cyclobutanes

Summary

Summary: Four carbon cycloparaffin cyclobutane (the structural formula (CH2)4) and its derivatives.

Top Publications

  1. Guzmán D, García E, Mejía G, Olguín H, Jiménez F, Soto E, et al. Effect of sibutramine on 5-hydroxyindole acetic acid levels and selected oxidative biomarkers on brain regions of female rats in the presence of zinc. Basic Clin Pharmacol Toxicol. 2012;110:421-6 pubmed publisher
    ..Our results suggest that sibutramine and zinc are associated with weight loss, an effect that was more pronounced in the group treated with both drugs. Reduction in oxidative stress may be involved in these effects. ..
  2. Bellentani F, Fernandes G, Perobelli J, Pacini E, Kiguti L, Pupo A, et al. Acceleration of sperm transit time and reduction of sperm reserves in the epididymis of rats exposed to sibutramine. J Androl. 2011;32:718-24 pubmed publisher
    ..In humans, use of this drug might present a threat for male fertility because sperm reserves in men are naturally lower than those in rats. ..
  3. Jurkiewicz N, da Silva Júnior E, de Souza B, Ferreira Verde L, Drawanz Pereira J, Mendes Sobrinho C, et al. Changes of cytosolic calcium and contractility of young rat vas deferens by acute treatment with amphetamine, fluoxetine or sibutramine. Eur J Pharmacol. 2012;691:52-60 pubmed publisher
    ..Therefore, the pretreatment with amphetamine, fluoxetine or sibutramine seems to affect the calcium contractility and homeostasis in young rat vas deferens...
  4. Viner R, Hsia Y, Neubert A, Wong I. Rise in antiobesity drug prescribing for children and adolescents in the UK: a population-based study. Br J Clin Pharmacol. 2009;68:844-51 pubmed publisher
    ..Further research into the effectiveness and safety of antiobesity drugs in clinical populations of children and adolescents is needed. ..
  5. Fiorentini S, Russo D, D Amato A, Limpido L, Bersani G. [Sibutramine-related panic attack: a clinical case of apparent resolution with paroxetine]. Riv Psichiatr. 2009;44:64-7 pubmed
    ..After six months from the suspension of the drugs, the patient can no longer be classified as affected by panic attack according to the DSM-IV criteria. ..
  6. Fu P, Hsu H, Wang P. Transient global amnesia after taking sibutramine: a case report. Neurologist. 2010;16:129-31 pubmed publisher
    ..Physicians should be careful to monitor for this adverse effect when sibutramine is prescribed. ..
  7. Waskiewicz A, Golinski P, Karolewski Z, Irzykowska L, Bocianowski J, Kostecki M, et al. Formation of fumonisins and other secondary metabolites by Fusarium oxysporum and F. proliferatum: a comparative study. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2010;27:608-15 pubmed publisher
    ..proliferatum and F. oxysporum (p < 0.001)...
  8. Madsen A, Hansen G, Paulsen S, Lykkegaard K, Tang Christensen M, Hansen H, et al. Long-term characterization of the diet-induced obese and diet-resistant rat model: a polygenetic rat model mimicking the human obesity syndrome. J Endocrinol. 2010;206:287-96 pubmed publisher
    ..Furthermore, the results underscore the effectiveness of GLP-1 mimetics both as anti-diabetes and anti-obesity agents. ..
  9. Derosa G, Maffioli P, Salvadeo S, Ferrari I, Gravina A, Mereu R, et al. Sibutramine and L-carnitine compared to sibutramine alone on insulin resistance in diabetic patients. Intern Med. 2010;49:1717-25 pubmed
    ..Furthermore, only sibutramine plus L-carnitine improved Tg, and visfatin. Sibutramine plus L-carnitine gave a faster improvement of lipid profile, insulin resistance parameters, glycemic control, and body weight compared to sibutramine. ..

More Information

Publications62

  1. James W, Caterson I, Coutinho W, Finer N, Van Gaal L, Maggioni A, et al. Effect of sibutramine on cardiovascular outcomes in overweight and obese subjects. N Engl J Med. 2010;363:905-17 pubmed publisher
    ..Funded by Abbott; ClinicalTrials.gov number, NCT00234832.) ..
  2. Derosa G, Maffioli P, Ferrari I, Palumbo I, Randazzo S, D Angelo A, et al. Effects of one year treatment of sibutramine on insulin resistance parameters in type 2 diabetic patients. J Pharm Pharm Sci. 2010;13:378-90 pubmed
    ..Sibutramine gave a faster improvement of insulin resistance parameters and glycemic control compared to placebo; furthermore sibutramine gave also an improvement of lipid profile, and body weight. ..
  3. He M, Su H, Gao W, Johansson S, Liu Q, Wu X, et al. Reversal of obesity and insulin resistance by a non-peptidic glucagon-like peptide-1 receptor agonist in diet-induced obese mice. PLoS ONE. 2010;5:e14205 pubmed publisher
    ..Boc5 may produce metabolic benefits via multiple synergistic mechanisms and may represent an attractive tool for therapeutic intervention of obesity and diabetes, by means of non-peptidic GLP-1R agonism. ..
  4. Janhunen S, van der Zwaal E, la Fleur S, Adan R. Inverse agonism at ?2A adrenoceptors augments the hypophagic effect of sibutramine in rats. Obesity (Silver Spring). 2011;19:1979-86 pubmed publisher
    ..All in all, the present data supports the ARs and 5-HT receptors involved in the effects of SIB on different aspects of caloric intake and locomotion. ..
  5. Choi J, Joo J, Kim D, Wang X, Oh T, Choi D, et al. Proteome changes in rat plasma in response to sibutramine. Proteomics. 2011;11:1300-12 pubmed publisher
  6. Bray G, Ryan D. Drug treatment of the overweight patient. Gastroenterology. 2007;132:2239-52 pubmed
    ..In addition there are several drugs and drug combinations in phase 2 or phase 2 trials that will be reported on in the coming years. ..
  7. Ernest D, Gershenzon A, Corallo C, Nagappan R. Sibutramine-associated QT interval prolongation and cardiac arrest. Ann Pharmacother. 2008;42:1514-7 pubmed publisher
    ..Clinicians prescribing sibutramine should monitor their patients for ECG abnormalities and be cautious in coprescribing drugs known to prolong the QT interval. ..
  8. Erondu N, Addy C, Lu K, Mallick M, Musser B, Gantz I, et al. NPY5R antagonism does not augment the weight loss efficacy of orlistat or sibutramine. Obesity (Silver Spring). 2007;15:2027-42 pubmed
    ..Blockade of the NPY5R with the potent antagonist MK-0557 did not significantly increase the weight loss efficacy of either orlistat or sibutramine monotherapy. ..
  9. Scholze J, Grimm E, Herrmann D, Unger T, Kintscher U. Optimal treatment of obesity-related hypertension: the Hypertension-Obesity-Sibutramine (HOS) study. Circulation. 2007;115:1991-8 pubmed
    ..These data may help to develop future comprehensive treatment strategies and guidelines for this high-risk patient population. ..
  10. Phelan S, Wadden T, Berkowitz R, Sarwer D, Womble L, Cato R, et al. Impact of weight loss on the metabolic syndrome. Int J Obes (Lond). 2007;31:1442-8 pubmed
    ..Moderate weight loss markedly reduced the odds of metabolic syndrome in this sample. ..
  11. Heusser K, Engeli S, Tank J, Diedrich A, Wiesner S, Janke J, et al. Sympathetic vasomotor tone determines blood pressure response to long-term sibutramine treatment. J Clin Endocrinol Metab. 2007;92:1560-3 pubmed
    ..The phenomenon might be explained by a sustained reduction in central sympathetic activity with sibutramine treatment. ..
  12. Haynes W, Egri Z. Sibutramine and the sympathetic nervous system in obese humans. Clin Auton Res. 2005;15:189-92 pubmed
  13. Henderson D, Copeland P, Daley T, Borba C, Cather C, Nguyen D, et al. A double-blind, placebo-controlled trial of sibutramine for olanzapine-associated weight gain. Am J Psychiatry. 2005;162:954-62 pubmed
    ..Sibutramine was an effective and well-tolerated adjunct to behavior modification for weight loss in patients with schizophrenia and schizoaffective disorder being treated with olanzapine. ..
  14. Birkenfeld A, Schroeder C, Boschmann M, Tank J, Franke G, Luft F, et al. Paradoxical effect of sibutramine on autonomic cardiovascular regulation. Circulation. 2002;106:2459-65 pubmed
    ..Our findings strongly suggest that current concepts regarding the action of sibutramine on the sympathetic nervous system should be reconsidered. ..
  15. Jestoi M, Rokka M, Yli Mattila T, Parikka P, Rizzo A, Peltonen K. Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples. Food Addit Contam. 2004;21:794-802 pubmed
    ..5%) measured as infected kernels. A significant correlation was found between F. avenaceum contamination level and the concentration levels of enniatins B and B1, as well as moniliformin. ..
  16. Sinninghe Damsté J, Strous M, Rijpstra W, Hopmans E, Geenevasen J, van Duin A, et al. Linearly concatenated cyclobutane lipids form a dense bacterial membrane. Nature. 2002;419:708-12 pubmed
    ..Our results further illustrate that microbial membrane lipid structures are far more diverse than previously recognized. ..
  17. Jordan J, Scholze J, Matiba B, Wirth A, Hauner H, Sharma A. Influence of Sibutramine on blood pressure: evidence from placebo-controlled trials. Int J Obes (Lond). 2005;29:509-16 pubmed
    ..However, blood pressure and HR should be monitored closely. In patients who experience a clinically significant and sustained increase in blood pressure, the drug should probably be discontinued. ..
  18. de Lemos H, Atallah A, de Lemos A. Can sibutramine alter systemic blood pressure in obese patients? Systematic review and meta-analysis. Sao Paulo Med J. 2008;126:342-6 pubmed
    ..69, CI 0.07 to 7.01. The meta-analyses presented in this systematic review show that sibutramine does not have a statistically significant effect on blood pressure, compared with placebo. ..
  19. Hauner H, Meier M, Jöckel K, Frey U, Siffert W. Prediction of successful weight reduction under sibutramine therapy through genotyping of the G-protein beta3 subunit gene (GNB3) C825T polymorphism. Pharmacogenetics. 2003;13:453-9 pubmed
    ..004) and for a weight loss greater than 10% was 9.6 (95% CI 1.7-53.8; P = 0.010). Genotyping for the GNB3 C825T polymorphism is highly predictive for the identification of obese individuals who will benefit from sibutramine treatment. ..
  20. Uhlig S, Jestoi M, Parikka P. Fusarium avenaceum -- the North European situation. Int J Food Microbiol. 2007;119:17-24 pubmed
    ..This paper summarises the results from mycological and chemical analyses of grain samples from Norway and Finland for major Fusarium species and F. avenaceum-related secondary metabolites. ..
  21. Barkeling B, Elfhag K, Rooth P, Rossner S. Short-term effects of sibutramine (Reductil) on appetite and eating behaviour and the long-term therapeutic outcome. Int J Obes Relat Metab Disord. 2003;27:693-700 pubmed
    ..Short-term sibutramine effects on eating behaviour are to some extent related to the long-term therapeutic outcome in obese subjects. ..
  22. Torp Pedersen C, Caterson I, Coutinho W, Finer N, Van Gaal L, Maggioni A, et al. Cardiovascular responses to weight management and sibutramine in high-risk subjects: an analysis from the SCOUT trial. Eur Heart J. 2007;28:2915-23 pubmed
    ..2 and 0.8 deaths per 100 years of exposure, respectively. Six-week treatment with sibutramine appears to be efficacious, tolerable and safe in this high-risk population for whom sibutramine is usually contraindicated. ..
