MESPIRENONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H30O4S
Molecular Weight	426.568
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@]1([H])[C@@]3(CCC(=O)O3)[C@@]4(C)CC[C@@]5([H])[C@@]([H])([C@@H](CC6=CC(=O)C=C[C@]56C)SC(C)=O)[C@]24[H]

InChI

InChIKey=CPHJTSJQUQZOLJ-ISIDMKFXSA-N

InChI=1S/C25H30O4S/c1-13(26)30-19-11-14-10-15(27)4-7-23(14,2)17-5-8-24(3)22(21(17)19)16-12-18(16)25(24)9-6-20(28)29-25/h4,7,10,16-19,21-22H,5-6,8-9,11-12H2,1-3H3/t16-,17+,18+,19-,21+,22+,23+,24+,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C25H30O4S
Molecular Weight	426.568
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28634268 | https://www.ncbi.nlm.nih.gov/pubmed/3028435 | https://www.ncbi.nlm.nih.gov/pubmed/1996630 | https://www.ncbi.nlm.nih.gov/pubmed/3245852 | https://www.ncbi.nlm.nih.gov/pubmed/1796922 |

Mespirenone (ZK 94679, 15β,16β-methylene-spironolactone) is a steroid aldosterone antagonist. In addition, it is a quite specific inhibitor of adrenocortical mineralocorticoid synthesis. In rodents mespirenone effectively prevents aldosterone-induced hypertension. It exerts natriuretic efficacy. Although it reached phase II clinical trials, it was discontinued in 1989.

Originator

Approval Year

PubMed

Title	Date	PubMed
Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists.	1986 Nov	3028435
Effect of a new mineralocorticoid antagonist mespirenone on aldosterone-induced hypertension.	1991 Feb	1996630
Potentiation of angiotensin II-induced drinking by glucocorticoids is a specific glucocorticoid type II receptor (GR)-mediated event.	1991 Jun 28	1913190
Inhibitory effects of the novel anti-aldosterone compound mespirenone on adrenocortical steroidogenesis in vitro.	1991 Sep	1796922
30 YEARS OF THE MINERALOCORTICOID RECEPTOR: Mineralocorticoid receptor antagonists: 60 years of research and development.	2017 Jul	28634268

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:11:35 GMT 2023` Edited by `admin` on `Fri Dec 15 16:11:35 GMT 2023`
Record UNII	E91TME2I23
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MESPIRENONE

Official Name

English

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

Common Name

English

mespirenone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C49186