Page last updated: 2024-12-10

methylestrenolone

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

Description

methylestrenolone: was MH 1963-92; METHYLESTRENOLONE & METHYLNORTESTOSTERONE were see NORMETHANDROLONE 1963-92; use ESTRENES to search NORMETHANDROLONE 1966-92 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5284597
CHEMBL ID2106801
CHEBI ID34896
SCHEMBL ID148631
MeSH IDM0198315

Synonyms (65)

Synonym
17alpha-methyl-17beta-hydroxyestr-4-en-3-one
unii-743f1z557a
743f1z557a ,
(17beta)-17-hydroxy-17-methylestr-4-en-3-one
estr-4-en-3-one, 17-hydroxy-17-methyl-, (17beta)-
17-beta-hydroxy-17-alpha-methyloestr-4-en-3-one
ai3-52808
estr-4-en-3-one, 17-beta-hydroxy-17-alpha-methyl-
19-nor-17-alpha-methyltestosterone
17alpha-methyl-17beta-hydroxy-19-nor-4-androsten-3-one
17alpha-methylestrenolone
orga-steron
estr-4-en-3-one, 17beta-hydroxy-17-methyl-
einecs 208-183-0
17-alpha-methyl-17-beta-hydroxy-4-estren-3-one
brn 2622263
nsc 10039
methylnortestosterone
orosteron
17-beta-hydroxy-17-methylestr-4-en-3-one
methyloestrenolone
17beta-hydroxy-17-methyl-4-estren-3-on
nsc-10039
17.alpha.-methyl-19-nortestosterone
17-methyl-19-nortestosterone
17.alpha.-methyl-17.beta.-hydroxy-19-nor-4-androsten-3-one
matronal
514-61-4
estr-4-en-3-one, 17.beta.-hydroxy-17-methyl-
normethandrone
metalutin
methalutin
lutenin
19-nortestosterone, 17-methyl-
orgasteron
methylestrenolone
normethanedrolone
normethandrolone
17.alpha.-methylestrenolone
17alpha-methyl-19-nortestosterone
(8r,9s,10r,13s,14s,17s)-17-hydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
normethisterone
A828605
(8r,9s,10r,13s,14s,17s)-13,17-dimethyl-17-oxidanyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
normetandrone
chebi:34896 ,
CHEMBL2106801
normethandrone [mart.]
normethandrone [mi]
normethandrone [who-dd]
17.alpha.-methyl-17.beta.-hydroxyestr-4-en-3-one
SCHEMBL148631
W-105887
19-nor-17-.alpha.-methyltestosterone
17-.alpha.-methyl-17-.beta.-hydroxy-4-estren-3-one
ZXSWTMLNIIZPET-ZOFHRBRSSA-N
17.alpha.-hydroxy-17.beta.-methylestr-4-en-3-one #
17-.beta.-hydroxy-17-methylestr-4-en-3-one
estr-4-en-3-one, 17-.beta.-hydroxy-17-.alpha.-methyl-
estr-4-en-3-one, 17-hydroxy-17-methyl-, (17.beta.)-
17.alpha.-methyl-19-norandrost-4-en-17.beta.-ol-3-one
DTXSID4023383
17beta-hydroxy-17alpha-methylestr-4-en-3-one
DB13533
Q6824007

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The contribution of lymphatic transport to the oral bioavailability of methylnortestosterone (M) after oral administration of the lipophilic prodrug methylnortestosterone undecanoate (MU) has been evaluated, and the sensitivity of lymphatic MU transport to lymphatic lipid transport has been investigated."( Lymphatic transport of Methylnortestosterone undecanoate (MU) and the bioavailability of methylnortestosterone are highly sensitive to the mass of coadministered lipid after oral administration of MU.
Charman, WN; Edwards, GA; Faassen, WA; Nguyen, G; Porter, CJ; White, KL, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" M and MU were administered intravenously and orally to greyhound dogs to determine absolute bioavailability after oral dosing of MU."( Lymphatic transport of Methylnortestosterone undecanoate (MU) and the bioavailability of methylnortestosterone are highly sensitive to the mass of coadministered lipid after oral administration of MU.
Charman, WN; Edwards, GA; Faassen, WA; Nguyen, G; Porter, CJ; White, KL, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
estrogenA hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. The oestrogens that occur naturally in the body, notably estrone, estradiol, estriol, and estetrol are steroids. Other compounds with oestrogenic activity are produced by plants (phytoestrogens) and fungi (mycoestrogens); synthetic compounds with oestrogenic activity are known as xenoestrogens.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
steroidAny of naturally occurring compounds and synthetic analogues, based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. Natural steroids are derived biogenetically from squalene which is a triterpene.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID87088The compound was tested for the seminal vesicle weight after -0.75 ug topical application for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID87091The compound was tested for the treated flank organ weight after -0.375 ug topical application for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID87087The compound was tested for the seminal vesicle weight after -0.375 ug topical application for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID87094The compound was tested for the treated flank organ weight after -5 mg sc administration for 14 days1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID87093The compound was tested for the treated flank organ weight after -1 mg sc administration for 14 days. 1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID87092The compound was tested for the treated flank organ weight after -0.75 ug topical application for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID87090The compound was tested for the seminal vesicle weight after -5 mg sc administration for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID162617Relative binding affinity against progestin receptor1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Correspondence analysis applied to steroid receptor binding.
AID74389Relative binding affinity against glucocorticoid receptor1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Correspondence analysis applied to steroid receptor binding.
AID87089The compound was tested for the seminal vesicle weight after -1 mg sc administration for 14 days.1983Journal of medicinal chemistry, Jan, Volume: 26, Issue:1
Novel 17 alpha-chloro-17 beta-sulfinyl steroids as specific inhibitors of sebaceous gland activity: potential antiacne agents.
AID162435Relative binding affinity for progesterone receptor(PgR) in human T47D cells1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
A potential radioiodinated ligand for androgen receptor: 7 alpha-methyl-17 alpha-(2'-(E)-iodovinyl)-19-nortestosterone.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID126441Relative binding affinity for the mineralocorticoid receptor1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Correspondence analysis applied to steroid receptor binding.
AID212922Relative binding affinity to the testosterone receptor.1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID39318Relative binding affinity for androgen receptor (AR) in rat uterus1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
A potential radioiodinated ligand for androgen receptor: 7 alpha-methyl-17 alpha-(2'-(E)-iodovinyl)-19-nortestosterone.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID39152Relative binding affinity for androgen receptor (AR) in human MCF-7 cells1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
A potential radioiodinated ligand for androgen receptor: 7 alpha-methyl-17 alpha-(2'-(E)-iodovinyl)-19-nortestosterone.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID69853Relative binding affinity against Estrogen receptor1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Correspondence analysis applied to steroid receptor binding.
AID39454Relative binding affinity against androgen receptor1986Journal of medicinal chemistry, Jan, Volume: 29, Issue:1
Correspondence analysis applied to steroid receptor binding.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID162462Relative binding affinity to the progesterone receptor.1994Journal of medicinal chemistry, Nov-11, Volume: 37, Issue:23
PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (58)

TimeframeStudies, This Drug (%)All Drugs %
pre-199042 (72.41)18.7374
1990's5 (8.62)18.2507
2000's7 (12.07)29.6817
2010's2 (3.45)24.3611
2020's2 (3.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.63

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.63 (24.57)
Research Supply Index4.26 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (2.94%)5.53%
Reviews1 (1.47%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other65 (95.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]