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Merck
CN

UC289

16β-Hydroxytestosterone

Synonym(s):

16β,17β-Dihydroxyandrost-4-en-3-one, 4-Androstene-16β,17β-diol-3-one

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About This Item

Empirical Formula (Hill Notation):
C19H28O3
CAS Number:
17528-90-4
Molecular Weight:
304.42
UNSPSC Code:
12161501
PubChem Substance ID:
329827664
MDL number:
MFCD00271245

Key Documents

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InChI

1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15+,16+,17+,18+,19+/m1/s1

SMILES string

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1C[C@H](O)[C@@H]2O

InChI key

YMCWOAZGWMZGQT-KYQPOWKGSA-N

form

powder

drug control

USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

mp

184-186

storage temp.

2-8°C

Application

16β-Hydroxytestosterone can be used as a standard for chromatographic assays of testosterone hydroxylases.

Biochem/physiol Actions

CYP3A2/2B1 (rat) metabolite; androgenic

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H351,H360

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
129K3351
119K3351
107K3261
066K3254
117K3252

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H B Lim et al.
Biochemistry international, 28(3), 543-550 (1992-11-01)
The metabolism of 16 alpha-hydroxytestosterone by cytochrome P-450 system was studied with two different inductions. At least 5 different metabolites with higher polarity were produced from 16 alpha-hydroxytestosterone. MT-B, one of their products, appeared to be specifically increased by 3-methylcholanthrene-
K Sugiyama et al.
Drug metabolism and disposition: the biological fate of chemicals, 22(4), 584-591 (1994-07-01)
P450 2C11 from rat liver is known to metabolize testosterone to 2 alpha-, 16 alpha-, and 6 beta-hydroxytestosterone, and to androstenedione and 16 alpha-hydroxyandrostenedione. Because Waxman (J. Biol. Chem. 259, 15481-15490) has reported that the enzyme converts androstenedione to 16
T L Klug et al.
Molecular genetics and metabolism, 89(4), 381-389 (2006-09-19)
Most, but not all, studies have found that women with a high urinary 2-hydroxyestrogen (2OHE) to 16alpha-hydroxyestrone (16alphaOHE1) ratio are at reduced risk for breast cancer and have a better prognosis. The aim was to identify factors associated with the
M Numazawa et al.
Analytical biochemistry, 146(1), 75-81 (1985-04-01)
A sensitive nonradiometric assay of aromatization of 16 alpha-hydroxylated androgens, 16 alpha-hydroxy-4-androstene-3,17-dione (16 alpha-OHA), and 16 alpha-hydroxytestosterone (16 alpha-OHT), has been developed using reverse-phase high-performance liquid chromatography with voltametric detector. The estrogens produced by human placental microsomes, estriol (E3) and
M Ringel et al.
Xenobiotica; the fate of foreign compounds in biological systems, 32(8), 653-666 (2002-09-26)
1. Steroids are known to act as permissive factors in hepatocytes. This study shows that dexamethasone (DEX) is a permissive factor for induction of CYP2B1/2, CYP3A1, CYP2A1 and probably also CYP2C11 in cultures with primary rat hepatocytes. 2. The induction
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