ABT-341
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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
Target Actions Organism UDipeptidyl peptidase 4 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- 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]
- External Links
- PubChem Compound
- 11974440
- PubChem Substance
- 99444515
- ChemSpider
- 10147795
- ZINC
- ZINC000014950371
- PDBe Ligand
- KIQ
- PDB Entries
- 2i78
Clinical Trials
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
Property Value Source Water Solubility 0.0141 mg/mL ALOGPS logP 2.29 ALOGPS logP 1.84 Chemaxon logS -4.5 ALOGPS pKa (Strongest Basic) 9.64 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 77.04 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 100.37 m3·mol-1 Chemaxon Polarizability 38.82 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9456 Caco-2 permeable - 0.6333 P-glycoprotein substrate Substrate 0.7507 P-glycoprotein inhibitor I Inhibitor 0.7706 P-glycoprotein inhibitor II Non-inhibitor 0.5461 Renal organic cation transporter Non-inhibitor 0.521 CYP450 2C9 substrate Non-substrate 0.9396 CYP450 2D6 substrate Non-substrate 0.723 CYP450 3A4 substrate Substrate 0.684 CYP450 1A2 substrate Non-inhibitor 0.7534 CYP450 2C9 inhibitor Inhibitor 0.6188 CYP450 2D6 inhibitor Non-inhibitor 0.7736 CYP450 2C19 inhibitor Inhibitor 0.7034 CYP450 3A4 inhibitor Inhibitor 0.5 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8513 Ames test Non AMES toxic 0.5874 Carcinogenicity Non-carcinogens 0.8585 Biodegradation Not ready biodegradable 0.9938 Rat acute toxicity 2.7606 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8366 hERG inhibition (predictor II) Inhibitor 0.8205
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0000900000-f6171fef552febc028a6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-002f-0000900000-fd816e06623763964b9c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0000900000-26c76f1b83cc6b189755 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002f-0101900000-cbafd88eb20057642f4a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0k9m-0132900000-192e6cfa6c21363f19f5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03xs-0930200000-9706b6cd9c02d01d14f0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.63829 predictedDeepCCS 1.0 (2019) [M+H]+ 196.03386 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.9464 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDipeptidyl peptidase 4
- 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
- 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]
- 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