CAS 53-43-0|Dehydroepiandrosterone

Introduction：Basic information about CAS 53-43-0|Dehydroepiandrosterone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Dehydroepiandrosterone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles196
8. Synonyms

Common Name	Dehydroepiandrosterone
CAS Number	53-43-0	Molecular Weight	288.424
Density	1.1±0.1 g/cm3	Boiling Point	426.7±45.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₈O₂	Melting Point	146-151ºC
MSDS	ChineseUSA	Flash Point	182.1±21.3 °C
Symbol	GHS02, GHS06, GHS08	Signal Word	Danger

Names

Name	dehydroepiandrosterone
Synonym	More Synonyms

Dehydroepiandrosterone BiologicalActivity

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 ReceptorNatural Products >>SteroidsResearch 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.

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
InChIKey	FMGSKLZLMKYGDP-USOAJAOKSA-N
SMILES	CC12CCC3C(CC=C4CC(O)CCC43C)C1CCC2=O

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

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%

Articles196

Assessment of the potential of polyphenols as a CYP17 inhibitor free of adverse corticosteroid elevation.

Biochem. Pharmacol. 90(3) , 288-96, (2014)

Inhibition of 17α-hydroxylase/17,20-lyase (CYP17), which dictates the proceeding of androgen biosynthesis, is recommended as an effective treatment for androgen-dependent diseases. However, androgen d...

Mechanistic Scrutiny Identifies a Kinetic Role for Cytochrome b5 Regulation of Human Cytochrome P450c17 (CYP17A1, P450 17A1).

PLoS ONE 10 , e0141252, (2015)

Cytochrome P450c17 (P450 17A1, CYP17A1) is a critical enzyme in the synthesis of androgens and is now a target enzyme for the treatment of prostate cancer. Cytochrome P450c17 can exhibit either one or...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Synonyms

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

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