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Also known as: Rad140, 1182367-47-0, Vosilasarm, Rad-140, 4o87q44knc, 2-chloro-4-[[(1r,2s)-1-[5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl]-2-hydroxypropyl]amino]-3-methylbenzonitrile

Molecular Formula

C₂₀H₁₆ClN₅O₂

Molecular Weight

393.8 g/mol

InChI Key

XMBUPPIEVAFYHO-KPZWWZAWSA-N

FDA UNII

4O87Q44KNC

Vosilasarm is an orally bioavailable, non-steroidal selective androgen receptor modulator (SARM), with potential tissue-selective androgenic/anti-androgenic activities. Upon oral administration, vosilasarm acts as an agonist in select tissues, such as skeletal muscle and bone, where it binds to and activates androgen receptors (ARs). In the prostate and breasts, RAD140 acts as an antagonist and blocks AR activation and AR-mediated cellular proliferation. Therefore, this agent may improve bone formation and muscle mass and strength, and may inhibit both the growth of the prostate in males and AR-dependent breast cancer cell proliferation. Compared to anabolic agents, SARMs have reduced androgenic properties.

1 2D Structure

Vosilasarm

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-chloro-4-[[(1R,2S)-1-[5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl]-2-hydroxypropyl]amino]-3-methylbenzonitrile

2.1.2 InChI

InChI=1S/C20H16ClN5O2/c1-11-16(8-7-15(10-23)17(11)21)24-18(12(2)27)20-26-25-19(28-20)14-5-3-13(9-22)4-6-14/h3-8,12,18,24,27H,1-2H3/t12-,18+/m0/s1

2.1.3 InChI Key

XMBUPPIEVAFYHO-KPZWWZAWSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC(=C1Cl)C#N)NC(C2=NN=C(O2)C3=CC=C(C=C3)C#N)C(C)O

2.1.5 Isomeric SMILES

CC1=C(C=CC(=C1Cl)C#N)N[C@@H](C2=NN=C(O2)C3=CC=C(C=C3)C#N)[C@H](C)O

2.2 Other Identifiers

2.2.1 UNII

4O87Q44KNC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-chloro-4-(((1r,2s)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropyl)amino)-3-methylbenzonitrile

2. Rad 140

3. Rad-140

4. Rad140

2.3.2 Depositor-Supplied Synonyms

1. Rad140

2. 1182367-47-0

3. Vosilasarm

4. Rad-140

5. 4o87q44knc

6. 2-chloro-4-[[(1r,2s)-1-[5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl]-2-hydroxypropyl]amino]-3-methylbenzonitrile

7. Chembl1672635

8. 2-chloro-4-(((1r,2s)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropyl)amino)-3-methylbenzonitrile

9. 2-chloro-4-((1r,2s)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropylamino)-3-methylbenzonitrile

10. Benzonitrile, 2-chloro-4-(((1r,2s)-1-(5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropyl)amino)-3-methyl-

11. Vosilasarm [inn]

12. Unii-4o87q44knc

13. Vosilasarm [who-dd]

14. Testolone [nflis-drug]

15. Schembl1363683

16. Ex-a725

17. Rad140,

18. Dtxsid201032907

19. Bcp16214

20. Bdbm50336997

21. Mfcd20527233

22. S5275

23. Zinc66097792

24. Ccg-268578

25. Cs-4670

26. Db13939

27. Ncgc00485476-01

28. 2-chloro-4-({1-[5-(4-cyanophenyl)-1,3,4-oxadiazol-2-yl]-2-hydroxypropyl}amino)-3-methylbenzonitrile

29. Ac-30220

30. Hy-14383

31. J-690050

32. Q25099854

33. 2-chloro-4-[[(1r,2s)-1-[5-(4-cyanophenyl)-1,3,4-oxadiazole-2-yl]-2-hydroxypropyl]amino]-3-methylbenzonitrile

2.4 Create Date

2009-09-21

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₆ClN₅O₂
Molecular Weight	393.8 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	393.0992525 g/mol
Monoisotopic Mass	393.0992525 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	623
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1