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[PMID]:26635068
[Au] Autor:Gudin J; Fudin J; Nalamachu S
[Ad] Endereço:a Pain Management and Palliative Care , Englewood Hospital and Medical Center , Englewood , NJ , USA.
[Ti] Título:Levorphanol use: past, present and future.
[So] Source:Postgrad Med;128(1):46-53, 2016 Jan.
[Is] ISSN:1941-9260
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Levorphanol is a potent opioid analgesic that was first approved for use in the United States in 1953. Levorphanol is approved for use in moderate to severe pain where an opioid analgesic is appropriate. Levorphanol has a wide range of activities including mu opioid agonism, delta agonism, kappa1 and kappa3 receptor agonism, N-methyl-d-aspartate receptor antagonism and reuptake inhibition of both norepinephrine and serotonin. This multimodal profile might prove effective for pain syndromes that are refractory to other opioid analgesics, such as central and neuropathic pain and opioid-induced hyperalgesia. Levorphanol is well suited as a first-line opioid and can also be used during opioid rotation. It has no known effect on the cardiac QT interval or drug-drug interactions involving hepatic cytochrome P450s enzymes. In these regards, levorphanol may offer a superior safety profile over methadone and other long-acting opioids. Despite its prospective value of multiple mechanisms of action and the potential for treating various types of pain, levorphanol use has been largely supplanted by other recently approved opioids. Its waning use over the years has caused it to be referred to as the "Forgotten Opioid" and resulted in what some consider its underutilization. In fact, levorphanol is relatively unfamiliar to most prescribers. The purpose of this review is to inform practitioners about the attributes of this opioid and reintroduce it to clinicians as an option for treating moderate to severe pain when alternative treatment options are inadequate, not indicated or contraindicated.
[Mh] Termos MeSH primário: Analgésicos Opioides/uso terapêutico
Levorfanol/uso terapêutico
Dor/tratamento farmacológico
[Mh] Termos MeSH secundário: Administração Oral
Analgésicos Opioides/química
Analgésicos Opioides/farmacocinética
Analgésicos Opioides/farmacologia
Esquema de Medicação
Seres Humanos
Levorfanol/química
Levorfanol/farmacocinética
Levorfanol/farmacologia
Índice de Gravidade de Doença
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Analgesics, Opioid); 27618J1N2X (Levorphanol)
[Em] Mês de entrada:1605
[Cu] Atualização por classe:160118
[Lr] Data última revisão:
160118
[Sb] Subgrupo de revista:AIM; IM
[Da] Data de entrada para processamento:151205
[St] Status:MEDLINE
[do] DOI:10.1080/00325481.2016.1128308


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[PMID]:26307179
[Au] Autor:Pham TC; Fudin J; Raffa RB
[Ad] Endereço:PGY2 Pain and Palliative Care Pharmacy Residency, Stratton VA Medical Center, Albany, New York, USA.
[Ti] Título:Is levorphanol a better option than methadone?
[So] Source:Pain Med;16(9):1673-9, 2015 Sep.
[Is] ISSN:1526-4637
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Methadone has been a stalwart pharmacologic option for the management of opioid drug dependence for many years. It substitutes for opioid agonists and possesses certain pharmacokinetic properties that confer characteristics preferable to those of other opioids for this application. Methadone is likewise used as an option for the treatment of pain, particularly chronic pain. It has a spectrum of pharmacodynamic activity, including contributions from non-opioid components, that translates to its specific clinical attributes as an analgesic. Unfortunately, basic science studies and accumulated clinical experience with methadone have revealed some undesirable, and even worrisome, features, including issues of safety. The benefit/risk ratio of methadone might be acceptable if there was no better alternative, but neither its pharmacokinetic nor pharmacodynamic properties are unique to methadone. OBJECTIVE: We review the basic and clinical pharmacology of methadone and suggest that levorphanol should receive attention as a possible alternative. CONCLUSION: Unlike methadone, levorphanol is a more potent NMDA antagonist, possesses a higher affinity for DOR and KOR, has a shorter plasma half-life yet longer duration of action, has no CYP450 interactions or QTc prolongation risk, can be a viable option in the elderly, palliative care, and SCI patients, requires little to no need for co-administration of adjuvant analgesics, and has potentially a lower risk of drug-related Emergency Department visits compared to other opioids.
[Mh] Termos MeSH primário: Analgésicos Opioides/uso terapêutico
Levorfanol/uso terapêutico
Metadona/uso terapêutico
Manejo da Dor/métodos
[Mh] Termos MeSH secundário: Analgésicos Opioides/farmacocinética
Seres Humanos
Levorfanol/farmacocinética
Metadona/farmacocinética
[Pt] Tipo de publicação:JOURNAL ARTICLE; REVIEW
[Nm] Nome de substância:
0 (Analgesics, Opioid); 27618J1N2X (Levorphanol); UC6VBE7V1Z (Methadone)
[Em] Mês de entrada:1607
[Cu] Atualização por classe:150916
[Lr] Data última revisão:
150916
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:150827
[St] Status:MEDLINE
[do] DOI:10.1111/pme.12795


