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1. Evaluation of the Pharmacokinetics of Trazpiroben (TAK-906), a Peripherally Selective D2/D3 Dopamine Receptor Antagonist, in the Presence and Absence of Itraconazole, a Potent CYP 3A4 Inhibitor

Author

Chen C, Zhang W, Bari M, Almansa C, Baratta M, and Rosario M

Subjects
drug–drug interactions, d2/d3 dopamine receptor antagonist, gastroparesis, pharmacokinetics, qt effects, Therapeutics. Pharmacology, RM1-950
Abstract

Chunlin Chen,1 Wenwen Zhang,1 Muhammad Bari,2 Cristina Almansa,1 Mike Baratta,1 Maria Rosario1 1Takeda Development Center Americas, Inc, Cambridge, MA, USA; 2Takeda International UK, Ltd, High Wycombe, UKCorrespondence: Chunlin Chen Email chen_chunlin@hotmail.comPurpose: Treatment options for gastroparesis, such as metoclopramide and domperidone, are limited because of safety concerns, which may be exacerbated in the presence of inhibitors of drug metabolism. This study evaluated the effect of itraconazole on the pharmacokinetics, safety, and tolerability of trazpiroben (previously TAK-906), a novel, peripherally selective D2/D3 dopamine receptor antagonist.Methods: This was a phase 1, two-period, crossover trial in healthy participants (NCT03161405). On day 1, period 1 (days 1– 3), participants received a single oral dose of trazpiroben 25 mg. During period 2 (days 4– 9), participants received oral itraconazole 200 mg once daily (days 1– 5) and one oral dose of trazpiroben 25 mg post itraconazole on day 4. Trazpiroben pharmacokinetics were assessed. Safety assessments included triplicate electrocardiograms.Results: Twelve healthy males (24– 45 years old) were studied. Co-administration of itraconazole increased trazpiroben area under the concentration–time curve from time 0 to infinity by 1.28-fold (90% confidence interval: 1.10, 1.49) and maximum plasma concentration (Cmax) by 1.98-fold (1.64, 2.39) versus trazpiroben alone. Placebo-corrected, change from baseline in corrected QT interval at the observed geometric mean Cmax for trazpiroben alone (9.53 ng/mL) and with itraconazole (18.00 ng/mL) was estimated at 1.31 ms (− 0.39, 3.01) and 1.54 ms (− 0.15, 3.24), respectively. There were no clinically relevant abnormalities in any safety parameters.Conclusion: These results indicate that TAK‑906 is relatively insensitive to inhibition of cytochrome P450 3A4, and cardiovascular safety concerns associated with domperidone are unlikely to be elicited by trazpiroben under similar conditions.Keywords: drug–drug interactions, D2/D3 dopamine receptor antagonist, gastroparesis, pharmacokinetics, QT effects

Published
2021

2. Co-crystals as a new approach to multimodal analgesia and the treatment of pain

Author

Almansa C, Frampton CS, Vela JM, Whitelock S, and Plata-Salamán CR

Subjects
co-crystal, efficacy, pain, multimodal, pharmacokinetics, physicochemical properties, safety, Medicine (General), R5-920
Abstract

