Compounds > mespirenone
Page last updated: 2024-11-06

mespirenone

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Description

mespirenone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65660
CHEMBL ID1908314
SCHEMBL ID637071
MeSH IDM0146061

Synonyms (21)

Synonym
sh-467
zk-94679
mespirenone
mespirenona [spanish]
mespirenonum
e91tme2i23 ,
mespirenone [inn]
mespirenona
87952-98-5
unii-e91tme2i23
15alpha,16alpha-dihydro-17-hydroxy-7alpha-mercapto-3-oxo-3'h-cyclopropa(15,16)-17alpha-pregna-1,4,15-triene-21-carboxylic acid, gamma-lactone, acetate
7alpha-acetylthio-15beta,16beta-methylen-3-oxo-1,4-pregnadien-21,17beta-carbolacton
mespirenonum [latin]
CHEMBL1908314
15.alpha.,16.alpha.-dihydro-17-hydroxy-7.alpha.-mercapto-3-oxo-3'h-cyclopropa(15,16)-17.alpha.-pregna-1,4,15-triene-21-carboxylic acid, g-lactone, acetate
SCHEMBL637071
CPHJTSJQUQZOLJ-ISIDMKFXSA-N
Q27277027
s-[(1'r,2s,2's,3's,5's,7's,10's,11'r,18'r)-7',11'-dimethyl-5,14'-dioxospiro[oxolane-2,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadeca-12,15-diene]-18'-yl] ethanethioate
(7alpha,15alpha,16alpha,17alpha)-7-(acetylthio)-15,16-dihydro-17-hydroxy-3-oxo-3'h-cyclopropa[15,16]pregna-1,4,15-triene-21-carboxylic acid gamma-lactone
DTXSID40868989

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" administration, mespirenone exhibited a short half-life and a high plasma clearance; after oral administration the unchanged compound was not detectable."( Pharmacokinetics and metabolism of mespirenone, a new aldosterone antagonist, in rat and cynomolgus monkey.
Hildebrand, M; Hoyer, GA; Krause, W; Kühne, G, 1987)		0.89
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID189720Antialdosterone activity in rats administered intravenously compared to Spironolactone(100)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID1177649Inhibition of aldosterone synthase in rat adrenal assessed as decrease in 18-OH-corticosterone level at 100 uM2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Aldosterone synthase inhibitors as promising treatments for mineralocorticoid dependent cardiovascular and renal diseases.
AID191663Antiandrogenic activity in rats as weight of prostate after oral administration at 10 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191655Antiandrogenic activity in rats as weight of prostate after subcutaneous administration at 4 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191665Antiandrogenic activity in rats as weight of prostate after oral administration at 30 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191669Antiandrogenic activity in rats as weight of seminal vesicle after oral administration at 1 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID39450Relative binding to androgen receptor compared to dihydrotesterone1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191660Antiandrogenic activity in rats as weight of seminal vesicle after subcutaneous administration at 4 mg/day1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191661Antiandrogenic activity in rats as weight of seminal vesicle after subcutaneous administration at 8 mg/day1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191801Antiandrogenic activity in rats as weight of seminal vesicle after oral administration at 3 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191667Antiandrogenic activity in rats as weight of seminal vesicle after oral administration at 100 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID167310Progestational activity by Clauberg test in rabbits as McPhail index after 100 mg peroral dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID167311Progestational activity by Clauberg test in rabbits as McPhail index after 300 mg peroral dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID74244Displacement of [3H]dexamethasone from Glucocorticoid receptor of rabbit kidney1993Journal of medicinal chemistry, Aug-06, Volume: 36, Issue:16
Synthesis of new 11 beta-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors.
AID126285Displacement of [3H]aldosterone from mineralocorticoid receptor of rabbit kidney1993Journal of medicinal chemistry, Aug-06, Volume: 36, Issue:16
Synthesis of new 11 beta-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors.
AID166630Ovulation inhibitory activity in rabbits after 30 mg peroral dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191670Antiandrogenic activity in rats as weight of seminal vesicle after oral administration at 30 mg/day1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID1177648Inhibition of aldosterone synthase in rat adrenal assessed as decrease in aldosterone level at 100 uM2014Journal of medicinal chemistry, Jun-26, Volume: 57, Issue:12
Aldosterone synthase inhibitors as promising treatments for mineralocorticoid dependent cardiovascular and renal diseases.
AID167313Progestational activity by Clauberg test in rabbits as McPhail index after 100 mg subcutaneous dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191657Antiandrogenic activity in rats as weight of seminal vesicle after subcutaneous administration at 16 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID167315Progestational activity by Clauberg test in rabbits as McPhail index after 30 mg subcutaneous dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191666Antiandrogenic activity in rats as weight of prostate after oral administration at 3 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191652Antiandrogenic activity as weight of prostate after subcutaneous administration at 16 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191656Antiandrogenic activity in rats as organ weight of prostate after subcutaneous administration at 8 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191662Antiandrogenic activity in rats as weight of prostate after oral administration at 100 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191664Antiandrogenic activity in rats as weight of prostate after oral administration at 1 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID162450Relative binding to progesterone receptor compared to progesterone1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID189726Antiandrogenic activity as seminal vesicle weight after subcutaneous administration compared to Spironolactone1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID189723Antiandrogenic activity after peroral administration as relative potency compared to Spironolactone1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID189725Antiandrogenic activity as prostate weight after subcutaneous administration compared to Spironolactone1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID166629Ovulation inhibitory activity in rabbits after 100 mg peroral dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID167314Progestational activity by Clauberg test in rabbits as McPhail index after 10 mg subcutaneous dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID167312Progestational activity by Clauberg test in rabbits as McPhail index after 30 mg peroral dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
AID191668Antiandrogenic activity in rats as weight of seminal vesicle after oral administration at 10 mg/day dose1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (53.85)18.7374
1990's5 (38.46)18.2507
2000's0 (0.00)29.6817
2010's1 (7.69)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: 11.62

