Fostemsavir tromethamineProduct ingredient for Fostemsavir

Name
Fostemsavir tromethamine
Drug Entry
Fostemsavir

Fostemsavir is the phosphonooxymethyl prodrug of temsavir, a novel HIV-1 attachment inhibitor.5 It binds to and inhibits the activity of gp120, a subunit within the HIV-1 gp160 envelope glycoprotein that facilitates the attachment of HIV-1 to host cell CD4 receptors - in doing so, temsavir prevents the first step in the HIV-1 viral lifecycle.5 The discovery of gp120 as a potential target of interest in the treatment of HIV-1 infection is relatively recent, and was born out of a desire to find alternative target proteins (i.e. mechanistically orthogonal therapies) for the treatment of HIV-1 patients with resistant infections.3 Fostemavir is the first attachment inhibitor to receive FDA approval, granted in July 2020 for use in combination with other antiretrovirals in highly treatment-experienced patients with multidrug-resistant HIV-1 infection whom are failing their current therapy.5,7 Targeting gp120 subunits is a new and novel therapeutic approach to HIV-1 infection, and the addition of attachment inhibitors, like temsavir, to the armament of therapies targeted against HIV-1 fills a necessary niche for therapeutic options in patients left with few, if any, viable treatments.

Accession Number
DBSALT002794
Structure
Synonyms
Fostemsavir trometamol / Fostemsavir tromethamine
External IDs
BMS-663068-03 / GSK-3684934A / GSK3684934A
UNII
2X513P36U0
CAS Number
864953-39-9
Weight
Average: 704.634
Monoisotopic: 704.231941041
Chemical Formula
C29H37N8O11P
InChI Key
RRGJSMBMTOKHTE-UHFFFAOYSA-N
InChI
InChI=1S/C25H26N7O8P.C4H11NO3/c1-16-27-14-32(28-16)23-21-20(19(39-2)12-26-23)18(13-31(21)15-40-41(36,37)38)22(33)25(35)30-10-8-29(9-11-30)24(34)17-6-4-3-5-7-17;5-4(1-6,2-7)3-8/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38);6-8H,1-3,5H2
IUPAC Name
({3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl}methoxy)phosphonic acid; 2-amino-2-(hydroxymethyl)propane-1,3-diol
SMILES
NC(CO)(CO)CO.COC1=CN=C(N2C=NC(C)=N2)C2=C1C(=CN2COP(O)(O)=O)C(=O)C(=O)N1CCN(CC1)C(=O)C1=CC=CC=C1
ChemSpider
28637754
ChEMBL
CHEMBL3301598
Wikipedia
Fostemsavir
Predicted Properties
PropertyValueSource
Water Solubility0.431 mg/mLALOGPS
logP0.64ALOGPS
logP-0.13Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.75Chemaxon
pKa (Strongest Basic)0.97Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area182.21 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity145.6 m3·mol-1Chemaxon
Polarizability55.12 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon