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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 NOMEGESTROL ACETATE

SMILES

[H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4C(C)=C[C@@]23[H]

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

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

Description
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

CNS Penetrant
2554
Curator's Comment: Nomegestrol acetate is CNS penetrant in animals. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 4.0 nM [Kd]
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
ZOELY

Approved Use

ZOELY is used for oral contraception.

Launch Date

2011
Primary
Approved
8429
NOGEST

Approved Use

NOGEST (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.
PubMed

PubMed

TitleDatePubMed
Reversal effects of nomegestrol acetate on multidrug resistance in adriamycin-resistant MCF7 breast cancer cell line.
2001
Implant contraception.
2001 Dec
[HRT in post-menopausal women: endometrial histology and bleeding patterns].
2002 Aug
Effects of transdermal hormone replacement therapy on levels of soluble P- and E-selectin in postmenopausal healthy women.
2002 Mar
In-vivo angiogenesis and progestogens.
2002 Mar
Classification and pharmacology of progestins.
2003 Dec 10
Newer progestogens.
2003 Jan
Postmenopausal femur bone loss: effects of a low dose hormone replacement therapy.
2003 Jul 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 May
[Nome gesrol (lutenyl) induced severe acute hepatitis].
2004 Jan
Serum leptin levels and body composition in postmenopausal women: effects of hormone therapy.
2004 Jul-Aug
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 Jun
Effects of estrogen-progestin therapy on serum levels of RANKL, osteoprotegerin, osteocalcin, leptin, and ghrelin in postmenopausal women.
2007 Jan-Feb
[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 Jun
Longitudinal evaluation of serum leptin and bone mineral density in early postmenopausal women.
2007 May-Jun
Effects of hormone treatment on hemostasis variables.
2007 Oct
Insulin resistance in postmenopausal women: concurrent effects of hormone replacement therapy and coffee.
2008 Oct
Classification and pharmacology of progestins.
2008 Sep-Oct
Patents

Patents

JP2002543155A
8
JP2002543157A
8

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 15:41:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:46 GMT 2023
Record UNII
83J78V5W05
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NOMEGESTROL ACETATE
DASH   EP   MART.   USAN   WHO-DD  
USAN  
Official Name English
TX-066
Code English
Nomegestrol acetate [WHO-DD]
Common Name English
19-NORPREGNA-4,6-DIENE-3,20-DIONE, 17-(ACETYLOXY)-6-METHYL-
Common Name English
ORG-10486-0
Code English
17-ACETOXY-6-METHYL-19-NORPREGN-4,6-DIEN-3,20-DIONE
Common Name English
6-Methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate
Common Name English
ZOELY
Brand Name English
ORG 10486-0
Code English
NOMEGESTROL ACETATE [USAN]
Common Name English
IOA
Brand Name English
NOMEGESTROL ACETATE [MART.]
Common Name English
TX 066
Code English
NOMEGESTROL ACETATE [EP MONOGRAPH]
Common Name English
NOMAC
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
EMA ASSESSMENT REPORTS ZOELY (AUTHORIZED: CONTRACEPTION)
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
EMA ASSESSMENT REPORTS IOA (WITHDRAWN: CONTRACEPTION)
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
261-379-8
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
CAS
58652-20-3
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
DRUG CENTRAL
1957
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
SMS_ID
100000090279
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID90207349
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
USAN
UU-158
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
EVMPD
SUB03449MIG
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
WIKIPEDIA
Nomegestrol acetate
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
MESH
C038501
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
NCI_THESAURUS
C87244
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
PUBCHEM
91668
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
FDA UNII
83J78V5W05
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
DRUG BANK
DB13981
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
RXCUI
53744
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1476022
Created by admin on Fri Dec 15 15:41:46 GMT 2023 , Edited by admin on Fri Dec 15 15:41:46 GMT 2023
PRIMARY
Related Record Type Details
ANDROGEN RECEPTOR
TARGET -> INHIBITOR
BINDING
Ki
PROGESTERONE RECEPTOR
TARGET -> AGONIST
Ki
Related Record Type Details
Structure of (2α)-17-(Acetyloxy)-2-hydroxy-6-(hydroxymethyl)-19-norpregna-4,6-diene-3,20-dione
METABOLITE -> PARENT
Structure of (2α)-17-(Acetyloxy)-2-glucoronide-6-methyl-19-norpregna-4,6-diene-3,20-dione
METABOLITE -> PARENT
PLASMA; URINE
Structure of 17α-Acetoxy-6-hydroxymethyl-3,20-dioxo-19-nor-pregna-4,6-diene
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.
Structure of (2α)-17-(Acetyloxy)-2-hydroxy-6-methyl-19-norpregna-4,6-diene-3,20-dione
METABOLITE -> PARENT
Related Record Type Details
Structure of NOMEGESTROL
IMPURITY -> PARENT
at 290 nm:
EP
Structure of 6α-methyl-3,20-dioxo-19-norpregn-4-en-17-yl acetate
IMPURITY -> PARENT
EP
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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