Carmen Almansa,1 Christopher S Frampton,2 José Miguel Vela,1 Steve Whitelock,3 Carlos R Plata-Salamán4 1Esteve Pharmaceuticals, S.A., Parc Cientific Barcelona, Barcelona 08028, Spain; 2Rbar3 Ltd, Cambridge, UK; 3Mundipharma Research Ltd, Cambridge, UK; 4Esteve Pharmaceuticals, S.A., Torre Esteve, Barcelona 08038, SpainCorrespondence: Carmen AlmansaEsteve Pharmaceuticals, S.A., Parc Cientific Barcelona, C/Baldiri Reixac 4–8, Barcelona 08028, SpainTel +34 93 446 6148Fax +34 93 446 6432Email calmansa@esteve.comAbstract: Pain is highly prevalent, but frequently untreated or under-treated, and health care professionals are faced with a range of treatment challenges. Multimodal therapy is recommended and can be achieved using open combinations (ie, concomitant administration) of individual agents, fixed-dose combinations (FDCs), or multimodal agents (ie, single agents with multiple mechanisms of action). Co-crystallization of active pharmaceutical ingredients (APIs) offers another approach, with the potential to provide drugs with unique properties and advantages for therapeutic applications compared to combinations. API–API co-crystals are single-entity forms that offer a unique possibility of improving the physicochemical properties of both constituent APIs, as well as permitting their synchronous release. Consequently, this may positively impact on their pharmacokinetic (PK) properties and profiles, providing a potential advantage over FDCs and translating into improved clinical efficacy and safety profiles. We report here a revision of the literature concerning API–API co-crystals for the treatment of pain. It becomes apparent that identifying APIs with complementary mechanisms of action that can be adequately co-crystallized in an appropriate molecular ratio applicable for therapeutic use is challenging. In addition, API–API co-crystals normally result in a mere increased exposure of an API without defined clinical benefits (since, to maintain the benefit-risk, the dose needs to be proportionally reduced to adjust for the increased exposure). An exception to this is the co-crystal of tramadol-celecoxib (CTC), that represents a unique concept in co-crystal technology. In CTC neither of its three active components that have complementary mechanisms of action (ie, the two enantiomers of tramadol and celecoxib) show increased exposure levels versus commercially available single-entity reference products, but rather show a change in their PK profile with potential clinical advantages. CTC is in Phase III clinical development for the treatment of pain.Keywords: co-crystal, efficacy, pain, multimodal, pharmacokinetics, physicochemical properties, safety

Published
2019

12. Blinded, Double-Dummy, Parallel-Group, Phase 2a Randomized Clinical Trial to Evaluate the Efficacy and Safety of a Highly Selective 5-Hydroxytryptamine Type 4 Receptor Agonist in Critically Ill Patients With Enteral Feeding Intolerance

Author

Chapman, MJ, Jones, KL, Almansa, C, Barnes, CN, Nguyen, D, Deane, AM, Chapman, MJ, Jones, KL, Almansa, C, Barnes, CN, Nguyen, D, and Deane, AM

Abstract

BACKGROUND: Delayed gastric emptying is the leading cause of enteral feeding intolerance (EFI) in critical illness. This phase 2a study compared TAK-954, a selective agonist of 5-hydroxytryptamine type 4 receptors, with metoclopramide in critically ill patients with EFI (NCT01953081). METHODS: A blinded, double-dummy trial was conducted in mechanically ventilated patients with EFI (>200 mL gastric residual volume within 24 hours before randomization). Patients were randomized to receive either 0.5 mg intravenous TAK-954 over 1 hour then 0.9% saline injection 4 times/d (sham metoclopramide) or the active comparator 10 mg intravenous metoclopramide 4 times/d and a 1-hour 0.9% saline infusion. After initial dosing, participants received a radiolabeled meal of liquid nutrient (Ensure; 106 kcal), and gastric emptying was measured (scintigraphy). Adverse events (AEs) were recorded from the time of consent through to day 5; serious AEs were collected to day 30. RESULTS: Thirteen patients (TAK-954, n = 7; metoclopramide, n = 6) participated. Five patients in the TAK-954 group and 4 in the metoclopramide group experienced AEs (2 and 3, respectively, were serious). All AEs except 1 (diarrhea in the metoclopramide group) were considered unrelated to study drug. Following treatment, a greater proportion of patients receiving TAK-954 had normal gastric retention (<13% retention at 180 minutes) than those receiving metoclopramide (6/7 vs 3/6 patients, respectively). CONCLUSION: A single dose of 0.5 mg intravenous TAK-954 appears to have at least similar efficacy in accelerating gastric emptying to multiple doses of 10 mg metoclopramide and was not associated with increased AEs.

