receptor (IGF-1R) Tyrosine Kinase as Anticancer agents. Mini reviews in medicinal chemistry 2013, 13 (5): 653-681.
38.Guardado-Mendoza R, Prioletta A, Jiménez-Ceja LM, Sosale A, Folli F: The role of nateglinide and repaglinide, derivatives of meglitinide, in the treatment of type 2 diabetes mellitus. 2013.
39.Fuhlendorff J, Rorsman P, Kofod H, Brand CL, Rolin B, MacKay P, Shymko R, Carr RD: Stimulation of insulin release by repaglinide and glibenclamide involves both common and distinct processes. Diabetes 1998, 47 (3): 345.
40.Mortimer R, Cannell G, Addison R, Johnson L, Roberts M, Bernus I: Methimazole and propylthiouracil equally cross the perfused human term placental lobule. Journal of Clinical Endocrinology & Metabolism 1997, 82 (9): 3099-3102.
41.Atkinson H, Begg E, Darlow B: Drugs in human milk. Clinical pharmacokinetics 1988, 14 (4): 217-240.
Published
2013-12-01
How to Cite
[1]
Negi, A. and Gill, B.S. 2013. Success Stories of Enolate Form of Drugs. PharmaTutor. 1, 2 (Dec. 2013), 45-53.
Section
Articles
