ABT-341

Identification

Generic Name
ABT-341
DrugBank Accession Number
DB08044
Background

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

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 445.3616
Monoisotopic: 445.133729421
Chemical Formula
C19H17F6N5O
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

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2,4-triazole / Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
913623-69-5
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

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. [Article]
PubChem Compound
11974440
PubChem Substance
99444515
ChemSpider
10147795
ZINC
ZINC000014950371
PDBe Ligand
KIQ
PDB Entries
2i78

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSsplash10-004i-0000900000-f6171fef552febc028a6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0000900000-fd816e06623763964b9c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-26c76f1b83cc6b189755
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0101900000-cbafd88eb20057642f4a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k9m-0132900000-192e6cfa6c21363f19f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xs-0930200000-9706b6cd9c02d01d14f0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.63829
predicted
DeepCCS 1.0 (2019)
[M+H]+196.03386
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.9464
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52