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词条 PPPA (drug)
释义

  1. List of PPPA derivatives

  2. See also

  3. References

  4. Further reading

{{Drugbox
| IUPAC_name = 3-Phenoxy-3-phenyl-1-propanamine
| image = 3-phenoxy-3-phenylpropan-1-amine.svg
| CAS_number =
| ATC_prefix = None
| ATC_suffix =
| PubChem =
| DrugBank =
| ChemSpiderID = 14379241
| chemical_formula =
| C=15 | H=17 | N=1 | O=1
| molecular_weight = 227.302 g/mol
| SMILES = c1ccc(cc1)C(CCN)Oc2ccccc2
| StdInChI = 1S/C15H17NO/c16-12-11-15(13-7-3-1-4-8-13)17-14-9-5-2-6-10-14/h1-10,15H,11-12,16H2
| StdInChIKey = XYWLZHPZECQHMB-UHFFFAOYSA-N
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
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}}PPPA, or 3-phenoxy-3-phenylpropan-1-amine, is a drug which is described as an antidepressant.[1] It was derived by Eli Lilly from the antihistamine diphenhydramine, a 2-diphenylmethoxyethanamine derivative with additional properties as a selective serotonin reuptake inhibitor (SSRI), and has been the basis for the subsequent discovery of a number of other antidepressant drugs.[2][3][4]

List of PPPA derivatives

  • Atomoxetine ((3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine) — NRI[1]
  • Fluoxetine (N-methyl-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI[2]
  • N-Methyl-PPPA (N-methyl-3-phenoxy-3-phenylpropan-1-amine) — SNRI[2][4]
  • Nisoxetine (N-methyl-3-(2-methoxyphenoxy)-3-phenylpropan-1-amine) — NRI[1]
  • Norfluoxetine (3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI[3]
  • Seproxetine ((S)-3-(4-(trifluoromethyl)phenoxy)-3-phenylpropan-1-amine) — SSRI[5]

Structurally related drugs include dapoxetine, duloxetine, edivoxetine, femoxetine, paroxetine, reboxetine, and viloxazine, all of which act, similarly, as monoamine reuptake inhibitors, and most of which are, again similarly, antidepressants.[1][3]

Zimelidine is an antidepressant and SSRI which was derived from the antihistamine pheniramine, which, similarly to its analogues brompheniramine and chlorpheniramine, possesses SNRI properties.[4] Fluvoxamine, another antidepressant and SSRI, was developed from the antihistamine tripelennamine, which possesses SNDRI actions.[6]

See also

  • Development and discovery of SSRI drugs
  • Aryloxypropanamine scaffold
  • Lometraline

References

1. ^{{cite book|author1=Thomas L. Lemke|author2=David A. Williams|title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA414|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=414–}}
2. ^{{cite book|author1=Francisco Lopez-Munoz|author2=Cecilio Alamo|title=Neurobiology of Depression|url=https://books.google.com/books?id=lmXRBQAAQBAJ&pg=PA132|date=9 September 2011|publisher=CRC Press|isbn=978-1-4398-3850-1|pages=132–}}
3. ^{{cite book|author1=Janos Fischer|author2=C. Robin Ganellin|title=Analogue-based Drug Discovery II|url=https://books.google.com/books?id=h2Kd8ci4Ln8C&pg=PA282|date=24 August 2010|publisher=John Wiley & Sons|isbn=978-3-527-63212-1|pages=35, 282, 284}}
4. ^{{cite book|author=Walter Sneader|title=Drug Discovery: A History|url=https://books.google.com/books?id=jglFsz5EJR8C&pg=PA416|date=31 October 2005|publisher=John Wiley & Sons|isbn=978-0-470-01552-0|pages=416–417}}
5. ^{{cite book|author=David G. Watson|title=Pharmaceutical Chemistry|url=https://books.google.com/books?id=-lQM4xHjWeUC&pg=PT1061|date=9 February 2011|publisher=Elsevier Health Sciences|isbn=0-7020-4850-X|pages=1061–}}
6. ^{{cite book|author=David Healy|title=Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression|url=https://books.google.com/books?id=5w64WC_-jbMC&pg=PA295|date=1 June 2004|publisher=NYU Press|isbn=978-0-8147-7300-0|pages=295–}}

Further reading

  • {{cite journal | vauthors = Wong DT, Bymaster FP, Engleman EA | title = Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication | journal = Life Sci. | volume = 57 | issue = 5 | pages = 411–41 | year = 1995 | pmid = 7623609 | doi = 10.1016/0024-3205(95)00209-o| url = http://linkinghub.elsevier.com/retrieve/pii/002432059500209O}}
{{Antidepressants}}{{Monoamine reuptake inhibitors}}{{Eli Lilly and Company}}{{nervous-system-drug-stub}}

4 : Amines|Antidepressants|Eli Lilly and Company|Serotonin-norepinephrine reuptake inhibitors

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