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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.)

    DRUG PRODUCT COMPOSITIONS

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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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