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Segesterone Acetate
Also known as: Nestoron, 7759-35-5, Elcometrine, Segesterone acetate, St-1435, Segesterone acetate [usan]
Molecular Formula
C23H30O4
Molecular Weight
370.5  g/mol
InChI Key
CKFBRGLGTWAVLG-GOMYTPFNSA-N
FDA UNII
9AMX4Q13CC

Segesterone acetate is a steroidal progestin or synthetic progesterone and a 19-norprogesterone derivative with no CH3 group radical in position 6. In animal studies, segesterone acetate was shown to be one of the most potent progestins. It mediates progestational activity 100 times higher than that of [progesterone]. It is commonly sold under the brand names Nestorone and Elcometrine and serves as an active component in hormonal contraceptives. It is also used as a treatment for endometriosis in South American countries. Segesterone acetate binds selectively to progesterone receptors and not androgen receptors. Due to its rapid hepatic metabolism, segesterone acetate must be administered parenterally. Segesterone acetate is not an orally active compound, but it is proved to be a potent anti-ovulatory agent when given in implants, vaginal rings or percutaneous gel. On August 10, 2018, Annovera containing segesterone acetate and [ethinyl estradiol] was granted approval by the U.S. Food and Drug Administration (FDA) as the first and only contraceptive that provides an entire year of protection against unintended pregnancy while entirely under a woman's control. According to the Center for Disease Control, more than 43 million women in the U.S. are at risk of unintended pregnancy, which may be associated with an elevated risk for improper prenatal care, premature and low-birth-weight infants, and physical and mental health risks. The introduction of this new contraceptive method offers an expansion of birth control options for women while maintaining high efficacy and acceptability similar to existing shorter-acting combined hormonal methods. In clinical trials, Annovera achieved a 97.3% success in pregnancy prevention. Annovera is administered as a vaginal ring that is in place for 21 days and removed for 7 days each cycle. As with other hormonal contraceptives, Annovera carries the risk for serious cardiovascular events.
1 2D Structure

Segesterone Acetate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-16-methylidene-3-oxo-2,6,7,8,9,10,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
2.1.2 InChI
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
2.1.3 InChI Key
CKFBRGLGTWAVLG-GOMYTPFNSA-N
2.1.4 Canonical SMILES
CC(=O)C1(C(=C)CC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)C
2.1.5 Isomeric SMILES
CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)OC(=O)C
2.2 Other Identifiers
2.2.1 UNII
9AMX4Q13CC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 16-methylene-17alpha-acetoxy-19-nor-4-pregnen-3,20-dione

2. St 1435

3. St-1435

2.3.2 Depositor-Supplied Synonyms

1. Nestoron

2. 7759-35-5

3. Elcometrine

4. Segesterone Acetate

5. St-1435

6. Segesterone Acetate [usan]

7. 17-hydroxy-16-methylene-19-norpregn-4-ene-3,20-dione Acetate

8. 9amx4q13cc

9. 16-methylene-17-alpha-acetoxy-19-nor-4-pregnene-3,20-dione

10. 19-norpregn-4-ene-3,20-dione, 17-(acetyloxy)-16-methylene-

11. Segesterone Acetate (usan)

12. St 1435

13. (8r,9s,10r,13s,14s,17r)-17-acetyl-13-methyl-16-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl Acetate

14. Unii-9amx4q13cc

15. Segesterone-acetate

16. Nestorone (tn)

17. [(8r,9s,10r,13s,14s,17r)-17-acetyl-13-methyl-16-methylidene-3-oxo-2,6,7,8,9,10,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Acetate

