Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01393)
Name
Rimegepant
Synonyms    Click to Show/Hide the Synonyms of This API
Rimegepant; BMS-927711; 1289023-67-1; BMS 927711; UNII-997WVV895X; CHEMBL2178422; C28H28F2N6O3; 997WVV895X; 1289023-67-1 (free base); (5S,6S,9R)-5-Amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate; Nurtec ODT; Rimegepant [USAN:INN]; BHV-3000; Rimegepant (USAN/INN); BMS-927711(Rimegepant); SCHEMBL1670580; Rimegepant (BMS-927711); GTPL10704; BHV3000; DTXSID70156003; EX-A1922; 3504AH; BDBM50400098; BMS927711; s6659; ZINC68267814; compound 8 [PMID: 23153230]; CS-1027; DB12457; NCGC00378677-01; HY-15498; A13102; D10662; W-5991; Q27272184; [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl] 4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate; [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl]4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
Clinical Status
Approved
PubChem CID
51049968
Formula
C28H28F2N6O3
Canonical SMILES
C1C[C@H](C2=C(C=CC=N2)[C@H]([C@@H]1C3=C(C(=CC=C3)F)F)N)OC(=O)N4CCC(CC4)N5C6=C(NC5=O)N=CC=C6
InChI
1S/C28H28F2N6O3/c29-20-6-1-4-17(23(20)30)18-8-9-22(25-19(24(18)31)5-2-12-32-25)39-28(38)35-14-10-16(11-15-35)36-21-7-3-13-33-26(21)34-27(36)37/h1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37)/t18-,22+,24-/m0/s1
InChIKey
KRNAOFGYEFKHPB-ANJVHQHFSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=51049968"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 534.6 Topological Polar Surface Area 114
XlogP 2.3 Complexity 891
Heavy Atom Count 39 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Rimegepant eq 75mg base Orally Disintegrating tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Benzyl Alcohol; Eucalyptol; Gelatin; Limonene; Mannitol; Menthol; Menthone; Menthyl Acetate; Sucralose; Vanillin
                   Dosage Form Orally Disintegrating Tablet
                   Company Biohaven Pharm
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [1]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [2]
Menthol DIG Info Transient receptor potential p8 (EC50 = 3000 nM) [3]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [4]
Vanillin DIG Info Aldehyde dehydrogenase 5A1 (IC50 = 15600 nM) [5]
Eucalyptol DIG Info Serotonin receptor 3A (IC50 = 257039.58 nM) [6]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [7]
References
1 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
2 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
3 Serendipity in drug-discovery: a new series of 2-(benzyloxy)benzamides as TRPM8 antagonists. Bioorg Med Chem Lett. 2013 Nov 15; 23(22):6118-22.
4 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
5 Inhibition of GABA shunt enzymes' activity by 4-hydroxybenzaldehyde derivatives. Bioorg Med Chem Lett. 2006 Feb; 16(3):592-5.
6 Progress in the discovery of small molecule modulators of the Cys-loop superfamily receptors. Bioorg Med Chem Lett. 2017 Aug 1; 27(15):3207-3218.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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