Anileridine is an opioid analgesic used to treat moderate to severe pain.
- Generic Name
- DrugBank Accession Number
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.
- Small Molecule
- Approved, Illicit
- Average: 352.4699
- Chemical Formula
- 1-[2-(4-aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl ester
- ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylate
- ethyl 1-(4-aminophenethyl)-4-phenylisonipecotate
- ethyl 1-(p-aminophenethyl)-4-phenylisonipecotate
- External IDs
For treatment and management of pain (systemic) and for use as an anesthesia adjunct.Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.
- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
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.
Target Actions Organism AMu-type opioid receptoragonist Humans
Anileridine is absorbed by all routes of administration.
- Volume of distribution
- Protein binding
- Route of elimination
- Adverse Effects
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Symptoms of overexposure include dizziness, perspiration, a feeling of warmth, dry mouth, visual difficulty, itching, euphoria, restlessness, nervousness and excitement have been reported.
Pathway Category Anileridine Action Pathway Drug action
- Pharmacogenomic Effects/ADRs
- Not Available
- 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.
Drug Interaction Alfentanil The therapeutic efficacy of Anileridine can be increased when used in combination with Alfentanil. Chloroform The therapeutic efficacy of Chloroform can be increased when used in combination with Anileridine. Clonidine The therapeutic efficacy of Anileridine can be increased when used in combination with Clonidine. Desflurane The therapeutic efficacy of Desflurane can be increased when used in combination with Anileridine. Dexmedetomidine The therapeutic efficacy of Anileridine can be increased when used in combination with Dexmedetomidine. Diazepam The therapeutic efficacy of Anileridine can be increased when used in combination with Diazepam. Enflurane The therapeutic efficacy of Anileridine can be increased when used in combination with Enflurane. Esketamine The therapeutic efficacy of Esketamine can be increased when used in combination with Anileridine. Etomidate The therapeutic efficacy of Anileridine can be increased when used in combination with Etomidate. Fentanyl The therapeutic efficacy of Anileridine can be increased when used in combination with Fentanyl.Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more
- Food Interactions
- Take with or without food. The absorption is unaffected by food.
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Anileridine hydrochloride 915Q054DLC 126-12-5 ZYTHLJLPPSSDIP-UHFFFAOYSA-N Anileridine phosphate 3584484N8V 1976-75-6 FLQCEKVTYABVSH-UHFFFAOYSA-N
- International/Other Brands
- Apodol (Bristol-Myers Squibb) / Leritine (Merck)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Leritine Inj 25mg/ml Liquid 25 mg / mL Intramuscular; Intravenous; Subcutaneous Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1966-12-31 2000-06-14 Leritine Tablets 25mg Tablet 25 mg / tab Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1966-12-31 2001-06-01
- ATC Codes
- N01AH05 — Anileridine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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.
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Sub Class
- Direct Parent
- 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 / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds show 4 more
- Amine / Amino acid or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenethylamine / Phenylpiperidine / Piperidinecarboxylic acid / Primary amine / Tertiary aliphatic amine / Tertiary amine show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- ethyl ester, substituted aniline, piperidinecarboxylate ester (CHEBI:61203)
- Affected organisms
- Humans and other mammals
- CAS number
- InChI Key
- IUPAC Name
- ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
- 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
- Merck and co inc
- Not Available
- Dosage Forms
Form Route Strength Liquid Intramuscular; Intravenous; Subcutaneous 25 mg / mL Tablet Oral 25 mg / tab
- Not Available
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 275-277 Weijlard, J.and Pfister, K., Ill; US. Patent 2,966,490; December 27, 1960; assigned to Merck & Co., Inc. logP 3.7 Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0124 mg/mL ALOGPS logP 4.05 ALOGPS logP 3.64 ChemAxon logS -4.5 ALOGPS pKa (Strongest Basic) 8.88 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 55.56 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 106.55 m3·mol-1 ChemAxon Polarizability 40.98 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon
- 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 inhibitor Non-inhibitor 0.6433 CYP450 2D6 inhibitor Inhibitor 0.7335 CYP450 2C19 inhibitor Non-inhibitor 0.6218 CYP450 3A4 inhibitor 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
- Mass Spec (NIST)
- Not Available
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on April 03, 2021 09:41