Androsterone

Names

[ CAS No. ]:
53-41-8

[ Name ]:
Androsterone

[Synonym ]:
3-α-hydroxy-5α-Androstan-17-one
MFCD01317504
Androkinine
5a-Androsterone
Androkinin
Androtine
3alpha-Hydroxy-5alpha-androstan-17-one
Atromide ICI
3-Epihydroxyetioallocholan-17-one
(3a,5a)-3-Hydroxyandrostan-17-one
(3α,5α)-3-Hydroxyandrostan-17-one
(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
3α-hydroxy-5α-androstane-17-one
Androtin
3alpha-Hydroxyetioallocholan-17-one
Androstan-3a-ol-17-one
5alpha-Androsterone
3a-Hydroxyetioallocholan-17-one
5alpha-Androstane-3alpha-ol-17-one
Androsterone
trans-Androsterone
Androstan-17-one, 3-hydroxy-, (3α,5α)-
EINECS 200-173-4
Androsterone, trans-
Atromide
(3α,5α)-3-hydroxy-Androstan-17-one
3a-Hydroxy-5a-androstan-17-one

Biological Activity

[Description]:

Androsterone is a metabolic product of testosterone and can activate Farnesoid X Receptor (FXR).

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> FXR

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Steroids

[Target]

Human Endogenous Metabolite

[In Vitro]

Androsterone activates both the mFXR-LBD and the hFXR-LBD, with Androsterone activating the mFXR-LBD more strongly than the hFXR-LBD. Furthermore, cotransfection studies with gal4-hFXR-LBD and SRC-1/VP16 expression plasmids demonstrate that Androsterone potentiates the interaction of SRC-1 with the hFXR-LBD. Several amino acid changes including H294S, S332V, R351H, and Y361F significantly reduce Androsterone activation[1]. Androsterone (5α, 3α-A) (10 to 100 μM) also inhibits epileptiform discharges in a concentration-dependent fashion in the in vitro slice model[2].

[In Vivo]

Androsterone treatment results in a significant induction of small heterodimer partner (SHP), suggesting Androsterone may activate endogenous FXR[1]. Intraperitoneal injection of Androsterone (5α, 3α-A) protects mice in a dose-dependent fashion from seizures in the following models (ED50, dose in mg/kg protecting 50% of animals): 6 Hz electrical stimulation (29.1), pentylenetetrazol (43.5), pilocarpine (105), 4-AP (215), and maximal electroshock (224)[2].

[Cell Assay]

AML-12 cells are used and cultured in a 1:1 mix of DMEM/Ham’s F12 medium supplemented with 10% fetal bovine serum, 1% insulin-transferrin-selenium mix, 40 ng/mL dexamethasone, 100 U/mL penicillin, and 100 μg/mL streptomycin. For gene regulation studies, AML-12 cells are plated in growth medium at 4×105 cells per well in six-well plates. The following day, treatments including Androsterone or dimethylsulfoxide (DMSO) vehicle are added to the medium. At various times after treatment addition, total RNA is prepared. mRNA levels for individual genes are determined by real-time PCR[1].

[Animal admin]

Castrated male mice 8 to10 wk of age are fed a casein diet for 2 wk before the start of the study. The mice receive daily sc injections of 0.1 mL 90% corn oil/10% ethanol vehicle or 10 mg/mL Androsterone in vehicle. Animals are killed 2 h after the fifth daily treatment, approximately 4 h after commencement of the light cycle. Total RNA is prepared, and mRNA levels for specific genes are determined by real-time PCR[1].

[References]

[1]. Wang S, et al. The nuclear hormone receptor farnesoid X receptor (FXR) is activated by androsterone. Endocrinology. 2006 Sep;147(9):4025-33.

[2]. Kaminski RM, et al. Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
413.1±45.0 °C at 760 mmHg

[ Melting Point ]:
180-185ºC

[ Molecular Formula ]:
C₁₉H₃₀O₂

[ Molecular Weight ]:
290.440

[ Flash Point ]:
176.4±21.3 °C

[ Exact Mass ]:
290.224579

[ PSA ]:
37.30000

[ LogP ]:
3.75

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.536

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BV8053000

CHEMICAL NAME :: 5-alpha-Androstan-17-one, 3-alpha-hydroxy-

CAS REGISTRY NUMBER :: 53-41-8

BEILSTEIN REFERENCE NO. :: 2217626

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C19-H30-O2

MOLECULAR WEIGHT :: 290.49

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 8400 ug/kg

SEX/DURATION :: male 21 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 21,313,1937

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 80 mg/kg

SEX/DURATION :: female 13-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 99,1490,1976 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3818 No. of Facilities: 53 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 767 (estimated) No. of Female Employees: 347 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H319-H334-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338-P342 + P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38-43

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
2811.0

[ WGK Germany ]:
3

[ RTECS ]:
BV8053000

[ Hazard Class ]:
6.1

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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