Androstanolone(DHT)

From DrugPedia: A Wikipedia for Drug discovery

Androstanolone(DHT) Pubchem(10635) A potent androgenic metabolite of TESTOSTERONE. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to ESTRADIOL therefore DHT is considered a pure androgenic steroid. KEGG Pathway(C03917, Pathway Androgen and estrogen metabolism Prostate cancer Activity Androgen MMDB ID: 13575 PDB ID: 1D2S Reference: Grishkovskaya I, Avvakumov GV, Sklenar G, Dales D, Hammond GL, Muller YACrystal structure of human sex hormone-binding globulin: steroid transport by a laminin G-like domainEMBO J. v19, p.504-512 Human sex hormone-binding globulin (SHBG) transports sex steroids in blood and regulates their access to target tissues. In biological fluids, SHBG exists as a homodimer and each monomer comprises two laminin G-like domains (G domains). The crystal structure of the N-terminal G domain of SHBG in complex with 5alpha-dihydrotestosterone at 1.55 A resolution reveals both the architecture of the steroid-binding site and the quaternary structure of the dimer....

MMDB ID: 13985 PDB ID: 1F5F Reference: Avvakumov GV, Muller YA, Hammond GLSteroid-binding specificity of human sex hormone-binding globulin is influenced by occupancy of a zinc-binding siteJ. Biol. Chem. v275, p.25920-25925 One calcium-binding site (site I) and a second poorly defined metal-binding site (site II) have been observed previously within the amino-terminal laminin G-like domain (G domain) of human sex hormone-binding globulin (SHBG). By soaking crystals of this structure in 2.5 mm ZnCl(2), site II and a new metal-binding site (site III) were found to bind Zn(2+)....

MMDB ID: 19532 PDB ID: 1KDK Reference: Grishkovskaya I, Avvakumov GV, Hammond GL, Muller YAResolution of a disordered region at the entrance of the human sex hormone-binding globulin steroid-binding siteJ. Mol. Biol. v318, p.621-626 The crystal structure of human sex hormone-binding globulin (SHBG) has revealed how 5alpha-dihydrotestosterone intercalates between the two seven-stranded beta-sheets of its amino-terminal laminin G-like domain. However, a region of disorder (residues 130 to 135 of SHBG) was identified together with a zinc-binding site in immediate proximity to the steroid....

MMDB ID: 19533 PDB ID: 1KDM Reference: Grishkovskaya I, Avvakumov GV, Hammond GL, Muller YAResolution of a disordered region at the entrance of the human sex hormone-binding globulin steroid-binding siteJ. Mol. Biol. v318, p.621-626 The crystal structure of human sex hormone-binding globulin (SHBG) has revealed how 5alpha-dihydrotestosterone intercalates between the two seven-stranded beta-sheets of its amino-terminal laminin G-like domain. However, a region of disorder (residues 130 to 135 of SHBG) was identified together with a zinc-binding site in immediate proximity to the steroid....

MMDB ID: 29012 PDB ID: 1T73 Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29013 PDB ID: 1T74 Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29014 PDB ID: 1T76 Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29015 PDB ID: 1T79 Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29016 PDB ID: 1T7F Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29017 PDB ID: 1T7M Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29018 PDB ID: 1T7R Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 29019 PDB ID: 1T7T Reference: Hur E, Pfaff SJ, Payne ES, Gron H, Buehrer BM, Fletterick RJRecognition and accommodation at the androgen receptor coactivator binding interfacePLoS Biol. v2, p.E274 Prostate cancer is a leading killer of men in the industrialized world. Underlying this disease is the aberrant action of the androgen receptor (AR). AR is distinguished from other nuclear receptors in that after hormone binding, it preferentially responds to a specialized set of coactivators bearing aromatic-rich motifs, while responding poorly to coactivators bearing the leucine-rich "NR box" motifs favored by other nuclear receptors....

MMDB ID: 31245 PDB ID: 1T5Z Reference: Estebanez-Perpina E, Moore JM, Mar E, Delgado-Rodrigues E, Nguyen P, Baxter JD, Buehrer BM, Webb P, Fletterick RJ, Guy RKThe molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptorJ. Biol. Chem. v280, p.8060-8068 Androgens drive sex differentiation, bone and muscle development, and promote growth of hormone-dependent cancers by binding the nuclear androgen receptor (AR), which recruits coactivators to responsive genes. Most nuclear receptors recruit steroid receptor coactivators (SRCs) to their ligand binding domain (LBD) using a leucine-rich motif (LXXLL)....

