Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H27NO3 |
Molecular Weight | 293.4012 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1
InChI
InChIKey=RGOVYLWUIBMPGK-UHFFFAOYSA-N
InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
DescriptionSources: https://gp2u.com.au/static/pdf/F/FINALGON-PI.pdfCurator's Comment: Description was created based on several sources, including http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/?gclid=CPb2kbG98M4CFULecgodQzgPcg and http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015186.pdf
Sources: https://gp2u.com.au/static/pdf/F/FINALGON-PI.pdf
Curator's Comment: Description was created based on several sources, including http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/?gclid=CPb2kbG98M4CFULecgodQzgPcg and http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015186.pdf
Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. Nonivamide (trade name Finalgon ) is used in topical ointments and creams to relieve minor aches and pains of muscles and joints. Nonivamide is also available in large adhesive bandages that can be applied to the back. Concentrations are typically between 0.025% and 0.075%. Nonivamide is a TRPV1 ion channel agonist.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6202305
Curator's Comment: Penetrant in rats
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Fatty acid uptake Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952 |
1.08 µM [IC50] | ||
Target ID: CHEMBL2924 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952 |
|||
Target ID: CHEMBL5102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22796184 |
223.0 nM [EC50] | ||
Target ID: CHEMBL4794 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination. | 2005 Jul 14 |
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Localization of SSeCKS in unmyelinated primary sensory neurons. | 2008 Mar 19 |
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A comparison of pretreatment with a topical combination of nonivamide and nicoboxil and surgical delay in a random pattern skin flap model. | 2009 Jul |
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Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation. | 2009 Jul 15 |
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Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides. | 2009 Mar |
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N-vanillylnonanamide tested as a non-toxic antifoulant, applied to surfaces in a polyurethane coating. | 2009 Sep |
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Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers. | 2010 |
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Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury. | 2012 Jan 1 |
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Transient receptor potential vanilloid-1 (TRPV1) is a mediator of lung toxicity for coal fly ash particulate material. | 2012 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://gp2u.com.au/static/pdf/F/FINALGON-PI.pdf
Curator's Comment: FINALGON cream contains nonivamide and butoxyethyl nicotinate
No more than 5 mm should be used to cover an area the size of a hand.
Route of Administration:
Topical
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952
Addition of 1 to 100 uM of nonivamide reduced fatty acid uptake in a dose-dependent manner in Caco-2 cells
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
70709
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100000083590
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DB11324
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NONIVAMIDE
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C005871
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ACTIVE MOIETY