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| Clinical data | |
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| Trade names | Aipuliete, Chuanliu |
| Other names | ONO-9302; SKF-105657; 17β-(tert-Butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid |
| Routes of administration | By mouth[1] |
| Drug class | 5α-Reductase inhibitor |
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| Legal status | |
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| Pharmacokinetic data | |
| Bioavailability | 93%[2] |
| Eliminationhalf-life | 26 hours[2] |
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| Chemical and physical data | |
| Formula | C25H37NO3 |
| Molar mass | 399.575 g·mol−1 |
| 3D model (JSmol) | |
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Epristeride, sold under the brand namesAipuliete andChuanliu, is amedication which is used in the treatment ofenlarged prostate inChina.[3][4][5] It is takenby mouth.[1]
Epristeride is a5α-reductase inhibitor and works bydecreasing theproduction ofdihydrotestosterone (DHT), anandrogensex hormone, in certain parts of the body like theprostate gland.[6][7][8] Itinhibits two of the threeforms of5α-reductase but is of relatively lowefficacy and can decrease DHT levels in the blood only by about 25 to 54%.[8]
Epristeride was under development for the treatment of enlarged prostate,scalp hair loss, andacne in theUnited States and other countries in the 1990s but did not complete development in these countries.[6][4] Instead, it was developed and introduced for the treatment of enlarged prostate in China in 2000.[4]
Epristeride is used in the treatment ofbenign prostatic hyperplasia (BPH), otherwise known as enlarged prostate.[3][4]
Epristeride is aselective,transition-state,non-competitive oruncompetitive,irreversibleinhibitor of5α-reductase,[6][7] and is specific to thetype IIisoform of theenzyme similarly tofinasteride andturosteride but unlikedutasteride.[8]
Epristeride is unique in itsmechanism of action relative to finasteride and dutasteride in that it binds irreversibly to 5α-reductase and results in the formation of an unproductive complex of the 5α-reductase enzyme, thesubstratetestosterone, and thecofactorNADPH.[8][9] For this reason, testosterone is caught in a trap, and it was initially speculated that the reciprocal increase in intraprostatic levels of testosterone seen with finasteride and dutasteride should not happen with epristeride.[8][9] However, subsequent clinical data have not supported this hypothesis.[8] Moreover, in spite of the fact that epristeride is a very potent inhibitor of 5α-reductase type II (0.18–2 nM), it has been found to reduce circulating levels ofdihydrotestosterone (DHT) by only 25 to 54% following 8 days of therapy over a dosage range of 0.4 to 160 mg/day.[8] For this reason, relative to other 5α-reductase inhibitors like finasteride and dutasteride, the degree of DHT suppression with epristeride falls short of that desirable for full clinical benefit.[8]
Theoralbioavailability of epristeride is 93%.[2] It has anelimination half-life of 26 hours.[2]
Epristeride, also known as 17β-(tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid, is asyntheticandrostanesteroid.
Oxidation of theacetyl group inprogesterone gives thecarboxylic acid (1).Halogenation withphosphorus tribromide converts theenone to the enol bromide and the acid to the acyl halide; mild basehydrolyzes the latter back to the free acid, giving (2). Halogenation withoxalyl chloride and aSchotten–Baumann reaction withtert-butylamine yields the amide (3). Epristeride is formed when the bromine atom in this compound is converted to a carboxylic acid via theorganolithium intermediate (4).[10][11][12][13]
Epristeride was under development for the treatment of BPH,androgenic alopecia (pattern hair loss), andacne vulgaris bySmithKline Beecham (nowGlaxoSmithKline) in the 1990s and reachedphase IIIclinical trials in theUnited States,United Kingdom, andJapan,[6] but ultimately was never marketed in these countries.[4] Instead, epristeride was developed by Ono Pharmaceutical and introduced for the treatment of BPH in China in 2000.[4]
Epristeride is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,USANTooltip United States Adopted Name,BANTooltip British Approved Name, andJANTooltip Japanese Accepted Name.[5]
Epristeride is marketed under the brand names Aipuliete and Chuanliu in China.[5][4]