MMDB ID: 31246 PDB ID: 1T63 Reference: Estebanez-Perpina E, Moore JM, Mar E, Delgado-Rodrigues E, Nguyen P, Baxter JD, Buehrer BM, Webb P, Fletterick RJ, Guy RKThe molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptorJ. Biol. Chem. v280, p.8060-8068 Androgens drive sex differentiation, bone and muscle development, and promote growth of hormone-dependent cancers by binding the nuclear androgen receptor (AR), which recruits coactivators to responsive genes. Most nuclear receptors recruit steroid receptor coactivators (SRCs) to their ligand binding domain (LBD) using a leucine-rich motif (LXXLL)....

MMDB ID: 31247 PDB ID: 1T65 Reference: Estebanez-Perpina E, Moore JM, Mar E, Delgado-Rodrigues E, Nguyen P, Baxter JD, Buehrer BM, Webb P, Fletterick RJ, Guy RKThe molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptorJ. Biol. Chem. v280, p.8060-8068 Androgens drive sex differentiation, bone and muscle development, and promote growth of hormone-dependent cancers by binding the nuclear androgen receptor (AR), which recruits coactivators to responsive genes. Most nuclear receptors recruit steroid receptor coactivators (SRCs) to their ligand binding domain (LBD) using a leucine-rich motif (LXXLL)....

MMDB ID: 31438 PDB ID: 1XJ7 Reference: Estebanez-Perpina E, Moore JM, Mar E, Delgado-Rodrigues E, Nguyen P, Baxter JD, Buehrer BM, Webb P, Fletterick RJ, Guy RKThe molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptorJ. Biol. Chem. v280, p.8060-8068 Androgens drive sex differentiation, bone and muscle development, and promote growth of hormone-dependent cancers by binding the nuclear androgen receptor (AR), which recruits coactivators to responsive genes. Most nuclear receptors recruit steroid receptor coactivators (SRCs) to their ligand binding domain (LBD) using a leucine-rich motif (LXXLL)....

MMDB ID: 39038 PDB ID: 2AMA Reference: Pereira de Je, Cote PL, Cantin L, Blanchet J, Labrie F, Breton RComparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinityProtein Sci. v15, p.987-999 Androgens exert their effects by binding to the highly specific androgen receptor (AR). In addition to natural potent androgens, AR binds a variety of synthetic agonist or antagonist molecules with different affinities. To identify molecular determinants responsible for this selectivity, we have determined the crystal structure of the human androgen receptor ligand-binding domain (hARLBD) in complex with two natural androgens, testosterone (Testo) and dihydrotestosterone (DHT), and with an androgenic steroid used in sport doping, tetrahydrogestrinone (THG), at 1.64, 1.90, and 1.75 A resolution,

MMDB ID: 59291 PDB ID: 2PIO Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59292 PDB ID: 2PIP Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59293 PDB ID: 2PIQ Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59294 PDB ID: 2PIR Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59295 PDB ID: 2PIT Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59296 PDB ID: 2PIU Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59297 PDB ID: 2PIV Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59298 PDB ID: 2PIW Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59299 PDB ID: 2PIX Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59302 PDB ID: 2PKL Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 59526 PDB ID: 2QPY Reference: Estebanez-Perpina E, Arnold LA, Nguyen P, Rodrigues ED, Mar E, Bateman R, Pallai P, Shokat KM, Baxter JD, Guy RK, Webb P, Fletterick RJA surface on the androgen receptor that allosterically regulates coactivator bindingProc. Natl. Acad. Sci. U. S. A. v104, p.16074-16079 Current approaches to inhibit nuclear receptor (NR) activity target the hormone binding pocket but face limitations. We have proposed that inhibitors, which bind to nuclear receptor surfaces that mediate assembly of the receptor"s binding partners, might overcome some of these limitations. The androgen receptor (AR) plays a central role in prostate cancer, but conventional inhibitors lose effectiveness as cancer treatments because anti-androgen resistance usually develops....

MMDB ID: 61083 PDB ID: 2Z4J Reference: Jouravel N, Sablin E, Arnold LA, Guy RK, Fletterick RJInteraction between the androgen receptor and a segment of its corepressor SHPActa Crystallogr. D Biol. Crystallogr. v63, p.1198-1200 The mechanisms of functional repression of the androgen receptor (AR) are crucial for the regulation of genes involved in physiological development as well as for the progression of prostate cancer. To date, only two in vivo inhibitors of AR-mediated transcription have been identified: DAX-1 and SHP (small heterodimer partner)....

Physical Property Value Units Temp (deg C) Source Melting Point 181 deg C EXP log P (octanol-water) 3.55 (none) EXP Water Solubility 5.25E+05 mg/L 25 EXP Vapor Pressure 2.79E-08 mm Hg 25 EST Henry's Law Constant 6.37E-09 atm-m3/mole 25 EST Atmospheric OH Rate Constant 4.17E-11 cm3/molecule-sec 25 EST