Anileridine

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); 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 ;
PubChem CID	8944;
IUPHAR/BPS	7115;
DrugBank	DB00913 ;
ChemSpider	8600 ;
UNII	71Q1A3O279;
KEGG	D02941 ;
ChEBI	CHEBI:61203 ;
ChEMBL	ChEMBL1201347 ;
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 ; Key:LKYQLAWMNBFNJT-UHFFFAOYSA-N ;
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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

As tablets or injection.^[7]

Pharmacokinetics

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

^ 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.