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Chemistry

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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
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 Weight 393.8 g/mol
Molecular Formula C20H16ClN5O2
XLogP33.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass393.0992525 g/mol
Monoisotopic Mass393.0992525 g/mol
Topological Polar Surface Area119 Ų
Heavy Atom Count28
Formal Charge0
Complexity623
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

API Reference Price

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12-Jul-2024
12-Jul-2024
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