Anileridine
Clinical data


Trade names	Leritine
AHFS/Drugs.com	Monograph
Routes of administration	Tablets, injection
ATC code	N01AH05 (WHO)
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class A1 (Narcotic drugs)^[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule II
Pharmacokinetic data
Protein binding	> 95%
Metabolism	Hepatic
Identifiers
IUPAC name Ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
CAS Number	144-14-9^Y
PubChem CID	8944
IUPHAR/BPS	7115
DrugBank	DB00913^Y
ChemSpider	8600^Y
UNII	71Q1A3O279
KEGG	D02941^Y
ChEBI	CHEBI:61203^Y
ChEMBL	ChEMBL1201347^N
CompTox Dashboard (EPA)	DTXSID8022610
Chemical and physical data
Formula	C₂₂H₂₈N₂O₂
Molar mass	352.478 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	83 °C (181 °F)
SMILES O=C(OCC)C3(c1ccccc1)CCN(CCc2ccc(N)cc2)CC3
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^Y Key:LKYQLAWMNBFNJT-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Anileridine (trade name: Leritine) is a synthetic analgesic drug^[2] and is a member of the piperidine class of analgesic agents^[3] developed by Merck & Co. in the 1950s.^[4] It differs from pethidine (meperidine) in that the N-methyl group of meperidine is replaced by an N-aminophenethyl group, which increases its analgesic activity.

Anileridine is no longer manufactured in the US or Canada.^[5] Anileridine is in Schedule II of the Controlled Substances Act 1970 of the United States as ACSCN 9020 with a zero aggregate manufacturing quota as of 2014. The free base conversion ratio for salts includes 0.83 for the dihydrochloride and 0.73 for the phosphate.^[6] It is also under international control per UN treaties.

Administration

[edit]

As tablets or injection.^[7]

Pharmacokinetics

[edit]

Anileridine usually takes effect within 15 minutes of either oral or intravenous administration, and lasts 2–3 hours.^[8] It is mostly metabolized by the liver.

References

[edit]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Orahovats PD, Lehman EG, Chapin EW (January 1957). "Pharmacology of ethyl-1-(4-aminophenethyl)-4-phenylisonipecotate, anileridine, a new potent synthetic analgesic". The Journal of Pharmacology and Experimental Therapeutics. 119 (1): 26–34. PMID 13417056.
^ Stage JT (August 1957). "Anileridine as an anesthetic agent". The Journal of the Florida Medical Association. Florida Medical Association. 44 (2): 143–5. PMID 13449255.
^ US 2897204, Frank A Cutler Jr FA, Chemerda JM, "Substituted piperidines and methods for making same", issued 28 July 1959, assigned to Merck and Co Inc
^ "Discontinued Prescription Drug Products". Canadian Pharmacists' Association. Archived from the original on 19 September 2008. Retrieved 28 July 2008.
^ "Federal Register Notices: Quotas - 2014". Diversion Control Division, Drug Enforcement Agency. U.S. Department of Justice. 25 August 2014. Archived from the original on 4 March 2016. Retrieved 26 February 2016.
^ "Pharmaceutical Information - LERITINE". RxMed. Retrieved 16 June 2010.
^ "Anileridine Consumer Information". MedicineNet. Archived from the original on 28 March 2012. Retrieved 28 July 2008.

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen ^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac ^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib ^‡ Parecoxib Rofecoxib ^‡ Valdecoxib ^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline^#) Na_v1.7/1.8-selective: DSP-2230^§ Funapide^§ PF-05089771^§
Potassium openers	Flupirtine^‡

Myorelaxants

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

General anesthetics (N01A)

Inhalational

Injection

Phenols	Ciprofol^† Fospropofol Propofol^#
Barbiturates	Amobarbital Hexobarbital Methohexital Narcobarbital Thiamylal Thiopental^# Thiotetrabarbital
Benzodiazepines	Midazolam^# Diazepam^# Lorazepam^# Remimazolam
Opioids	Morphine^# Oxycodone Anileridine^‡ Embutramide^‡ Fentanyl^# Alfentanil Phenoperidine Remifentanil÷ Sufentanil
Arylcyclohexylamines	Esketamine Ketamine^# Phencyclidine^‡ Tiletamine
Neuroactive steroids	Alfadolone Alfaxalone Hydroxydione
Others	Etomidate Propanidid^‡