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
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
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.
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 |
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Preventing | ELMETRIN Approved UseUnknown |
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Preventing | ANNOVERA Approved Useis indicated for use by females of reproductive potential to prevent pregnancy Launch Date2018 |
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 |
---|---|---|
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
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11108869
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
Edited
Fri Dec 15 15:16:26 GMT 2023
by
admin
on
Fri Dec 15 15:16:26 GMT 2023
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Record UNII |
9AMX4Q13CC
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C776
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C152316
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DB14583
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DE-09
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Segesterone acetate
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9AMX4Q13CC
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CHEMBL3707377
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m4856
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2055977
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
EC50
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TARGET -> AGONIST |
EC50
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET->ANALOGUE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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