Sample records for butyrophenones

  1. Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone

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    Fengli Xin


    Full Text Available A novel synthetic approach towards 5-fluoro-2-hydroxy butyrophenone is reported. Using 4-fluorophenol as a raw material, the processes of etherification protection, Friedel-Crafts acylation and demethylation provide the target compound under mild conditions. The structure was characterized by the melting point and IR, MS, 1H-NMR, and 13C-NMR spectroscopy. The bioassay results indicate that the target compound exhibits potent antifungal activities against Valsa mali, Coniella dipodiella, and other agricultural plant fungi. The target compound also shows potent herbicidal activities for Lactuca sativa, a dicotyledon, and Echinochloa crus-galli, a monocotyledon. The toxicity regression C50 values of the compound against Valsa mali, Coniothyrium diplodiella, Lactuca sativa seedling, and Echinochloa crusgalli seedling were calculated by SPSS. The Hormesis effect for roots of Echinochloa crusgalli was confirmed.

  2. Drug: D02621 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available D02621 Drug Fluanisone (INN) C21H25FN2O2 356.19 356.4338 D02621.gif ATC code: N05AD...M N05 PSYCHOLEPTICS N05A ANTIPSYCHOTICS N05AD Butyrophenone derivatives N05AD09 Fluanisone D02621 Fluanisone

  3. Regional localization of halopemide, a new psychotropic agent, in the rat brain

    NARCIS (Netherlands)

    Loonen, A.J.M.; Van Wijngaarden, I.; Janssen, P.A.J.; Soudijn, W.


    Halopemide is a new psychotropic agent, structurally related to the neuroleptics of the butyrophenone type, but with a different pharmacological and clinical profile. The concentration of halopemide in the rat brain is about 10 times less than that of R 29800, its chemical congener and of spiperone,

  4. Regional distribution of halopemide, a new psychotropic agent, in the rat brain at different time intervals and after chronic administration

    NARCIS (Netherlands)

    Loonen, A.J.M.; Van Wijngaarden, I.; Janssen, P.A.J.; Soudijn, W.


    Only a very small amount of halopemide, a new psychotropic agent, structurally related to the butyrophenones, but with a different pharmacological and clinical profile, penetrates into the rat brain. The maximum concentration is reached between 1 and 2 hours after injection. Halopemide is evenly dis

  5. Sulpiride in tardive dyskinesia.


    Schwartz, M.; Moguillansky, L; Lanyi, G; Sharf, B


    The abnormal involuntary movements in tardive dyskinesia can be reduced by the dopamine antagonist drugs, phenothiazines and butyrophenones, but most cause an increase in Parkinsonian signs. Sulpiride, a benzamide derivative, and selective antagonist of D2 receptors had a significantly beneficial effect on most of 15 patients (p less than 0.01). In 12 patients the improvement was marked. The reduction of abnormal movements was observed even with low doses, and it was not necessary to increase...

  6. Olanzapine as an antiemetic in refractory nausea and vomiting in advanced cancer. (United States)

    Srivastava, Manish; Brito-Dellan, Norman; Davis, Mellar P; Leach, Marie; Lagman, Ruth


    Nausea and vomiting are difficult symptoms to manage in patients with advanced cancer. Several classes of antiemetics are available, including phenothiazines, butyrophenones, substituted benzamides and selective serotonin antagonists, as well as corticosteroids. Most patients will respond to either single agents or combinations that frequently include corticosteroids. A minority of patients will have nausea that fails to respond. The atypical antipsychotic, olanzapine, relieves nausea in some patients failing to respond to the usual antiemetics. Two case reports are presented and the rationale for olanzapine's benefit is discussed.

  7. Accidental haloperidol poisoning in children

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    Mona P Gajre


    Full Text Available Haloperidol, a butyrophenone neuroleptic drug, is an antipsychotic used in the treatment of adult schizophrenia and mania. It is used in children with neurological disorders like chorea and developmental disorders such as hyperactivity. With the advent of newer selective neuroleptics use of haloperidol is now on decline. However, in adults it is still the preferred drug especially in resource challenged settings. Extrapyramidal reactions occur frequently with haloperidol predominantly as parkinsonian symptoms. There are few case reports of accidental haloperidol poisoning in children and this one of them.

