U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
56.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ANNOVERA
Primary
Preventing
ELMETRIN
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

Sample Use Guides

In Vivo Use Guide
One ANNOVERA™ (segesterone acetate and ethinyl estradiol) should be placed in the vagina. For maximum contraceptive effectiveness, ANNOVERA™ is to remain in the vagina continuously for 21 days (3 complete weeks). It is removed for a 1-week dose-free interval, and during this time a withdrawal bleed usually occurs.
Route of Administration: parenteral; vaginal; transdermal
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