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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEGESTERONE

SMILES

CC(=O)[C@@]1(O)C(=C)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C

InChI

InChIKey=SFLXYFZGKSGFKA-XUDSTZEESA-N
InChI=1S/C21H28O3/c1-12-10-19-18-6-4-14-11-15(23)5-7-16(14)17(18)8-9-20(19,3)21(12,24)13(2)22/h11,16-19,24H,1,4-10H2,2-3H3/t16-,17+,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Description

Elcometrine (Segesterone acetate, Nestorone) is a steroidal progestin which is used as a hormonal contraceptive and as a treatment of endometriosis. Upon oral administration, Nestorone undergoes rapid metabolism and inactivation. Several clinical trials have been performed with Nestorone administered via subdermal implants.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
56.0 nM [EC50]
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
Preventing
ELMETRIN
PMID

PMID

TitleDatePMID
Use of a single implant of elcometrine (ST-1435), a nonorally active progestin, as a long acting contraceptive for postpartum nursing women.
1999 Feb
Nestorone: a progestin with a unique pharmacological profile.
2000 Oct-Nov
Subdermal progestin implant (Nestorone) in the treatment of endometriosis: clinical response to various doses.
2003 Feb
Comparison of the impact of vaginal and oral administration of combined hormonal contraceptives on hepatic proteins sensitive to estrogen.
2007 Jun
Relative progestational and androgenic activity of four progestins used for male hormonal contraception assessed in vitro in relation to their ability to suppress LH secretion in the castrate male rat.
2010 Oct 26
Patent

Patent

Sample Use Guides

In Vivo Use Guide
Elcometrine is delivered within a single subdermal capsule of medical grade polydimethylsiloxane, containing 50 mg of elcometrine. In clinical trials, administration by a vaginal ring was investigated (150 mg of Nestorone and 15 mg of ethinyl estradiol). The development of transdermal gel containing elcometrine is also reported.
Route of Administration: parenteral; vaginal; transdermal
In Vitro Use Guide
Female Sprague–Dawley rats were ovariectomized and 1 week later, injected daily for 3 days with 1 mg 17 b-estradiol (E2) to induce synthesis of PR. The animals were killed on day 4, uteri were collected over dry ice and homogenized. Aliquot of cytosol were incubated overnight at 4°C in glass tubes with [3H]promegestone with or without cold nestorone at different concentrations. The bound and free radioactivity was separated by the dextran-charcoal method.
Name Type Language
SEGESTERONE
INN   USAN  
USAN   INN  
Official Name English
SEGESTERONE [INN]
Common Name English
SEGESTERONE [USAN]
Common Name English
Code System Code Type Description
INN
8221
Created by admin on Tue Mar 06 17:13:07 UTC 2018 , Edited by admin on Tue Mar 06 17:13:07 UTC 2018
PRIMARY
ChEMBL
CHEMBL2107778
Created by admin on Tue Mar 06 17:13:07 UTC 2018 , Edited by admin on Tue Mar 06 17:13:07 UTC 2018
PRIMARY
NCI_THESAURUS
C66532
Created by admin on Tue Mar 06 17:13:07 UTC 2018 , Edited by admin on Tue Mar 06 17:13:07 UTC 2018
PRIMARY
CAS
7690-08-6
Created by admin on Tue Mar 06 17:13:07 UTC 2018 , Edited by admin on Tue Mar 06 17:13:07 UTC 2018
PRIMARY
PUBCHEM
11823650
Created by admin on Tue Mar 06 17:13:07 UTC 2018 , Edited by admin on Tue Mar 06 17:13:07 UTC 2018
PRIMARY SWITZERF