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[PMID]:22741803
[Au] Autor:Gyulai Z; Udvardy A; Cs Bényei A; Fichna J; Gach K; Storr M; Tóth G; Antus S; Berényi S; Janecka A; Sipos A
[Ad] Endereço:Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary.
[Ti] Título:Synthesis and opioid activity of novel 6-ketolevorphanol derivatives.
[So] Source:Med Chem;9(1):1-10, 2013 Feb.
[Is] ISSN:1875-6638
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:Novel 6-ketolevorphanol analogs with diverse substitution patterns at ring C were synthesized and their binding affinities at the µ,δ and κ opioid receptors were investigated. The in vitro activity of the new analogs was then evaluated in the functional assay based on the electrically-stimulated contractions of the mouse ileum. It was shown that analogs with Δ7,8 bond had no significant potency at any of the opioid receptor types. In contrast, analogs with the saturated ring C were either potent κ agonist or antagonist depending on the absence or presence of the hydroxyl group in position 14.
[Mh] Termos MeSH primário: Analgésicos Opioides/síntese química
Analgésicos Opioides/farmacologia
Contração Muscular/efeitos dos fármacos
[Mh] Termos MeSH secundário: Analgésicos Opioides/química
Animais
Cristalografia por Raios X
Relação Dose-Resposta a Droga
Íleo/citologia
Íleo/efeitos dos fármacos
Cetonas/síntese química
Cetonas/química
Cetonas/farmacologia
Levorfanol/síntese química
Levorfanol/química
Levorfanol/farmacologia
Masculino
Camundongos
Estrutura Molecular
Células Swiss 3T3
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Analgesics, Opioid); 0 (Ketones); 27618J1N2X (Levorphanol)
[Em] Mês de entrada:1309
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:120630
[St] Status:MEDLINE


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[PMID]:21699425
[Au] Autor:Loitman JE
[Ti] Título:Levorphanol #240.
[So] Source:J Palliat Med;14(7):875-6, 2011 Jul.
[Is] ISSN:1557-7740
[Cp] País de publicação:United States
[La] Idioma:eng
[Mh] Termos MeSH primário: Analgésicos Opioides/farmacologia
Levorfanol/farmacologia
[Mh] Termos MeSH secundário: Analgésicos Opioides/administração & dosagem
Analgésicos Opioides/economia
Levorfanol/administração & dosagem
Levorfanol/economia
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Analgesics, Opioid); 27618J1N2X (Levorphanol)
[Em] Mês de entrada:1111
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:110625
[St] Status:MEDLINE
[do] DOI:10.1089/jpm.2011.9673


