Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00491)
Name
Orlistat
Synonyms    Click to Show/Hide the Synonyms of This API
orlistat; 96829-58-2; Tetrahydrolipstatin; Xenical; Orlipastat; (-)-Tetrahydrolipstatin; Orlipastatum [INN-Latin]; Ro-18-0647; [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate; Ro 18-0647/002; UNII-95M8R751W8; N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; Orlistat (Alli, Xenical); (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate; C29H53NO5; MLS002207022; CHEMBL175247; MFCD05662360; L-Leucine, N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; 95M8R751W8; Orlipastatum; SMR000466339; (S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl formyl-L-leucinate; L-Leucine, N-formyl-, (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; tetrahydrolipastatin; Xenical (TN); SR-01000759417; orlistatum; Orlistat [USAN:INN:BAN]; HSDB 7556; N-formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester; zlchem 13; N-Formyl-L-leucine, ester with (3S,4S)-3-hexyl-4-((2S)-2-hydroxytridecyl)-2-oxetanone; KS-1183; PubChem18271; (-)-tetrahydrolipostatin; Orlistat (JAN/USP/INN); Orlistat, >=98%, solid; SCHEMBL16408; L-Leucine, N-formyl-, 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester, (2S-(2alpha(R*),3beta))-; MLS000759448; MLS001423955; BIDD:GT0853; GTPL5277; LEU002; DTXSID8023395; BDBM24567; CHEBI:94686; AOB6737; ZLA0015; Tetrahydrolipstatin;Ro-18-0647; HMS2051I08; HMS3413P06; HMS3677P06; HY-B0218; ZINC8214635; AKOS015894875; BCP9001031; CCG-100851; DB01083; NC00101; (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate; NCGC00165856-01; NCGC00165856-02; [(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate; BCP0726000044; Tetrahydrolipstatin; Ro 18-0647/002; Ro-180647002; Ro-180647-002; SW197481-2; Ro-18-0647/002; D04028; J90006; AB00639987-09; AB00639987_10; 829O582; Q424163; Q-201519; SR-01000759417-5; SR-01000759417-7; Z2379810072; Orlistat, United States Pharmacopeia (USP) Reference Standard; Orlistat, Pharmaceutical Secondary Standard; Certified Reference Material; 2-formamido-3-[(3-hexyl-4-oxo-oxetan-2-yl)methyl]-2-isobutyl-tetradecanoate; N-formyl-L-leucine (S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; N-formyl-L-leucine-(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]-dodecyl ester; (2S)-2-formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester; (S)-((S)-1-((2S,3S)-3-hexyl-4-oxooxetan-2-yl)tridecan-2-yl) 2-formamido-4-methylpentanoate; 104872-04-0
Clinical Status
Approved
Disease Indication Obesity ICD-11: 5B81 [1]
PubChem CID
3034010
Formula
C29H53NO5
Canonical SMILES
CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI
1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChIKey
AHLBNYSZXLDEJQ-FWEHEUNISA-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=3034010"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 495.7 Topological Polar Surface Area 81.7
XlogP 10 Complexity 579
Heavy Atom Count 35 Rotatable Bond Count 23
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Orlistat 120 mg capsule Click to Show/Hide the Full List of Formulation(s):          3 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
Sodium lauryl sulfate; Butyl alcohol; Fd&c blue no. 2; Isopropyl alcohol; Ammonia; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Talc; Titanium dioxide; Alcohol; Cellulose, microcrystalline; Gelatin; Povidones; Shellac; Sodium starch glycolate type a potato
                   Dosage Form Oral Capsule
                   Company A-S Medication Solutions
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             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
Sodium lauryl sulfate; Fd&c blue no. 2; Ammonia; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Talc; Titanium dioxide; Gelatin, unspecified; Microcrystalline cellulose; Povidone, unspecified; Shellac; Sodium starch glycolate type a potato
                   Dosage Form Oral Capsule
                   Company Genentech
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             Drug Formulation 3 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
Sodium lauryl sulfate; Fd&c blue no. 1; Talc; Titanium dioxide; Cellulose, microcrystalline; Gelatin; Povidones; Shellac; Sodium starch glycolate type a potato
                   Dosage Form Oral Capsule
                   Company Genentech
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
          Orlistat 60 mg 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
Sodium lauryl sulfate; Fd&c blue no. 2; Ferrous oxide; Talc; Titanium dioxide; Cellulose, microcrystalline; Gelatin; Povidones; Sodium starch glycolate type a potato
                   Dosage Form Oral Capsule
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
References
1 FDA label for approved orlistat from the official website of the U.S. Food and Drug Administration.
2 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.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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