  8. Identification of rat faecal metabolites of ebastine by B/E linked scanning liquid secondary ion mass spectrometry. (United States)

    Yoshida, K; Hatoyama, T; Fujii, T; Kagemoto, A; Miyazaki, H; Naruto, S


    The identification of rat faecal metabolites of a new antihistaminic agent, ebastine, 4'-tert-butyl-4-[4-(diphenylmethoxy)piperidino]butyrophenone, is presented. After oral administration of (14C)ebastine (20 mg kg-1) to rats, 84% of the radioactive dose was excreted in the 24 h faeces. Unchanged drug and five metabolites were isolated from the faeces by thin-layer chromatography and solid-phase extraction, and their structures were identified by liquid secondary ion mass spectrometry using the B/E linked scanning technique. The main metabolic pathways were oxidation of a terminal methyl group to give the hydroxymethyl and carboxyl derivatives, and hydroxylation of a phenyl ring in the diphenylmethoxy moiety. In addition to the oxidative mechanism, metabolism of ebastine involved sulphate conjugation. It is noteworthy that M-4, having both phenolic and alcoholic hydroxyl groups, was sulphated selectively in the latter position.

  9. Drug: D01101 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available D01101 Drug Bromperidol (JAN/USAN/INN); Impromen (TN) C21H23BrFNO2 419.0896 420.3152 D01101...cting central nervous system 117 Psychotropics 1179 Others D01101 Bromperidol (JAN/USAN/INN) Anatomical Ther...TICS N05A ANTIPSYCHOTICS N05AD Butyrophenone derivatives N05AD06 Bromperidol D01101 Bromperidol (JAN/USAN/IN...opamine D2-receptor [HSA:1813] [KO:K04145] Bromperidol [ATC:N05AD06] D01101 Bromp...eridol (JAN/USAN/INN) CAS: 10457-90-6 PubChem: 7848164 LigandBox: D01101 NIKKAJI: J10.460D ATOM 26 1 C1b C 1

  10. Structural requirements of Na+-dependent antidopaminergic agents: Tropapride, Piquindone, Zetidoline, and Metoclopramide Comparison with Na+-independent ligands (United States)

    Collin, Sonia; Vercauteren, Daniel P.; Vanderveken, Didier; Evrard, Guy; Durant, François


    Molecular graphic design coupled with PCILO and crystallographic results have been used to investigate the three-dimensional structure of Tropapride, Piquindone, Zetidoline, and Metoclopramide, four dopamine D-2 receptor antagonists showing Na+-dependent binding. Three putative pharmacophoric elements, a nitrogen lone pair, a phenyl ring and a carbonyl moiety, are similarly oriented in all the Na+-dependent drugs. Conversely, for Na+-independent analogs, the two latter pharmacophoric elements play a subordinate role, but two Π-electron regions are systematically localized on the other side of the molecule: the first is a phenyl group while the second is a carbonyl function as in butyrophenones, a cyano group as in R48455, or a phenyl ring as in diphenylbutylpiperidines or tricyclics. The presence of a benzyl ring on this side in Tropapride might explain its weak extrapyramidal effects.

  11. Design and synthesis of dual 5-HT1A and 5-HT7 receptor ligands. (United States)

    Ofori, Edward; Zhu, Xue Y; Etukala, Jagan R; Peprah, Kwakye; Jordan, Kamanski R; Adkins, Adia A; Bricker, Barbara A; Kang, Hye J; Huang, Xi-Ping; Roth, Bryan L; Ablordeppey, Seth Y


    5-HT1A and 5-HT7 receptors have been at the center of discussions recently due in part to their major role in the etiology of major central nervous system diseases such as depression, sleep disorders, and schizophrenia. As part of our search to identify dual targeting ligands for these receptors, we have carried out a systematic modification of a selective 5HT7 receptor ligand culminating in the identification of several dual 5-HT1A and 5-HT7 receptor ligands. Compound 16, a butyrophenone derivative of tetrahydroisoquinoline (THIQ), was identified as the most potent agent with low nanomolar binding affinities to both receptors. Interestingly, compound 16 also displayed moderate affinity to other clinically relevant dopamine receptors. Thus, it is anticipated that compound 16 may serve as a lead for further exploitation in our quest to identify new ligands with the potential to treat diseases of CNS origin.

