Anileridine

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Anileridine
Anileridine2DCSD.svg
Anileridine 3D BS.png
Clinical data
Trade names Leritine
AHFS/Drugs.com Monograph
Routes of
administration
Tablets, injection
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding > 95%
Metabolism Hepatic
Identifiers
  • 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
Formula C22H28N2O2
Molar mass 352.478 g·mol−1
3D model (JSmol)
Melting point 83 °C (181 °F)
  • O=C(OCC)C3(c1ccccc1)CCN(CCc2ccc(N)cc2)CC3
  • 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 Yes check.svgY
  • Key:LKYQLAWMNBFNJT-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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.

Contents

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

Related Research Articles

<span class="mw-page-title-main">Pethidine</span> Opioid analgesic

Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines, the prodines, bemidones and others more distant, including diphenoxylate and analogues.

<span class="mw-page-title-main">Dipipanone</span> Opioid analgesic drug

Dipipanone (Pipadone) is a strong opioid analgesic drug, used for acute pain by mouth (PO) for adults — initially 10 mg every 6 hours, then increased if necessary up to 30 mg every 6 hours, with the dose to be increased gradually. It is often used in instances where morphine is indicated but cannot be used due to the patient being allergic to morphine. In analgesic potency 25 mg dipipanone is approximately equivalent to 10 mg morphine.

<span class="mw-page-title-main">Phenoperidine</span> Opioid analgesic drug

Phenoperidine, is an opioid analgesic which is structurally related to pethidine and is used clinically as a general anesthetic.

<span class="mw-page-title-main">Metopon</span> Analgesic drug

Metopon is an opioid analogue that is a methylated derivative of hydromorphone which was invented in 1929 as an analgesic.

<span class="mw-page-title-main">Phenadoxone</span> Opioid analgesic drug

Phenadoxone is an opioid analgesic of the open chain class invented in Germany by Hoechst in 1947. It is one of a handful of useful synthetic analgesics which were used in the United States for various lengths of time in the 20 or so years after the end of the Second World War but which were withdrawn from the market for various or no known reason and which now are mostly in Schedule I of the United States' Controlled Substances Act of 1970, or in Schedule II but not produced or marketed in the US. Others on this list are ketobemidone (Ketogin), dextromoramide, phenazocine, dipipanone, piminodine (Alvodine), propiram (Algeril), anileridine (Leritine) and alphaprodine (Nisentil).

<span class="mw-page-title-main">Hydroxypethidine</span> Chemical compound

Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency, and it also has NMDA antagonist properties like its close relative ketobemidone.

<span class="mw-page-title-main">Prodine</span> Opioid analgesic

Prodine is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s.

<span class="mw-page-title-main">Allylprodine</span> Chemical compound

Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic & non-phenolic opioids bind at different sites of the opiate receptor.

<span class="mw-page-title-main">Meprodine</span> Chemical compound

Meprodine is an opioid analgesic that is an analogue of pethidine (meperidine). It is closely related to the drug prodine, the only difference being that meprodine has an ethyl group rather than a methyl at the 3-position of the piperidine ring.

<span class="mw-page-title-main">Piminodine</span> Opioid analgesic drug

Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine). It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2–4 hours; 7.5–10 mg via the subcutaneous route is the most common starting dose, being equal to 80–100 mg of pethidine, 40–60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.

<span class="mw-page-title-main">Propiram</span> Opioid analgesic drug

Propiram is a partial μ-opioid receptor agonist and weak μ antagonist analgesic from the ampromide family of drugs related to other drugs such as phenampromide and diampromide. It was invented in 1963 in the United Kingdom by Bayer but was not widely marketed, although it saw some limited clinical use, especially in dentistry. Propiram reached Phase III clinical trials in the United States and Canada.

<span class="mw-page-title-main">Phenampromide</span> Chemical compound

Phenampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and diampromide. It was invented in the 1960s by American Cyanamid Co. Although never given a general release, it was trialled and 50mg codeine ≈ 60mg phenampromide. Tests on the 2 isomers showed that all of the analgesic effects were caused by the (S) isomer. In the book a 4-phenyl group added to the piperidine-ring produces a drug some x60 morphine. The potency derives from the fact that it similar in structure to fentanyl. Like fentanyl, the addition of a 4-hydroxy group to the 4-piperidylphenyl derivative increases potency to x150 morphine for the racemic compound

<span class="mw-page-title-main">Norpethidine</span> Chemical compound

Norpethidine is a 4-phenylpiperidine derivative that is both a precursor to, and the toxic metabolite of, pethidine (meperidine). It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9233. The 2014 annual manufacturing quota was 11 grams (0.39 oz).

<span class="mw-page-title-main">Benzethidine</span> Chemical compound

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine.

<span class="mw-page-title-main">Etoxeridine</span> Chemical compound

Etoxeridine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">Furethidine</span> Chemical compound

Furethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine), but with around 25x higher potency. According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine.

<span class="mw-page-title-main">Morpheridine</span> Chemical compound

Morpheridine (Morpholinoethylnorpethidine) is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine). It is a strong analgesic with around 4 times the potency of pethidine, and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.

<span class="mw-page-title-main">Pethidine intermediate A</span> Chemical compound

Pethidine intermediate A is a 4-phenylpiperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active, so pethidine intermediate A might also show opioid effects. It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232. The 2014 annual manufacturing quota was 6 grammes.

<span class="mw-page-title-main">Isomethadone</span> Chemical compound

Isomethadone (INN, BAN; trade nameLiden; also known as isoamidone) is a synthetic opioid analgesic and antitussive related to methadone that was used formerly as a pharmaceutical drug but is now no longer marketed. Isomethadone was used as both an analgesic and antitussive. It binds to and activates both the μ- and δ-opioid receptors, with the (S)-isomer being the more potent of its two enantiomers. Isomethadone is a Schedule II controlled substance in the United States, with an ACSCN of 9226 and a 2014 aggregate manufacturing quota of 5 g. The salts in use are the hydrobromide (HBr, free base conversion ratio 0.793), hydrochloride (HCl, 0.894), and HCl monohydrate (0.850). Isomethadone is also regulated internationally as a Schedule I controlled substance under the United Nations Single Convention on Narcotic Drugs of 1961.

<span class="mw-page-title-main">Noracymethadol</span> Chemical compound

Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed. In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness. Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone. Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961. The salts known are the gluconate and hydrochloride (0.903).

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. 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.