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Velnacrine

From Wikipedia, the free encyclopedia
Active metabolite of tacrine
Velnacrine
Names
IUPAC name
9-amino-1,2,3,4-tetrahydroacridin-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C13H14N2O/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15)
    Key: HLVVITIHAZBPKB-UHFFFAOYSA-N
  • C1CC(C2=C(C3=CC=CC=C3N=C2C1)N)O
Properties
C13H14N2O
Molar mass214.268 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Velnacrine, also known as1-hydroxytacrine,[1] is an inhibitor ofcholinesterase enzymes. It is also ametabolite oftacrine.[2]

Pharmacology

[edit]

Velnacrine is able to inhibitacetylcholinesterase (AChE),[3] this results in elevated levels ofacetylcholine, as AChE is the enzyme that hydrolyzes acetylcholine.[4] It is also able to inhibitbutyrylcholinesterase.[5]

Therapeutic potential

[edit]

Velnacrine, as many othercholinergics, has been described as possibly useful to help manage symptoms of Alzheimer's disease. Some research has described the drug as having benefits over placebo[6] and an acceptable safety profile.[7] However, a review described available data as not proving efficacy and showing evidence of toxicity.[8] Additionally, theFDA voted against recommending approval of velnacrine.[8]

References

[edit]
  1. ^PubChem."Velnacrine".pubchem.ncbi.nlm.nih.gov. Retrieved2025-07-31.
  2. ^Viau, C. J.; Curren, R. D.; Wallace, K. (1993). "Cytotoxicity of tacrine and velnacrine metabolites in cultured rat, dog and human hepatocytes".Drug and Chemical Toxicology.16 (3):227–239.doi:10.3109/01480549309081817.ISSN 0148-0545.PMID 8404544.
  3. ^"AID 31170 - Inhibition of acetylcholinesterase (AChE) of human red blood cell (type XIII) by modified radiometric AChE assay - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2025-07-31.
  4. ^Trang, Amy; Khandhar, Paras B. (2025),"Physiology, Acetylcholinesterase",StatPearls, Treasure Island (FL): StatPearls Publishing,PMID 30969557, retrieved2025-07-31
  5. ^"AID 44453 - Inhibition of (BChE) Butyrylcholinesterase of horse serum - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2025-07-31.
  6. ^Antuono, P. G. (1995-09-11). "Effectiveness and safety of velnacrine for the treatment of Alzheimer's disease. A double-blind, placebo-controlled study. Mentane Study Group".Archives of Internal Medicine.155 (16):1766–1772.doi:10.1001/archinte.1995.00430160102010.ISSN 0003-9926.PMID 7654110.
  7. ^Puri, S. K.; Ho, I.; Hsu, R.; Lassman, H. B. (October 1990). "Multiple dose pharmacokinetics, safety, and tolerance of velnacrine (HP 029) in healthy elderly subjects: a potential therapeutic agent for Alzheimer's disease".Journal of Clinical Pharmacology.30 (10):948–955.doi:10.1002/j.1552-4604.1990.tb03576.x.ISSN 0091-2700.PMID 2229455.
  8. ^abBirks, J.; Wilcock, G. G. W. (2004). "Velnacrine for Alzheimer's disease".The Cochrane Database of Systematic Reviews (2) CD004748.doi:10.1002/14651858.CD004748.ISSN 1469-493X.PMID 15106259.
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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