Rolapitant hydrochloride monohydrateProduct ingredient for Rolapitant
- Name
- Rolapitant hydrochloride monohydrate
- Drug Entry
- Rolapitant
Rolapitant is a potent, highly selective, long-acting Neurokinin-1 (NK-1) receptor antagonist approved for the prevention of delayed chemotherapy-induced nausea and vomiting (CINV) in adults. Delayed-phase CINV typically occurs >24 hours after chemotherapy treatment and is principally mediated by Neurokinin-1 and its ligand Substance P, which is released in the gut following chemotherapy administration. Neurokinin-1 is also known as Tachykinin Receptor 1 (TACR1), Neurokinin 1 Receptor (NK1R), and Substance P Receptor (SPR). By blocking Substance P from interacting with NK-1 receptors in the gut and the central nervous system, rolapitant prevents late-phase CINV. Unlike other available NK-1 receptor antagonists, rolapitant is not an inhibitor of Cytochrome P450 enzyme CYP3A4 and has a long elimination half-life, allowing a single dose to prevent both acute and late-phase CINV during the first 120 hours post-chemotherapy.
- Accession Number
- DBSALT001286
- Structure
Structure for Rolapitant hydrochloride monohydrate (DBSALT001286)
- Synonyms
- Rolapitant hydrochloride
- External IDs
- SCH-619734 / SCH619734
- UNII
- 57O5S1QSAQ
- CAS Number
- 914462-92-3
- Weight
- Average: 554.96
Monoisotopic: 554.1770895 - Chemical Formula
- C25H29ClF6N2O3
- InChI Key
- GZQWMYVDLCUBQX-WVZIYJGPSA-N
- 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
- IUPAC Name
- (5S,8S)-8-{[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl}-8-phenyl-1,7-diazaspiro[4.5]decan-2-one hydrate hydrochloride
- SMILES
- O.Cl.C[C@@H](OC[C@]1(CC[C@]2(CCC(=O)N2)CN1)C1=CC=CC=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F
- External Links
- KEGG Drug
- D08988
- ChemSpider
- 17332043
- ChEBI
- 90911
- ChEMBL
- CHEMBL3707330
- Predicted Properties
Property Value Source Water Solubility 0.00166 mg/mL ALOGPS logP 4.07 ALOGPS logP 5 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 14.15 Chemaxon pKa (Strongest Basic) 8.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 50.36 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 118.28 m3·mol-1 Chemaxon Polarizability 46.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon