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
CC(=O)O[C@@]1(CC[C@H]2[C@@H]3C=C(C)C4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C)C(C)=O
InChI
InChIKey=IIVBFTNIGYRNQY-YQLZSBIMSA-N
InChI=1S/C23H30O4/c1-13-11-20-18(17-6-5-16(26)12-19(13)17)7-9-22(4)21(20)8-10-23(22,14(2)24)27-15(3)25/h11-12,17-18,20-21H,5-10H2,1-4H3/t17-,18-,20-,21+,22+,23+/m1/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 |
DescriptionSources: http://adis.springer.com/drugs/800010246Curator's Comment: Description was created based on several sources, including
http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/001213/WC500115831.pdf | https://www.ncbi.nlm.nih.gov/pubmed/20329803 | https://www.ncbi.nlm.nih.gov/pubmed/22364709
Sources: http://adis.springer.com/drugs/800010246
Curator's Comment: Description was created based on several sources, including
http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/001213/WC500115831.pdf | https://www.ncbi.nlm.nih.gov/pubmed/20329803 | https://www.ncbi.nlm.nih.gov/pubmed/22364709
Nomegestrol acetate (NOMAC) is a 19-norprogesterone derivative with high biological activity at the progesterone receptor, a weak anti-androgenic effect, but with no binding to estrogen, glucocorticoid or mineralocorticoid receptors. Nomegestrol has been developed by the Monaco-based company Théramex SAM (a Teva subsidiary). Nomegestrol acetate has been used successfully for the treatment of some gynaecological disorders (menstrual disturbances, dysmenorrhoea, premenstrual syndrome) and as a component of hormone replacement therapy in combination with estradiol for the relief of menopausal symptoms; it has been approved in Europe as monotherapy for the treatment of the menopausal syndrome, uterine diseases and menorrhagia, and in combination with an estrogen for the treatment of menopausal symptoms. Nomegestrol acetate in combination with estradiol is used as an oral contraceptive.
CNS Activity
Sources: https://www.tga.gov.au/auspar/auspar-nomegestrol-acetate-oestradiol | https://www.ncbi.nlm.nih.gov/pubmed/25168884
Curator's Comment: Nomegestrol acetate is CNS penetrant in animals. No human data available.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL208 |
4.0 nM [Kd] | ||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21757063 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | ZOELY Approved UseZOELY is used for oral contraception. Launch Date2011 |
|||
| Primary | NOGEST Approved UseNOGEST (nomegestrol acetate) is used:
In women before menopause: for the treatment of menstrual cycle disorders caused by the absence or low secretion of progesterone. These troubles of the menstrual cycle can be:
- Menstrual cycle length abnormalities,
- Bleeding abnormalities during or outside menstruation,
- Painful menstruation,
- Troubles before menstruation such as nervousness or irritability (premenstrual syndrome),
- Breast tenderness.
In post menopausal women: as Hormone Replacement Therapy (HRT) for the treatment of menopause disorders in addition with a treatment containing estrogen in non-hysterectomized women with at least 6 months since their last natural period. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE food status: UNKNOWN |
|
6.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
12.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg 1 times / day steady-state, oral dose: 2.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
7.19 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
96 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE food status: UNKNOWN |
|
106 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
106 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg 1 times / day steady-state, oral dose: 2.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
50.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADOLESCENT sex: FEMALE food status: UNKNOWN |
|
48.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26365792/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
45.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg 1 times / day steady-state, oral dose: 2.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
41.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22898360/ |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: ESTRADIOL |
NOMEGESTROL ACETATE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2% |
NOMEGESTROL ACETATE serum | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12.5 mg 1 times / day multiple, oral Highest studied dose|Higher than recommended Dose: 12.5 mg, 1 times / day Route: oral Route: multiple Dose: 12.5 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Headaches, Irritability... AEs leading to discontinuation/dose reduction: Headaches (8.3%) Sources: Irritability (8.3%) Emotional lability (8.3%) |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Bleeding, Amenorrhea... AEs leading to discontinuation/dose reduction: Bleeding (2.82%) Sources: Amenorrhea (0.91%) Weight loss (0.61%) Weight gain (0.61%) Headache (0.28%) Dizziness (0.28%) Increased blood pressure (0.22%) Nausea (0.17%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Emotional lability | 8.3% Disc. AE |
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Headaches | 8.3% Disc. AE |
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Irritability | 8.3% Disc. AE |