  12. [Rhabdomyolysis with acute renal failure and malignant neuroleptic syndrome]. (United States)

    Kleinknecht, D; Parent, A; Blot, P; Bochereau, G; Lallement, P Y; Pourriat, J L


    Seven episodes of rhabdomyolysis with acute renal failure (ARF) have been observed in 6 patients treated with various short-acting tranquilizers and antidepressants. Clinical features usually included severe hyperthermia, diffuse hypertonicity with or without coma, circulatory failure or unstable blood pressure, and often acute respiratory failure. Serum CPK were always elevated. The type of ARF was prerenal failure without oliguria in 5/7 episodes, and acute tubular necrosis in 2/7 episodes, requiring hemodialyses in one patient. Three patients died. In any case, the tranquilizers and antidepressants responsible for this syndrome were stopped, and electrolyte disorders and acidosis were corrected. Associated acute circulatory failure, septicemia and/or acute hepatic failure required prompt therapy, and artificial ventilation was required in 4 instances. The further use of phenothiazines, butyrophenones, sulpiride and their derivatives should be avoided in any patient having developed such an accident, whose pathophysiology is similar to that described in malignant hyperthermia of various origin.

  13. Methyl Chloroacetate as Extraction Solvent for Coupling Liquid-liquid Semimicroextraction with Micellar Electrokinetic Chromatography for the Separation of Neutral Compounds with Concentration Enhancement%氯乙酸甲酯为萃取剂的液-液半微萃取与胶束电动色谱耦联富集分离中性化合物

    Institute of Scientific and Technical Information of China (English)

    唐婧; 郑胜彪; 朱金坤; 王田霖


    This paper reports the use of methyl chloroacetate ( MCA) as an extraction solvent for coupling liquid-liquid semimicroextraction( LLsME ) with micellar electrokinetic chromatography ( MEKC) through on-capillary decomposition for the separation of neutral compounds with concentration enhancement. Alkylphenones butyrophenone, valerophenone and acetophenone were chosen as modeling compounds. Aqueous samples of the alkylphenones were extracted by LLsME into MCA. The organic phase was directly subjected to separate by MEKC. The detection limits(S/N≥3) were 50, 50 and 100 |xg/L for butyrophenone, valerophenone and acetophenone in water, respectively, and the concentration factors of the extraction were in a range of 63 to 151-fold in terms of peak area. The method developed has no requirement for any special experimental apparatus other than a basic CE setup and is time-saving and easy-ope-rated. Recoveries of 4-t-BP and BPA in drink water were examined. The recoveries were obtained as 99.87% and 102.8%, respectively. Therefore, it would be readily acceptable for routine analysis, especially for environmental samples.%建立了液-液半微萃取与胶束电动色谱耦联的富集分离方法,以氯乙酸甲酯为萃取剂,通过萃取剂的柱上分解来富集分离中性化合物.选取苯酮类化合物作为模型,将水中的苯酮类化合物通过液-液半微萃取进人氯乙酸甲酯相中,氯乙酸甲酯相直接进人胶束电动色谱中分离.对于苯乙酮(C8)、苯丁酮(C10)和苯戊酮(C11)的检出限分别为50,50和100μg/L(S/N≧3),三者的富集因子达到63~151.本方法设备简单,省时且操作简便.用此方法对环境雌激素叔丁基苯酚(4-tBP)和双酚A(BPA)进行加标回收实验,回收率分别为99.87%和102.8%.该方法具有用于实际环境样品分析的潜力.

