17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one (DMAA; 4-MA) is a 5α-reductase inhibitor with a Ki 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.
For research use only. We do not sell to patients.
- CAS No.: 73671-86-0
- Formula: C24H40N2O2
- Molecular Weight:388.59
-
Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Biological Activity
-
Chemical Information
- Protocols
- Purity & Documentation
- References
-
Help & FAQs
Biological Activity
Description
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 (30-60 min) binds to rat prostate microsomes in an NADPH-dependent manner with a Kd of 7 nM and a Bmax 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 Ki 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
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].
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.
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date |
Phase
|
|---|---|---|---|---|
| NCT01329991 | 2011-05 | PHASE1 |
Chemical Information
-
CAS No. 73671-86-0
-
Molecular Weight 388.59
-
Formula 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
-
Initial Source
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one Related Classifications
HY-153528 Related Classifications
Powered by Bioz
Keywords
- 17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one
- 73671-86-0
- DMAA
- 4-MA
- 5 alpha Reductase
- 3β-hydroxysteroid oxidoreductase
- 5α-dihydrotestosterone
- 5α-reductase
- NADPH
- androgen receptor
- androgen-dependent prostate tumor xenograft
- benign prostatic hyperplasia
- prostate
- rat
- testosterone
- Inhibitor
- inhibitor
- inhibit