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

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30O4
Molecular Weight 370.4819
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEGESTERONE ACETATE

SMILES

[H][C@@]12CC(=C)[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=CKFBRGLGTWAVLG-GOMYTPFNSA-N
InChI=1S/C23H30O4/c1-13-11-21-20-7-5-16-12-17(26)6-8-18(16)19(20)9-10-22(21,4)23(13,14(2)24)27-15(3)25/h12,18-21H,1,5-11H2,2-4H3/t18-,19+,20+,21-,22-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H30O4
Molecular Weight 370.4819
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Segesterone acetate (elcometrine), a progestin, is sold in combination with ethinyl estradiol under the brand name Annovera. Annovera is indicated for use by females of reproductive potential to prevent pregnancy. Segesterone acetate acts as an agonist of the progesterone receptor and it doesn’t possess estrogenic, androgenic, antiandrogenic, or antimineralocorticoid activity.

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

2018
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

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: Other
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:26 GMT 2023
Record UNII
9AMX4Q13CC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEGESTERONE ACETATE
USAN  
USAN  
Official Name English
16-METHYLENE-17.ALPHA.-ACETOXY-19-NOR-PREGN-4-ENE-3,20-DIONE
Common Name English
19-NORPREGN-4-ENE-3,20-DIONE, 17-(ACETYLOXY)-16-METHYLENE-
Common Name English
ANNOVERA COMPONENT SEGESTERONE ACETATE
Brand Name English
Segesterone acetate [WHO-DD]
Common Name English
ELCOMETRINE [MI]
Common Name English
17-(ACETYOXY)-16- METHYLENE -19-NONPREGN-4-ENE-3,20-DIONE
Common Name English
ST-1435
Code English
NESTORONE
Brand Name English
SEGESTERONE ACETATE [ORANGE BOOK]
Common Name English
SEGESTERONE ACETATE [USAN]
Common Name English
SEGESTERONE ACETATE COMPONENT OF ANNOVERA
Brand Name English
ELCOMETRINE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152316
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
DRUG BANK
DB14583
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
USAN
DE-09
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
WIKIPEDIA
Segesterone acetate
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
FDA UNII
9AMX4Q13CC
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL3707377
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
MERCK INDEX
m4856
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY Merck Index
RXCUI
2055977
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
CAS
7759-35-5
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
DAILYMED
9AMX4Q13CC
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID70998804
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
PUBCHEM
108059
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
DRUG CENTRAL
3175
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
SMS_ID
300000034700
Created by admin on Fri Dec 15 15:16:26 GMT 2023 , Edited by admin on Fri Dec 15 15:16:26 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> AGONIST
EC50
TARGET -> AGONIST
EC50
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET->ANALOGUE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC