Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00210)
Name
Dolutegravir
Synonyms    Click to Show/Hide the Synonyms of This API
Dolutegravir; 1051375-16-6; GSK1349572; S/GSK1349572; Tivicay; GSK 1349572; Dolutegravir (GSK1349572); GSK-1349572; S-349572; UNII-DKO1W9H7M1; (4r,12as)-N-(2,4-Difluorobenzyl)-7-Hydroxy-4-Methyl-6,8-Dioxo-3,4,6,8,12,12a-Hexahydro-2h-Pyrido[1',2':4,5]pyrazino[2,1-B][1,3]oxazine-9-Carboxamide; CHEBI:76010; (4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide; DKO1W9H7M1; 1051375-16-6 (free); Tivicay (TN); S-GSK1349572; Dolutegravir [USAN:INN]; Soltegravir; HSDB 8152; Dolutegravir (USAN); (4R,12aS)-N-[(2,4-difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,12,12a-tetrahydro-2H-pyrido[[?]:[?]]pyrazino[[?]][1,3]oxazine-9-carboxamide; SCHEMBL82071; MLS006011137; GTPL7365; QCR-34; CHEMBL1229211; DTXSID90909356; C20H19F2N3O5; AOB87150; EX-A1695; methyl-9,12-dioxo-4-oxa-1,8-; ABP000915; BDBM50062551; MFCD20488027; ZINC58581064; AKOS025396657; S/GSK-1349572; BCP9000620; CCG-268876; CS-0454; DB08930; PB33506; NCGC00346629-01; NCGC00346629-02; 2H-Pyrido(1',2':4,5)pyrazino(2,1-b)(1,3)oxazine-9-carboxamide, N-((2,4-difluorophenyl)methyl)-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-, (4R,12aS)-; AC-28371; AS-75277; HY-13238; SMR004702915; AB0033823; S/GSK1349572,GSK1349572; D10066; Q-4931; Q937224; J-501471; diazatricyclo[8.4.0.0?,?]tetradeca-10,13-diene-13-; (3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-; (3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-methyl-9,12-dioxo-4-oxa-1,8-diazatricyclo[8.4.0.0(3),?]tetradeca-10,13-diene-13-carboxamide; (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-[1,3]oxazino[3,2-a]pyrido[1,2-d]pyrazine-9-carboxamide; (4R,12aS)-N-(2,4-Difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-9-carboxamide; (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1,2:4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide; (4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1 ,3]oxazine-9-carboxamide; (4R,12aS)-N-[(2,4-difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,12,12a-tetrahydro-2H-pyrido[5,6]pyrazino[2,6-b][1,3]oxazine-9-carboxamide; N-[(2,4-Difluorophenyl)methyl]-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboximidic acid
Clinical Status
Approved
Disease Indication Human immunodeficiency virus infection ICD-11: 1C60 [1]
PubChem CID
54726191
Formula
C20H19F2N3O5
Canonical SMILES
C[C@@H]1CCO[C@@H]2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O
InChI
1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1
InChIKey
RHWKPHLQXYSBKR-BMIGLBTASA-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=54726191"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 419.4 Topological Polar Surface Area 99.2
XlogP 2.4 Complexity 829
Heavy Atom Count 30 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Dolutegravir 25 mg 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
Sodium stearyl fumarate; Mannitol; Ferric oxide yellow; Talc; Titanium dioxide; Polyvinyl alcohol; Cellulose, microcrystalline; Polyethylene glycols; Povidones; Sodium starch glycolate type a corn
                   Dosage Form Oral Tablet
                   Company ViiV Healthcare Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
          Dolutegravir 50 mg 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
Sodium stearyl fumarate; Mannitol; Ferric oxide yellow; Talc; Titanium dioxide; Polyvinyl alcohol; Cellulose, microcrystalline; Polyethylene glycols; Povidones; Sodium starch glycolate type a corn
                   Dosage Form Oral Tablet
                   Company RemedyRepack; ViiV Healthcare Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
          Dolutegravir 10 mg 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
Sodium stearyl fumarate; Mannitol; Talc; Titanium dioxide; Polyvinyl alcohol; Cellulose, microcrystalline; Polyethylene glycols; Povidones; Sodium starch glycolate type a corn
                   Dosage Form Oral Tablet
                   Company ViiV Healthcare Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
          Dolutegravir Sodium eq 5mg base tablet for suspension 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
Calcium Sulfate Dihydrate; Crospovidone; Mannitol; Microcrystalline Cellulose; Povidone K29/32; Silicified Microcrystalline Cellulose; Sodium Starch Glycolate; Strawberry Cream Flavor; Sucralose; Sodium Stearyl Fumarate; Hypromellose; Polyethylene Glycol; Titanium Dioxide
                   Dosage Form Tablet For Suspension
                   Company Viiv Hlthcare
                   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) [5]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [7]
          Dolutegravir Sodium eq 50mg base 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
D-Mannitol; Microcrystalline Cellulose; Povidone K29/32; Sodium Starch Glycolate; And Sodium Stearyl Fumarate; Macrogol/Peg; Polyvinyl Alcohol-Part Hydrolyzed; Talc; Titanium Dioxide; Iron Oxide Yellow
                   Dosage Form Tablet
                   Company Viiv Hlthcare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [7]
          Dolutegravir Sodium eq 25mg base 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
D-Mannitol; Microcrystalline Cellulose; Povidone K29/32; Sodium Starch Glycolate; Sodium Stearyl Fumarate; Macrogol/Peg; Polyvinyl Alcohol-Part Hydrolyzed; Talc; Titanium Dioxide; Iron Oxide Yellow
                   Dosage Form Tablet
                   Company Viiv Hlthcare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [7]
          Dolutegravir Sodium eq 10mg base 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
D-Mannitol; Microcrystalline Cellulose; Povidone K29/32; Sodium Starch Glycolate; And Sodium Stearyl Fumarate; Macrogol/Peg; Polyvinyl Alcohol-Part Hydrolyzed; Talc; Titanium Dioxide
                   Dosage Form Tablet
                   Company Viiv Hlthcare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [7]
References
1 FDA label for approved dolutegravir from the official website of the U.S. Food and Drug Administration.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
3 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
7 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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