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 Index11.62 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.110dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
metyrapone
Metyrapone: An inhibitor of the enzyme STEROID 11-BETA-MONOOXYGENASE. It is used as a test of the feedback hypothalamic-pituitary mechanism in the diagnosis of CUSHING SYNDROME.. metyrapone : An aromatic ketone that is 3,3-dimethylbutan-2-one in which the methyl groups at positions 1 and 4 are replaced by pyridin-3-yl groups. A steroid 11beta-monooxygenase (EC 1.14.15.4) inhibitor, it is used in the diagnosis of adrenal insufficiency.		2.110aromatic ketoneantimetabolite;
diagnostic agent;
EC 1.14.15.4 (steroid 11beta-monooxygenase) inhibitor
corticosterone
[no description available]		1.971011beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite
carbachol
Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.		1.9710ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
spironolactone
Spironolactone: A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827). spironolactone : A steroid lactone that is 17alpha-pregn-4-ene-21,17-carbolactone substituted by an oxo group at position 3 and an alpha-acetylsulfanyl group at position 7.		3.841203-oxo-Delta(4) steroid;
oxaspiro compound;
steroid lactone;
thioester		aldosterone antagonist;
antihypertensive agent;
diuretic;
environmental contaminant;
xenobiotic
aldosterone
[no description available]		3.236011beta-hydroxy steroid;
18-oxo steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid hormone;
mineralocorticoid;
primary alpha-hydroxy ketone;
steroid aldehyde		human metabolite;
mouse metabolite
desoxycorticosterone
Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE		1.971020-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
mineralocorticoid;
primary alpha-hydroxy ketone		human metabolite;
mouse metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9710antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		1.97101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
canrenone
Canrenone: A synthetic pregnadiene compound with anti-aldosterone activity.		2.3820steroid lactone
staurosporine
[no description available]		2.110indolocarbazole alkaloid;
organic heterooctacyclic compound		apoptosis inducer;
bacterial metabolite;
EC 2.7.11.13 (protein kinase C) inhibitor;
geroprotector
fadrozole
Fadrozole: A selective aromatase inhibitor effective in the treatment of estrogen-dependent disease including breast cancer.		2.110imidazopyridine
zk 91587
[no description available]		1.9710
ru-28362
11,17-dihydroxy-6-methyl-17-(1-propynyl)androsta-1,4,6-triene-3-one: glucocorticoid receptor agonist; RN given refers to (11beta,17beta)-isomer		2.3920
angiotensin ii
Giapreza: injectable form of angiotensin II used to increase blood pressure in adult patients with septic or other distributive shock. Ile(5)-angiotensin II : An angiotensin II that acts on the central nervous system (PDB entry: 1N9V).		2.3820amino acid zwitterion;
angiotensin II		human metabolite
eplerenone
Eplerenone: A spironolactone derivative and selective ALDOSTERONE RECEPTOR antagonist that is used in the management of HYPERTENSION and CONGESTIVE HEART FAILURE, post-MYOCARDIAL INFARCTION.		2.1103-oxo-Delta(4) steroid;
epoxy steroid;
gamma-lactone;
methyl ester;
organic heteropentacyclic compound;
oxaspiro compound;
steroid acid ester		aldosterone antagonist;
antihypertensive agent
etomidate
Etomidate: Imidazole derivative anesthetic and hypnotic with little effect on blood gases, ventilation, or the cardiovascular system. It has been proposed as an induction anesthetic.. etomidate : The ethyl ester of 1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylic acid. It is an intravenous general anaesthetic with no analgesic activity.		2.110ethyl ester;
imidazoles		intravenous anaesthetic;
sedative
osilodrostat
Osilodrostat: an orally active aldosterone-synthase inhibitor		2.110
ConditionIndicatedRelationship StrengthStudiesTrials
Cardiovascular Diseases
Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.		02.110
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		01.9710
Blood Pressure, High
[description not available]		01.9710
Hypertension
Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.		06.9710
Diseases of Endocrine System
[description not available]		01.9710
Endocrine System Diseases
Pathological processes of the ENDOCRINE GLANDS, and diseases resulting from abnormal level of available HORMONES.		01.9710