Apamin

Modify Date: 2025-10-24 09:13:56

Apamin Structure
Apamin structure
 Common Name Apamin
CAS Number 24345-16-2 Molecular Weight 2027.339
Density 1.6±0.1 g/cm3 Boiling Point N/A
Molecular Formula C79H131N31O24S4 Melting Point N/A
MSDS Chinese USA Flash Point N/A
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Apamin


Apamin, an 18 amino acid peptide neurotoxin found in apitoxin (bee venom), is known to block Ca2+-activated K+ channels and prevent carbon tetrachloride-induced liver fibrosis.

 Names

Name Apamin
Synonym More Synonyms

 Apamin Biological Activity

Description Apamin, an 18 amino acid peptide neurotoxin found in apitoxin (bee venom), is known to block Ca2+-activated K+ channels and prevent carbon tetrachloride-induced liver fibrosis.
Related Catalog
Target

K+ channel[1]

In Vitro Apamin is an 18 amino acid peptide neurotoxin found in apitoxin (bee venom). It has long been known as a specifically selective blocker of Ca2+-activated K+ (SK) channels. Apamin inhibits liver fibrosis in a 3,5-diethoxycarbonyl-1,4-dihydrocollidine (DDC)-induced mouse model as determined by hematoxylin and eosin staining. Apamin treatment attenuates inflammatory cytokine expression, including IL-6, IFN-γ, TNF-α and IL-1β compared with expression levels in the DDC-fed group[1]. Apamin is an 18 amino acid peptide neurotoxin found in apitoxin (bee venom). Apamin, a neurotoxin extracted from bee venom, specifically binds to a particular class of Ca2+-activated K+ channels which are involved in the slow afterhyperpolarization (S-AHP) that follows action potentials in many excitable cell[2].
In Vivo To investigate the anti-fibrotic effect of Apamin on ECM deposition in the DDC-fed mice, Liver fibrosis induced by DDC is confirmed by induction of fibrogenic genes, FSP-1, α-smooth muscle actin (α-SMA) and collagen I expression. Expression of α-SMA is strongly expressed in the myofibroblasts and HSCs around the proliferated bile duct in the DDC-fed group and clearly with the Apamin treatment. Moreover, expression of collagen I in the DDC-fed group is significantly increased, especially in the portal tracts[1].
Cell Assay HSC-T6 cells, an immortalized rat hepatic stellate cell line, which has a stable phenotype and biochemical characteristics. Cells are cultured at 37°C in a humidified incubator under a 5% CO2 atmosphere. HSC-T6 cells are seeded in complete medium for 24 h. The cells are changed to fresh serum-free media containing the indicated concentrations of Apamin (0.5, 1 and 2 µg/mL). After 24 h, the cells are replaced with fresh serum-free media containing 2 ng/mL of TGF-β1 for 24 h[1].
Animal Admin Mice[1] For induction of liver injury, 8-week-old C57BL/6 male mice (20-25 g) are selected. Male C57BL/6 mice are fed a control diet or a DDC supplemented diet (0.1%) for 4 weeks to induce advanced biliary fibrosis. The mice receive an intraperitoneal injection of Apamin (0.1 mg/kg) dissolved in saline twice a week. Mice are sacrificed after 4 weeks from the first DDC diet administration.
References

[1]. Kim JY, et al. Apamin suppresses biliary fibrosis and activation of hepatic stellate cells. Int J Mol Med. 2017 May;39(5):1188-1194.

[2]. Messier C, et al. Effect of apamin, a toxin that inhibits Ca(2+)-dependent K+ channels, on learning and memory processes. Brain Res. 1991 Jun 14;551(1-2):322-6.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Molecular Formula C79H131N31O24S4
Molecular Weight 2027.339
Exact Mass 2025.886597
PSA 1021.52000
LogP -14.24
Index of Refraction 1.724
InChIKey YVIIHEKJCKCXOB-UHFFFAOYSA-N
SMILES CC(C)CC1NC(=O)C(C)NC(=O)C(C(C)O)NC(=O)C(CCC(=O)O)NC(=O)C2CCCN2C(=O)C(C)NC(=O)C(CCCCN)NC(=O)C2CSSCC(C(=O)NC(CCC(N)=O)C(=O)NC(CCC(N)=O)C(=O)NC(Cc3c[nH]cn3)C(N)=O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CCCNC(=N)N)NC(=O)C(C)NC(=O)C(CSSCC(N)C(=O)NC(CC(N)=O)C(=O)N2)NC1=O

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CD6899900
CHEMICAL NAME :
Apamin
CAS REGISTRY NUMBER :
24345-16-2
LAST UPDATED :
198708
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C79-H131-N31-O24-S4
MOLECULAR WEIGHT :
2027.65

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 22,308,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2900 ug/kg
TOXIC EFFECTS :
Behavioral - ataxia
REFERENCE :
EJBCAI European Journal of Biochemistry. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1967- Volume(issue)/page/year: 56,35,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 mg/kg
TOXIC EFFECTS :
Behavioral - excitement Behavioral - changes in motor activity (specific assay)
REFERENCE :
NSAPCC Naunyn-Schmiedeberg's Archives of Pharmacology. (Springer Verlag, Heidelberger, Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.272- 1972- Volume(issue)/page/year: 300,189,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1800 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 22,308,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 20,157,1982

 Safety Information

Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H334
Precautionary Statements P261-P342 + P311
Hazard Codes Xn
Safety Phrases S22-S24/25
RIDADR UN 2811
WGK Germany 3
RTECS CD6899900
Packaging Group III
Hazard Class 6.1(b)

 Articles91

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 Synonyms

apamine
MFCD00167944
N-{[(1R,4S,7S,13S,16S,19S,22S,25S,28R,31S,34S,37S,40R,47S,50R)-50-Amino-4-(4-aminobutyl)-47-(2-amino-2-oxoethyl)-34,37-bis(3-carbamimidamidopropyl)-16-(2-carboxyethyl)-19-(1-hydroxyethyl)-25-isobut yl-7,22,31-trimethyl-2,5,8,14,17,20,23,26,29,32,35,38,46,49-tetradecaoxo-42,43,52,53-tetrathia-3,6,9,15,18,21,24,27,30,33,36,39,45,48-tetradecaazatricyclo[26.16.10.0]tetrapentacont-40-yl]carbony ;l}-L-glutaminyl-L-glutaminyl-L-histidinamide
Apamin
APAMIN,BEE VENOM
APAMIN FROM BEE VENOM
CNCKAPETALCARRCQQH-NH2
M.W. 2027.34 C79H131N31O24S4
APAMIN FROM HONEY BEE VENOM
EINECS 246-182-7
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