Avanafil
Avanafil|
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| Systematic (IUPAC) name |
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(S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide |
| Clinical data |
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| Trade names |
Stendra |
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| Licence data |
US FDA:link |
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- US: C (Risk not ruled out)
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Oral |
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| Identifiers |
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330784-47-9  Y |
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G04BE10 |
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| PubChem |
CID 9869929 |
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| ChemSpider |
8045620 Y |
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| UNII |
DR5S136IVO Y |
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| KEGG |
D03217 Y |
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| ChEMBL |
CHEMBL1963681  N |
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| Chemical data |
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| Formula |
C23H26ClN7O3 |
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483.951 g/mol |
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SMILES
- Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
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InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
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Key:WEAJZXNPAWBCOA-INIZCTEOSA-N
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| N (what is this?) (verify) |
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Avanafil is a PDE5 inhibitor approved for erectile dysfunction by FDA on April 27, 2012 [1] and by EMA on June 21, 2013.[2] Avanafil is known by the trademark names Stendra and Spedra and was developed by Vivus Inc. In July 2013 Vivus announced partnership with Menarini Group, which will commercialise and promote Spedra in over 40 European countries plus Australia and New Zealand.[3] Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme which is found in various body tissues, but primarily in the corpus cavernosum penis, as well as the retina.[4] Other similar drugs are sildenafil, tadalafil and vardenafil. The advantage of avanafil is that it has very fast onset of action compared with other PDE5 inhibitors.[5] It is absorbed quickly, reaching a maximum concentration in about 30–45 minutes.[6] About two-thirds of the participants were able to engage in sexual activity within 15 minutes.[6]
Synthesis
Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[7]
See also
References
- ↑ "FDA approves Stendra for erectile dysfunction" (Press release). Food and Drug Administration (FDA). April 27, 2012.
- ↑ "Spedra (avanafil)". European Medicines Agency. Retrieved 17 April 2014.
- ↑ http://ir.vivus.com/releasedetail.cfm?releaseid=775706
- ↑ "avanafil, Spedra". Medicine Net. Retrieved 17 April 2014.
- ↑ "Spedra". HealthExpress. Retrieved 17 April 2014.
- ↑ 6.0 6.1 Kyle, Jeffery; Brown, Dana (2013). "Avanafil for Erectile Dysfunction". Annals of Pharmacotherapy (Sage Publishing). doi:10.1177/1060028013501989. Retrieved 28 September 2013.
- ↑ Yamada, K.; Matsuki, K.; Omori, K.; Kikkawa, K.; 2004, U.S. Patent 6,797,709
External links
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| | For erectile dysfunction | |
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| | For premature ejaculation | |
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| | Description |
- Anatomy
- Physiology
- Development
- sex determination and differentiation
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| | Disease |
- Infections
- Congenital
- Neoplasms and cancer
- male
- female
- gonadal
- germ cell
- Other
- Symptoms and signs
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| | Treatment |
- Procedures
- Drugs
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
- sexual dysfunction
- infection
- hormones
- androgens
- estrogens
- progestogens
- GnRH
- prolactin
- Assisted reproduction
- Birth control
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