  5 / 549 MEDLINE  
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[PMID]:21051498
[Au] Autor:Paronis CA; Bergman J
[Ad] Endereço:Preclinical Pharmacology Laboratory, McLean Hospital/Harvard Medical School, Belmont, Massachusetts 02115, USA. c.paronis@neu.edu
[Ti] Título:Buprenorphine and opioid antagonism, tolerance, and naltrexone-precipitated withdrawal.
[So] Source:J Pharmacol Exp Ther;336(2):488-95, 2011 Feb.
[Is] ISSN:1521-0103
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The dual antagonist effects of the mixed-action µ-opioid partial agonist/κ-opioid antagonist buprenorphine have not been previously compared in behavioral studies, and it is unknown whether they are comparably modified by chronic exposure. To address this question, the dose-related effects of levorphanol, trans-(-)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] benzeneacetamide (U50,488), heroin, and naltrexone on food-maintained behavior in rhesus monkeys were studied after acute and chronic treatment with buprenorphine (0.3 mg/kg/day). In acute studies, the effects of levorphanol and U50,488 were determined at differing times after buprenorphine (0.003-10.0 mg/kg i.m.). Results show that buprenorphine produced similar, dose-dependent rightward shifts of the levorphanol and U50,488 dose-response curves that persisted for ≥ 24 h after doses larger than 0.1 mg/kg buprenorphine. During chronic treatment with buprenorphine, the effects of levorphanol, U50,488, heroin, and naltrexone were similarly determined at differing times (10 min to 48 h) after intramuscular injection. Overall, results show that buprenorphine produced comparable 3- to 10-fold rightward shifts in the U50,488 dose-response curve under both acute and chronic conditions, but that chronic buprenorphine produced larger (10- to ≥ 30-fold) rightward shifts in the heroin dose-effect function than observed acutely. Naltrexone decreased operant responding in buprenorphine-treated monkeys, and the position of the naltrexone dose-effect curve shifted increasingly to the left as the time after daily buprenorphine treatment increased from 10 min to 48 h. These results suggest that the µ-antagonist, but not the κ-antagonist, effects of buprenorphine are augmented during chronic treatment. In addition, the leftward shift of the naltrexone dose-effect function suggests that daily administration of 0.3 mg/kg buprenorphine is adequate to produce opioid dependence.
[Mh] Termos MeSH primário: Buprenorfina/farmacologia
Naltrexona/farmacologia
Antagonistas de Entorpecentes/farmacologia
Síndrome de Abstinência a Substâncias/etiologia
[Mh] Termos MeSH secundário: (trans)-Isômero de 3,4-Dicloro-N-metil-N-(2-(1-pirrolidinil)-ciclo-hexil)-benzenoacetamida/antagonistas & inibidores
Animais
Buprenorfina/sangue
Relação Dose-Resposta a Droga
Tolerância a Medicamentos
Feminino
Levorfanol/antagonistas & inibidores
Macaca mulatta
Masculino
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL
[Nm] Nome de substância:
0 (Narcotic Antagonists); 27618J1N2X (Levorphanol); 40D3SCR4GZ (Buprenorphine); 5S6W795CQM (Naltrexone); 67198-13-4 (3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer)
[Em] Mês de entrada:1103
[Cu] Atualização por classe:161019
[Lr] Data última revisão:
161019
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:101106
[St] Status:MEDLINE
[do] DOI:10.1124/jpet.110.173823


