Identification

Name
ABT-341
Accession Number
DB08044
Type
Small Molecule
Groups
Experimental
Description

ABT-341 is a potent and selective DPP-4 inhibitor with a structure very similar to sitagliptin (in 2D; the 3D structure is significantly different). [1]

Structure
Thumb
Synonyms
  • (1S,6R)-3-{[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]CARBONYL}-6-(2,4,5-TRIFLUOROPHENYL)CYCLOHEX-3-EN-1-AMINE
External IDs
ABT-341
Categories
UNII
Not Available
CAS number
913623-69-5
Weight
Average: 445.3616
Monoisotopic: 445.133729421
Chemical Formula
C19H17F6N5O
InChI Key
NVVSPGQEXMJZIR-BMIGLBTASA-N
InChI
InChI=1S/C19H17F6N5O/c20-12-7-14(22)13(21)6-11(12)10-2-1-9(5-15(10)26)17(31)29-3-4-30-16(8-29)27-28-18(30)19(23,24)25/h1,6-7,10,15H,2-5,8,26H2/t10-,15+/m1/s1
IUPAC Name
(1S,6R)-3-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]-6-(2,4,5-trifluorophenyl)cyclohex-3-en-1-amine
SMILES
[H][C@]1(N)CC(=CC[C@]1([H])C1=CC(F)=C(F)C=C1F)C(=O)N1CCN2C(C1)=NN=C2C(F)(F)F

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Pei Z: From the bench to the bedside: dipeptidyl peptidase IV inhibitors, a new class of oral antihyperglycemic agents. Curr Opin Drug Discov Devel. 2008 Jul;11(4):512-32. [PubMed:18600568]
External Links
PubChem Compound
11974440
PubChem Substance
99444515
ChemSpider
10147795
HET
KIQ
PDB Entries
2i78

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0141 mg/mLALOGPS
logP2.29ALOGPS
logP1.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.04 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.37 m3·mol-1ChemAxon
Polarizability38.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9456
Caco-2 permeable-0.6333
P-glycoprotein substrateSubstrate0.7507
P-glycoprotein inhibitor IInhibitor0.7706
P-glycoprotein inhibitor IINon-inhibitor0.5461
Renal organic cation transporterNon-inhibitor0.521
CYP450 2C9 substrateNon-substrate0.9396
CYP450 2D6 substrateNon-substrate0.723
CYP450 3A4 substrateSubstrate0.684
CYP450 1A2 substrateNon-inhibitor0.7534
CYP450 2C9 inhibitorInhibitor0.6188
CYP450 2D6 inhibitorNon-inhibitor0.7736
CYP450 2C19 inhibitorInhibitor0.7034
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8513
Ames testNon AMES toxic0.5874
CarcinogenicityNon-carcinogens0.8585
BiodegradationNot ready biodegradable0.9938
Rat acute toxicity2.7606 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8366
hERG inhibition (predictor II)Inhibitor0.8205
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Triazolopyrazines / Aralkylamines / Fluorobenzenes / Pyrazines / Aryl fluorides / Triazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds / Hydrocarbon derivatives
show 6 more
Substituents
Gamma amino acid or derivatives / Triazolopyrazine / Halobenzene / Aralkylamine / Fluorobenzene / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Pyrazine
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
  2. Pei Z, Li X, von Geldern TW, Madar DJ, Longenecker K, Yong H, Lubben TH, Stewart KD, Zinker BA, Backes BJ, Judd AS, Mulhern M, Ballaron SJ, Stashko MA, Mika AK, Beno DW, Reinhart GA, Fryer RM, Preusser LC, Kempf-Grote AJ, Sham HL, Trevillyan JM: Discovery of ((4R,5S)-5-amino-4-(2,4,5- trifluorophenyl)cyclohex-1-enyl)-(3- (trifluoromethyl)-5,6-dihydro- [1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methanone (ABT-341), a highly potent, selective, orally efficacious, and safe dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem. 2006 Nov 2;49(22):6439-42. doi: 10.1021/jm060955d. [PubMed:17064063]

Drug created on September 15, 2010 15:27 / Updated on November 02, 2018 06:42