Anileridine

Identification

Summary

Anileridine is an opioid analgesic used to treat moderate to severe pain.

Generic Name
Anileridine
DrugBank Accession Number
DB00913
Background

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.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Weight
Average: 352.4699
Monoisotopic: 352.21507815
Chemical Formula
C22H28N2O2
Synonyms
  • 1-[2-(4-aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl ester
  • Anileridina
  • Anileridine
  • Anileridinum
  • ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylate
  • ethyl 1-(4-aminophenethyl)-4-phenylisonipecotate
  • ethyl 1-(p-aminophenethyl)-4-phenylisonipecotate
  • N-(β-(p-aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidine
  • N-β-(p-aminophenyl)ethylnormeperidine
External IDs
  • IDS-NA-012

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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Toxicity

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

Pathways
PathwayCategory
Anileridine Action PathwayDrug action
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.
DrugInteraction
AlfentanilThe therapeutic efficacy of Anileridine can be increased when used in combination with Alfentanil.
ChloroformThe therapeutic efficacy of Chloroform can be increased when used in combination with Anileridine.
ClonidineThe therapeutic efficacy of Anileridine can be increased when used in combination with Clonidine.
DesfluraneThe therapeutic efficacy of Desflurane can be increased when used in combination with Anileridine.
DexmedetomidineThe therapeutic efficacy of Anileridine can be increased when used in combination with Dexmedetomidine.
Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Anileridine hydrochloride915Q054DLC126-12-5ZYTHLJLPPSSDIP-UHFFFAOYSA-N
Anileridine phosphate3584484N8V1976-75-6FLQCEKVTYABVSH-UHFFFAOYSA-N
International/Other Brands
Apodol (Bristol-Myers Squibb) / Leritine (Merck)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Leritine Inj 25mg/mlLiquid25 mg / mLIntramuscular; Intravenous; SubcutaneousMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1966-12-312000-06-14Canada flag
Leritine Tablets 25mgTablet25 mg / tabOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1966-12-312001-06-01Canada flag

Categories

ATC Codes
N01AH05 — Anileridine
Drug Categories
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
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
Amine / Amino acid or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
ethyl ester, substituted aniline, piperidinecarboxylate ester (CHEBI:61203)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
71Q1A3O279
CAS number
144-14-9
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

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
Human Metabolome Database
HMDB0015049
KEGG Drug
D02941
PubChem Compound
8944
PubChem Substance
46505199
ChemSpider
8600
RxNav
17933
ChEBI
61203
ChEMBL
CHEMBL1201347
ZINC
ZINC000000608179
Therapeutic Targets Database
DAP001135
PharmGKB
PA164768817
Wikipedia
Anileridine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidIntramuscular; Intravenous; Subcutaneous25 mg / mL
TabletOral25 mg / tab
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-MSsplash10-004i-1290000000-5ad6d8738bbf2736cf67
GC-MS Spectrum - EI-BGC-MSsplash10-0002-4490000000-1f331ba53cfcca295590
Mass Spectrum (Electron Ionization)MSsplash10-0002-1290000000-ba6e571da24e144b4e13
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-08a9e580a6af10e24b39
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0019000000-6138b7382cf056e573d6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fi0-0589000000-11cfc3478388b73b93b0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfr-1019000000-bb368f4f29504c7dea0c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ul0-0954000000-c0c210e2638153e9e6a1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1941000000-8bba712b06f7f37825b1
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]-193.6024361
predicted
DarkChem Lite v0.1.0
[M-H]-188.80054
predicted
DeepCCS 1.0 (2019)
[M+H]+193.6624361
predicted
DarkChem Lite v0.1.0
[M+H]+191.34564
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.9185361
predicted
DarkChem Lite v0.1.0
[M+Na]+199.80392
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:54