Anileridine

Anileridine (trade name: Leritine) is a synthetic analgesic drug[1] and is a member of the piperidine class of analgesic agents[2] developed by Merck & Co. in the 1950s.[3] 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
Clinical data
Trade namesLeritine
AHFS/Drugs.comMonograph
Routes of
administration		Tablets, injection
ATC code
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule II
Pharmacokinetic data
Protein binding> 95%
MetabolismHepatic
Identifiers
IUPAC name
  • Ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28N2O2
Molar mass352.478 g·mol−1
3D model (JSmol)
Melting point83 °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 is no longer manufactured in the US or Canada.[4] 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.[5] It is also under international control per UN treaties.

Administration

As tablets or injection.[6]

Pharmacokinetics

Anileridine usually takes effect within 15 minutes of either oral or intravenous administration, and lasts 2–3 hours.[7] It is mostly metabolized by the liver.

References
  1. 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.
  2. 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.
  3. 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
  4. "Discontinued Prescription Drug Products". Canadian Pharmacists' Association. Archived from the original on 19 September 2008. Retrieved 28 July 2008.
  5. "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.
  6. "Pharmaceutical Information - LERITINE". RxMed. Retrieved 16 June 2010.
  7. "Anileridine Consumer Information". MedicineNet. Archived from the original on 28 March 2012. Retrieved 28 July 2008.



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