Pengitoxin

• CAT Number: I034385
• CAS Number: 7242-04-8
• Molecular Formula: C51H74O19
• Molecular Weight: 991.13
• Purity: 98%
• Synonyms: Pengitoxin; Cordoval; Pentagit; EINECS 230-645-5
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (2R,3R,4S,6S)-6-(((2R,3R,4S,6S)-4-acetoxy-6-(((2R,3R,4S,6R)-4-acetoxy-6-(((3S,5R,8R,9S,10S,13R,14S,16S,17R)-16-acetoxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate
• InChI: InChI=1S/C51H74O19/c1-24-46(67-31(8)56)37(63-27(4)52)20-43(61-24)69-48-26(3)62-44(21-39(48)65-29(6)54)70-47-25(2)60-42(19-38(47)64-28(5)53)68-34-13-15-49(9)33(18-34)11-12-36-35(49)14-16-50(10)45(32-17-41(57)59-23-32)40(66-30(7)55)22-51(36,50)58/h17,24-26,33-40,42-48,58H,11-16,18-23H2,1-10H3/t24-,25-,26-,33-,34+,35+,36-,37+,38+,39+,40+,42+,43+,44+,45+,46-,47-,48-,49+,50-,51+/m1/s1
• InChIKey: JDYLJSDIEBHXPO-ALNZGLKXSA-N
• SMILES: C[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@@]5([C@@H](C6=CC(OC6)=O)[C@@H](OC(C)=O)C[C@]45O)C)C)C[C@@H]([C@@H]1O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)OC(C)=O)OC(C)=O)OC(C)=O)OC(C)=O

Pengitoxin (Cat No.: I034385) is a marine-derived toxin known for its potent bioactivity in neurotoxicity and ion channel modulation research. It interacts with voltage-gated sodium channels, disrupting normal neuronal signaling and muscle function. Due to its high specificity, pengitoxin is used as a tool in neuropharmacology to study ion channel physiology and potential therapeutic targets for neurological disorders. Its structural complexity and biological activity make it a valuable compound for toxinology, drug discovery, and understanding mechanisms of neurotoxic effects in biomedical research.

Reference

1: Haustein KO, Alken RG, Lach HJ, Becker U, Rietbrock N. On the pharmacokinetics of pengitoxin and its cardioactive derivative 16-acetyl- gitoxin. Eur J Clin Pharmacol. 1983;25(3):369-73. doi: 10.1007/BF01037950. PMID: 6628525.
2: Haustein KO, Wesser M. Pharmacokinetics of pengitoxin and its therapeutic efficacy in congestive heart failure. Int J Clin Pharmacol Ther Toxicol. 1988 Jan;26(1):8-15. PMID: 3403092.
3: Haustein KO, Oltmanns G, Rietbrock N, Alken RG. Differences in color vision impairment caused by digoxin, digitoxin, or pengitoxin. J Cardiovasc Pharmacol. 1982 Jul-Aug;4(4):536-41. doi: 10.1097/00005344-198207000-00003. PMID: 6181326.
4: Haustein KO. On the pharmacokinetics of 16-acetyl-gitoxin and its bioavailability from pengitoxin-containing tablet formulations. J Pharmacokinet Biopharm. 1986 Aug;14(4):357-64. doi: 10.1007/BF01059196. PMID: 3772737.
5: Haustein KO, Hentschel H. Dose-dependent shortening of systolic time intervals after intake of pengitoxin. Int J Clin Pharmacol Res. 1987;7(1):19-25. PMID: 3583485.
6: Emmrich R, Wagner J, Axthelm EH. Die Bindungskapazitäten der Serumproteine für Herzglykoside (speziell für Pengitoxin) [The binding capacity of serum proteins for cardiac glycosides (especially for pengitoxin)]. Munch Med Wochenschr. 1969 Feb 21;111(8):401-4. German. PMID: 5818954.
7: Kozák P. Untersuchungen über die Herzwirkung eines neuen, fünffach azetylierten Gitoxins (Pengitoxin [Cardiac effect of a new penta-acetylated gitoxin (pengitoxin)]. Ther Ggw. 1974 Mar;113(3):430-2 passim. German. PMID: 4818043.
8: Haustein KO, Wesser M. Kliniko-farmakologicheskoe i klinicheskoe issledovanie pengitoksina [Clinico-pharmacological and clinical evaluation of pengitoxin]. Farmakol Toksikol. 1982 May-Jun;45(3):67-8. Russian. PMID: 7095131.
9: Haustein KO. Measurement of plasma glycoside level following pengitoxin administration. Eur J Clin Pharmacol. 1978 Jul 30;13(5):389-91. doi: 10.1007/BF00644614. PMID: 668799.
10: Haustein KO, Schmidt C. Differences in color discrimination between three cardioactive glycosides. Int J Clin Pharmacol Ther Toxicol. 1988 Oct;26(10):517-20. PMID: 3235219.