Identification

Name
Anileridine
Accession Number
DB00913  (APRD00741)
Type
Small Molecule
Groups
Approved, Illicit
Description

Anileridine is a synthetic opioid and strong analgesic medication. It is a narcotic pain reliever used to treat moderate to severe pain. Narcotic analgesics act in the central nervous system (CNS) to relieve pain. Some of their side effects are also caused by actions in the CNS.

Structure
Thumb
Synonyms
  • 1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl ester
  • Anileridina
  • Anileridinum
  • Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylate
  • ethyl 1-(4-aminophenethyl)-4-phenylisonipecotate
  • Ethyl 1-(P-aminophenethyl)-4-phenylisonipecotate
  • N-(beta-(P-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidine
  • N-beta-(P-Aminophenyl)ethylnormeperidine
  • N-β-(p-aminophenyl)ethylnormeperidine
External IDs
IDS-NA-012
Product Ingredients
IngredientUNIICASInChI Key
Anileridine hydrochloride915Q054DLC126-12-5ZYTHLJLPPSSDIP-UHFFFAOYSA-N
Anileridine phosphate3584484N8V1976-75-6FLQCEKVTYABVSH-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Leritine Inj 25mg/mlLiquid25 mgIntramuscular; Intravenous; SubcutaneousMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1966-12-312000-06-14Canada
Leritine Tablets 25mgTablet25 mgOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1966-12-312001-06-01Canada
International/Other Brands
Apodol (Bristol-Myers Squibb) / Leritine (Merck)
Categories
UNII
71Q1A3O279
CAS number
144-14-9
Weight
Average: 352.4699
Monoisotopic: 352.21507815
Chemical Formula
C22H28N2O2
InChI Key
LKYQLAWMNBFNJT-UHFFFAOYSA-N
InChI
InChI=1S/C22H28N2O2/c1-2-26-21(25)22(19-6-4-3-5-7-19)13-16-24(17-14-22)15-12-18-8-10-20(23)11-9-18/h3-11H,2,12-17,23H2,1H3
IUPAC Name
ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
SMILES
CCOC(=O)C1(CCN(CCC2=CC=C(N)C=C2)CC1)C1=CC=CC=C1

Pharmacology

Indication

For treatment and management of pain (systemic) and for use as an anesthesia adjunct.

Structured Indications
Not Available
Pharmacodynamics

Anileridine, a potent analgesic, is an analog of pethidine. Anileridine is useful for the relief of moderate to severe pain. It may also be used as an analgesic adjunct in general anesthesia in the same manner as meperidine to reduce the amount of anesthetic needed, to facilitate relaxation, and to reduce laryngospasm. In addition, anileridine exerts mild antihistaminic, spasmolytic and antitussive effects. Anileridine's main pharmacologic action is exerted on the CNS. Respiratory depression, when it occurs, is of shorter duration than that seen with morphine or meperidine when equipotent analgesic doses are used.

Mechanism of action

Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Opioids such as anileridine close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
Absorption

Anileridine is absorbed by all routes of administration.

Volume of distribution
Not Available
Protein binding

> 95%

Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Symptoms of overexposure include dizziness, perspiration, a feeling of warmth, dry mouth, visual difficulty, itching, euphoria, restlessness, nervousness and excitement have been reported.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Anileridine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Weijlard, J.and Pfister, K., Ill; US. Patent 2,966,490; December 27, 1960; assigned to Merck & Co., Inc.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015049
PubChem Compound
8944
PubChem Substance
46505199
ChemSpider
8600
ChEBI
61203
ChEMBL
CHEMBL1201347
Therapeutic Targets Database
DAP001135
PharmGKB
PA164768817
Wikipedia
Anileridine
ATC Codes
N01AH05 — Anileridine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous; Subcutaneous25 mg
TabletOral25 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)275-277Weijlard, J.and Pfister, K., Ill; US. Patent 2,966,490; December 27, 1960; assigned to Merck & Co., Inc.
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0124 mg/mLALOGPS
logP4.05ALOGPS
logP3.64ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.55 m3·mol-1ChemAxon
Polarizability40.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9915
Blood Brain Barrier+0.9819
Caco-2 permeable+0.5093
P-glycoprotein substrateSubstrate0.7222
P-glycoprotein inhibitor INon-inhibitor0.6472
P-glycoprotein inhibitor IINon-inhibitor0.5191
Renal organic cation transporterNon-inhibitor0.5323
CYP450 2C9 substrateNon-substrate0.8596
CYP450 2D6 substrateNon-substrate0.7164
CYP450 3A4 substrateNon-substrate0.5894
CYP450 1A2 substrateNon-inhibitor0.5629
CYP450 2C9 inhibitorNon-inhibitor0.6433
CYP450 2D6 inhibitorInhibitor0.7335
CYP450 2C19 inhibitorNon-inhibitor0.6218
CYP450 3A4 inhibitorNon-inhibitor0.7506
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7202
Ames testNon AMES toxic0.7635
CarcinogenicityNon-carcinogens0.8296
BiodegradationNot ready biodegradable0.9874
Rat acute toxicity3.1563 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9098
hERG inhibition (predictor II)Inhibitor0.6709
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-4490000000-1f331ba53cfcca295590
Mass Spectrum (Electron Ionization)MSsplash10-0002-1290000000-ba6e571da24e144b4e13
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-51d5aa3665f062055774
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uk9-0509000000-da80cc1781c8dd21ddf0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-4c29e57b70578de9cb54
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-f69077c57a03477473bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-2900000000-1a76eeca83116d6bdacd

Taxonomy

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
Piperidinecarboxylic acids / Phenethylamines / Aniline and substituted anilines / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Primary amines
show 4 more
Substituents
Phenylpiperidine / Phenethylamine / Piperidinecarboxylic acid / Aniline or substituted anilines / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid or derivatives / Carboxylic acid ester / Tertiary aliphatic amine
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ethyl ester, substituted aniline, piperidinecarboxylate ester (CHEBI:61203)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:52