Silodosin
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| Systematic (IUPAC) name | |
|---|---|
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1-(3-hydroxypropyl)-5-[(2R)-({2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]indoline-7-carboxamide | |
| Clinical data | |
| Pregnancy category |
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| Legal status |
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| Routes of administration | Oral |
| Pharmacokinetic data | |
| Bioavailability | 32% |
| Protein binding | 97% |
| Metabolism | Hepatic glucuronidation (UGT2B7-mediated); also minor CYP3A4 involvement |
| Biological half-life | 13±8 hours |
| Excretion | Renal and fecal |
| Identifiers | |
| CAS Number |
160970-54-7  |
| ATC code | G04CA04 |
| PubChem | CID 5312125 |
| IUPHAR/BPS | 493 |
| ChemSpider |
4471557  |
| UNII |
CUZ39LUY82 |
| ChEMBL |
CHEMBL24778 |
| Synonyms | KAD-3213, KMD-3213 |
| Chemical data | |
| Formula | C25H32F3N3O4 |
| Molar mass | 495.534 g/mol |
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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
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.
FDA approved silodosin 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
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 be the cause of silodosin's typical side effect of retrograde 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
- ↑ "Drugs.com, Watson Announces Silodosin NDA Accepted for Filing by FDA for the Treatment of Benign Prostatic Hyperplasia". Retrieved 2008-02-13.
- ↑ European Medicines Agency: Assessment report for Silodyx
- ↑ Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
- ↑ 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.
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