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
SMILES
[H][C@@]12CC(=C)[C@](O)(C(C)=O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]
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
Molecular Formula | C21H28O3 |
Molecular Weight | 328.4452 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P06401 Gene ID: 5241.0 Gene Symbol: PGR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11108869 |
56.0 nM [EC50] | ||
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11108869 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Preventing | ELMETRIN Approved UseUnknown |
|||
Preventing | ANNOVERA Approved Useis indicated for use by females of reproductive potential to prevent pregnancy Launch Date1.53377282E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29409834/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29409834/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Other AEs:Migraine headache (1.3%) Vulvovaginal mycotic infection (1.3%) Nausea and vomiting (1.2%) Uterine myoma expulsion (1.4%) Migraine headache (38.6%) Sources: Page: 13Nausea 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/209627Orig1s000MultidisciplineR.pdf#page=70 Page: 227.0 |
unlikely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 17:44:01 UTC 2022
by
admin
on
Fri Dec 16 17:44:01 UTC 2022
|
Record UNII |
09Q5UV3747
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C776
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
8221
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
DTXSID00998190
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
DB14584
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
Segesterone
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
DE-08
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
CHEMBL2107778
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
C66532
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
Segesterone
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
7690-08-6
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
09Q5UV3747
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
11823650
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
09Q5UV3747
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY | |||
|
2055978
Created by
admin on Fri Dec 16 17:44:01 UTC 2022 , Edited by admin on Fri Dec 16 17:44:01 UTC 2022
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |