Alpidem

Alpidem
Clinical data
Trade namesAnanxyl
Other namesSL 80.0342; SL800342; SL-800342
Routes of
administration		Oral administration
Drug classNonbenzodiazepine; GABAA receptor positive allosteric modulator; Anxiolytic
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability32–35% (estimated)[1][2]
Protein binding99.4%[1]
MetabolismExtensive (hydroxylation, dealkylation, conjugation)[1]
MetabolitesMany (some active)[1]
Onset of action1.0–2.5 hours (Cmax)[1]
Elimination half-lifeYoung adults: 19 hours (7–44 hours)[1]
Elderly: 22.6 ± 2.3 hours[1]
Children: 11.4 ± 1.9 hours[1]
ExcretionMainly feces[1]
Identifiers
  • 2-[6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]-N,N-dipropylacetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.216.305 Edit this at Wikidata
Chemical and physical data
FormulaC21H23Cl2N3O
Molar mass404.34 g·mol−1
3D model (JSmol)
  • CCCN(CCC)C(=O)CC1=C(N=C2N1C=C(C=C2)Cl)C3=CC=C(C=C3)Cl
  • InChI=1S/C21H23Cl2N3O/c1-3-11-25(12-4-2)20(27)13-18-21(15-5-7-16(22)8-6-15)24-19-10-9-17(23)14-26(18)19/h5-10,14H,3-4,11-13H2,1-2H3 checkY
  • Key:JRTIDHTUMYMPRU-UHFFFAOYSA-N checkY
  (verify)

Alpidem, sold under the brand name Ananxyl, is a nonbenzodiazepine anxiolytic medication which was briefly used to treat anxiety disorders but is no longer marketed.[3] It was previously marketed in France, but was discontinued due to liver toxicity.[3] Alpidem is taken by mouth.[1]

Side effects of alpidem include sedation, fatigue, dizziness, and headache, among others.[3][2][4] It has much less to no impact on cognition, memory, and psychomotor function relative to benzodiazepines.[3][5] Similarly, no rebound anxiety or withdrawal symptoms have been observed with alpidem.[3][2] Rarely, alpidem can cause serious liver toxicity, including liver failure and death.[3] Alpidem is a nonbenzodiazepine of the imidazopyridine family, structurally related to the Z-drug zolpidem,[1] and acts as a GABAA receptor positive allosteric modulator of the benzodiazepine site of the receptor complex.[3] In contrast to zolpidem however, alpidem has anxiolytic effects rather than sedative or hypnotic effects at normal therapeutic doses.[3]

Alpidem was first described by 1982[6][7] and was introduced for medical use in France in 1991.[3][8][9] It was also under development for use in other countries in the 1990s, but development was discontinued and the drug was never marketed in any other country.[8][9] Alpidem was withdrawn from the market in France in 1993 due to liver toxicity.[10][11][12][13][3]

  1. ^ a b c d e f g h i j k Durand A, Thénot JP, Bianchetti G, Morselli PL (1992). "Comparative pharmacokinetic profile of two imidazopyridine drugs: zolpidem and alpidem". Drug Metabolism Reviews. 24 (2): 239–266. doi:10.3109/03602539208996294. PMID 1576937.
  2. ^ a b c Morselli PL (May 1990). "On the therapeutic action of alpidem in anxiety disorders: an overview of the European data". Pharmacopsychiatry. 23 (Suppl 3): 129–134. doi:10.1055/s-2007-1014549. PMID 1974073.
  3. ^ a b c d e f g h i j Skolnick P (November 2012). "Anxioselective anxiolytics: on a quest for the Holy Grail". Trends in Pharmacological Sciences. 33 (11): 611–620. doi:10.1016/j.tips.2012.08.003. PMC 3482271. PMID 22981367.
  4. ^ Cite error: The named reference pmid1974071 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid1974069 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  7. ^ Saletu B, Grünberger J, Linzmayer L (April 1986). "Pharmacokinetic and dynamic studies with a new anxiolytic imidazo-pyridine alpidem utilizing pharmaco-EEG and psychometry". International Clinical Psychopharmacology. 1 (2): 145–164. doi:10.1097/00004850-198604000-00006. PMID 2883214.
  8. ^ a b Cite error: The named reference AdisInsight was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
  10. ^ Guengerich FP (2011). "Mechanisms of drug toxicity and relevance to pharmaceutical development". Drug Metabolism and Pharmacokinetics. 26 (1): 3–14. doi:10.2133/dmpk.dmpk-10-rv-062. PMC 4707670. PMID 20978361.
  11. ^ "ANANXYL WITHDRAWN FROM MARKET IN FRANCE - Pharmaceutical industry news".
  12. ^ "La commercialisation de l'Ananxyl est suspendue pour un an". Le Monde.fr. 26 October 1993.
  13. ^ WHO Drug Information Vol. 8, No. 2, 1994, page 64