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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H27N5O5
Molecular Weight 477.5124
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVN-944

SMILES

CC[C@H](CC#N)OC(=O)N[C@@H](C)C1=CC=CC(NC(=O)NC2=CC(OC)=C(C=C2)C3=CN=CO3)=C1

InChI

InChIKey=GYCPCOJTCINIFZ-OXJNMPFZSA-N
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

HIDE SMILES / InChI
Molecular Formula C25H27N5O5
Molecular Weight 477.5124
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

AVN-944 is an IMPDH (inosine 5-monophosphate dehydrogenase) inhibitor which is now being tested in phase I of clinical trials for the treatment of hematologic malignancies and solid tumors and in phase II for pancreatic cancer (in combination with gemcitabine). The drug showed good inhibition of IMPDH isoforms I and II with Ki=6-10 nM.

Originator

Vertex
26
Curator's Comment: Licensed by Avalon Pharmaceuticals.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5418 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18971325
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AVN-944 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14540 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18971325
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AVN-944 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18971325
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AVN-944 plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
250 mg single, oral
Highest studied dose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/18971325
healthy
Health Status: healthy
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/18971325
Sources:
https://pubmed.ncbi.nlm.nih.gov/18971325
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00BFM8
https://www.1pchem.com/search?query=1P00BFM8
AK Scientific
SYN5575
https://aksci.com/item_detail.php?cat=SYN5575
AOBIOUS INC
AOB5557
http://aobious.com/aobious/search?search_query=AOB5557
AstaTech
F13061
http://astatechinc.com/CPSResult.php?CRNO=F13061
BLD Pharm
BD450430
http://www.bldpharm.com/search/Search.html?keyword=BD450430
Cayman Chemical
21284
http://www.caymanchem.com/app/template/Product.vm/catalog/21284
Chem Scene
CS-3427
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3427
ChemShuttle
157279
https://www.chemshuttle.com/catalogsearch/result/?q=157279
Combi-Blocks
QV-3655
http://www.combi-blocks.com/cgi-bin/find.cgi?QV-3655
eMolecules
301195741
https://orderbb.emolecules.com/search/#?query=301195741
eMolecules
50282741
https://orderbb.emolecules.com/search/#?query=50282741
eMolecules
89937146
https://orderbb.emolecules.com/search/#?query=89937146
KeyOrganics
AS-16899
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-16899
Lab Seeker
SC-82478
http://www.labseeker.com/search.php?keywords=SC-82478&category=0
LabSeeker
SC-82478
http://www.labseeker.com/search.php?keywords=SC-82478&category=0
mcule
MCULE-4503400571
https://mcule.com/MCULE-4503400571/
mcule
MCULE-9404960723
https://mcule.com/MCULE-9404960723/
MedChem Express
HY-13560
https://www.medchemexpress.com/search.html?q=HY-13560&ft=&fa=&fp=
Molnova
M13910
https://www.molnova.com/en/serch-list.html?keywords=M13910
MolPort
MolPort-044-181-293
https://www.molport.com/shop/molecule-link/MolPort-044-181-293
MuseChem
I003029
https://www.musechem.com/product/I003029.html
Ryan Scientific
MK3697
https://ryansci.com/products?q=MK3697&list_q=&search_type=exact
TargetMol
T1979
https://www.targetmol.com/search?keyword=T1979
Toronto Research Chemicals
A794720
https://www.trc-canada.com/product-detail/?CatNum=A794720
PubMed

PubMed

TitleDatePubMed
Depletion of guanine nucleotides leads to the Mdm2-dependent proteasomal degradation of nucleostemin.
2009-04-01
Gateways to clinical trials.
2009-03
A phase I dose-ranging study of the pharmacokinetics, pharmacodynamics, safety, and tolerability of AVN944, an IMPDH inhibitor, in healthy male volunteers.
2009-01
Antiproliferative effects of AVN944, a novel inosine 5-monophosphate dehydrogenase inhibitor, in prostate cancer cells.
2008-11-15
Guanine nucleotide depletion inhibits pre-ribosomal RNA synthesis and causes nucleolar disruption.
2008-01
Recent development of IMP dehydrogenase inhibitors for the treatment of cancer.
2007-07

Sample Use Guides

In Vivo Use Guide
Pancreatic Cancer: patients took 150, 200, 250, 300, or 400 mg q12h. Advanced Stage Solid Tumors: 150 mg twice per day escalating to 750 mg twice per day.
Route of Administration: Oral
In Vitro Use Guide
CCRF-CEM, K562, and Raji cells were plated in 0.5 ml aliquots of growth medium into 48-well plates at 2×10(4) cells per well and then incubated with various concentrations of AVN-944 (1-10 uM). In cell proliferation the IC50s ranged from 0.13 to 0.16 uM for AVN-944.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:13:31 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:31 GMT 2025
Record UNII
I3NPL1V48Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AVN-944
Common Name English
CARBAMIC ACID, ((1S)-1-(3-((((3-METHOXY-4-(5-OXAZOLYL)PHENYL)AMINO)CARBONYL)AMINO)PHENYL)ETHYL)-, (1R)-1-(CYANOMETHYL)PROPYL ESTER
Preferred Name English
AVN 944
Code English
AVN944
Code English
AVN 944 [WHO-DD]
Common Name English
CARBAMIC ACID, N-((1S)-1-(3-((((3-METHOXY-4-(5-OXAZOLYL)PHENYL)AMINO)CARBONYL)AMINO)PHENYL)ETHYL)-, (1R)-1-(CYANOMETHYL)PROPYL ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2087
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C49181
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
FDA UNII
I3NPL1V48Q
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
PUBCHEM
9918559
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
CAS
297730-17-7
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID80183921
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
DRUG BANK
DB05500
Created by admin on Mon Mar 31 18:13:31 GMT 2025 , Edited by admin on Mon Mar 31 18:13:31 GMT 2025
PRIMARY
NIH
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