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Nausea | 0.17% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Increased blood pressure | 0.22% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Dizziness | 0.28% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Headache | 0.28% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Weight gain | 0.61% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Weight loss | 0.61% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Amenorrhea | 0.91% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Bleeding | 2.82% Disc. AE |
55 mg single, subcutaneous Studied dose Dose: 55 mg Route: subcutaneous Route: single Dose: 55 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Classification and pharmacology of progestins. | 2009-05-13 |
|
| Insulin resistance in postmenopausal women: concurrent effects of hormone replacement therapy and coffee. | 2008-10 |
|
| Effects of hormone treatment on hemostasis variables. | 2007-10 |
|
| [Evaluation of the hematochemical parameters and bone mineral density of women in physiological menopause treated with hormone replacement therapy with nomegestrol acetate and surgical menopause treated with estrogen replacement. Part II]. | 2007-06 |
|
| Longitudinal evaluation of serum leptin and bone mineral density in early postmenopausal women. | 2007-01-24 |
|
| Effects of estrogen-progestin therapy on serum levels of RANKL, osteoprotegerin, osteocalcin, leptin, and ghrelin in postmenopausal women. | 2006-11-01 |
|
| Nomegestrol acetate may enhance the skeletal effects of estradiol on biochemical markers of bone turnover in menopausal women after a 12-week treatment period. | 2005-06 |
|
| Serum leptin levels and body composition in postmenopausal women: effects of hormone therapy. | 2004-07-10 |
|
| [Nome gesrol (lutenyl) induced severe acute hepatitis]. | 2004-01 |
|
| Classification and pharmacology of progestins. | 2003-12-10 |
|
| Postmenopausal femur bone loss: effects of a low dose hormone replacement therapy. | 2003-07-25 |
|
| [Comparison of changes in biochemical markers of bone turnover after 6 months of hormone replacement therapy with either transdermal 17 beta-estradiol or equine conjugated estrogen plus nomegestrol acetate]. | 2003-05 |
|
| Newer progestogens. | 2003-01 |
|
| [HRT in post-menopausal women: endometrial histology and bleeding patterns]. | 2002-08 |
|
| Effects of transdermal hormone replacement therapy on levels of soluble P- and E-selectin in postmenopausal healthy women. | 2002-03 |
|
| In-vivo angiogenesis and progestogens. | 2002-03 |
|
| Implant contraception. | 2001-12 |
|
| Reversal effects of nomegestrol acetate on multidrug resistance in adriamycin-resistant MCF7 breast cancer cell line. | 2001 |
Patents
Sample Use Guides
ZOELY (2.5 mg nomegestrol acetate/1.5 mg estradiol) tablets:
One tablet is to be taken daily for 28 consecutive days. Each pack starts with 24 white active tablets, followed by 4 yellow placebo tablets. A subsequent pack is started immediately after finishing the previous pack, without a break in daily tablet intake and irrespective of presence or absence of withdrawal bleeding. Withdrawal bleeding usually starts on day 2-3 after intake of the last white tablet and may not have finished before the next pack is started.
NOGEST (nomegestrol acetate): the usual dosage is one tablet per day (5 mg/day)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25961213
0.5-50 uM nomegestrol acetate inhibits aromatase activity in a stable aromatase-expressing human breast cancer cell line
| Substance Class |
Chemical
Created
by
admin
on
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Mon Mar 31 18:05:48 GMT 2025
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admin
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Mon Mar 31 18:05:48 GMT 2025
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| Record UNII |
83J78V5W05
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Validated (UNII)
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NCI_THESAURUS |
C776
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EMA ASSESSMENT REPORTS |
ZOELY (AUTHORIZED: CONTRACEPTION)
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EMA ASSESSMENT REPORTS |
IOA (WITHDRAWN: CONTRACEPTION)
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1957
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UU-158
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Nomegestrol acetate
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CHEMBL1476022
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TARGET -> INHIBITOR |
BINDING
Ki
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TARGET -> AGONIST |
Ki
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
PLASMA; URINE
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PARENT -> METABOLITE LESS ACTIVE |
NOMAC was shown to undergo hepatic metabolism via the cytochrome P450 (CYP) system (CYP3A3, 3A4, and 2A6), with hydroxylation to six primary metabolites that have little or no progestational activity.
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IMPURITY -> PARENT |
at 290 nm:
EP
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IMPURITY -> PARENT |
EP
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Volume of Distribution | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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