Basic Description

Synonyms	AVN-944 \| HY-13560 \| DTXSID80183921 \| 501345-02-4 \| CARBAMIC ACID, N-((1S)-1-(3-((((3-METHOXY-4-(5-OXAZOLYL)PHENYL)AMINO)CARBONYL)AMINO)PHENYL)ETHYL)-, (1R)-1-(CYANOMETHYL)PROPYL ESTER \| NSC-767601 \| (R)-1-cyanobutan-2-yl ((S)-1-(3-(3-(3-methoxy-4-(oxazol
Specifications & Purity	≥99%
Biochemical and Physiological Mechanisms	AVN-944 (VX-944) is an orally active, potent, selective, noncompetitive and specific inhibitor of IMPDH (inosine monophosphate dehydrogenase). AVN-944 is an essential rate-limiting enzyme in de novo guanine nucleotide synthesis. AVN-944 is also an inhibit
Storage Temp	Store at -20°C
Shipped In	Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available.
Action Type	INHIBITOR
Mechanism of action	Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor
Product Description	AVN-944 (VX-944) is an orally active, potent, selective, noncompetitive and specific inhibitor of IMPDH (inosine monophosphate dehydrogenase). AVN-944 is an essential rate-limiting enzyme in de novo guanine nucleotide synthesis. AVN-944 is also an inhibitor of arenavirus RNA synthesis , and blocks arenavirus infection. AVN-944 has broad anti-cancer activities, and can be used for multiple myeloma (MM) and acute myeloid leukemia (AML) research . In Vitro AVN-944 (0-1 μM, 48 h) inhibits growth of human multiple myeloma (MM) cell lines in a dose-dependent manner. AVN-944 (800 nM, 0-72 h) induces apoptosis in MM cell lines via a caspase-independent, Bax/AIF/Endo G pathway. AVN-944 (0-200 nM) enhances the cytotoxicity of Doxorubicin and Melphalan . AVN-944 inhibits the proliferation of the human MV-4-11 and murine Ba/F3-Flt3-ITD-dependent cell lines with IC 50 values of 26 and 30 nM, respectively. AVN-944 (0-32 μM, 48 h) shows good activity against arenavirus infection at low doses (7.5 μM) with less cytotoxicity. AVN-944 (0-6.4 μM, 48 h) does not reduce the viability of peripheral blood mononuclear cells (PBMNCs). MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Proliferation AssayCell Line: RPMI8226, MM.1S, and U266 cells Concentration: 0, 100, 200, 300, 400, 600, 1000 nM Incubation Time: 48 h Result: Significantly inhibited the growth of RPMI8226, MM.1S, and U266 cells in a dose-dependent fashion, with 50% inhibition (IC 50 ) values at 48 h of 450, 450, and 600 nM, respectively. Inhibited growth of drug-resistant cell lines, including Doxorubicin (Dox)-resistant RPMI8226-Dox40, Melphalan (Mel) resistant RPMI8226-LR5, and Dex (Dexamethasone) resistant MM.1R cells, with IC 50 values similar to the parental drug-sensitive cell lines. Apoptosis AnalysisCell Line: MM.1S and RPMI8226 cells Concentration: 800 nM Incubation Time: 48 and 72 h Result: Induced apoptosis in MM cell lines. Western Blot AnalysisCell Line: MM.1S and RPMI8226 cells Concentration: 800 nM Incubation Time: 12, 24, 48 h Result: Induced modest cleavage of caspase 3, 8 and 9 in MM.1S cells and RPMI8226 cells. Markedly upregulated Bax and Bak, without significant changes in Bcl-2, Mcl-1, XIAP, and Bad. Observed translocation of mitochondrial proapoptotic proteins, apoptosis-inducing factor (AIF) and endonuclease G (Endo G) to cytosolic fractions. Cell Cytotoxicity AssayCell Line: MM.1S cells, MM.1S cells cultured with BMSCs Concentration: 0, 50, 200 nM Incubation Time: 24 h Result: Enhanced the cytotoxicity of of Doxorubicin and Melphalan in MM.1S cells. Additive effects were also observed in MM.1S cells cultured with BMSCs derived from MM patient. In Vivo AVN-944 (0-150 mg/kg, Orally, twice daily) significantly increases the median survival time of leukemia model mice. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Balb/c mice (leukemia model, using Ba/F3 cells transduced with an activating human Flt-3 mutation injected into mice)Dosage: 75 or 150 mg/kg Administration: Orally, twice daily Result: Provided a significant increase in median survival time. Three of the 12 mice treated with 150 mg/kg AVN-944 were still alive on Day 35 when the study was terminated. Form:Solid

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Organoheterocyclic compounds
  - Class Azoles
    - Subclass Oxazoles

Kingdom	Organic compounds
Superclass	Organoheterocyclic compounds
Class	Azoles
Subclass	Oxazoles
Intermediate Tree Nodes	Not available
Direct Parent	Phenyl-1,3-oxazoles
Alternative Parents	N-phenylureas Methoxyanilines Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers Heteroaromatic compounds Carbamate esters Ureas Oxacyclic compounds Nitriles Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework	Aromatic heteromonocyclic compounds
Substituents	Phenyl-1,3-oxazole - N-phenylurea - Methoxyaniline - Phenoxy compound - Anisole - Phenol ether - Methoxybenzene - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Carbamic acid ester - Heteroaromatic compound - Urea - Nitrile - Carbonitrile - Ether - Oxacycle - Azacycle - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Carbonyl group - Cyanide - Aromatic heteromonocyclic compound
Description	This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
External Descriptors	Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

Product Properties

ALogP	3.1

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

IUPAC Name	[(2R)-1-cyanobutan-2-yl] N-[(1S)-1-[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]ethyl]carbamate
INCHI	InChI=1S/C25H27N5O5/c1-4-20(10-11-26)35-25(32)28-16(2)17-6-5-7-18(12-17)29-24(31)30-19-8-9-21(22(13-19)33-3)23-14-27-15-34-23/h5-9,12-16,20H,4,10H2,1-3H3,(H,28,32)(H2,29,30,31)/t16-,20+/m0/s1
InChIKey	GYCPCOJTCINIFZ-OXJNMPFZSA-N
Smiles	CC[C@H](CC#N)OC(=O)N[C@@H](C)C1=CC(=CC=C1)NC(=O)NC2=CC(=C(C=C2)C3=CN=CO3)OC
Isomeric SMILES	CC[C@H](CC#N)OC(=O)N[C@@H](C)C1=CC(=CC=C1)NC(=O)NC2=CC(=C(C=C2)C3=CN=CO3)OC
PubChem CID	9918559
Molecular Weight	477.51

Certificates（CoA,COO,BSE/TSE and Analysis Chart)

C of A & Other Certificates(BSE/TSE, COO):

Analytical Chart:

Chemical and Physical Properties

Solubility	DMSO : 100 mg/mL (209.42 mM; Need ultrasonic)
Molecular Weight	477.500 g/mol
XLogP3	3.100
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	10
Exact Mass	477.201 Da
Monoisotopic Mass	477.201 Da
Topological Polar Surface Area	139.000 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	743.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

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SKU	Size	Availability	Price
A646297-1mg	1mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$57.90
A646297-5mg	5mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$120.90
A646297-10mg	10mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$191.90
A646297-50mg	50mg	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$754.90

AVN-944 - 99%, high purity , Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor, CAS No.297730-17-7, Inosine-5'-monophosphate dehydrogenase (IMPDH) inhibitor