Lofentanil

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

Identification

Name
Lofentanil
Accession Number
DB09174
Type
Small Molecule
Groups
Illicit
Description

Lofentanil is one of the most potent opioid analgesics known and is an analogue of fentanyl, which was developed in 1960. It is most similar to the highly potent opioid carfentanil (4-carbomethoxyfentanyl), only slightly more potent. Lofentanil can be described as 3-methylcarfentanil, or 3-methyl-4-carbomethoxyfentanyl. While 3-methylfentanyl is considerably more potent than fentanyl itself, lofentanil is only slightly stronger than carfentanil. This suggests that substitution at both the 3 and 4 positions of the piperidine ring introduces steric hindrance which prevents μ-opioid affinity from increasing much further. As with other 3-substituted fentanyl derivatives such as ohmefentanyl, the stereoisomerism of lofentanil is very important, with some stereoisomers being much more potent than others.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
7H7YQ564XV
CAS number
61380-40-3
Weight
Average: 408.542
Monoisotopic: 408.241292898
Chemical Formula
C25H32N2O3
InChI Key
IMYHGORQCPYVBZ-NLFFAJNJSA-N
InChI
InChI=1S/C25H32N2O3/c1-4-23(28)27(22-13-9-6-10-14-22)25(24(29)30-3)16-18-26(19-20(25)2)17-15-21-11-7-5-8-12-21/h5-14,20H,4,15-19H2,1-3H3/t20-,25+/m1/s1
IUPAC Name
methyl (3R,4S)-3-methyl-1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
SMILES
CCC(=O)N(C1=CC=CC=C1)[C@]1(CCN(CCC2=CC=CC=C2)C[C@H]1C)C(=O)OC

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Lofentanil.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Lofentanil.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may increase the analgesic activities of Lofentanil.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Lofentanil.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Lofentanil.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Lofentanil is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Lofentanil.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Lofentanil.
AcetazolamideThe risk or severity of adverse effects can be increased when Lofentanil is combined with Acetazolamide.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Lofentanil.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
10070040
PubChem Substance
310265083
ChemSpider
8245580
BindingDB
50027473
ChEMBL
CHEMBL28198
Wikipedia
Lofentanil

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 Solubility0.0166 mg/mLALOGPS
logP3.93ALOGPS
logP4.15ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.85 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity118.79 m3·mol-1ChemAxon
Polarizability46.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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/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 fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Fentanyls
Direct Parent
Fentanyls
Alternative Parents
Alpha amino acids and derivatives / Piperidinecarboxylic acids / Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Methyl esters / Trialkylamines / Monocarboxylic acids and derivatives / Azacyclic compounds
show 4 more
Substituents
Fentanyl / Alpha-amino acid or derivatives / Phenethylamine / Piperidinecarboxylic acid / Anilide / Aralkylamine / Benzenoid / Monocyclic benzene moiety / Methyl ester / Tertiary carboxylic acid amide
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 14, 2015 14:58 / Updated on August 02, 2018 06:15