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Namespace Prefixes

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Statements

Subject Item
n2:DB08930
rdf:type
n3:Drug
n3:description
Dolutegravir is indicated for HIV-1 infection for adults and children and adolescents ≥12 years of age and weighing ≥40 kg. It is marketed as Tivicay as dolutegravir sodium. 52.6 mg of dolutegravir sodium is equivalent to 50 mg dolutegravir free acid. FDA approved on August 12, 2013.
n3:dosage
n17:271B5D9A-363D-11E5-9242-09173F13E4C5 n17:271B5D9B-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# FDA label # Min S, Song I, Borland J, Chen S, Lou Y, Fujiwara T, Piscitelli SC: Pharmacokinetics and safety of S/GSK1349572, a next-generation HIV integrase inhibitor, in healthy volunteers. Antimicrob Agents Chemother. 2010 Jan;54(1):254-8. doi: 10.1128/AAC.00842-09. Epub 2009 Nov 2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19884365 # Lenz JC, Rockstroh JK: S/GSK1349572, a new integrase inhibitor for the treatment of HIV: promises and challenges. Expert Opin Investig Drugs. 2011 Apr;20(4):537-48. doi: 10.1517/13543784.2011.562189. Epub 2011 Mar 8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21381981 # Min S, Sloan L, DeJesus E, Hawkins T, McCurdy L, Song I, Stroder R, Chen S, Underwood M, Fujiwara T, Piscitelli S, Lalezari J: Antiviral activity, safety, and pharmacokinetics/pharmacodynamics of dolutegravir as 10-day monotherapy in HIV-1-infected adults. AIDS. 2011 Sep 10;25(14):1737-45. doi: 10.1097/QAD.0b013e32834a1dd9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21716073 # Hare S, Smith SJ, Metifiot M, Jaxa-Chamiec A, Pommier Y, Hughes SH, Cherepanov P: Structural and functional analyses of the second-generation integrase strand transfer inhibitor dolutegravir (S/GSK1349572). Mol Pharmacol. 2011 Oct;80(4):565-72. doi: 10.1124/mol.111.073189. Epub 2011 Jun 30. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21719464 # Katlama C, Murphy R: Dolutegravir for the treatment of HIV. Expert Opin Investig Drugs. 2012 Apr;21(4):523-30. doi: 10.1517/13543784.2012.661713. Epub 2012 Mar 2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22380682 # Cahn P, Pozniak AL, Mingrone H, Shuldyakov A, Brites C, Andrade-Villanueva JF, Richmond G, Buendia CB, Fourie J, Ramgopal M, Hagins D, Felizarta F, Madruga J, Reuter T, Newman T, Small CB, Lombaard J, Grinsztejn B, Dorey D, Underwood M, Griffith S, Min S: Dolutegravir versus raltegravir in antiretroviral-experienced, integrase-inhibitor-naive adults with HIV: week 48 results from the randomised, double-blind, non-inferiority SAILING study. Lancet. 2013 Aug 24;382(9893):700-8. doi: 10.1016/S0140-6736(13)61221-0. Epub 2013 Jul 3. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23830355 # Dolutegravir (Tivicay) for HIV. Med Lett Drugs Ther. 2013 Sep 30;55(1426):77-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/24081387 # Cottrell ML, Hadzic T, Kashuba AD: Clinical pharmacokinetic, pharmacodynamic and drug-interaction profile of the integrase inhibitor dolutegravir. Clin Pharmacokinet. 2013 Nov;52(11):981-94. doi: 10.1007/s40262-013-0093-2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23824675 # Ballantyne AD, Perry CM: Dolutegravir: first global approval. Drugs. 2013 Sep;73(14):1627-37. doi: 10.1007/s40265-013-0121-4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/24052331 # Boyd MA, Donovan B: Antiretroviral therapy: dolutegravir sets SAIL(ING). Lancet. 2013 Aug 24;382(9893):664-6. doi: 10.1016/S0140-6736(13)61456-7. Epub 2013 Jul 3. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23830358
n3:group
approved
n3:halfLife
Terminal half life = 14 hours
n3:indication
Dolutegravir is indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in adults and children aged 12 years and older and weighing at least 40 kg.
owl:sameAs
n14:DB08930
dcterms:title
Dolutegravir
adms:identifier
n5:Dolutegravir n10:D10066 n11:49702-228-13 n12:76014 n15:DB08930
n3:mechanismOfAction
Dolutegravir is an HIV-1 antiviral agent. It inhibits HIV integrase by binding to the active site and blocking the strand transfer step to retroviral DNA integration. This is an essential step of the HIV replication cycle and will result in an inhibition of viral activity. Dolutegravir has a mean EC50 value of 0.5 nM (0.21 ng/mL) to 2.1 nM (0.85 ng/mL) in peripheral blood mononuclear cells (PBMCs) and MT-4 cells.
n3:patent
n9:8129385
n3:routeOfElimination
When a single oral dose of dolutegravir is given, 53% was excreted unchanged in the feces. 31% is excreted in urine in which consists of the ether glucuronide of dolutegravir (18.9%), a metabolite formed by oxidation at the benzylic carbon (3.0%), and its hydrolytic N-dealkylation product (3.6%). Renal elimination of unchanged drug was low (<1%).
n3:toxicity
The most common adverse reactions of moderate to severe intensity and incidence ≥2% (in those receiving TIVICAY in any one adult trial) are insomnia and headache.
n3:volumeOfDistribution
Volume of distribution (Vd/F), 50 mg once daily = 17.4 L. The median dolutegravir concentration in the CSF was 18 ng/mL after 2 weeks of treatment.
n6:hasAHFSCode
n7:8-18-08-12
n3:proteinBinding
Dolutegravir is highly protein bound (≥98.9%) to human plasma proteins.
n3:salt
foaf:page
n20:dolutegravir.html
n3:IUPAC-Name
n8:271B5DA0-363D-11E5-9242-09173F13E4C5
n3:InChI
n8:271B5DA6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n8:271B5DA5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n8:271B5DA2-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n8:271B5DA3-363D-11E5-9242-09173F13E4C5
n3:SMILES
n8:271B5DA4-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n8:271B5D9E-363D-11E5-9242-09173F13E4C5 n8:271B5DB6-363D-11E5-9242-09173F13E4C5
n3:logP
n8:271B5D9C-363D-11E5-9242-09173F13E4C5 n8:271B5D9F-363D-11E5-9242-09173F13E4C5
n3:logS
n8:271B5D9D-363D-11E5-9242-09173F13E4C5
n6:hasATCCode
n16:J05AX12
n3:H-Bond-Acceptor-Count
n8:271B5DAC-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n8:271B5DAD-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n8:271B5DA7-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n8:271B5DA8-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n8:271B5DAA-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n8:271B5DA9-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n8:271B5DAB-363D-11E5-9242-09173F13E4C5
n3:absorption
When 50 mg of dolutegravir once daily was orally administered to HIV-1 infected adults, the AUC (0-24), Cmax, and Cmin is 53.6 mcg.h/mL, 3.67 mcg/mL, and 1.11 mcg/mL, respectively. The peak plasma concentration was observed 2 to 3 hours post dose. Steady state is achieved within approximately 5 days with average accumulation ratios for AUC, Cmax, and C24h ranging from 1.2 to 1.5. When 50 mg once daily is given to pediatric patients (12 to <18 years and weighing ≥40 kg) the Cmax, AUC (0-24), and C24 is 3.49 mcg/mL, 46 mcg.h/mL, and 0.90 mcg/mL respectively.
n3:affectedOrganism
Human Immunodeficiency Virus
n3:casRegistryNumber
1051375-16-6
n3:clearance
Apparent clearance (CL/F) = 1.0 L/h
n3:Bioavailability
n8:271B5DB2-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n8:271B5DB4-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n8:271B5DB5-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n8:271B5DB1-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n8:271B5DB0-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n8:271B5DB3-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n8:271B5DA1-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n8:271B5DAE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n8:271B5DAF-363D-11E5-9242-09173F13E4C5