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Identification
NameAnileridine
Accession NumberDB00913  (APRD00741)
Typesmall molecule
Groupsapproved, 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
SynonymLanguageCode
1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl esterNot AvailableNot Available
AnileridinaSpanishINN
AnileridinumLatinINN
Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylateNot AvailableNot Available
ethyl 1-(4-aminophenethyl)-4-phenylisonipecotateNot AvailableNot Available
Ethyl 1-(P-aminophenethyl)-4-phenylisonipecotateNot AvailableNot Available
N-(beta-(P-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineNot AvailableNot Available
N-beta-(P-Aminophenyl)ethylnormeperidineNot AvailableNot Available
N-β-(p-aminophenyl)ethylnormeperidineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
ApodolBristol-Myers Squibb
LeritineMerck
Brand mixturesNot Available
CategoriesNot Available
CAS number144-14-9
WeightAverage: 352.4699
Monoisotopic: 352.21507815
Chemical FormulaC22H28N2O2
InChI KeyLKYQLAWMNBFNJT-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassPhenylpiperidines
Direct parentPhenylpiperidines
Alternative parentsPhenylacetic Acid Derivatives; Phenethylamines; Piperidinecarboxylic Acids; Anilines; Primary Aromatic Amines; Tertiary Amines; Carboxylic Acid Esters; Ethers; Enolates; Polyamines
Substituentsphenylacetate; piperidinecarboxylic acid; phenethylamine; aniline; primary aromatic amine; benzene; carboxylic acid ester; tertiary amine; polyamine; ether; carboxylic acid derivative; enolate; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Pharmacology
IndicationFor treatment and management of pain (systemic) and for use as an anesthesia adjunct.
PharmacodynamicsAnileridine, 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 actionOpiate 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.
AbsorptionAnileridine is absorbed by all routes of administration.
Volume of distributionNot Available
Protein binding> 95%
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwayCategorySMPDB ID
Anileridine Action PathwayDrug actionSMP00674
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9915
Blood Brain Barrier + 0.9819
Caco-2 permeable + 0.5093
P-glycoprotein substrate Substrate 0.7222
P-glycoprotein inhibitor I Non-inhibitor 0.6472
P-glycoprotein inhibitor II Non-inhibitor 0.5191
Renal organic cation transporter Non-inhibitor 0.5323
CYP450 2C9 substrate Non-substrate 0.8596
CYP450 2D6 substrate Non-substrate 0.7164
CYP450 3A4 substrate Non-substrate 0.5894
CYP450 1A2 substrate Non-inhibitor 0.5629
CYP450 2C9 substrate Non-inhibitor 0.6433
CYP450 2D6 substrate Inhibitor 0.7335
CYP450 2C19 substrate Non-inhibitor 0.6218
CYP450 3A4 substrate Non-inhibitor 0.7506
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7202
Ames test Non AMES toxic 0.7635
Carcinogenicity Non-carcinogens 0.8296
Biodegradation Not ready biodegradable 0.9874
Rat acute toxicity 3.1563 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9098
hERG inhibition (predictor II) Inhibitor 0.6709
Pharmacoeconomics
Manufacturers
  • Merck and co inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point275-277Weijlard, 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 solubility1.24e-02 g/lALOGPS
logP4.05ALOGPS
logP3.64ChemAxon
logS-4.5ALOGPS
pKa (strongest basic)8.88ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area55.56ChemAxon
rotatable bond count7ChemAxon
refractivity106.55ChemAxon
polarizability40.98ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

General ReferenceNot Available
External Links
ResourceLink
PubChem Compound8944
PubChem Substance46505199
ChemSpider8600
ChEBI61203
ChEMBLCHEMBL1201347
Therapeutic Targets DatabaseDAP001135
PharmGKBPA164768817
Drug Product Database10014
WikipediaAnileridine
ATC CodesN01AH05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

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
  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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 28, 2014 10:06