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[PMID]:19797609
[Au] Autor:Bonn B; Masimirembwa CM; Castagnoli N
[Ad] Endereço:Department of Chemistry, Medicinal Chemistry, University of Gothenburg, Gothenburg, Sweden. kjelland@chem.gu.se
[Ti] Título:Exploration of catalytic properties of CYP2D6 and CYP3A4 through metabolic studies of levorphanol and levallorphan.
[So] Source:Drug Metab Dispos;38(1):187-99, 2010 Jan.
[Is] ISSN:1521-009X
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:CYP2D6 and CYP3A4, two members of the cytochrome P450 superfamily of monooxygenases, mediate the biotransformation of a variety of xenobiotics. The two enzymes differ in substrate specificity and size and characteristics of the active site cavity. The aim of this study was to determine whether the catalytic properties of these isoforms, reflected by the differences observed from crystal structures and homology models, could be confirmed with experimental data. Detailed metabolite identification, reversible inhibition, and time-dependent inhibition were examined for levorphanol and levallorphan with CYP2D6 and CYP3A4. The studies were designed to provide a comparison of the orientations of substrates, the catalytic sites of the two enzymes, and the subsequent outcomes on metabolism and inhibition. The metabolite identification revealed that CYP3A4 catalyzed the formation of a variety of metabolites as a result of presenting different parts of the substrates to the heme. CYP2D6 was a poorer catalyst that led to a more limited number of metabolites that were interpreted in terms to two orientations of the substrates. The inhibition studies showed evidence for strong reversible inhibition of CYP2D6 but not for CYP3A4. Levallorphan acted as a time-dependent inhibitor on CYP3A4, indicating a productive binding mode with this enzyme not observed with CYP2D6 that presumably resulted from close interactions of the N-allyl moiety oriented toward the heme. All the results are in agreement with the large and flexible active site of CYP3A4 and the more restricted active site of CYP2D6.
[Mh] Termos MeSH primário: Biocatálise
Citocromo P-450 CYP2D6/metabolismo
Citocromo P-450 CYP3A/metabolismo
Levalorfano/metabolismo
Levorfanol/metabolismo
[Mh] Termos MeSH secundário: Domínio Catalítico
Cromatografia Líquida de Alta Pressão
Citocromo P-450 CYP2D6/química
Inibidores do Citocromo P-450 CYP2D6
Citocromo P-450 CYP3A/química
Inibidores Enzimáticos/química
Inibidores Enzimáticos/metabolismo
Glutationa/metabolismo
Seres Humanos
Interações Hidrofóbicas e Hidrofílicas
Cinética
Levalorfano/análogos & derivados
Levalorfano/análise
Levalorfano/química
Levorfanol/análogos & derivados
Levorfanol/análise
Levorfanol/química
Modelos Químicos
Modelos Moleculares
Estrutura Molecular
Proteínas Recombinantes/química
Proteínas Recombinantes/metabolismo
Espectrometria de Massas por Ionização por Electrospray
Eletricidade Estática
Espectrometria de Massas em Tandem
Termodinâmica
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Cytochrome P-450 CYP2D6 Inhibitors); 0 (Enzyme Inhibitors); 0 (Recombinant Proteins); 27618J1N2X (Levorphanol); 353613BU4U (Levallorphan); EC 1.14.13.67 (CYP3A4 protein, human); EC 1.14.14.1 (Cytochrome P-450 CYP2D6); EC 1.14.14.1 (Cytochrome P-450 CYP3A); GAN16C9B8O (Glutathione)
[Em] Mês de entrada:1003
[Cu] Atualização por classe:141120
[Lr] Data última revisão:
141120
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:091003
[St] Status:MEDLINE
[do] DOI:10.1124/dmd.109.028670


  7 / 549 MEDLINE  
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[PMID]:19719367
[Au] Autor:McNulty JP
[Ti] Título:Chronic pain: levorphanol, methadone, and the N-methyl-D-aspartate receptor.
[So] Source:J Palliat Med;12(9):765-6, 2009 Sep.
[Is] ISSN:1557-7740
[Cp] País de publicação:United States
[La] Idioma:eng
[Mh] Termos MeSH primário: Analgésicos Opioides/uso terapêutico
Levorfanol/uso terapêutico
Metadona/uso terapêutico
N-Metilaspartato/efeitos dos fármacos
Entorpecentes/uso terapêutico
Dor/tratamento farmacológico
Cuidados Paliativos
Receptores de N-Metil-D-Aspartato/antagonistas & inibidores
[Mh] Termos MeSH secundário: Doença Crônica
Cuidados Paliativos na Terminalidade da Vida
Seres Humanos
[Pt] Tipo de publicação:LETTER
[Nm] Nome de substância:
0 (Analgesics, Opioid); 0 (Narcotics); 0 (Receptors, N-Methyl-D-Aspartate); 27618J1N2X (Levorphanol); 6384-92-5 (N-Methylaspartate); UC6VBE7V1Z (Methadone)
[Em] Mês de entrada:1009
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:090902
[St] Status:MEDLINE
[do] DOI:10.1089/jpm.2009.0105


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[PMID]:18095794
[Au] Autor:Prommer EE
[Ti] Título:Levorphanol revisited.
[So] Source:J Palliat Med;10(6):1228-30, 2007 Dec.
[Is] ISSN:1096-6218
[Cp] País de publicação:United States
[La] Idioma:eng
[Mh] Termos MeSH primário: Analgésicos Opioides
Levorfanol
[Mh] Termos MeSH secundário: Analgésicos Opioides/administração & dosagem
Analgésicos Opioides/efeitos adversos
Analgésicos Opioides/farmacocinética
Analgésicos Opioides/farmacologia
Levorfanol/administração & dosagem
Levorfanol/efeitos adversos
Levorfanol/farmacocinética
Levorfanol/farmacologia
Metadona
Morfina
[Pt] Tipo de publicação:COMMENT; LETTER
[Nm] Nome de substância:
0 (Analgesics, Opioid); 27618J1N2X (Levorphanol); 76I7G6D29C (Morphine); UC6VBE7V1Z (Methadone)
[Em] Mês de entrada:0803
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:071222
[St] Status:MEDLINE


