| Identification | Back Directory | [Name]
Galeterone | [CAS]
851983-85-2 | [Synonyms]
CS-232
VN 124
TOK-001
NX41765
VN/124-1
Galeterone
Galaterone
synthesis-008
synthesis-1-007
TOK-001 impurity
Galeterone,TOK-001
TOK-001 (Galeterone)
Galeterone USP/EP/BP
GALETERONE;TOK001;TOK 001;TOK-001
VN/124-1; GALETERONE;TOK001;TOK 001;TOK-001
(3β)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol
(3beta)-17-(1H-Benzimidazol-1-yl)androsta-5,16-dien-3-ol
Androsta-5,16-dien-3-ol, 17-(1H-benzimidazol-1-yl)-, (3β)-
(3S,8R,9S,10R,13S,14S)-17-(benzimidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,10R,13S)-17-(1H-benzo[d]imidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8R,9S,10R,13S,14S)-17-(1H-Benzo[d]imidazol-1-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | [EINECS(EC#)]
806-537-4 | [Molecular Formula]
C26H32N2O | [MDL Number]
MFCD16660907 | [MOL File]
851983-85-2.mol | [Molecular Weight]
388.545 |
| Chemical Properties | Back Directory | [Melting point ]
189-190℃ | [Boiling point ]
564.5±60.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), Ethyl Aceatae (Slightly, Heated) | [form ]
Solid | [pka]
14.71±0.70(Predicted) | [color ]
White to Off-White | [InChIKey]
PAFKTGFSEFKSQG-MRFMOSGMNA-N | [SMILES]
C1C[C@]2(C)C3CC[C@]4(C)C([n]5cnc6ccccc56)=CCC4C3CC=C2C[C@H]1O |&1:2,7,27,r| |
| Hazard Information | Back Directory | [Description]
The cytochrome P450 (CYP) isoform CYP17 is also known as steroid 17α-hydroxylase/17,20 lyase because it catalyzes both 17α-hydroxylase and 17,20 lyase reactions in the synthesis of steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids.1 Galeterone is a CYP17 inhibitor (IC50 = 300 nM) that has been shown to competitively block synthetic androgen binding (EC50 = 845 nM) and to antagonize the androgen receptor in transcriptional activation assays.2 Galeterone can inhibit the growth of castration-resistant prostate cancer cells with an IC50 value of 2.9 μM and demonstrates synergy with everolimus (Item No. 11597) or gefitinib (Item No. 13166) for growth inhibition.2,3 | [Uses]
Galeterone is an androgen receptor antagonist and CYP17A1 enzyme inhibitor. | [Definition]
ChEBI: Galeterone is a 3-hydroxy steroid. It has a role as an androgen. | [Biological Activity]
The cytochrome P450 (CYP) isoform CYP17 is also known as steroid 17α-hydroxylase/17,20 lyase because it catalyzes both 17α-hydroxylase and 17,20 lyase reactions in the synthesis of steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids. Galeterone is a CYP17 inhibitor (IC50 = 300 nM) that has been shown to competitively block synthetic androgen binding (EC50 = 845 nM) and to antagonize the androgen receptor in transcriptional activation assays. Galeterone can inhibit the growth of castration-resistant prostate cancer cells with an IC50 value of 2.9 μM and demonstrates synergy with everolimus or gefitinib for growth inhibition. | [target]
CYP17 | [storage]
Store at -20°C | [Mode of action]
Galeterone is an orally bioavailable small-molecule androgen receptor modulator and CYP17 lyase inhibitor with potential antiandrogen activity. Galeterone exhibits three distinct mechanisms of action: 1) as an androgen receptor antagonist, 2) as a CYP17 lyase inhibitor and 3) by decreasing overall androgen receptor levels in prostate cancer tumors, all of which may result in a decrease in androgen-dependent growth signaling. Localized to the endoplasmic reticulum (ER), the cytochrome P450 enzyme CYP17 (P450C17 or CYP17A1) exhibits both 17alpha-hydroxylase and 17,20-lyase activities, and plays a key role in the steroidogenic pathway that produces progestins, mineralocorticoids, glucocorticoids, androgens, and estrogens. | [References]
[1]. devore n m, & scott e e. structures of cytochrome p450 17a1 with prostate cancer drugs abiraterone and tok-001. nature, 2012, 482: 116-119.
[2]. mallik i, davila m, tapia t, et al. androgen regulates cdc6 transcription through interactions between androgen receptor and e2f transcription factor in prostate cancer cells. biochimica et biophysica acta (bba) - molecular cell research, 2008,1783:1737-1744.
[3]. bruno r d, vasaitis t s, gediya l. k, et al. synthesis and biological evaluations of putative metabolically stable analogs of vn/124-1 (tok-001): head to head anti-tumor efficacy evaluation of vn/124-1 (tok-001) and abiraterone in lapc-4 human prostate cancer xenograft model. steroids, 2011,76: 1268-1279. |
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