Published
2021

22. Influence of tank bottom surface on growth and welfare of Senegalese sole (Solea senegalensis)

Author

Universitat Politècnica de Catalunya. Departament d'Enginyeria Agroalimentària i Biotecnologia, Universitat Politècnica de Catalunya. SPAq - Sistemes de Producció Aqüícola, Universitat Politècnica de Catalunya. TECTEX - Grup de Recerca en Tecnologia Tèxtil, Almansa, C., Oca Baradad, Joan, Claramunt Blanes, Josep, Reig Puig, Lourdes, Universitat Politècnica de Catalunya. Departament d'Enginyeria Agroalimentària i Biotecnologia, Universitat Politècnica de Catalunya. SPAq - Sistemes de Producció Aqüícola, Universitat Politècnica de Catalunya. TECTEX - Grup de Recerca en Tecnologia Tèxtil, Almansa, C., Oca Baradad, Joan, Claramunt Blanes, Josep, and Reig Puig, Lourdes

Abstract

Tank bottom surface is an important question to take into account in flatfish aquaculture considering the intimate contact that the fish have with it. The most usual materials in aquaculture tank surfaces are inert materials such as epoxy resins or plastics with null porosity, and cement that presents a high alkalinity, roughness and porosity. To improve the cement characteristics, silica fume admixture is usually added in construction industry. The aim of this study was to evaluate the effect of three types of tank bottom surfaces on growth and welfare over a Solea senegalensis population. Moreover, the degree of fin erosion, the appearance of skin lesions and malpigmentation patterns were also monitored. The bottom surfaces tested were plain cement (CE), the same plain cement blended with silica fume (10%) (SF) and epoxy coated surface (EP). Specific growth rate for each bottom surface were compared. The Image Processing Activity Index (IPAI) was used to evaluate the Senegalese sole welfare. Higher SGR and lower IPAI values were obtained in the surface of cement with silica fume, suggesting a higher welfare. The use of plain cement affected negatively the performance of fish, probably due to the high pH and alkalinity of the water in direct contact with fish skin. The null porosity of EP seems to be related to the main cause of higher activity level of fish kept on it outcoming in lower growth. Silica fume that is frequently use to improve the mechanical characteristics of plain cement, also provides benefits in terms of fish welfare., Postprint (author's final draft)

Published
2017

23. Tasas de aparición y desaparición de los síntomas de reflujo gastroesofágico en la población española y su impacto sobre la calidad de vida

Author

Rey, E., Álvarez-Sánchez, A., Rodríguez-Artalejo, F., Moreno Elola-Olaso, C., Almansa, C., and Díaz-Rubio, M.

Subjects
Quality of life, Gastroesophageal reflux, fungi
Abstract

Background: few studies have reported the onset and disappearance rates of gastroesophageal reflux symptoms (GERS) in the population. Aim: to assess the occurrence and disappearance rates of GERS in Spain, and their impact on health-related quality of life (HRQL). Participants and methods: participants were selected at random from the general population of Madrid in age and sex strata. They were interviewed at home twice, 6 months apart. Heartburn, acid regurgitation and consultation were assessed with the gastroesophageal reflux questionnaire, and HRQL with the SF-36. Results: 709 individuals were included, and 451 (63.6%) were re-interviewed 6 months later. Among the 325 individuals without GERS, 9 developed weekly symptoms (2.2% [95% CI: 0.8, 3.4%]); 2 (22%) consulted because of GERS. Among the 34 subjects reporting weekly GERS initially, 26 did not report them at 6-months. Onset of GERS was associated with worsening scores in the physical summary of SF-36 (delta = -6.6 [95% CI: -11.8, -1.42]), while disappearance with an improved score (delta = -3.0 [95% CI: 0.0, 5.9]). Conclusion: despite the lower prevalence of GERS in Spain, the occurrence rate is 2.2% in 6 months; however symptoms disappeared in more than half of subjects six months later. Developing GERS was associated with reduced HRQL, and their disappearance with improvement.

Published
2009

24. Opinión de los médicos españoles sobre el síndrome de intestino irritable: Resultados de un estudio utilizando el método Delphi

Author

Almansa, C., Rey, E., Bolaños, E., Palma, M., Álvarez Sánchez, A., and Díaz-Rubio, M.

