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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:44 UTC |
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HMDB ID | HMDB0014794 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Trazodone |
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Description | A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309) |
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Structure | ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1 InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2 |
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Synonyms | Value | Source |
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2-(3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one | ChEBI | Trazodona | ChEBI | Trazodonum | ChEBI | Trittico | Kegg | Aventis brand OF trazodone hydrochloride | HMDB | Desyrel | HMDB | Farma lepori brand OF trazodone hydrochloride | HMDB | Gen-trazodone | HMDB | Genpharm brand OF trazodone hydrochloride | HMDB | Novopharm brand OF trazodone hydrochloride | HMDB | Nu pharm brand OF trazodone hydrochloride | HMDB | Ratiopharm brand OF trazodone hydrochloride | HMDB | Searle brand OF trazodone hydrochloride | HMDB | Trazodon-neuraxpharm | HMDB | Apo-trazodone | HMDB | Apotex brand OF trazodone hydrochloride | HMDB | Boehringer ingelheim brand OF trazodone hydrochloride | HMDB | Bristol myers squibb brand OF trazodone hydrochloride | HMDB | Bristol-myers squibb brand OF trazodone hydrochloride | HMDB | Gen trazodone | HMDB | Molipaxin | HMDB | Sidmark brand OF trazodone hydrochloride | HMDB | Tradozone | HMDB | Trazodon hexal | HMDB | Trazodone hydrochloride | HMDB | Ratio trazodone | HMDB | Apo trazodone | HMDB | Deprax | HMDB | Novo-trazodone | HMDB | Nu trazodone | HMDB | Nu-trazodone | HMDB | Pharmascience brand OF trazodone hydrochloride | HMDB | Thombran | HMDB | Neuraxpharm brand OF trazodone hydrochloride | HMDB | Apothecon brand OF trazodone hydrochloride | HMDB | Aventis pharma brand OF trazodone hydrochloride | HMDB | Hexal brand OF trazodone hydrochloride | HMDB | Novo trazodone | HMDB | Nu-pharm brand OF trazodone hydrochloride | HMDB | PMS Trazodone | HMDB | PMS-Trazodone | HMDB | Trazodon neuraxpharm | HMDB | Trazon | HMDB | Ratio-trazodone | HMDB | RatioTrazodone | HMDB | TrazodonNeuraxpharm | HMDB |
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Chemical Formula | C19H22ClN5O |
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Average Molecular Weight | 371.864 |
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Monoisotopic Molecular Weight | 371.151288058 |
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IUPAC Name | 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one |
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Traditional Name | trazodone |
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CAS Registry Number | 19794-93-5 |
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SMILES | ClC1=CC=CC(=C1)N1CCN(CCCN2N=C3C=CC=CN3C2=O)CC1 |
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InChI Identifier | InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2 |
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InChI Key | PHLBKPHSAVXXEF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazinanes |
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Sub Class | Piperazines |
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Direct Parent | Phenylpiperazines |
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Alternative Parents | |
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Substituents | - Phenylpiperazine
- N-arylpiperazine
- Aryl 1,2,4-triazol-3-one
- Triazolopyridine
- Tertiary aliphatic/aromatic amine
- Aniline or substituted anilines
- Dialkylarylamine
- Pyridinone
- Chlorobenzene
- N-alkylpiperazine
- Halobenzene
- Aryl chloride
- Aryl halide
- Pyridine
- Monocyclic benzene moiety
- Benzenoid
- 1,2,4-triazole
- Azole
- Heteroaromatic compound
- Triazole
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition
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Biological location
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 86 - 87 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.29 g/L | Not Available | LogP | 2.9 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 182.046 | 30932474 | DeepCCS | [M-H]- | 179.688 | 30932474 | DeepCCS | [M-2H]- | 213.405 | 30932474 | DeepCCS | [M+Na]+ | 188.632 | 30932474 |
Predicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Trazodone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4j-3940000000-a9996f74a013c4cd5f34 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trazodone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-7980000000-5d2bde624fdd9a946993 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone , positive-QTOF | splash10-00di-0609000000-cee74b5bf3182c2aa324 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 75V, Positive-QTOF | splash10-0002-6900000000-cad4ab75befff3f2968b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 90V, Positive-QTOF | splash10-0002-9400000000-c7d8f0dfcdffc01eea38 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 60V, Positive-QTOF | splash10-0002-1900000000-28ba21055e54b4402211 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 50V, Positive-QTOF | splash10-0002-0900000000-6fb990f5da8a065e9e2d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF | splash10-004j-0900000000-3e00b6f236166b87e556 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 15V, Positive-QTOF | splash10-00di-0009000000-389ead4eddc071685054 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 30V, Positive-QTOF | splash10-00b9-0905000000-7559d512fbf6d562d524 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 30V, Positive-QTOF | splash10-004i-0902000000-32913e34f1b8199d47e2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF | splash10-004j-0900000000-eba2f098618563ae8d8d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF | splash10-00di-0209000000-df47170d3861120bdd95 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF | splash10-00di-0009000000-bcfc1f78608d8da92b69 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 90V, Positive-QTOF | splash10-0002-9400000000-e57c89e0b5532e2d9949 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trazodone 35V, Positive-QTOF | splash10-00ba-0904000000-6d3af981b3cc1292370a | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF | splash10-00di-0409000000-aa395fcbb17de632c6bd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF | splash10-009j-3943000000-2a70b3bfe44c6f0cbc7b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF | splash10-0f7d-6910000000-98fd05d57a2cfaca1e18 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 10V, Negative-QTOF | splash10-00di-1509000000-86e48f5bf6cb797c7455 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 20V, Negative-QTOF | splash10-001i-4903000000-dbd293226ccdf09ec683 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 40V, Negative-QTOF | splash10-053r-2900000000-cc4d58e26d8dc2a62148 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 10V, Positive-QTOF | splash10-00di-0009000000-6eafab677fc7a5bcdc94 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 20V, Positive-QTOF | splash10-00di-0429000000-7ff66c2ff10e98b15b9b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 40V, Positive-QTOF | splash10-0f6x-2935000000-39b0f2302534fa91975f | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 10V, Negative-QTOF | splash10-00di-0009000000-46b6e1f93b93a9142b29 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trazodone 20V, Negative-QTOF | splash10-00di-1009000000-fb123f08ae47e01d90aa | 2021-10-11 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00656 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00656 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00656 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5332 |
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KEGG Compound ID | C07156 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Trazodone |
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METLIN ID | Not Available |
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PubChem Compound | 5533 |
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PDB ID | Not Available |
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ChEBI ID | 9654 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Rotzinger S, Fang J, Baker GB: Trazodone is metabolized to m-chlorophenylpiperazine by CYP3A4 from human sources. Drug Metab Dispos. 1998 Jun;26(6):572-5. [PubMed:9616194 ]
- Kalgutkar AS, Henne KR, Lame ME, Vaz AD, Collin C, Soglia JR, Zhao SX, Hop CE: Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4. Chem Biol Interact. 2005 Jun 30;155(1-2):10-20. Epub 2005 Apr 18. [PubMed:15978881 ]
- Marek GJ, McDougle CJ, Price LH, Seiden LS: A comparison of trazodone and fluoxetine: implications for a serotonergic mechanism of antidepressant action. Psychopharmacology (Berl). 1992;109(1-2):2-11. [PubMed:1365657 ]
- Jauch R, Kopitar Z, Prox A, Zimmer A: [Pharmacokinetics and metabolism of trazodone in man (author's transl)]. Arzneimittelforschung. 1976;26(11):2084-9. [PubMed:1037253 ]
- Otani K, Yasui N, Kaneko S, Ishida M, Ohkubo T, Osanai T, Sugawara K, Fukushima Y: Trazodone treatment increases plasma prolactin concentrations in depressed patients. Int Clin Psychopharmacol. 1995 Jun;10(2):115-7. [PubMed:7673654 ]
- Saletu-Zyhlarz GM, Abu-Bakr MH, Anderer P, Gruber G, Mandl M, Strobl R, Gollner D, Prause W, Saletu B: Insomnia in depression: differences in objective and subjective sleep and awakening quality to normal controls and acute effects of trazodone. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):249-60. [PubMed:11817501 ]
- Fink HA, MacDonald R, Rutks IR, Wilt TJ: Trazodone for erectile dysfunction: a systematic review and meta-analysis. BJU Int. 2003 Sep;92(4):441-6. [PubMed:12930437 ]
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