Silodosin

From Wikipedia, the free encyclopedia
  (Redirected from Rapaflo)
Jump to: navigation, search
Silodosin
Silodosin.png
Systematic (IUPAC) name
1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]indoline-7-carboxamide
Clinical data
Pregnancy cat.
  • US: B
  • Not approved for use in women
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 32%
Protein binding 97%
Metabolism Hepatic glucuronidation (UGT2B7-mediated); also minor CYP3A4 involvement
Half-life 13±8 hours
Excretion Renal and fecal
Identifiers
CAS number 160970-54-7 N
ATC code G04CA04
PubChem CID 5312125
IUPHAR ligand 493
ChemSpider 4471557 YesY
UNII CUZ39LUY82 YesY
ChEMBL CHEMBL24778 YesY
Synonyms KAD-3213, KMD-3213
Chemical data
Formula C25H32F3N3O4 
Mol. mass 495.534 g/mol
 N (what is this?)  (verify)

Silodosin (trade names Rapaflo (USA), Silodyx (Europe and South Africa), Rapilif (India), Silodal (India), Urief (Japan), Urorec (Russia)) is a medication for the symptomatic treatment of benign prostatic hyperplasia. It acts as an α1-adrenoceptor antagonist with high uroselectivity (selectivity for the prostate).

History[edit]

Silodosin received its first marketing approval in Japan in May 2006 under the tradename Urief, which is jointly marketed by Kissei Pharmaceutical Co., Ltd. and Daiichi Sankyo Pharmaceutical Co., Ltd.

Kissei licensed the US, Canadian, and Mexican rights for silodosin to Watson Pharmaceuticals, Inc. in 2004.

On February 12, 2008, Watson announced that the New Drug Application submitted to the United States Food and Drug Administration for silodosin has been accepted for filing. FDA approved this drug on October 9, 2008.[1] Silodosin is marketed under the trade names Rapaflo in the US and Silodyx in Europe.[2] and Rapilif in India (Ipca Urosciences)

Pharmacology[edit]

Since silodosin has high affinity for the α1A adrenergic receptor, it causes practically no orthostatic hypotension (in contrast to other α1 blockers). On the other side, the high selectivity seems to cause more problems with ejaculation.[3]

As α1A adrenoceptor antagonists are being investigated as a means to male birth control due to their ability to inhibit ejaculation but not orgasm, a trial with 15 male volunteers was conducted. While silodosin was completely efficacious in preventing the release of semen in all subjects, 12 out of the 15 patients reported mild discomfort upon orgasm. The men also reported the psychosexual side effect of being strongly dissatisfied by their lack of ejaculation.[4]

References[edit]

  1. ^ "Drugs.com, Watson Announces Silodosin NDA Accepted for Filing by FDA for the Treatment of Benign Prostatic Hyperplasia". Retrieved 2008-02-13. 
  2. ^ European Medicines Agency: Assessment report for Silodyx
  3. ^ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
  4. ^ Kobayashi K, Masumori N, Kato R, Hisasue S, Furuya R, Tsukamoto T. (December 2009). "Orgasm is preserved regardless of ejaculatory dysfunction with selective alpha1A-blocker administration.". Int J Impot Res. 21 (5): 306–10. doi:10.1038/ijir.2009.27. PMC 2834370. PMID 19536124. 

External links[edit]