Subjects
Irritable bowel syndrome, Estudio Delphi, Síndrome del intestino irritable, Delphi survey
Abstract

Introducción: el síndrome del intestino irritable (SII) es una patología controvertida, donde ante la escasez de evidencia científica las recomendaciones sobre su manejo clínico y su definición vienen determinadas por métodos de consenso de expertos. Objetivo: obtener la opinión de los médicos de nuestro país implicados en el manejo de pacientes con SII y conocer los puntos de acuerdo en las principales cuestiones clínicas que plantea. Material y métodos: se realizó un estudio Delphi a nivel nacional mediante dos envíos a 100 médicos de atención primaria y gastroenterólogos. El cuestionario incluía preguntas sobre el concepto, diagnóstico y tratamiento del SII, evaluando el grado de acuerdo entre los participantes. Resultados: el 55% de los encuestados completó los dos envíos. Se obtuvo acuerdo respecto a los síntomas que caracterizan al SII y los de alarma. No existió una actitud clara ante el paciente sin síntomas de alarma, pero sí acuerdo respecto a la realización de colonoscopia en su presencia. Se señaló la necesidad de realizar estudios complementarios en mayores de 40 años. En el tratamiento no encontramos una actitud uniforme, aunque parece existir una orientación diferente según el síntoma predominante. Conclusiones: los médicos participantes en el estudio demuestran a través de sus respuestas un buen conocimiento conceptual del SII, si bien las discrepancias observadas en las cuestiones sobre diagnóstico y tratamiento demuestran la complejidad y falta de uniformidad que existe en el manejo diario de este síndrome. Introduction: lack of evidence in most clinical situations regarding irritable bowel syndrome (IBS) enhances the importance of an expert's opinion, which will guide management and even the concept underlying the disease. Objective: to delve into the knowledge and degree of agreement on main clinical skills for this syndrome among physicians involved in its management. Material and method: two rounds of a Delphi survey were conducted on 100 physicians: general practitioners (GPs) and gastroenterologists. The questionnaire evaluated agreement among participants in some aspects regarding the definition, diagnosis, and treatment of IBS. Results: fifty-five percent of participants completed the two-round survey. Agreement was achieved regarding the definition of typical symptoms and red flags characterizing IBS. Although there was no consensus regarding the appropriate management of patients without alarm symptoms, the performance of a colonoscopy on any patient presenting red flags was suggested. Patients were thought to require a wider examination when older than 40. A well defined line of IBS treatment was not found, albeit most physicians tended to choose it depending on the main complaint. Conclusion: interviewed physicians showed adequate theoretical knowledge of IBS, but lack of uniformity on diagnosis and treatment approach reflects the controversial day-by-day management of this syndrome.

Published
2007

25. Has the identification of rectal hypersensitivity any implication in the clinical outcome of irritable bowel syndrome?

Author

Izquierdo, S., Rey, E., García Alonso, M., Almansa, C., and Díaz-Rubio, M.

Subjects
Irritable bowel syndrome, Sensitivity, Sensibilidad, Síndrome intestino irritable, Use of health resources, Consumo de recursos sanitarios
Abstract