  14. Alteration of dopamine receptor sensitivity by opiates and the subsequent effect of this alteration on opiate tolerance and dependence

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    Martin, J.R.


    The present study was undertaken to determine whether there is an alteration of dopamine receptor sensitivity following opiate administration, and whether this alteration has any influence on the development of opiate tolerance and dependence. Behavioral hypersensitivity to direct-acting dopamine agonists was observed in mice following acute or chronic morphine administration. Acute levorphanol administration also resulted in potentiation of dopamine agonist-induced behaviors. An increase in density of dopamine receptors, as measured by (/sup 3/H)butyrophenone binding accompanied the development of behavioral hypersensitivity. This increase was localized to the striatum, an area important in the mediation of dopamine-agonist induced behaviors. Naloxone or LiCl coadministered with the opiates prevented the development of hypersensitivity and the increase in density of dopamine receptors. Coadministration of lithium enhanced the development of acute and chronic tolerance. Lithium enhanced the development of dependence as determined by naloxone-induced hypothermia in chronically morphine-treated mice. Apomorphine enhanced naloxone-induced withdrawal in acutely dependent mice. This enhancement was blocked by coadministration of lithium with the opiates. These results suggest that dopamine receptor supersensitivity influences the degree of tolerance and dependence.

  15. Photoaddition reactions of silyl ketene acetals with aromatic carbonyl compounds: a new procedure for {beta}-hydroxyester synthesis

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    Yoon, Ung Chan; Kim, Moon Jung; Moon, Jae Joon; Oh, Sun Wha; Kim, Hyun Jin [Pusan National Univ., Pusan (Korea, Republic of); Mariano, Patrick S. [University of New Mexico, Albuquerque (United States)


    Photochemical reactions of aromatic carbonyl compounds with silyl ketene acetals have been explored. Irradiation of acetonitrile or benzene solutions containing aryl aldehydes or ketones in the presence of silyl ketene acetals is observed to promote formation of {beta}-hydroxyester, 2,2-dioxyoxetane and 3,3-dioxyoxetane products. The ratios of these photoproducts, which arise by competitive single electron transfer (SET) and classical Paterno-Buchi mechanistic pathway, is found to be dependent on the degree of methyl-substitution on the vinyl moieties of the ketene acetals in a manner which reflects expected alkyl substituent effects on the oxidation potentials of these electron rich donors. An analysis of the product distribution arising by irradiation of a solution containing butyrophenone (6) and the silyl ketene acetal 9, derived from methyl isobutyrate, provides an estimate of the rate constants for the competitive Norrish type II, SET and Paterno-Buchi processes occurring. Finally, sequences involving silyl ketene acetal-aryl aldehyde or ketone photoaddition followed by 2,2-dioxyoxetane hydrolysis represent useful procedures for Claisen-condensation type, {beta}-hydroxyester synthesis.

  16. Influence of neurotropic compounds on the calmodulin- and troponin C-dependent processes

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    Baldenkov, G.N.; Men' shikov, M.Yu.; Feoktistov, I.A.; Tkachuk, V.A.


    An analysis was made of the effects of neurotropic compounds on the Ca-binding proteins - calmodulin and troponin C. It was shown that most of the neuroleptics of the phenothiazine group interact effectively both with calmodulin and with troponin C and also inhibit the calmodulin-dependent phosphodiesterase of cyclic nucleotides and calcium-activated actomyosin ATPase. Neuroleptics of the butyrophenone group, as well as imipramine and diphenhydramine, are capable of a low-efficiency interaction only with calmodulin. It was found that one of the phenothiazines - methophenazine, which is an effective inhibitor of calmodulin and calmodulin-dependent phosphodiesterase - does not affect troponin C and Ca-dependent actomyosin ATPase. As a result of this, methophenazine can serve as a convenient tool for studying processes regulated by these Ca-binding proteins. It was concluded that troponin C possesses Ca-dependent binding sites for drugs structurally similar to those of calmodulin but binding the drugs less effectively and exhibiting selectivity with respect to certain preparations. It was shown that despite the homology of the two Ca-binding proteins, calmodulin and troponin C, a selective action on the processes regulated by them is possible.

