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Chemistry

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Also known as: Rolapitant hydrochloride hydrate, 914462-92-3, Rolapitant hcl, Varubi, Sch619734, Rolapitant hcl h20
Molecular Formula
C25H29ClF6N2O3
Molecular Weight
555.0  g/mol
InChI Key
GZQWMYVDLCUBQX-WVZIYJGPSA-N
FDA UNII
57O5S1QSAQ

Rolapitant HCl
Rolapitant Hydrochloride is the hydrochloride salt form of rolapitant, an orally bioavailable, centrally-acting, selective, neurokinin 1 receptor (NK1-receptor) antagonist with potential antiemetic activity. Upon oral administration, rolapitant competitively binds to and blocks the activity of the NK1-receptor in the central nervous system, thereby inhibiting the binding of the endogenous ligand, substance P (SP). This may prevent both SP-induced emesis and chemotherapy-induced nausea and vomiting (CINV). The interaction of SP with the NK1-receptor plays a key role in the induction of nausea and vomiting caused by emetogenic cancer chemotherapy. Compared to other NK1-receptor antagonists, rolapitant has both a more rapid onset of action and a much longer half-life.
1 2D Structure

Rolapitant HCl

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(5S,8S)-8-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-8-phenyl-1,9-diazaspiro[4.5]decan-2-one;hydrate;hydrochloride
2.1.2 InChI
InChI=1S/C25H26F6N2O2.ClH.H2O/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22;;/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34);1H;1H2/t16-,22-,23-;;/m1../s1
2.1.3 InChI Key
GZQWMYVDLCUBQX-WVZIYJGPSA-N
2.1.4 Canonical SMILES
CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OCC2(CCC3(CCC(=O)N3)CN2)C4=CC=CC=C4.O.Cl
2.1.5 Isomeric SMILES
C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC[C@]2(CC[C@]3(CCC(=O)N3)CN2)C4=CC=CC=C4.O.Cl
2.2 Other Identifiers
2.2.1 UNII
57O5S1QSAQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (5s,8s)-8-(((1r)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro(4.5)decan-2-one

2. 8-((1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro(4,5)decan-2-one

3. Rolapitant

4. Sch 619734

5. Varubi

2.3.2 Depositor-Supplied Synonyms

1. Rolapitant Hydrochloride Hydrate

2. 914462-92-3

3. Rolapitant Hcl

4. Varubi

5. Sch619734

6. Rolapitant Hcl H20

7. Rolapitant Hydrochloride [usan]

8. Rolapitant Hydrochloride Monohydrate

9. 57o5s1qsaq

10. Varubi (tn)

11. (5s,8s)-8-(((1r)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro(4.5)decan-2-one Monohydrochloride Monohydrate

12. (5s,8s)-8-[[(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-8-phenyl-1,9-diazaspiro[4.5]decan-2-one;hydrate;hydrochloride

13. Rolapitant Hydrochloride (usan)

14. Rolapitant Hcl Hydrate

15. 1,7-diazaspiro(4.5)decan-2-one, 8-(((1r)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-, Monohydrochloride, Monohydrate, (5s,8s)-

16. Unii-57o5s1qsaq

17. Rolapitant.hcl.h2o

18. Schembl2173125

19. Chembl3707330

20. Chebi:90911

21. Dtxsid70238570

22. Bcp15968

23. Mfcd19443696

24. Rolapitant Hydrochloride [mi]

25. Rolapitant Monohydrochloride Monohydrate

26. Ac-35397

27. Bs-17849

28. Rolapitant Hydrochloride [orange Book]

29. D08988

30. D83025

31. Rolapitant Hydrochloride Monohydrate [who-dd]

32. Q27162902

33. (5s,8s)-8-({(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-2-oxo-8-phenyl-1,7-diazaspiro[4.5]decan-7-ium Chloride--water (1/1)

34. (5s,8s)-8-({(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-8-phenyl-1,7-diazaspiro[4.5]decan-2-one Hydrochloride--water (1/1)

2.4 Create Date
2007-07-09
3 Chemical and Physical Properties
Molecular Weight 555.0 g/mol
Molecular Formula C25H29ClF6N2O3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count5
Exact Mass554.1770895 g/mol
Monoisotopic Mass554.1770895 g/mol
Topological Polar Surface Area51.4 Ų
Heavy Atom Count37
Formal Charge0
Complexity731
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Neurokinin-1 Receptor Antagonists

Compounds that inhibit or block the activity of NEUROKININ-1 RECEPTORS. (See all compounds classified as Neurokinin-1 Receptor Antagonists.)


INTERMEDIATES SUPPLIERS

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01

BOS Manchester
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BOS Manchester
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CAS Number : 171284-84-7

End Use API : Rolapitant HCl

About The Company : Chengdu Yazhong Bio-pharmaceutical Co., Ltd., founded in 2002, is a leading company with plant extracts, APIs and medical intermediates. Our company is equipped...

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02

BOS Manchester
Not Confirmed
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BOS Manchester
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CAS Number : 1214741-19-1

End Use API : Rolapitant HCl

About The Company : Chengdu Yazhong Bio-pharmaceutical Co., Ltd., founded in 2002, is a leading company with plant extracts, APIs and medical intermediates. Our company is equipped...

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03

BOS Manchester
Not Confirmed
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BOS Manchester
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CAS Number : 1214741-20-4

End Use API : Rolapitant HCl

About The Company : Chengdu Yazhong Bio-pharmaceutical Co., Ltd., founded in 2002, is a leading company with plant extracts, APIs and medical intermediates. Our company is equipped...

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04

BOS Manchester
Not Confirmed
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BOS Manchester
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CAS Number : 1214741-21-5

End Use API : Rolapitant HCl

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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05

BOS Manchester
Not Confirmed
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BOS Manchester
Not Confirmed
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CAS Number : 1214741-20-4

End Use API : Rolapitant HCl

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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06

BOS Manchester
Not Confirmed
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BOS Manchester
Not Confirmed
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CAS Number : 1214741-19-1

End Use API : Rolapitant HCl

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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07

BOS Manchester
Not Confirmed
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BOS Manchester
Not Confirmed
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CAS Number : 1214741-14-6

End Use API : Rolapitant HCl

About The Company : Established in 2011 and situated in Hangzhou, Zhejiang, China, Hangzhou Longshine Bio-Tech CO., Ltd is dedicated to providing services for pharmaceutical and ch...

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DOSAGE - TABLET;ORAL - EQ 90MG BASE

USFDA APPLICATION NUMBER - 206500

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DOSAGE - EMULSION;INTRAVENOUS - EQ 166.5MG BA...DOSAGE - EMULSION;INTRAVENOUS - EQ 166.5MG BASE/92.5ML (EQ 1.8MG BASE/ML)

USFDA APPLICATION NUMBER - 208399

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