Dolutegravir is a two-metal-bound HIV integrase inhibitor with an IC50 of 2.7 nM in cell-free trials and moderate activity against the significant Raltegravir resistant mutants Y143R, Q148K, N155H, and G140S/Q148H.

 

Brand: BCM

 

Target: HIV Protease

 

Signaling Pathways: Microbiology/Virology; Proteases/Proteasome

 

In Vitro: S/GSK1349572 shows the potent inhibitory effect on nine clinical isolates from integrase inhibitor-naive HIV-2-infected patients with EC50 ranging from 0.2 nM -1.4 nM. In vitro, S/GSK1349572 inhibits recombinant HIV-1 integrase-catalyzed strand transfer with IC50 of 2.7 nM. Furthermore, S/GSK1349572 potently inhibits HIV replication in cells such as peripheral blood mononuclear cells (PBMCs), MT-4 cells and CIP4 cells infected with a self-inactivating PHIV lentiviral vector with EC50 of 0,51 nM, 0.71 nM and 2.2 nM, respectively. In vitro, S/GSK1349572 exhibits potent activity against five different nonnucleoside reverse transcription inhibitor--resistant or nucleoside reverse transcription inhibitor--resistant viruses with EC50 ranging from 1.3 nM -2.1 nM. Similarly to that against wild-type virus, S/GSK1349572 shows equivalent activity against two protease inhibitor-resistant viruses with EC50 of 0.36 nM and 0.37 nM, respectively.

 

Melting Point: 187-189°C

 

Boiling Point: 669.0±55.0 °C(Predicted)

 

pKa: 4.50±1.00(Predicted)

 

Solubility: Soluble in DMSO. Insoluble in Water; Insoluble in Ethanol.

 

GHS: GHS07

 

Isomeric 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  

 

InChIKey: RHWKPHLQXYSBKR-BMIGLBTASA-N  

 

InChI: 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

 

Attribute
[Chem Name]	(3S,7R)-N-[(2,4-difluorophenyl)methyl]-11-hydroxy-7-methyl-9,12-dioxo-4-oxa-1,8-diazatricyclo[8.4.0.03,8]tetradeca-10,13-diene-13-carboxamide
[Synonym]	Dolutegravir; GSK1349572; S/GSK1349572
[CAS No.]	1051375-16-6
[MDL No.]	MFCD20488027
[Formula]	C20H19F2N3O5
[Molecular]	419.38
[Form]	White to Pale Beige Solid
[Storage]	Sealed in dry, 2-8°C

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