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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.446
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEGESTERONE

SMILES

C=C1C[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4([H])[C@@]3([H])CC[C@]2(C)[C@]1(C(=O)C)O

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P06401
Gene ID: 5241.0
Gene Symbol: PGR
Target Organism: Homo sapiens (Human)
56.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
ELMETRIN

Approved Use

Unknown
Preventing
ANNOVERA

Approved Use

is indicated for use by females of reproductive potential to prevent pregnancy

Launch Date

1.53377282E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
294 pg/mL
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1147 pg/mL
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
942.9 pg/mL
200 μg 1 times / day steady-state, vaginal
dose: 200 μg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.9 ng × h/mL
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
15 ng × h/mL
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
38685.7 pg × h/mL
200 μg 1 times / day steady-state, vaginal
dose: 200 μg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.5 h
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
4.5 h
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
5%
0.15 mg 1 times / day steady-state, vaginal
dose: 0.15 mg
route of administration: Vaginal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
SEGESTERONE ACETATE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Disc. AE: Menometrorrhagia, Migraine headache...
Other AEs: Migraine headache, Nausea and vomiting...
AEs leading to
discontinuation/dose reduction:
Menometrorrhagia (1.7%)
Migraine headache (1.3%)
Vulvovaginal mycotic infection (1.3%)
Nausea and vomiting (1.2%)
Uterine myoma expulsion (1.4%)
Other AEs:
Migraine headache (38.6%)
Nausea and vomiting (25%)
Vulvovaginal mycotic infection (14.5%)
Abdominal pain lower (13.3%)
Dysmenorrhea (12.5%)
Vaginal discharge (11.8%)
Genitourinary tract infection (10%)
Breast discomfort (9.5%)
Disorder menstrual (7.5%)
Diarrhea (7.2%)
Pruritus genital (5.5%)
Thrombosis NOS (>= 2 patients)
Psychiatric disorder NOS (>= 2 patients)
Drug hypersensitivity (>= 2 patients)
Abortions spontaneous (>= 2 patients)
Sources: Page: 13
AEs

AEs

AESignificanceDosePopulation
Nausea and vomiting 1.2%
Disc. AE
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Migraine headache 1.3%
Disc. AE
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Vulvovaginal mycotic infection 1.3%
Disc. AE
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Uterine myoma expulsion 1.4%
Disc. AE
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Menometrorrhagia 1.7%
Disc. AE
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Genitourinary tract infection 10%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Vaginal discharge 11.8%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Dysmenorrhea 12.5%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Abdominal pain lower 13.3%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Vulvovaginal mycotic infection 14.5%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Nausea and vomiting 25%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Migraine headache 38.6%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Pruritus genital 5.5%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Diarrhea 7.2%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Disorder menstrual 7.5%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Breast discomfort 9.5%
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Abortions spontaneous >= 2 patients
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Drug hypersensitivity >= 2 patients
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Psychiatric disorder NOS >= 2 patients
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
Thrombosis NOS >= 2 patients
0.15 mg 1 times / day multiple, vaginal
Recommended
Dose: 0.15 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.15 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.013 mg/day)
Sources: Page: 13
healthy, 18 - 40 years
n = 2308
Health Status: healthy
Age Group: 18 - 40 years
Sex: F
Population Size: 2308
Sources: Page: 13
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
Drug as victim

Drug as victim

Tox targets

Tox targets

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

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: Vaginal
In Vitro Use Guide
Unknown
Name Type Language
SEGESTERONE
INN   USAN  
USAN   INN  
Official Name English
SEGESTERONE [INN]
Common Name English
SEGESTERONE [WHO-DD]
Common Name English
SEGESTERONE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
Code System Code Type Description
INN
8221
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
DRUG BANK
DB14584
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
LACTMED
Segesterone
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107778
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
NCI_THESAURUS
C66532
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
CAS
7690-08-6
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
FDA UNII
09Q5UV3747
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
PUBCHEM
11823650
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY
RXCUI
2055978
Created by admin on Sat Jun 26 03:31:15 UTC 2021 , Edited by admin on Sat Jun 26 03:31:15 UTC 2021
PRIMARY