  17. Behavioral indices in antipsychotic drug discovery. (United States)

    Porsolt, Roger D; Moser, Paul C; Castagné, Vincent


    Schizophrenia is characterized by three major symptom classes: positive symptoms, negative symptoms, and cognitive deficits. Classical antipsychotics (phenothiazines, thioxanthenes, and butyrophenones) are effective against positive symptoms but induce major side effects, in particular, extrapyramidal symptoms (EPS). The discovery of clozapine, which does not induce EPS and is thought effective against all three classes of symptom, has driven research for novel antipsychotics with a wider activity spectrum and lower EPS liability. To increase predictiveness, current efforts aim to develop translational models where direct parallels can be drawn between the processes studied in animals and in humans. The present article reviews existing procedures in animals for their ability to predict compound efficacy and EPS liability in relation to their translational validity. Rodent models of positive symptoms include procedures related to dysfunction in central dopamine and glutamatergic (N-methyl-D-aspartate) and serotonin (5-hydroxytryptamine) neurotransmission. Procedures for evaluating negative symptoms include rodent models of anhedonia, affective flattening, and diminished social interaction. Cognitive deficits can be assessed in rodent models of attention (prepulse inhibition) and of learning/memory (object and social recognition, Morris water maze and operant-delayed alternation). The relevance of the conditioned avoidance response is also discussed. A final section reviews procedures for assessing EPS liability, in particular, parkinsonism (catalepsy in rodents), acute dystonia (purposeless chewing in rodents, dystonia in monkeys), akathisia (defecation in rodents), and tardive dyskinesia (long-term antipsychotic treatment in rodents and monkeys). It is concluded that, with notable exceptions (attention, learning/memory, EPS liability), current predictive models for antipsychotics fall short of clear translational validity.

  18. The consolidation of neuroleptic therapy: Janssen, the discovery of haloperidol and its introduction into clinical practice. (United States)

    López-Muñoz, Francisco; Alamo, Cecilio


    The discovery of haloperidol at the end of the 1950s constitutes one of the greatest advances of 20th century psychiatry. This antipsychotic drug has their origin in the research process of central analgesic molecules derived from pethidine and methadone, carried out by the Belgian company Janssen Phamaceutica. After the synthesis of phenoperidine, numerous analogues of this compound were studied, and chemists at Janssen took the decision to substitute the propiophenone group for a butyrophenone group. One of these compounds went the R-1625, a stronger agent with specifically neuroleptic properties but lacking morphine-like activity. This substance was synthesized on the 11th February 1958 and received the generic name of haloperidol because of the two halogenated substitutes incorporated into the molecule. Clinical development of haloperidol was conducted, primarily, by psychiatric research team at the University of Liège that confirmed its efficacy in the treatment of various psychiatric disorders such as acute and chronic paranoid psychosis, mania, or chronic treatment-resistant schizophrenia. Under the brand name Haldol((R)), haloperidol was licensed and marketed in Belgium in October 1959. The direct and differed consequences of its introduction into the psychiatric practice have been multiple, involving different areas of socio-sanitary reality. Moreover, haloperidol has contributed substantially to the development of biological psychiatry and currently neuroscience, because it made possible the development of new experimental models for predicting the effects of antipsychotics, and allowed the postulate of the firsts biological hypotheses about the schizophrenia etiology. Haloperidol has been included in the World Health Organisation's list of essential medicines.

