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SML1375

Sigma-Aldrich

Galeterone

≥98% (HPLC)

Synonym(s):

3β-Hydroxy-17-(1H-benzimidazole-1-yl)androsta-5,16-diene, TOK-001, VN-124-1, VN/124-1

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About This Item

Empirical Formula (Hill Notation):
C26H32N2O
CAS Number:
851983-85-2
Molecular Weight:
388.55
MDL number:
MFCD16660907
UNSPSC Code:
51111800
PubChem Substance ID:
329825826
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

C[C@]12C(C[C@@H](O)CC2)=CC[C@]3([H])[C@]1([H])CC[C@@]4(C)[C@@]3([H])CC=C4N5C=NC6=C5C=CC=C6

InChI

1S/C26H32N2O/c1-25-13-11-18(29)15-17(25)7-8-19-20-9-10-24(26(20,2)14-12-21(19)25)28-16-27-22-5-3-4-6-23(22)28/h3-7,10,16,18-21,29H,8-9,11-15H2,1-2H3/t18-,19-,20-,21-,25-,26-/m0/s1

InChI key

PAFKTGFSEFKSQG-PAASFTFBSA-N

Gene Information

human ... AR(367) , CYP17A1(1586)

Biochem/physiol Actions

Galeterone is an inhibitor of CYP17A1 (CYP450c17), an enzyme that catalyzes two key serial reactions (17-α hydroxylase and 17,20 lyase) in androgen and estrogen biosynthesis resulting in the formation of DHEA and androstenedione, which may ultimately be metabolized into testosterone. CYP17 is the key enzyme for androgen biosynthesis in both the testes and adrenals, so its inhibition should stop the production of androgens in both places. Galeterone, moreover, is a potent blocker of the androgen receptor and causes down-regulation of androgen receptor (AR) protein expression in vitro and in vivo.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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