73671-86-0
Chemical Structure
17β-N,N-Diethylcarbamoyl-4-methyl-4-aza-5α-androstan-3-one
Synonym(s): DMAA; 4-MA
- CAS No.: 73671-86-0
- Formula:C24H40N2O2
- Molecular Weight:388.59
IUPAC Name: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N,N-diethyl-1,4a,6a-trimethyl-2-oxohexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
InChIKey: GNWBLLYJQXKPIP-ZOGIJGBBSA-N
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
Biological Activity: 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[1][2][3][4].
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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. | |||||||||||||||||||||
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References
- [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]