  23. Gietema J, de Vries E, Sleijfer D, Willemse P, Guchelaar H, Uges D, et al. A phase I study of 1,2-diamminomethyl-cyclobutane-platinum (II)-lactate (D-19466; lobaplatin) administered daily for 5 days. Br J Cancer. 1993;67:396-401 pubmed
    ..The recommended dose of lobaplatin i.v. bolus daily for 5 days for phase II studies depends on renal function, namely 30 mg m-2 at CRCL 60-80 ml min-1; 55 mg m-2 at CRCL 81-100 ml min-1; 70 mg m-2 at CRCL > 100 ml min-1. ..
  24. Wadden T, Berkowitz R, Sarwer D, Prus Wisniewski R, Steinberg C. Benefits of lifestyle modification in the pharmacologic treatment of obesity: a randomized trial. Arch Intern Med. 2001;161:218-27 pubmed
    ..05 for all). The addition of group lifestyle modification to the pharmacologic management of obesity significantly improved weight loss and patients' satisfaction with treatment outcome. ..
  25. Levin B, Dunn Meynell A. Sibutramine alters the central mechanisms regulating the defended body weight in diet-induced obese rats. Am J Physiol Regul Integr Comp Physiol. 2000;279:R2222-8 pubmed
    ..Thus sibutramine lowered the defended body weight in association with compensatory changes in those central pathways involved in energy homeostasis...
  26. Arunkumar E, Forbes C, Noll B, Smith B. Squaraine-derived rotaxanes: sterically protected fluorescent near-IR dyes. J Am Chem Soc. 2005;127:3288-9 pubmed
    ..It should be possible to prepare squaraine-derived rotaxanes with improved properties for a wide range of photophysical, photochemical, and biomedical applications. ..
  27. Nisoli E, Carruba M. An assessment of the safety and efficacy of sibutramine, an anti-obesity drug with a novel mechanism of action. Obes Rev. 2000;1:127-39 pubmed
    ..Finally, sibutramine does not have the potential for abuse that is characteristic of amphetamine and it is indistinguishable from placebo in abuse potential studies. ..
  28. Bray G, Blackburn G, Ferguson J, Greenway F, Jain A, Mendel C, et al. Sibutramine produces dose-related weight loss. Obes Res. 1999;7:189-98 pubmed
    ..Improvements in serum lipids and uric acid accompany sibutramine-induced weight loss. Most of the adverse events observed on sibutramine are related to its pharmacology, including small mean increases in blood pressure and heart rate. ..
  29. Hansen D, Toubro S, Stock M, Macdonald I, Astrup A. Thermogenic effects of sibutramine in humans. Am J Clin Nutr. 1998;68:1180-6 pubmed
    ..Sibutramine increased satiety more than did placebo (5-h area under the curve, P < 0.05). Sibutramine caused a significant increase in both EE and satiety, which may both contribute to its weight-reducing properties. ..
  30. Grudell A, Sweetser S, Camilleri M, Eckert D, Vazquez Roque M, Carlson P, et al. A controlled pharmacogenetic trial of sibutramine on weight loss and body composition in obese or overweight adults. Gastroenterology. 2008;135:1142-54 pubmed publisher
    ..02). Patient selection based on candidate genes may enhance response to multidimensional sibutramine and behavioral therapy for obesity. ..
  31. Mersebach H, Klose M, Svendsen O, Astrup A, Feldt Rasmussen U. Combined dietary and pharmacological weight management in obese hypopituitary patients. Obes Res. 2004;12:1835-43 pubmed
    ..However, the long-term effect on risk factors associated with type 2 diabetes and cardiovascular disease as well as on mortality needs to be established. ..
  32. Kaya A, Aydin N, Topsever P, Filiz M, Ozturk A, Dağar A, et al. Efficacy of sibutramine, orlistat and combination therapy on short-term weight management in obese patients. Biomed Pharmacother. 2004;58:582-7 pubmed
    ..Sibutramine and sibutramine in combination with orlistat seemed to be equally effective in terms of weight reduction compared to orlistat monotherapy. Attention should be paid to the possibility of adverse effects. ..
