Page last updated: 2024-11-11

17-n,n-diethylcarbamoyl-4-methyl-4-azaandrostane-3-one

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

17-N,N-diethylcarbamoyl-4-methyl-4-azaandrostane-3-one: inhibitor of testosterone 5-alpha reductase, receptor binding & nuclear uptake of androgens in the prostate [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6917653
CHEMBL ID2298601
SCHEMBL ID852296
MeSH IDM0099071

Synonyms (16)

Synonym
n,n-diethyl-4-methyl-3-oxo-5-alpha-4-azaandrostane-17-beta-carboxamide
brn 4269357
17-beta-n,n-diethylcarbamoyl-4-methyl-4-aza-5-alpha-androstan-3-one
5-alpha-4-azaandrostane-17-beta-carboxamide, n,n-diethyl-4-methyl-3-oxo-
4-azaandrostane-17-carboxamide, n,n-diethyl-4-methyl-3-oxo-, (5alpha,17beta)-
17-n,n-diethylcarbamoyl-4-methyl-4-azaandrostane-3-one
4-ma
73671-86-0
(1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide
dmaa [steroid]
SCHEMBL852296
CHEMBL2298601 ,
bdbm50213061
PD182245
HY-153528
CS-0783044

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The higher dosage of 4-MA also abolished odour-based discrimination between females shown by normal males."( Precopulatory behaviour in the male hamster: effect of the 5 alpha-reductase inhibitor 17 beta-N,N-diethylcarbamoyl-4-aza-5 alpha-androstan-3-one.
Hutchison, JB; Steel, E, 1988
)
0.27
" Six delta 1 analogs of the potent 5 alpha-reductase inhibitor, 4-MA (17 beta-N,N-diethylcarbamoyl-4-aza-4-methyl-5 alpha-androstan-3-one) were uniformly active at low dosage levels (less than or equal to 3 mg/kg) in both types of assay whereas several C1-C2 saturated analogs exhibited little activity in the chronic test."( Prostatic effects induced in dogs by chronic or acute oral administration of 5 alpha-reductase inhibitors.
Berman, C; Brooks, JR; Garnes, D; Giltinan, D; Gordon, LR; Malatesta, PF; Primka, RL; Rasmusson, GH; Reynolds, GF, 1986
)
0.27
" First, while administration of testosterone to eggs incubating at all male-producing and male-biased intermediate temperatures produced females in a dose- and temperature-dependent manner, significant numbers of intersex individuals resulted from high dosage testosterone treatment to eggs incubating at a female-biased intermediate temperature."( Role of reductase and aromatase in sex determination in the red-eared slider (Trachemys scripta), a turtle with temperature-dependent sex determination.
Bergeron, JM; Crews, D, 1994
)
0.29
" In the conditioned place-preference assay, DMAA produced an inverted-U-shaped dose-response curve, with intermediate doses producing significant place preference."( Abuse liability of the dietary supplement dimethylamylamine.
Dolan, SB; Gatch, MB, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorRattus norvegicus (Norway rat)IC50 (µMol)2.80000.00101.979414.1600AID39178
3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)IC50 (µMol)0.00290.00170.48807.5000AID207456; AID207917
3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)Ki0.00500.00500.53031.6000AID207920
Androgen receptorMus musculus (house mouse)IC50 (µMol)0.46300.00100.87503.0000AID201917
3-oxo-5-alpha-steroid 4-dehydrogenase 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.01060.00427.468021.1000AID207301; AID207907
3-oxo-5-alpha-steroid 4-dehydrogenase 1 Rattus norvegicus (Norway rat)Ki0.00500.00500.04010.0882AID207435
3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)IC50 (µMol)0.00230.00010.526710.0000AID205603; AID205611; AID207440
3-oxo-5-alpha-steroid 4-dehydrogenase 2Rattus norvegicus (Norway rat)IC50 (µMol)0.01060.00037.329421.1000AID207301; AID207907
3-oxo-5-alpha-steroid 4-dehydrogenase 2Rattus norvegicus (Norway rat)Ki0.00500.00501.711010.0000AID207435
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
urogenital system development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
liver development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
androgen biosynthetic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
androgen catabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
sex determination3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
male gonad development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to starvation3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to xenobiotic stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to muscle activity3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
diterpenoid metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
spinal cord development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
hippocampus development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
thalamus development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
hypothalamus development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
pituitary gland development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cerebral cortex development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cell differentiation3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
male genitalia development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
female genitalia development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to follicle-stimulating hormone3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to insulin stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
serotonin metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
progesterone metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to estrogen3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
bone development3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to growth hormone3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
response to fungicide3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to cAMP3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to growth factor stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to estradiol stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to testosterone stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to dexamethasone stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cellular response to epinephrine stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
steroid biosynthetic process3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
androgen biosynthetic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
steroid catabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
cell-cell signaling3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
androgen metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
male gonad development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to xenobiotic stimulus3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
biphenyl metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
dibenzo-p-dioxin metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
phthalate metabolic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
hippocampus development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
hypothalamus development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
cell differentiation3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
male genitalia development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
female genitalia development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to nutrient levels3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to follicle-stimulating hormone3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to testosterone3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to peptide hormone3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
response to steroid hormone3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
bone development3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
testosterone biosynthetic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
steroid biosynthetic process3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
3-oxo-5-alpha-steroid 4-dehydrogenase activity3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
electron transfer activity3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
amide binding3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) activity3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
NADPH binding3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
3-oxo-5-alpha-steroid 4-dehydrogenase activity3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
protein binding3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
testosterone dehydrogenase [NAD(P)] activity3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
amide binding3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) activity3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membrane3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
neuronal cell body3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
perinuclear region of cytoplasm3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
cell body fiber3-oxo-5-alpha-steroid 4-dehydrogenase 1Homo sapiens (human)
endoplasmic reticulum membrane3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
neuronal cell body3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
cell body fiber3-oxo-5-alpha-steroid 4-dehydrogenase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID207920In vitro inhibitory activity against human type 1 5-alpha reductase1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
6-Azasteroids: structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase.
AID207435Apparent inhibitory constant value for rat prostatic steroid 5alpha reductase was determined1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.
AID207285Ratio of IC50 to that of 10x compound against Steroid 5-alpha-reductase1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.
AID207907Inhibition of rat 5-alpha reductase isozyme.1997Journal of medicinal chemistry, Apr-25, Volume: 40, Issue:9
Pharmacological options in the treatment of benign prostatic hyperplasia.
AID207917Inhibitory concentration was tested on human 5-alpha reductase 1 isozyme1997Journal of medicinal chemistry, Apr-25, Volume: 40, Issue:9
Pharmacological options in the treatment of benign prostatic hyperplasia.
AID212917Comparative activity against Testosterone 5 alpha-Reductase evaluated by setting Ki of 7-(2-Hydroxy-1-methyl-ethyl)-1,4a,6a-trimethyl-hexadecahydro-indeno[5,4-f]quinolin-2-one at 1; 1/21985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one as an inhibitor of testosterone 5 alpha-reductase.
AID205611Inhibition of human 5-alpha reductase 2 isozyme.1997Journal of medicinal chemistry, Apr-25, Volume: 40, Issue:9
Pharmacological options in the treatment of benign prostatic hyperplasia.
AID207912In vitro inhibitory activity against rat prostatic 5-alpha-reductase (150 ng/tube)1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Azasteroids as inhibitors of rat prostatic 5 alpha-reductase.
AID212914Compound was evaluated for in vitro inhibition of Testosterone 5 alpha-Reductase using substrate concentration 3 x 10e-7 M1985Journal of medicinal chemistry, Jun, Volume: 28, Issue:6
Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one as an inhibitor of testosterone 5 alpha-reductase.
AID207301In vitro inhibitory activity against rat prostatic steroid 5-alpha-reductase1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.
AID205603In vitro inhibitory activity against human type 2 5-alpha reductase1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
6-Azasteroids: structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase.
AID201917In vitro inhibition of DHT (dihydrotestosterone) on proliferation of androgen-sensitive cancer Schionogi (SC-3) cells1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Synthesis and in vitro activity of 17 beta-(N-alkyl/arylformamido)- and 17 beta-[(N-alkyl/aryl)alkyl/arylamido]-4-methyl-4-aza-3-oxo-5 alpha-androstan-3-ones as inhibitors of human 5 alpha-reductases and antagonists of the androgen receptor.
AID3434In vitro inhibitory activity against human adrenal 3-beta hydroxy-delta 5-teroid isomerase1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
6-Azasteroids: structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase.
AID207440In vitro inhibition of human steroid 5-alpha-reductase type 2 in SW-13-transfected cells1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Synthesis and in vitro activity of 17 beta-(N-alkyl/arylformamido)- and 17 beta-[(N-alkyl/aryl)alkyl/arylamido]-4-methyl-4-aza-3-oxo-5 alpha-androstan-3-ones as inhibitors of human 5 alpha-reductases and antagonists of the androgen receptor.
AID207456In vitro inhibition of human steroid 5-alpha-reductase type I in Du-145 cells1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Synthesis and in vitro activity of 17 beta-(N-alkyl/arylformamido)- and 17 beta-[(N-alkyl/aryl)alkyl/arylamido]-4-methyl-4-aza-3-oxo-5 alpha-androstan-3-ones as inhibitors of human 5 alpha-reductases and antagonists of the androgen receptor.
AID39178In vitro antagonist activity against rat prostatic androgen receptor (AR)1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (76)

TimeframeStudies, This Drug (%)All Drugs %
pre-199027 (35.53)18.7374
1990's38 (50.00)18.2507
2000's6 (7.89)29.6817
2010's5 (6.58)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.91

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.91 (24.57)
Research Supply Index4.41 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.47%)6.00%
Case Studies1 (1.23%)4.05%
Observational0 (0.00%)0.25%
Other78 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]