18. 16-methylene-17alpha-acetoxy-19-nor-4-pregnen-3,20-dione

19. Elcometrine [mi]

20. Schembl1261001

21. Chembl3707377

22. Elcometrine;nestorone;st-1435

23. Nestorone, >=97% (hplc)

24. Dtxsid70998804

25. Chebi:135563

26. 16-methylene-17-hydroxy-19-norpregn-4-ene-3,20-dione Acetate

27. Bcp12737

28. Zinc5167230

29. 19-norpregn-4-ene-3,20-dione, 17-hydroxy-16-methylene-, Acetate

30. Segesterone Acetate [who-dd]

31. Akos025402243

32. Ac-6844

33. Cs-0411

34. Db14583

35. Ncgc00487114-02

36. Segesterone Acetate [orange Book]

37. Hy-13071

38. Annovera Component Segesterone Acetate

39. D10986

40. E89278

41. Segesterone Acetate Component Of Annovera

42. 759n355

43. A914499

44. Elcometrine;nestorone;st-1435;st 1435;st1435

45. Q1978481

46. 1-tert-butoxycarbonylamino-cyclopent-3-enecarboxylicacid

47. 16-methylene-17.alpha.-acetoxy-19-nor-pregn-4-ene-3,20-dione

48. 17-(acetyoxy)-16- Methylene -19-nonpregn-4-ene-3,20-dione

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 370.5 g/mol
Molecular Formula C23H30O4
XLogP32.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass370.21440943 g/mol
Monoisotopic Mass370.21440943 g/mol
Topological Polar Surface Area60.4 Ų
Heavy Atom Count27
Formal Charge0
Complexity762
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Segesterone acetate in combination with ethinyl estradiol is indicated for use by females of reproductive potential to prevent pregnancy as a combination hormonal contraceptive (CHC). It induces contraception for thirteen 28-day cycles (1 year) following vaginal administration. The vaginal system must remain in place continuously for 3 weeks (21 days) followed by a 1-week (7-day) vaginal system-free interval. The use in females with a body mass index of >29 kg/m^2 has not been adequately evaluated.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Segesterone acetate suppresses ovulation. In a Phase I randomized, placebo-controlled, randomized crossover study involving healthy adult female subjects, there was no clinically significant QTc interval prolongation following a single intravenous bolus dose of segesterone acetate. Segesterone acetate shows no androgenic, anabolic, or estrogenic activity. It also did not show uterotropic activity in ovariectomized rats. In the endometrial transformation test to assess the progestational activity, dose-dependent increases in both uterine weight was observed following subcutaneous administration of segesterone acetate.


5.2 MeSH Pharmacological Classification

Contraceptive Agents, Female

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)


Contraceptive Agents, Hormonal

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)


5.3 Absorption, Distribution and Excretion

Absorption

Contraceptive vaginal rings provided sustained release of contraceptive levels of segesterone acetate over 90 days in a pharmacokinetic study of healthy women. Following vaginal administration for up to 13 cycles, segesterone acetate was absorbed into systemic administration and reached the peak plasma concentration in 2 hours in Cycle 1, Cycle 3, and Cycle 13. Concentrations declined after time to reach plasma concentration (Tmax) and became more constant after 96 hours post-dose.Over subsequent cycles of use, the peak serum concentrations of segesterone acetate decreased. In Cycle 1, 3 and 13, the peak plasma concentrations were 1147, 363, and 294 pg/mL.


Route of Elimination

In a pharmacokinetic study, approximately 81.4% and 7.62% of the subcutaneously-administered dose in rats was excreted via feces and urine, respectively.


Volume of Distribution

The volume of distribution of segesterone acetate is 19.6 L/kg.


Clearance

No pharmacokinetic data available.


5.4 Metabolism/Metabolites

Segesterone acetate undergoes rapid metabolism and inactivation in the liver. Based on the findings _in vitro_, the major oxidative metabolites in the serum include 5-dihydro- and 17-hydroxy-5-dihydro metabolites constitute about 50% of exposure relative to segesterone acetate. The metabolites are not pharmacologically active with EC50 to progesterone receptor 10-fold higher than that of the parent compound. It was shown that 3, 5-tetrahydrosegesterone acetate acts as an activator at the GABA-A receptors in the brain.


5.5 Biological Half-Life

The mean (SD) half life of segesterone acetate is 4.5 (3.4) hours.


5.6 Mechanism of Action

Segesterone acetate selectively binds to the progesterone receptor (PR), a transcription factor belonging to the nuclear receptor superfamily, where it acts as an agonist and transactivator. According to the findings from docking experiments, it adopts the same docking position within the PR ligand-binding domain (LBD) as progesterone but due to additional stabilizing contacts between 17-acetoxy and 16-methylene groups and PR LBD, segesterone acetate display higher potency than progesterone. As with other progestins, segesterone acetate prevents ovulation by blocking the midcycle surge in luteinizing hormone (LH) secretion, thereby inhibiting the development of ovarian follicles. When used in combination with segesterone acetate, ethinyl estradiol potentiates the antigonadotropic of the progestin and prevents irregular shedding of the endometrium. Segesterone acetate lacks androgenic activity, and displayed binding affinity to androgen receptors that was 500- to 600-fold less than that of testosterone. It does not display binding affinity toward estrogen receptors. When the relative binding affinities of segesterone acetate to human steroid receptors were investigated _in vitro_, it was demonstrated that segesterone acetate binds to the glucocorticoid receptor. However, segesterone acetate did not exert any glucocorticoid activity in the _in vivo_ assays showing no increase in liver glycogen and tyrosine transaminase TAT.


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