  33. Hauner H, Meier M, Wendland G, Kurscheid T, Lauterbach K. Weight reduction by sibutramine in obese subjects in primary care medicine: the SAT Study. Exp Clin Endocrinol Diabetes. 2004;112:201-7 pubmed
    ..P (- 0.9 beats/min) (p < 0.05). Under primary care conditions, sibutramine 15 mg daily proved to be a safe and effective drug for additional weight loss in obese subjects undergoing a comprehensive weight reduction program. ..
  34. Florentin M, Liberopoulos E, Elisaf M. Sibutramine-associated adverse effects: a practical guide for its safe use. Obes Rev. 2008;9:378-87 pubmed
    ..Hypertension, if adequately treated and frequently monitored, is not an absolute contraindication for the prescription of sibutramine. ..
  35. Casado A, Rodriguez V, Portillo M, Macarulla M, Abecia L, Echevarria E, et al. Sibutramine decreases body weight gain and increases energy expenditure in obese Zucker rats without changes in NPY and orexins. Nutr Neurosci. 2003;6:103-11 pubmed
    ..The reduction in body weight and adiposity induced by sibutramine was achieved by both a reduction in food intake and an increase in energy expenditure. NPY and orexins do not seem to be involved in the anorectic effect of sibutramine. ..
  36. Baranowska B, Wolinska Witort E, Martynska L, Chmielowska M, Mazurczak Pluta T, Boguradzka A, et al. Sibutramine therapy in obese women--effects on plasma neuropeptide Y (NPY), insulin, leptin and beta-endorphin concentrations. Neuro Endocrinol Lett. 2005;26:675-9 pubmed
    ..We suggest that the effects on the disturbed activity of NPY, beta-endorphin, insulin and leptin may be involved in the mechanism of sibutramine action. ..
  37. Kim S, Ahn H, Choi B, Jang H, Kim M, Rhie D, et al. Open channel block of A-type, kv4.3, and delayed rectifier K+ channels, Kv1.3 and Kv3.1, by sibutramine. J Pharmacol Exp Ther. 2007;321:753-62 pubmed
    ..3 and Kv3.1, resulting in a crossover phenomenon. These results indicate that sibutramine acts on Kv4.3, Kv1.3, and Kv3.1 as an open channel blocker. ..
  38. Davis R, Carroll A, Duffy S, Avery V, Guymer G, Forster P, et al. Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum. J Nat Prod. 2007;70:1118-21 pubmed
    ..All compounds were tested in a glucocorticoid receptor binding assay and displayed IC50 values ranging from 0.9 to 35 microM...
  39. Jestoi M. Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008;48:21-49 pubmed publisher
    ..Based on the available studies, attention should be paid to the studies on the distinct significance of these compounds in the human and animal food chains. ..
  40. Van Gaal L, Caterson I, Coutinho W, Finer N, Maggioni A, Sharma A, et al. Weight and blood pressure response to weight management and sibutramine in diabetic and non-diabetic high-risk patients: an analysis from the 6-week lead-in period of the sibutramine cardiovascular outcomes (SCOUT) trial. Diabetes Obes Metab. 2010;12:26-34 pubmed publisher
    ..A small median increase in pulse rate was recorded. ..
  41. Wilfley D, Crow S, Hudson J, Mitchell J, Berkowitz R, Blakesley V, et al. Efficacy of sibutramine for the treatment of binge eating disorder: a randomized multicenter placebo-controlled double-blind study. Am J Psychiatry. 2008;165:51-8 pubmed
    ..This trial demonstrated the efficacy of sibutramine in reducing binge eating, weight, and associated psychopathology. ..
  42. Neovius M, Narbro K. Cost-effectiveness of pharmacological anti-obesity treatments: a systematic review. Int J Obes (Lond). 2008;32:1752-63 pubmed publisher
    ..Modeling of head-to-head comparisons and attrition is needed, as are analyses conducted independently of manufacturing companies. ..
  43. Svacina S, Owen K, Hendl J, Matoulek M, Brychta T. Comparison of lipid lowering effect of sibutramine in patients treated or not treated with statins--3 month follow-up. Prague Med Rep. 2007;108:333-8 pubmed
    ..We can therefore preliminarily conclude that sibutramine therapy has significant positive effect on the lipid profile even in patients who were started on statins prior to initiation of sibutramine treatment. ..
  44. Appolinario J, Bacaltchuk J, Sichieri R, Claudino A, Godoy Matos A, Morgan C, et al. A randomized, double-blind, placebo-controlled study of sibutramine in the treatment of binge-eating disorder. Arch Gen Psychiatry. 2003;60:1109-16 pubmed
    ..Sibutramine is effective and well tolerated in the treatment of obese patients with BED. Its effects address 3 main domains of the BED syndrome, ie, binge eating, weight, and related depressive symptoms. ..
  45. Florakis D, Diamanti Kandarakis E, Katsikis I, Nassis G, Karkanaki A, Georgopoulos N, et al. Effect of hypocaloric diet plus sibutramine treatment on hormonal and metabolic features in overweight and obese women with polycystic ovary syndrome: a randomized, 24-week study. Int J Obes (Lond). 2008;32:692-9 pubmed
    ..Total testosterone, FAI and TG levels reduction could be a possible mechanism. Finally, sibutramine increased compliance to diet and it was well tolerated from these patients. ..
  46. Trapali M, Liapi C, Perelas A, Perrea D, Stroubini T, Dontas I, et al. Effect of isocaloric diets and sibutramine on food intake, body mass variation and serum TNF-alpha levels in rats. Pharmacology. 2008;82:15-21 pubmed publisher
    ..However, sibutramine did not affect TNF-alpha. ..
  47. Mashiko S, Ishihara A, Iwaasa H, Moriya R, Kitazawa H, Mitobe Y, et al. Effects of a novel Y5 antagonist in obese mice: combination with food restriction or sibutramine. Obesity (Silver Spring). 2008;16:1510-5 pubmed publisher
    ..These findings demonstrate that the Y5 receptor is an important mediator of energy homeostasis in rodents. ..
  48. Valsamakis G, McTernan P, Chetty R, Al Daghri N, Field A, Hanif W, et al. Modest weight loss and reduction in waist circumference after medical treatment are associated with favorable changes in serum adipocytokines. Metabolism. 2004;53:430-4 pubmed
    ..Modest weight loss is also associated with potentially favourably changes in serum adipocytokines, particularly in a rise of serum adiponectin. Reduction of waist circumference is associated with a change in serum resistin. ..
  49. McNulty S, Ur E, Williams G. A randomized trial of sibutramine in the management of obese type 2 diabetic patients treated with metformin. Diabetes Care. 2003;26:125-31 pubmed
    ..01). Sibutramine can be an effective adjunct to metformin treatment in selected obese type 2 diabetic subjects and improves metabolic control in individuals who lose weight. ..
  50. Cordeiro Q, Vallada H. Sibutramine-induced mania episode in a bipolar patient. Int J Neuropsychopharmacol. 2002;5:283-4 pubmed
  51. McLaughlin T, Abbasi F, Lamendola C, Kim H, Reaven G. Metabolic changes following sibutramine-assisted weight loss in obese individuals: role of plasma free fatty acids in the insulin resistance of obesity. Metabolism. 2001;50:819-24 pubmed
  52. Finer N, Bloom S, Frost G, Banks L, Griffiths J. Sibutramine is effective for weight loss and diabetic control in obesity with type 2 diabetes: a randomised, double-blind, placebo-controlled study. Diabetes Obes Metab. 2000;2:105-12 pubmed
    ..m.i. > 26 kg/m2) with type 2 diabetes. Sibutramine was well tolerated, and significant improvement in diabetic control was seen in conjunction with weight reduction on sibutramine treatment. ..
  53. Fisas A, Codony X, Romero G, Dordal A, Giraldo J, Mercè R, et al. Chronic 5-HT6 receptor modulation by E-6837 induces hypophagia and sustained weight loss in diet-induced obese rats. Br J Pharmacol. 2006;148:973-83 pubmed
    ..These results show that the 5-HT(6) receptor partial agonist, E-6837, is a promising new approach to the management of obesity with the potential to produce greater sustained weight loss than sibutramine. ..