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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
Structure of NEOSAXITOXIN

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Multiple saxitoxin-binding sites in bullfrog muscle: tetrodotoxin-sensitive sodium channels and tetrodotoxin-insensitive sites of unknown function.
1988 Feb
Interactions of neosaxitoxin with the sodium channel of the frog skeletal muscle fiber.
1991 Mar
Liquid chromatographic determination of paralytic shellfish poisons in shellfish after prechromatographic oxidation.
1991 Nov-Dec
Neosaxitoxin as a local anesthetic: preliminary observations from a first human trial.
2007 Feb
Patents

Sample Use Guides

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
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 Fri Dec 15 19:15:11 UTC 2023
Edited
by admin
on Fri Dec 15 19:15:11 UTC 2023
Record UNII
6YRL8BWD9H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEOSAXITOXIN
INCI  
Official Name English
NEOSTX
Brand Name English
(3AS,4R,10AS)-2-AMINO-4-(((AMINOCARBONYL)OXY)METHYL)-3A,4,5,6,8,9-HEXAHYDRO-5-HYDROXY-6-IMINO-1H,10H-PYRROLO(1,2-C)PURINE-10,10-DIOL
Systematic Name English
1H,10H-PYRROLO(1,2-C)PURINE-10,10-DIOL, 2-AMINO-4-(((AMINOCARBONYL)OXY)METHYL)-3A,4,5,6,8,9-HEXAHYDRO-5-HYDROXY-6-IMINO-, (3AS-(3A.ALPHA.,4.ALPHA.,10AR*))-
Systematic Name English
Code System Code Type Description
CAS
64296-20-4
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
PRIMARY
FDA UNII
6YRL8BWD9H
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
PRIMARY
MESH
C034902
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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EPA CompTox
DTXSID70880098
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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DRUG BANK
DB12989
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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WIKIPEDIA
Neosaxitoxin
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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CHEBI
167561
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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SMS_ID
300000042530
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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PUBCHEM
21117946
Created by admin on Fri Dec 15 19:15:11 UTC 2023 , Edited by admin on Fri Dec 15 19:15:11 UTC 2023
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ACTIVE MOIETY