Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00380)
Name
Lubiprostone
Synonyms    Click to Show/Hide the Synonyms of This API
Lubiprostone; Amitiza; 333963-40-9; RU-0211; 136790-76-6; SPI-0211; UNII-7662KG2R6K; 333963-40-9 (hemiketal); Lubiprostone [USAN:INN:JAN]; (2R,4aR,5R,7aR)-2-(1,1-Difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-heptanoic acid; 7662KG2R6K; 7-((2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxooctahydrocyclopenta[b]pyran-5-yl)heptanoic acid; 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[b]pyran-5-yl]heptanoic acid; 7-[(1R,3R,6R,7R)-3-(1,1-Difluoropentyl)-3-hydroxy-8-oxo-2-oxabicyclo[4.3.0]non-7-yl]heptanoic acid; Amitiza (TN); Bicyclic lubiprostone; Lubiprostone hemiketal; NCGC00183105-01; DSSTox_CID_28565; DSSTox_RID_82837; DSSTox_GSID_48639; SCHEMBL217184; GTPL4242; Lubiprostone (JAN/USAN/INN); CHEMBL1201134; DTXSID5048639; C20H32F2O5; C28H28F2O5; EX-A1771; ZINC4217732; Tox21_112986; MFCD08444045; AKOS015896639; AC-1863; DB01046; YF10093; NCGC00183105-02; AS-39360; CAS-136790-76-6; C13707; CAS# 333963-40-9; D04790; 963L409; J-006909; Q6695342; Prostan-1-oic acid, 11,15-epoxy-16,16-difluoro-15-hydroxy-9-oxo-, (11alpha,15R)-; 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[e]pyran-5-yl]heptanoic acid
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
157920
Formula
C20H32F2O5
Canonical SMILES
CCCCC([C@]1(CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)O)(F)F
InChI
1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15-,17-,20-/m1/s1
InChIKey
WGFOBBZOWHGYQH-MXHNKVEKSA-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=157920"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 390.5 Topological Polar Surface Area 83.8
XlogP 4 Complexity 525
Heavy Atom Count 27 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Lubiprostone 0.024 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 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
D&c yellow no. 10; Fd&c red no. 40; Sorbitol; Water; Medium-chain triglycerides; Gelatin, unspecified
                   Dosage Form Oral Capsule
                   Company Takeda Pharmaceuticals America
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [4]
             Drug Formulation 2 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
D&c yellow no. 10; Fd&c red no. 40; Sorbitol; Water; Medium-chain triglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Carilion Materials Management; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [4]
          Lubiprostone 0.008 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 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
Sorbitol; Ferric oxide red; Titanium dioxide; Water; Medium-chain triglycerides; Gelatin, unspecified
                   Dosage Form Oral Capsule
                   Company Takeda Pharmaceuticals America
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [4]
             Drug Formulation 2 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
Sorbitol; Ferric oxide red; Titanium dioxide; Water; Medium-chain triglycerides; Gelatin
                   Dosage Form Oral Capsule
                   Company Physicians Total Care; Stat Rx USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [4]
References
1 FDA label for approved lubiprostone from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.

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