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Elacestrant

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Chemistry

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Also known as: 722533-56-4, Rad1901, Elacestrant [inn], Elacestrant [usan], Rad-1901, Er-306323

Molecular Formula

C₃₀H₃₈N₂O₂

Molecular Weight

458.6 g/mol

InChI Key

SIFNOOUKXBRGGB-AREMUKBSSA-N

FDA UNII

FM6A2627A8

Elacestrant is an orally available, selective estrogen receptor degrader (SERD) and selective estrogen receptor modulator (SERM), with potential antineoplastic and estrogen-like activities. Upon oral administration of higher doses of elacestrant, this agent acts as a SERD, which binds to the estrogen receptor (ER) and induces a conformational change that results in the degradation of the receptor. This may inhibit the growth and survival of ER-expressing cancer cells. At lower doses of this agent, RAD1901 acts as a SERM and has estrogen-like effects in certain tissues, which can both reduce hot flashes and protect against bone loss. In addition, elacestrant is able to cross the blood-brain barrier (BBB).

1 2D Structure

Elacestrant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R)-6-[2-[ethyl-[[4-[2-(ethylamino)ethyl]phenyl]methyl]amino]-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

2.1.2 InChI

InChI=1S/C30H38N2O2/c1-4-31-17-16-22-6-8-23(9-7-22)21-32(5-2)30-20-28(34-3)14-15-29(30)26-11-10-25-19-27(33)13-12-24(25)18-26/h6-9,12-15,19-20,26,31,33H,4-5,10-11,16-18,21H2,1-3H3/t26-/m1/s1

2.1.3 InChI Key

SIFNOOUKXBRGGB-AREMUKBSSA-N

2.1.4 Canonical SMILES

CCNCCC1=CC=C(C=C1)CN(CC)C2=C(C=CC(=C2)OC)C3CCC4=C(C3)C=CC(=C4)O

2.1.5 Isomeric SMILES

CCNCCC1=CC=C(C=C1)CN(CC)C2=C(C=CC(=C2)OC)[C@@H]3CCC4=C(C3)C=CC(=C4)O

2.2 Other Identifiers

2.2.1 UNII

FM6A2627A8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (6r)-6-(2-(ethyl((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

2.3.2 Depositor-Supplied Synonyms

1. 722533-56-4

2. Rad1901

3. Elacestrant [inn]

4. Elacestrant [usan]

5. Rad-1901

6. Er-306323

7. Fm6a2627a8

8. (6r)-6-[2-[ethyl-[[4-[2-(ethylamino)ethyl]phenyl]methyl]amino]-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

9. (6r)-6-{2-[ethyl({4-[2-(ethylamino)ethyl]phenyl}methyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

10. (2r)-2-(2-(ethyl-((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxy-phenyl)tetralin-6-ol

11. (6r)-6-(2-(ethyl((4-(2- (ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)- 5,6,7,8-tetrahydronaphthalen-2-ol

12. 2-naphthalenol, 6-(2-(ethyl((4-(2-(ethylamino)ethyl)phenyl)methyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydro-, (6r)-

13. Elacestrant (usan/inn)

14. Elacestrant [usan:inn]

15. Elacestrant [who-dd]

16. Schembl229431

17. Unii-fm6a2627a8

18. Chembl4297509

19. Bdbm349630

20. Dtxsid901045846

21. Glxc-26208

22. Ex-a5070

23. Us10208011, Compound Rad-

24. Mfcd30532693

25. Who 10247

26. Cs-6306

27. Db06374

28. Hy-19822

29. D11671

30. Q27278069

31. (r)-6-(2-(ethyl(4-(2-(ethylamino)ethyl)benzyl)amino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

32. I0v

2.4 Create Date

2008-01-14

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₃₈N₂O₂
Molecular Weight	458.6 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Exact Mass	458.293328459 g/mol
Monoisotopic Mass	458.293328459 g/mol
Topological Polar Surface Area	44.7 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	578
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in menopause and female hormonal deficiencies/abnormalities.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

RAD1901 is a novel selective estrogen receptor modulator(SERM). SERMs are small molecules that bind to and selectively modulate estrogen receptors. These molecules have the ability to stimulate or block estrogen's activity in different types of tissue, functioning as estrogen receptor agonists in some tissues and as estrogen receptor antagonists in others. RAD1901 has potential to reduce vasomotor symptoms, along with a simultaneous bone-protective effect, without stimulating breast or uterine tissues. RAD1901 is distinctive from other SERMs in its unique biological profile, combined with its significant ability to penetrate the blood-brain barrier, which enables RAD1901 to function as an estrogen agonist within the central nervous system and thereby relieve hot flashes.

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