Art. -Nr.: HY-153528

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one

Name: 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one
Brand: MedChemExpress
SKU: HY-153528
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(Synonyms: DMAA; 4-MA)

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (DMAA; 4-MA) is a 5α-reductase inhibitor with a K_i of 5.3 nM. 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one inhibits the NADPH-dependent conversion of testosterone to 5α-DHT through competitive binding to the testosterone site, and inhibits both the membrane-bound and solubilized forms of the enzyme. 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one partially inhibits prostatic epithelial 3β-hydroxysteroid oxidoreductase and inhibits prostatic cytosolic androgen binding. 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one reduces prostatic 5α-dihydrotestosterone and elevates testosterone in vivo, inhibits androgen-dependent prostate and seminal vesicle growth, reduces prostate volume, and inhibits the growth of androgen-dependent prostate tumors. 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one can be used in research related to benign prostatic hyperplasia and prostate cancer.

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CAS. Nr.: 73671-86-0
Formel: C₂₄H₄₀N₂O₂
Molecular Weight:388.59

Speicherung:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (292 KB)

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one Chemical Structure

CAS. Nr.: 73671-86-0

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

Cellular Effect

Cell Line	Type	Value	Description	References
DU-145	IC₅₀	4.14 nM Compound: 4-MA	In vitro inhibition of human steroid 5-alpha-reductase type I in Du-145 cells In vitro inhibition of human steroid 5-alpha-reductase type I in Du-145 cells	[PMID: 7707319]

In Vitro

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (0-60 min) reversibly binds to male rat liver microsomes with a K_d of 6.5 nM and a B_max of 26.2 pmol/mg protein^[1].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (30-60 min) binds to rat prostate microsomes in an NADPH-dependent manner with a K_d of 7 nM and a B_max of 0.18 pmol/mg protein^[1].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (1 nM-100 μM; 10 min) inhibits 5α-reductase in rat liver microsomes and prostate particulate fraction, with an IC₅₀ of 11 nM in both systems^[1].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (1-1,000 nM; 6 h) is a potent inhibitor of 5α-reductase in cultured rat ventral prostate epithelial cells (IC₅₀ of 7.4 nM), with only partial inhibition of 3β-HSORox/3β-HSORred and no effect on the other enzymes tested^[2].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (1-1,000 nM; 6 h) is a potent inhibitor of 5α-reductase in rat ventral prostate stromal cell cultures (IC₅₀ = 9.0 nM) and does not affect 3α-HSORox, 3α-HSORred, or 6/7-HSH; no stromal 3β-HSOR or 17β-HSORox activity is detected^[2].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (5-15 nM; 10 min) is a competitive inhibitor of rat ventral prostate 5α-reductase with an apparent K_i of 5.3 nM^[3].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (60 min) inhibits the binding of 5α-[³H]DHT to rat ventral prostate cytosolic androgen receptor with an IC₅₀ of 2.8 μM^[3].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (90 min) inhibits the binding of 5α-[³H]DHT and [³H]testosterone to rat ventral prostate cytosolic androgen receptor as determined by the dextran-coated charcoal method, with IC₅₀ values of 2.0 and 2.5 μM, respectively^[3].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (0.1-1 μM; 5-15 min) does not inhibit the nuclear uptake of pre-bound 5α-[³H]DHT-receptor complexes in isolated rat ventral prostate nuclei^[3].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (>20 Ci/mmol) shows no detectable binding to rat or human serum proteins in the charcoal assay at serum dilutions of 160×-800×^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Anti-cancerOthers

Anti-cancer

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (6 mg/kg/day; subcutaneous sustained-release tablet implantation; 30 days) significantly inhibits the growth of androgen-dependent human prostate cancer PC-82 xenografts in castrated and hormone-replaced male Balb/c athymic nude mice [4].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (6 mg/kg/day; subcutaneous sustained-release tablet implantation; 30 days) significantly inhibits the growth of androgen-responsive human genitourinary tumor R198 xenografts in intact mature male Balb/c athymic nude mice, with an inhibition extent comparable to castration [4].
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (6 mg/kg/day; subcutaneous sustained-release pellets) inhibits androgen-dependent tumor growth in PC-82 and R198 tumor-bearing nude mice without altering plasma 5α-dihydrotestosterone (DHT) levels, and only reduces plasma testosterone (T) levels^[4].

Others

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (5 μg-10 mg per animal; injection) reduces prostate 5α-dihydrotestosterone levels and increases testosterone levels in intact male rats; in castrated male rats, it inhibits testosterone propionate-induced accumulation of 5α-DHT in the ventral prostate and attenuates the accumulation of testosterone and 5α-DHT in the prostate, and it selectively inhibits testosterone-induced growth of the ventral prostate and seminal vesicles, while at high doses it further inhibits tissue growth induced by 5α-DHT and its propionate derivative^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Castrated male BALB/c athymic nude mice (age-matched) with hormonal replacement (physiologic T, supraphysiologic T, or supraphysiologic T and DHT)^[4]
Dosage:

6 mg/kg/day (released over 30 days)
Administration:

Subcutaneous implantation of cholesterol-lactate time-release pellets
Result:

Significantly inhibited PC-82 growth in all T- and DHT-replaced groups (-40% / -86% / -90% vs +308% / +249% / +510% in controls)

Animal Model:

Intact mature male BALb/c athymic nude mice (age-matched)^[4]
Dosage:

6 mg/kg/day (released over 30 days)
Administration:

Subcutaneous implantation of cholesterol-lactate time-release pellets
Result:

Significantly inhibited R198 growth, comparable to that achieved by castration.

Related Protocols :

Research Protocol for Endocrine Diseases

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991			2011-05	PHASE1

Chemical Information

CAS. Nr. 73671-86-0
Molecular Weight 388.59
Formel C₂₄H₄₀N₂O₂
SMILES

C[C@@]12[C@]3([H])[C@](CC[C@@]1([H])N(C(CC2)=O)C)([H])[C@@]4([H])[C@](CC3)([C@H](CC4)C(N(CC)CC)=O)C
Synonyms

DMAA; 4-MA
Structure Classification
- Others
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (292 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Liang T, et al. Binding of a 4-methyl-4-aza-steroid to 5 alpha-reductase of rat liver and prostate microsomes. Endocrinology. 1983 Apr;112(4):1460-8.

[2]. Orlowski J, et al. Effect of a 4-methyl-4-aza steroid on androgen metabolism by rat ventral prostate epithelial and stromal cell cultures: selective inhibition of 5 alpha-reductase activity. Prostate. 1988;13(4):289-97.

[3]. Liang T, et al. Inhibition of 5 alpha-reductase, receptor binding, and nuclear uptake of androgens in the prostate by a 4-methyl-4-aza-steroid. J Biol Chem. 1981 Aug 10;256(15):7998-8005.

[4]. Andriole GL, et al. The effect of 4MA, a potent inhibitor of 5 alpha-reductase, on the growth of androgen-responsive human genitourinary tumors grown in athymic nude mice. Prostate. 1987;10(3):189-97. [Content Brief]

Calculators

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Bioz

Keywords

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one

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17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one

Biologische Aktivität

Beschreibung

Cellular Effect

In Vitro

In Vivo

Clinical Trial

Chemical Information

Reinheit & Dokumentation

Verweise

Calculators

Help & FAQs

17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one Related Classifications

HY-153528 Related Classifications

Bioz

Keywords

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