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Dehydroepiandrosterone

Names

[ CAS No. ]:
53-43-0

[ Name ]:
Dehydroepiandrosterone

[Synonym ]:
3β-Hydroxy-androst-5-ene-17-one
DHEA
17-Hormoforin
3-β-hydroxyandrost-5-en-17-one
3b-hydroxy-Androst-5-en-17-one
(3b)-3-Hydroxyandrost-5-en-17-one
3β-hydroxy-androst-5-en-17-one
(3β)-3-hydroxy-Androst-5-en-17-one
D5-Androsten-3b-ol-17-one
(3β)-3-Hydroxyandrost-5-en-17-one
MFCD00003613
Psicosterone
Prasterone
trans-Dehydroandrosterone
3b-Hydroxyandrost-5-ene-17-one
Androst-5-en-17-one, 3β-hydroxy-
Androst-5-en-17-one, 3-hydroxy-, (3β)-
3b-Hydroxyandrost-5-en-17-one
Prestara
3β-Hydroxy-5-androsten-17-one
Intrarosa
Deandros
dehydroisoandrosterone
(3β)-3-Hydroxyandrost-5-ene-17-one
Androst-5-ene-3b-ol-17-one
Androst-5-ene-3β-ol-17-one
5-Androsten-3β-ol-17-one
Dehydro-epi-androsterone
17-Chetovis
Dehydroepiandrosterone
didehydroepiandrosterone
3β-Hydroxyandrost-5-ene-17-one
D5-Androsten-3β-ol-17-one
Diandrone
EINECS 200-175-5
Astenile
3β-Hydroxyandrost-5-en-17-one
UNII-459AG36T1B
Diandron

Biological Activity

[Description]:

DHEA is one of the most abundant steroid hormones. DHEA mediates its action via multiple signaling pathways involving specific membrane receptors and via transformation into androgen and estrogen derivatives (e.g., androgens, estrogens, 7α and 7β DHEA, and 7α and 7β epiandrosterone derivatives) acting through their specific receptors.

[Related Catalog]:

Signaling Pathways >> Others >> Androgen Receptor
Natural Products >> Steroids
Research Areas >> Endocrinology

[Target]

Human Endogenous Metabolite


[In Vitro]

DHEA is an effective antiapoptotic factor, reversing the serum deprivation-induced apoptosis in prostate cancer cells (DU145 and LNCaP cell lines) as well as in colon cancer cells (Caco2 cell line). DHEA significantly reduces serum deprivation-induced apoptosis in all 3 cancer cell types, quantitated with the APOPercentage assay (apoptosis is reduced from 0.587±0.053 to 0.142±0.0016 or 0.059±0.002 after treatment for 12 hours with DHEA or NGF, respectively; n=3, P<0.01), and by flow cytometry analysis (FACS) for DU145 cells. The antiapoptotic effect of DHEA is dose dependent with an EC50 at nanomolar concentrations (EC50: 11.2±3.6 nM and 12.4±2.2 nM in DU145 and Caco2 cells, respectively)[1]. DHEA is the principal sex steroid precursor in humans and can be converted directly to androgens. DHEA (≥1 μM) causes a dose-dependent inhibition of Chub-S7 proliferation, as assessed by thymidine incorporation assays. DHEA treatment inhibits expression of the key glucocorticoid-regulating genes H6PDH (≥100 nM) and HSD11B1 (≥1 μM) in differentiating preadipocytes in a dose-dependent manner. In keeping with this finding, DHEA treatment (≥1 μM) results in a marked reduction in 11β-HSD1 oxoreductase activity (≥1 μM) and a concurrent increase in dehydrogenase activity at the highest DHEA dose used (25 μM DHEA) in differentiated adipocytes[2].

[In Vivo]

DHEA in the diet (0.45 % w/w) of male B6 mice (groups of five mice) treated for 8 weeks led to significant decreases in body temperature compared with mice fed the control AIN-76A diet. A similar comparison indicated that control and pair-fed mice are also significantly different. Animals fed DHEA have significantly lower temperatures than mice fed the control diet 26/29 times tested; mice pair fed to those on the DHEA diet are less affected, with 8/29 values significantly lower than in mice fed AIN-76A ad libitum. The temperatures of mice fed DHEA or pair fed to DHEA are significantly different 21/29 times tested. Body weights are significantly greater in mice fed the control diet than in mice fed DHEA or pair fed to DHEA. Food intake (grams per day) from cages are averaged for each week (n=7), except for Week 9 (n=3). The amount of food intake is significantly decreased in mice fed DHEA. By design, mice pair fed to DHEA ate about the same amount. Thus, it appears that DHEA reduces body temperature by food restriction and by a separate mechanism[3].

[Kinase Assay]

Chub-S7 cells are incubated in DMEM containing cold DHEA (20 nM) and tritiated DHEA (0.2 μCi/well) for 48 h. Following incubation, steroids are extracted using dichloromethane separated by thin-layer chromatography using n-hexane/1-hexanol (75:25) as the mobile phase system. Metabolites are identified by comigration with unlabeled reference steroids that are visualized by exposure to Lieberman-Burchard reagent (ethanol-acetic anhydride-sulfuric acid). Steroid conversion is quantified using a LabLogic AR-200 scanner. Protein concentration is measured using a colorimetric 96-well plate assay and used to normalize conversion. Activity is expressed as percent conversion[2].

[Cell Assay]

Chub-S7 preadipocytes and human primary preadipocytes are seeded into a 24-well plate at densities 1×105 and 2.5×105 respectively. Following overnight culture, medium is supplemented with DHEA, androstenediol, or DHEAS (0-100 μM). Following 24-, 48-, or 72 h incubation, cell proliferation is assessed by incubation with radiolabeled thymidine (0.2 μCi/well) for the final 6 h of culture. Proteins are precipitated with TCA, and cells are scraped in NaOH. The respective content of radiolabeled nuclear material in the resulting lysates is analyzed by scintillation counting. Data are expressed as percentage of control[2].

[Animal admin]

Mice[3] Mice are fed Purina Lab Chow until the start of experiments (Day 0). Groups of five mice are then fed pelleted AIN-76A diet containing either no additive or DHEA (0.45% w/w) between 0900 and 1000 hr. Diets are stored at 4°C for no longer than six months to maintain optimal activity. Mice are given the diets ad libitum, except for mice that are pair fed to mice treated with DHEA. The amounts of AIN-76A diet the pair-fed mice received are determined by the weight of food consumed by the DHEA-fed mice on a daily basis. Body weights (grams) are measured at different time points starting at Day 1 and ending at Day 59. Daily food intakes (grams per day) are determined by weighing the food consumed per cage of five mice. The mean±SEM values are calculated for weeks 1 to 8 (n=7); week 9 had only 3 days.

[References]

[1]. Anagnostopoulou V, et al. Differential effects of dehydroepiandrosterone and testosterone in prostate and colon cancer cell apoptosis: the role of nerve growth factor (NGF) receptors. Endocrinology. 2013 Jul;154(7):2446-56.

[2]. McNelis JC, et al. Dehydroepiandrosterone exerts anti-glucocorticoid action on human preadipocyte proliferation, differentiation and glucose uptake. Am J Physiol Endocrinol Metab. 2013 Nov 1;305(9):E1134-44.

[3]. Catalina F, et al. Decrease of core body temperature in mice by dehydroepiandrosterone. Exp Biol Med (Maywood). 2002 Jun;227(6):382-8.


[Related Small Molecules]

3-Methyladenine | Hydrocortisone | Acetylcysteine(N-acetylcysteine) | Retinoic acid | Melatonine | Dinoprostone | Nicotinamide | Adenosine triphosphate | 4-Acetamidophenol | Prostaglandin E1 | ARN-509 | Corticosterone | Progesterone | Docosahexaenoic Acid | NAD+

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
426.7±45.0 °C at 760 mmHg

[ Melting Point ]:
146-151ºC

[ Molecular Formula ]:
C19H28O2

[ Molecular Weight ]:
288.424

[ Flash Point ]:
182.1±21.3 °C

[ Exact Mass ]:
288.208923

[ PSA ]:
37.30000

[ LogP ]:
3.42

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.560

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BV8396000
CHEMICAL NAME :
Androst-5-en-17-one, 3-beta-hydroxy-
CAS REGISTRY NUMBER :
53-43-0
BEILSTEIN REFERENCE NO. :
2058110
LAST UPDATED :
199707
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C19-H28-O2
MOLECULAR WEIGHT :
288.47
WISWESSER LINE NOTATION :
L E5 B666 FV LUTJ A1 E1 OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
159 gm/kg/84W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 gm/kg/52D-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
400 mg/kg/50D-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1800 mg/kg
SEX/DURATION :
female 2-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
300 mg/kg
SEX/DURATION :
female 15-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
357 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
300 mg/kg
SEX/DURATION :
female 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
600 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Endocrine - changes in luteinizing hormone Endocrine - estrogenic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
240 mg/kg
SEX/DURATION :
female 13-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
240 mg/kg
SEX/DURATION :
female 13-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
Unscheduled DNA synthesis

MUTATION DATA

TEST SYSTEM :
Rodent - rat
DOSE/DURATION :
3780 mg/kg/14D (Continuous)
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 52,2977,1992 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81794 No. of Facilities: 28 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 700 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81794 No. of Facilities: 39 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 2085 (estimated) No. of Female Employees: 1457 (estimated)

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

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

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
UN1230 - class 3 - PG 2 - Methanol, solution

[ WGK Germany ]:
2

[ RTECS ]:
BV8396000

[ HS Code ]:
2937290090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2937290014

[ Summary ]:
HS:2937290014 (3s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17(2h)-one VAT:17.0% Tax rebate rate:9.0% Supervision conditions:l MFN tariff:4.0% General tariff:30.0%

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