Background: sixty percent of patients with irritable bowel disease (IBS) are hypersensitive to rectal distension. It is uncertain to what extend the identification of this abnormality has an impact in the clinical outcome. Objective: to evaluate if rectal hypersensitivity is associated with a different clinical outcome, prognosis and use of medical resources. Material and methods: patients with IBS (Rome II criteria) who underwent a rectal distension study at least one year before were eligible if they have not been included in any research protocol since then. We reviewed how many times in the last year they came to emergency room, underwent an endoscopy, and consulted a gastroenterologist or other medical physician for any reason. Also, a telephone interview was done by a gastroenterology fellow using a structured questionnaire to evaluate the frequency and severity of their symptoms in the last year and last month. Results: a total of 52 patients were eligible and 38 were included. Forteen were not included because inability to made a phone contact or did not consent to phone interview. Twenty six patients were hypersensitive and 12 normosensitive. Both groups had similar symptoms (frequency and severity) but hypersensitive patients visited less to the gastroenterologist (1.2 ± 0.2 vs. 2.9 ± 0.6 times yearly, p < 0.01). Conclusion: identification of rectal hypersensitivity to distension is associated to less consultation to gastroenterologist, although severity and frequency of symptoms are not modified. Finding of an objective explanation of the symptoms seems to help patients to understand their disease, leading to a decrease in resources' use. Introducción: el 60% de los pacientes con SII tienen hipersensibilidad a la distensión rectal. Se desconoce si la identificación de esta alteración puede modificar su evolución. Objetivo: evaluar si la hipersensibilidad a la distensión rectal se asocia con un diferente pronóstico respecto a la presentación de síntomas y la utilización de recursos sanitarios en pacientes con SII. Material y métodos: se incluyeron pacientes con SII según criterios de Roma II, que habían sido sometidos a un estudio de distensión rectal. Se recogieron datos de los registros informáticos sobre asistencia a consultas especializadas, realización de endoscopias, asistencia a urgencias e ingresos hospitalarios. Además, se realizó entrevista telefónica en la que se interrogó acerca de la existencia de síntomas a lo largo del último año y último mes (características, duración y severidad). Resultados: se evaluaron 38 pacientes, 26 con hipersensibilidad en el estudio de distensión basal y 12 normosensibles. En el momento de la recogida de datos (registro informático y entrevista telefónica) el seguimiento medio era de 2,39 años después del estudio de distensión. Los sujetos hipersensibles presentaron una clínica similar a aquellos normosensibles. Se registró una menor tasa de frecuentación anual en las consultas de Aparato Digestivo (1,2 ± 0,2 vs. 2,9 ± 0,6, p < 0,01) por parte de los pacientes hipersensibles sin existir diferencias en el resto de variables estudiadas. Conclusión: la identificación de hipersensibilidad visceral en pacientes con SII conlleva una notable reducción de las consultas al gastroenterólogo, sin que esto pueda explicarse por la mejoría de los síntomas, ni por una menor tendencia a realizar otras consultas médicas.

Published
2005

44. New Water-Soluble Sulfonylphosphoramidic Acid Derivatives of the COX-2 Selective Inhibitor Cimicoxib. A Novel Approach to Sulfonamide Prodrugs

Author

Almansa, C., Bartroli, J., Belloc, J., Cavalcanti, F. L., Ferrando, R., Gomez, L. A., Ramis, I., Carceller, E., Merlos, M., and Garcia-Rafanell, J.

Abstract

The synthesis and pharmacological evaluation of new water-soluble phosphoramidate derivatives of the COX-2 selective inhibitor cimicoxib (4) are described. The sulfonylphosphoramidic acid derivative 10 was converted to 4 in human plasma and showed excellent in vivo activity in the rat carrageenan-edema test. Pharmacokinetic evaluation in dogs indicated that 10 behaved as a prodrug, immediately converting to 4 and giving an identical profile to that of the parent compound. These results represent the first description of phosphoramidic acids as prodrugs for the sulfonamido group. Compound 10 also exhibited an important and sustained analgesic effect in the hyperalgesia test in rats and a high aqueous solubility at pH higher than 7. This profile led to the selection of 10 (UR-14048) for further development in the parenteral treatment of acute pain.

Published
2004

45. Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors:  1,5-Diarylimidazoles

Author

Almansa, C., Alfon, J., Arriba, A. F. de, Cavalcanti, F. L., Escamilla, I., Gomez, L. A., Miralles, A., Soliva, R., Bartroli, J., Carceller, E., Merlos, M., and Garcia-Rafanell, J.

Abstract

The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole cores led to the identification of 4-[4-chloro-5-(3-fluoro-4-methoxyphenyl)imidazol-1-yl]benzenesulfonamide (UR-8880, 51f) as the best candidate, which is now undergoing Phase I clinical trials.

Published
2003

46. Theoretical Studies on the Inhibition Mechanism of Cyclooxygenase-2. Is There a Unique Recognition Site?

Author

Soliva, R., Almansa, C., Kalko, S. G., Luque, F. J., and Orozco, M.

Abstract

The mechanism of binding of different nonsteroidal anti-inflammatory drugs to the cyclooxygenase active site of cyclooxygenase-2 (COX-2) has been studied by means of a wide range of theoretical techniques including molecular dynamics and free energy calculations. It is found that theoretical methods predict accurately the binding of different drugs based on different scaffolds. Calculations allow us to describe in detail the key recognition sites and to analyze how these recognition sites change depending on the scaffold of the drug. It is concluded that the recognition site of COX-2 is very flexible and can adapt its structure to very subtle structural changes in the drug.

Published
2003

47. Synthesis and SAR of a New Series of COX-2-Selective Inhibitors:  Pyrazolo[1,5-a]pyrimidines

Author

Almansa, C., Arriba, A. F. de, Cavalcanti, F. L., Gomez, L. A., Miralles, A., Merlos, M., Garcia-Rafanell, J., and Forn, J.

Abstract

The synthesis and pharmacological activity of a series of bicyclic pyrazolo[1,5-a]pyrimidines as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema and air-pouch model). Modification of the pyrimidine substituents showed that 6,7-disubstitution provided the best activity and led to the identification of 3-(4-fluorophenyl)-6,7-dimethyl-2-(4-methylsulfonylphenyl)pyrazolo[1,5-a]pyrimidine (10f) as one of the most potent and selective COX-2 inhibitor in this series.

Published
2001

48. Diphenylpropionic Acids as New AT<INF>1</INF> Selective Angiotensin II Antagonists

Author

Almansa, C., Gomez, L. A., Cavalcanti, F. L., Arriba, A. F. de, Rodriguez, R., Carceller, E., Garcia-Rafanell, J., and Forn, J.

Abstract

The synthesis and pharmacological evaluation of a new series of potent AT1 selective diphenylpropionic acid nonpeptide angiotensin II receptor antagonists are reported. The new compounds were evaluated for in vitro AT1 (rat liver) and AT2 (rat adrenal) binding affinity as well as for in vivo inhibition of angiotensin II-induced increase in mean arterial blood pressure in pithed rats. Unsaturation of the diphenylpropionic acids as well as substitution or replacement by alkyl groups of the pendant phenyl ring resulted in a decrease of potency. On the other hand, the presence of small alkyl groups in the α-position to the carboxylic acid was important for activity, with one of the resultant diastereoisomers (R*,R*) being ca. 10-fold more active than the other (R*,S*). Oral evaluation of the most active compounds in a furosemide-treated sodium-depleted rat model showed that compound 36g (UR-7198) reduced blood pressure dose dependently. This compound showed in vitro and iv potencies similar to that of the reference compound losartan but faster onset of action and somewhat greater oral activity, presumably due to its improved bioavailability.

Published
1996

49. Synthesis and Structure−Activity Relationship of a New Series of Potent AT<INF>1</INF> Selective Angiotensin II Receptor Antagonists:  5-(Biphenyl-4-ylmethyl)pyrazoles

Author

Almansa, C., Gomez, L. A., Cavalcanti, F. L., Arriba, A. F. de, Garcia-Rafanell, J., and Forn, J.

Abstract

The synthesis and pharmacological activity of a new series of 5-(biphenyl-4-ylmethyl)pyrazoles as potent angiotensin II antagonists both in vitro (binding of [3H]AII) and in vivo (iv, inhibition of AII-induced increase in blood pressure, pithed rats; po, furosemide-treated sodium-depleted rats) are reported. The various substituents of the pyrazole ring have been modified taking into account the receptor's requirements derived from related structure−activity relationship studies. A propyl or butyl group at position 1 as well as a carboxylic acid group at position 4 were shown to be essential for high affinity. Different groups at position 3 (H, small alkyl, phenyl, benzyl) provided good binding affinity, but oral activity was highly discriminating:  bulky alkyl groups provided the highest potencies. Among the acidic isosteres tested in the biphenyl moiety, the tetrazole group proved to be the best. Compound 14n (3-tert-butyl-1-propyl-5-[[2‘-(1H-tetrazol-5-yl)-1,1‘-biphenyl-4-yl]methyl]-1H-pyrazole-4-carboxylic acid, UR-7280) shows high potency both in vitro (IC50 = 3 nM) and in vivo (iv, 61.2 ± 10% decrease in blood pressure at 0.3 mg/kg; po, 30 mmHg fall in blood pressure at 0.3 mg/kg), in comparison to losartan (IC50 = 59 nM; iv, 62.5 ± 8.9% decrease in blood pressure at 1 mg/kg; po, 13 mmHg fall in blood pressure at 3 mg/kg). These data, together with the good pharmacokinetic profile of 14n in different species, have led to its selection for clinical evaluation as an antihypertensive agent.

Published
1997

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