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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ApodolBristol-Myers Squibb
LeritineMerck
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Phenylacetate
  • Piperidinecarboxylic acid
  • Phenethylamine
  • Substituted aniline
  • Aralkylamine
  • Aniline
  • Benzenoid
  • Primary aromatic amine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
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 substrateNon-inhibitor0.6433
CYP450 2D6 substrateInhibitor0.7335
CYP450 2C19 substrateNon-inhibitor0.6218
CYP450 3A4 substrateNon-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
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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
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
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