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VX-148

CAT: 0804-HY-118917Size: 1 EachDry Ice: NoHazardous: No
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Description
VX-148 is an orally active immunosuppressant, which is a non-competitive inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor with Ki values for IMPDH II and IMPDH I of 6 and 14 nM respectively. VX-148 can significantly inhibit the proliferation of human peripheral blood mononuclear cells (PBMC) stimulated by T-cell mitogen (PHA) or B-cell mitogen (SPAS) . VX-148 has high selectivity for lymphocytes (such as L1210, Jurkat T cells, and Raji B cells), but has no significant toxicity to non-lymphoid cells. VX-148 can inhibit antibody responses in mouse models and significantly prolong the survival time of transplanted skin in allogeneic skin transplantation models. VX-148 can be used in the research of autoimmune diseases (such as rheumatoid arthritis, psoriasis) and organ transplantation anti-rejection[1][2].
CAS Number
297730-05-3
UNSPSC
12352005
Target
IMPDH
Related Pathways
Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Smiles
O=C(O[C@@H](CC#N)CC)N[C@H](C1=CC=CC(NC(NC2=CC=C(C#N)C(OC)=C2)=O)=C1)C
Molecular Formula
C23H25N5O4
Molecular Weight
435.48
References & Citations
[1]Pankiewicz KW, et al. Cofactor mimics as selective inhibitors of NAD-dependent inosine monophospate dehydrogenase (IMPDH) -the major therapeutic target. Current medicinal chemistry. 2004 Apr 1;11 (7) :887-900.|[2]Jain J, et al. Characterization of pharmacological efficacy of VX-148, a new, potent immunosuppressive inosine 5′-monophosphate dehydrogenase inhibitor. The Journal of pharmacology and experimental therapeutics. 2002 Jan 1;302 (3) :1272-7.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
IMPDH1; IMPDH2

Chemical Information

VX-148

VX-148 is a second-generation, orally administered inhibitor of inosine monophosphate dehydrogenase (IMPDH). The IMPDH enzyme plays a key role in regulating immune response and proliferation of specific cell types, including lymphocytes. VX-148 is a developed for the treatment of autoimmune diseases.

CAS Number297730-05-3
PubChem CID9845837
IUPAC Name[(2R)-1-cyanobutan-2-yl] N-[(1S)-1-[3-[(4-cyano-3-methoxyphenyl)carbamoylamino]phenyl]ethyl]carbamate
Molecular FormulaC23H25N5O4
Molecular Weight435.5
XLogP2.7
Topological Polar Surface Area136
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Heavy Atom Count32
Formal Charge0
Complexity726
SMILES
CC[C@H](CC#N)OC(=O)N[C@@H](C)C1=CC(=CC=C1)NC(=O)NC2=CC(=C(C=C2)C#N)OC
InChI
InChI=1S/C23H25N5O4/c1-4-20(10-11-24)32-23(30)26-15(2)16-6-5-7-18(12-16)27-22(29)28-19-9-8-17(14-25)21(13-19)31-3/h5-9,12-13,15,20H,4,10H2,1-3H3,(H,26,30)(H2,27,28,29)/t15-,20+/m0/s1
InChIKey
PJFQWSNOXLEDDZ-MGPUTAFESA-N
Chemical Structure
2D Structure
2D structure of VX-148
CAS: 297730-05-3
CID: 9845837
Formula: C23H25N5O4
MW: 435.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight435.5
XLogP32.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass435.19065430
Monoisotopic Mass435.19065430
Topological Polar Surface Area136 Ų
Heavy Atom Count32
Formal Charge0
Complexity726
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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