  19. Perbandingan Granisetron 0,01 mg/KgBb dengan Ondansetron 0,08 Mg/Kg.Bb Untuk Mencegah Mual Muntah Pascaoperasi Dini Mastektomi Radikal Modifikasi

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    Budi Fitriyana


    Full Text Available Postoperative nausea and vomiting not only cause discomfort to the patient, but also lead to electrolyte imbalance, regurgitation and aspiration, bleeding and loss of surgical sutures. Patients who experience postoperative nausea and vomiting will require further attention and treatment which of course increases the cost of medical services. Women who underwent mastectomy with accompanying decision underarm lymph nodes have a high risk of postoperative nausea and vomiting. Many anti-vomiting are given including antihistamines, butyrophenon, and dopamine receptor antagonists have been reported to have undesirable side effects including excessive sedation, hypotension, dry mouth, dysphoria, hallucinations and extrapyramidal effects. 5 HT3 receptor antagonists provide a major advancement for treatment of postoperative nausea and vomiting due to fewer side effects when compared with anti-vomiting medications before. This study will compare the two drugs 5 HT3 receptor antagonist granisetron with ondansetron in preventing postoperative nausea and vomiting modified radical mastectomy early. Conducted research on 58 patients ASA I and II modified radical mastectomy is performed under general anesthesia. Sampling was carried out using double-blind randomized controlled trial. Samples were divided into two groups by block randomization. Group G is given granisetron 0.01 gr / and group O is given ondansetron 0.08 mg / Drug treatment is administered intravenously 30 minutes before the surgery ended on a complete evaluation of blood pressure, heart rate, oxygen saturation and length of surgery. Postoperative nausea and vomiting shortly after surgery assessed every hour until 6 hours after surgery (early postoperative nausea and vomiting to 4 scale (0-3. Data were analyzed by t-test, Chi-square test, Mann-Whitney test and Fisher's Exact test on Windows SPSS ver.16 The results suggest there is a tendency complaints of postoperative nausea and

  20. On the clinical impact of cerebral dopamine D{sub 2} receptor scintigraphy; Zur klinischen Wertigkeit der zerebralen Dopamin-D{sub 2}-Rezeptorszintigraphie

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    Larisch, R. [Duesseldorf Univ. (Germany). Klinik fuer Nuklearmedizin; Klimke, A. [Duesseldorf Univ. (Germany). Psychiatrische Klinik


    The present review describes findings and clinical indications for the dopamine D{sub 2} receptor scintigraphy. Methods for the examination of D{sub 2} receptors are positron emission tomography (PET) using {sup 11}C- or {sup 18}F-labelled butyrophenones or benzamides or single photon emission tomography (SPECT) using {sup 123}I-iodobenzamide (IBZM) respectively. The most important indication in neurology is the differential diagnosis of Parkinsonism: Patients with early Parkinson`s disease show an increased D{sub 2} receptor binding (D{sub 2}-RB) compared to control subjects. However, patients suffering from Steele-Richardson-Olszewski-Syndrome or Multiple System Atrophy show a decreased D{sub 2}-RB and are generally non-responsive to treatment. Postsynaptic blockade of D{sub 2} receptors results in a drug induced Parkinsonian syndrome, which can be diagnosed by D{sub 2} scintigraphy. Further possible indications occur in psychiatry: The assessment of receptor occupancy is useful in schizophrenic patients treated with neuroleptics. Additionally, D{sub 2} receptor scintigraphy might help to clarify the differential diagnosis between neuroleptic malignant syndrome and lethal catatonia. The method might be useful for supervising neurobiochemical changes in drug dependency and during withdrawal. Assessment of dopamine D{sub 2} receptor binding can simplify the choice of therapy in depressive disorder: Patients showing a low D{sub 2} binding are likely to improve following an antidepressive drug treatment whereas sleep deprivation is promising in patients with high D{sub 2} binding. (orig.) [Deutsch] Die vorliegende Arbeit gibt eine Uebersicht ueber Befunde und klinische Indikationen zur Dopamin-D{sub 2}-Rezeptorszintigraphie. Methoden zur Untersuchung der D{sub 2}-Rezeptoren sind die Positronen-Emissions-Tomographie (PET) mit {sup 11}C- oder {sup 18}F-markierten Butyrophenonen oder Benzamiden oder die Einzelphotonen-Emissions-Tomographie (SPECT) mit {sup 123}I