Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01264)
Name
Nabilone
Synonyms    Click to Show/Hide the Synonyms of This API
Nabilone; 51022-71-0; Cesamet; CHEMBL947; Lilly 109514; (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-9-one; Nabilona; Nabilonum; Nabilonum [Latin]; Nabilona [Spanish]; Nabilone [USAN:INN:BAN]; CPD 109514; CPD-109514; 9H-Dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-rel-; 9H-Dibenzo[b,d]pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, (6aR,10aR)-rel-; Cesamet (TN); (-)-Nabilone; (?)-Nabilone; Nabilone (USAN/INN); SCHEMBL33339; DEA No. 7379; DTXSID8023341; DTXSID401015800; ZINC1542930; BDBM50287941; Nabilone, solid, >=98% (HPLC); DB00486; (+-)-3-(1,1-Dimethylheptyl)-6,6abeta,7,8,10,10aalpha-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo(b,d)pyran-9-one; (+-)-trans-3-(1,1-Dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo(b,d)pyran-9-on; (+-)-trans-3-(1,1-Dimethylheptyl-7,8,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo(b,d)pyran-9(6aH)-on; D05099; N-0100; 022N710; Q419079; UNII-2N4O9L084N component GECBBEABIDMGGL-RTBURBONSA-N; (+-)-trans-3-(1,1-Dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo(b,d)pyran-9-one; (-)-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one; (-)-trans-1-Hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one; (-)-trans-3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9h-dibenzo[b,d]pyran-9-one; (6AR,10AR)-1-HYDROXY-6,6-DIMETHYL-3-(2-METHYLOCTAN-2-YL)-6H,6AH,7H,8H,9H,10H,10AH-BENZO[C]ISOCHROMEN-9-ONE; (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-7,8,10,10a-tetrahydro-6H-benzo[c]chromen-9(6aH)-one; (6aR,10aR)-3-(1,1-Dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-benzo[c]chromen-9-one; (6aR,10aR)-3-(1,1-dimethylheptyl)-1-hydroxy-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-benzo[c]chromen-9-one; 61617-09-2; 9H-Dibenzo(b,d)pyran-9-one, 3-(1,1-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-, trans-, (+-)-; trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-one; trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one; trans-3-(1',1'-dimethylheptyl)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-9H-dibenzo[b,d]pyran-9-one
Clinical Status
Approved
PubChem CID
5284592
Formula
C24H36O3
Canonical SMILES
CCCCCCC(C)(C)C1=CC(=C2[C@@H]3CC(=O)CC[C@H]3C(OC2=C1)(C)C)O
InChI
1S/C24H36O3/c1-6-7-8-9-12-23(2,3)16-13-20(26)22-18-15-17(25)10-11-19(18)24(4,5)27-21(22)14-16/h13-14,18-19,26H,6-12,15H2,1-5H3/t18-,19-/m1/s1
InChIKey
GECBBEABIDMGGL-RTBURBONSA-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=5284592"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 372.5 Topological Polar Surface Area 46.5
XlogP 6.4 Complexity 524
Heavy Atom Count 27 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Nabilone 1mg capsule 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
Povidone; Corn Starch; Fd&C Blue No 1; Red D&C Nos 28 33; Gelatin; Titanium Dioxide
                   Dosage Form Capsule
                   Company Bausch
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [1]
Food blue 1 aluminum lake DIG Info Leukemia MT4 cells (IC50 = 1288.25 nM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [4]
References
1 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
2 Synthesis and structure-activity relationship studies of CD4 down-modulating cyclotriazadisulfonamide (CADA) analogues. J Med Chem. 2006 Feb 23; 49(4):1291-312.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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