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[PMID]:17488103
[Au] Autor:Zhang A; Li F; Ding C; Yao Q; Knapp BI; Bidlack JM; Neumeyer JL
[Ad] Endereço:Bioorganic and Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. aozhang@mail.shcnc.ac.cn
[Ti] Título:Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.
[So] Source:J Med Chem;50(11):2747-51, 2007 May 31.
[Is] ISSN:0022-2623
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and micro receptors was slightly reduced.
[Mh] Termos MeSH primário: Analgésicos Opioides/síntese química
Indóis/síntese química
Levorfanol/análogos & derivados
Levorfanol/síntese química
Tiazóis/síntese química
[Mh] Termos MeSH secundário: Analgésicos Opioides/farmacologia
Animais
Células CHO
Cricetinae
Cricetulus
Indóis/farmacologia
Levorfanol/farmacologia
Ensaio Radioligante
Relação Estrutura-Atividade
Tiazóis/farmacologia
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, N.I.H., EXTRAMURAL; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Analgesics, Opioid); 0 (Indoles); 0 (Thiazoles); 27618J1N2X (Levorphanol)
[Em] Mês de entrada:0707
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:070510
[St] Status:MEDLINE


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[PMID]:17472497
[Au] Autor:McNulty JP
[Ad] Endereço:Palliative Care Institute of Southeast LA, Covington, Louisiana 70433, USA. jmcnulty@palliativecare-la.org
[Ti] Título:Can levorphanol be used like methadone for intractable refractory pain?
[So] Source:J Palliat Med;10(2):293-6, 2007 Apr.
[Is] ISSN:1096-6218
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:BACKGROUND: Levorphanol has been reported to provide analgesia at doses that suggest it does not act like other pure agonist opioids. A dual effect of action on both opioid receptors and n-methyl, d-aspartate (NMDA) receptors has been proposed to be responsible for this effect. METHOD: Case series of patients treated with levorphanol when pain did not respond adequately to other opioids, including methadone. RESULTS: During a 5-year period in a single palliative medicine practice, 20 of 244 patients with chronic nonmalignant pain in a palliative care clinic and 11 of 1508 terminally ill patients enrolled in hospice care whose severe chronic pain was not relieved by treatment with other opioids were treated with oral levorphanol. Of those 31 patients, 16 (52%) reported excellent relief of pain and 7 (22%) reported fair relief for a total response rate of 74%. DISCUSSION: These results suggest that levorphanol has a role in the treatment of pain syndromes that are refractory to other opioids. The pattern of relief seen in this case series is similar to that reported for methadone. Could it be that levorphanol may have a role like methadone for pain that is poorly controlled with other pure agonist opioids? We summarize what is known about levorphanol and provide a table for converting other opioids to levorphanol that was used for this case series.
[Mh] Termos MeSH primário: Analgésicos Opioides/uso terapêutico
Levorfanol/uso terapêutico
Dor Intratável/tratamento farmacológico
Cuidados Paliativos
[Mh] Termos MeSH secundário: Analgésicos Opioides/administração & dosagem
Analgésicos Opioides/farmacologia
Doença Crônica
Cuidados Paliativos na Terminalidade da Vida
Seres Humanos
Levorfanol/administração & dosagem
Levorfanol/farmacologia
Louisiana
Metadona/administração & dosagem
Metadona/farmacologia
Metadona/uso terapêutico
Medição da Dor
Dor Intratável/classificação
Falha de Tratamento
Resultado do Tratamento
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (Analgesics, Opioid); 27618J1N2X (Levorphanol); UC6VBE7V1Z (Methadone)
[Em] Mês de entrada:0712
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:070503
[St] Status:MEDLINE



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