NAV

Trefentanil

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Trefentanil
DrugBank Accession Number
DB09181
Background

Trefentanil (A-3665) is a fentanyl analogue opioid developed in 1992. It is more potent and shorter acting than alfentanil. Trefentanil is not used in clinics due to the severity of its respiratory depression, though it is still used in research.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 466.561
Monoisotopic: 466.249252425
Chemical Formula
C25H31FN6O2
Synonyms
  • Trefentanil
External IDs
  • A-2665
  • A-3665
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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

Products

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Product Ingredients
IngredientUNIICASInChI Key
Trefentanil hydrochloride20742ZOB3G120656-93-1YMRJQYDWCFOMRR-UHFFFAOYSA-N

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Anilides / Fluorobenzenes / Aralkylamines / Aryl fluorides / Tetrazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Amino acids and derivatives / Azacyclic compounds
show 5 more
Substituents
Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
36QM58LVGU
CAS number
120656-74-8
InChI Key
RJSCINHYBGMIFT-UHFFFAOYSA-N
InChI
InChI=1S/C25H31FN6O2/c1-3-23(33)32(22-13-9-8-12-21(22)26)25(20-10-6-5-7-11-20)14-16-29(17-15-25)18-19-31-24(34)30(4-2)27-28-31/h5-13H,3-4,14-19H2,1-2H3
IUPAC Name
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl}-N-(2-fluorophenyl)propanamide
SMILES
CCN1N=NN(CCN2CCC(CC2)(N(C(=O)CC)C2=CC=CC=C2F)C2=CC=CC=C2)C1=O

References

General References
Not Available
PubChem Compound
60728
PubChem Substance
310265089
ChemSpider
54732
ChEMBL
CHEMBL84617
Wikipedia
Trefentanil

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 Solubility0.0261 mg/mLALOGPS
logP3.72ALOGPS
logP4.72Chemaxon
logS-4.2ALOGPS
pKa (Strongest Basic)7.59Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area71.82 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity132.38 m3·mol-1Chemaxon
Polarizability49.61 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-63b7760cb8ca01045b1c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1000900000-73114fa2219e3d3969a1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0239500000-d4595a37e7d7442e752d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014r-3109700000-7ef995fc93ed51a1332a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0429100000-92de0411c18321693299
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-0109100000-e3629b94a734b78fa8c5
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]-194.55249
predicted
DeepCCS 1.0 (2019)
[M+H]+196.91049
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.35542
predicted
DeepCCS 1.0 (2019)

Drug created at October 14, 2015 21:21 / Updated at February 21, 2021 18:52