Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H17N7O5 |
Molecular Weight | 315.2859 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12N=C(N)N[C@]13N(CCC3(O)O)C(=N)N(O)[C@H]2COC(N)=O
InChI
InChIKey=PPEKGEBBBBNZKS-HGRQIUPRSA-N
InChI=1S/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1
Molecular Formula | C10H17N7O5 |
Molecular Weight | 315.2859 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Neosaxitoxin is a site-1 specific sodium channel blocker which acts synergistically with local anesthetics to provide surgical anesthesia by peripheral nerve blocks or local infiltration and markedly increases the duration of post-operative analgesia. Saxitoxin and neosaxitoxin, small molecules synthesized by marine dinoflagellates and freshwater cyanobacteria. Neosaxitoxin, one of the saxitoxin analogs, differs from saxitoxin by the addition of one oxygen atom, wherein the hydrogen (-H) at Nitrogen 1 in saxitoxin is replaced by a hydroxyl group (-OH) in neosaxitoxin. Neosaxitoxin has shown greater potency than saxitoxin and its analogs and is also more potent than tetrodotoxin in in vitro and in vivo animal studies.Neosaxitoxin showed an effective local anesthetic effect when injected in the subcutaneous plane. The efficacy of a 50-ug dose of neosaxitoxin was shown. Neosaxitoxin has poor affinity for the cardiac isoform of the sodium channel and does not cross the blood–brain barrier, thus this compound is virtually devoid of cardiac and central nervous system toxicity—the limiting toxicities of traditional local anesthetics.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Multiple saxitoxin-binding sites in bullfrog muscle: tetrodotoxin-sensitive sodium channels and tetrodotoxin-insensitive sites of unknown function. | 1988 Feb |
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Interactions of neosaxitoxin with the sodium channel of the frog skeletal muscle fiber. | 1991 Mar |
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A study of ten toxins associated with paralytic shellfish poison using prechromatographic oxidation and liquid chromatography with fluorescence detection. | 1991 Mar-Apr |
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Liquid chromatographic determination of paralytic shellfish poisons in shellfish after prechromatographic oxidation. | 1991 Nov-Dec |
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Neosaxitoxin as a local anesthetic: preliminary observations from a first human trial. | 2007 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17264729
Subcutaneous injections were made in the middle posterior skin of the calf: one leg received 50 ug neosaxitoxin, and the contra-lateral leg received placebo.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18232710
Curator's Comment: The ability of Neosaxitoxin to inhibit the veratridine-induced
cell depolarization in cultured neurons was evaluated using a fixed concentration of 50 uM veratridine to evoke complete cell
depolarization in primary cultures of mouse cerebellar neurons.
Neosaxitoxin inhibited veratridine-induced cell depolarization with an IC50 value of 6.2 nM
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:15:11 UTC 2023
by
admin
on
Fri Dec 15 19:15:11 UTC 2023
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Record UNII |
6YRL8BWD9H
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Record Status |
Validated (UNII)
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Record Version |
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64296-20-4
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6YRL8BWD9H
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C034902
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DTXSID70880098
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DB12989
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Neosaxitoxin
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167561
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300000042530
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21117946
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR RESISTANT |
NaV1.5, NaV1.8, and NaV1.9 are tetrodotoxin-resistant to varying degrees
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR RESISTANT |
NaV1.5, NaV1.8, and NaV1.9 are tetrodotoxin-resistant to varying degrees
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR RESISTANT |
NaV1.5, NaV1.8, and NaV1.9 are tetrodotoxin-resistant to varying degrees
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Related Record | Type | Details | ||
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ACTIVE MOIETY |