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) [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

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.

See also

• Pheneridine

References

1. 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.
2. 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. doi:10.1016/S0022-3565(25)11805-3. PMID   13417056.
3. 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.
4. 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 
5. "Discontinued Prescription Drug Products". Canadian Pharmacists' Association. Archived from the original on 19 September 2008. Retrieved 28 July 2008.
6. "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.
7. "Pharmaceutical Information - LERITINE". RxMed. Retrieved 16 June 2010.
8. "Anileridine Consumer Information". MedicineNet. Archived from the original on 28 March 2012. Retrieved 28 July 2008.