MedKoo Cat#: 329407 | Name: Acetyldigoxin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acetyldigoxin, also known as AD-125, is a sodium/potassium-transporting ATPase inhibitor used to treat arrhythmia and heart failure. beta-Acetyldigoxin can be transferred to alpha-Acetyldigoxin in alkaline solutions.

Chemical Structure

Acetyldigoxin
Acetyldigoxin
CAS#5511-98-8

Theoretical Analysis

MedKoo Cat#: 329407

Name: Acetyldigoxin

CAS#: 5511-98-8

Chemical Formula: C43H66O15

Exact Mass: 822.4402

Molecular Weight: 822.99

Elemental Analysis: C, 62.76; H, 8.08; O, 29.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
5511-98-8 (acetyl) 20830-75-5 (free)
Synonym
Acetyldigoxin; digoxin; AD 125; AD 125; AD 125; Desglucolanatosid; Betagoxin
IUPAC/Chemical Name
(2R,3R,4S,6S)-6-(((2R,3S,4S,6S)-6-(((2R,3S,4S,6R)-6-(((3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-10,13-dimethyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl acetate
InChi Key
HWKJSYYYURVNQU-DXJNJSHLSA-N
InChi Code
InChI=1S/C43H66O15/c1-20-38(49)32(55-23(4)44)18-37(52-20)58-40-22(3)54-36(17-31(40)46)57-39-21(2)53-35(16-30(39)45)56-26-9-11-41(5)25(14-26)7-8-28-29(41)15-33(47)42(6)27(10-12-43(28,42)50)24-13-34(48)51-19-24/h13,20-22,25-33,35-40,45-47,49-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27-,28-,29+,30+,31+,32+,33-,35+,36+,37+,38-,39-,40-,41+,42+,43+/m1/s1
SMILES Code
O=C1OCC([C@H]2CC[C@]3([C@@]2([C@@H](C[C@H]4[C@H]3CC[C@H]5[C@@]4(CC[C@@H](C5)O[C@@H]6O[C@@H]([C@H]([C@H](C6)O)O[C@@H]7O[C@H](C)[C@H]([C@H](C7)O)O[C@@H]8O[C@H](C)[C@H]([C@H](C8)OC(C)=O)O)C)C)O)C)O)=C1
Appearance
White to off-white solid powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 822.99 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Pauli-Magnus C, Mürdter T, Godel A, Mettang T, Eichelbaum M, Klotz U, Fromm MF. P-glycoprotein-mediated transport of digitoxin, alpha-methyldigoxin and beta-acetyldigoxin. Naunyn Schmiedebergs Arch Pharmacol. 2001 Mar;363(3):337-43. PubMed PMID: 11284449. 2: Sukoyan GV, Gongadze NV. Mechanism of cardioprotective effect of adenocine and non-glycoside cardiotonic drugs during experimental chronic cardiac insufficiency. Bull Exp Biol Med. 2011 Mar;150(5):610-3. PubMed PMID: 22235397. 3: Moore WN, Taylor LT. Extraction and quantitation of digoxin and acetyldigoxin from the Digitalis lanata leaf via near-supercritical methanol-modified carbon dioxide. J Nat Prod. 1996 Jul;59(7):690-3. PubMed PMID: 8759168. 4: Reisch J, Zappel J, Rao AR. Photostability studies of ouabain, alpha-acetyldigoxin and digoxin in solid state. Pharm Acta Helv. 1994 Jul;69(1):47-50. PubMed PMID: 7938076. 5: Sukoyan GV, Gongadze NV. Comparative therapeutic efficacy of adenocin and non-glycoside cardiotonic drugs in chronic heart failure at rest and under conditions of heart overload. Bull Exp Biol Med. 2010 Nov;149(6):714-7. PubMed PMID: 21165427. 6: Menke T, Neppert B. [Bilateral reduction in vision in the morning, cardiological intensive care in the evening]. Ophthalmologe. 2008 Jun;105(6):584-7. doi: 10.1007/s00347-007-1630-x. German. PubMed PMID: 18299848. 7: Dreyer M, Dammann HG, Endell W, Rudolph M, Iven H. [Absolute bioavailability of beta-acetyldigoxin from tablets and drops in healthy subjects]. Arzneimittelforschung. 1992 Mar;42(3):303-6. German. PubMed PMID: 1497688. 8: Ikeda Y, Fujii Y, Yamazaki M. High-performance liquid chromatographic determination of alpha-acetyldigoxin in Digitalis lanata leaves. Anal Biochem. 1991 Aug 1;196(2):451-5. PubMed PMID: 1776696. 9: Karsanov NV, Sukoian GV, Tatulashvili DR, Karsanov VN, Mamulashvili LD. [Differences in mechanisms of action of beta-acetyldigoxin, strophanthin K and ouabain]. Biull Eksp Biol Med. 1992 Feb;113(2):146-9. Russian. PubMed PMID: 1611058. 10: Kuhlmann J, Marcin S. [Pharmacokinetic and cardiac efficacy of beta-acetyldigoxin and digitoxin in combination therapy with diltiazem]. Klin Wochenschr. 1985 Jul 15;63(14):636-42. German. PubMed PMID: 4032988. 11: Karsanov NV, Magaldadze VA, Macharashvili TN. [Effects of strophanthin K and beta-acetyldigoxin in vitro on energy transformation of myocardial contractile protein system in toxic-allergic lesions of the cardiac muscle]. Biull Eksp Biol Med. 1991 May;111(5):534-6. Russian. PubMed PMID: 1878573. 12: Rameis H, Bonelli J, Waginger H, Hruby K. [Pharmacokinetics of beta-methyldigoxin and beta-acetyldigoxin in patients with cirrhosis of the liver (author's transl)]. Wien Klin Wochenschr. 1981 Oct 2;93(18):572-6. German. PubMed PMID: 7303703. 13: Clasen R, Kemmeter H, Gilfrich HJ. [Biological availability of digoxin and beta-acetyldigoxin after single-dose administration (author's transl)]. Dtsch Med Wochenschr. 1979 Apr 13;104(15):543-6. German. PubMed PMID: 436626. 14: Kuhlmann J, Zilly W, Wilke J. Effects of cytostatic drugs on plasma level and renal excretion of beta-acetyldigoxin. Clin Pharmacol Ther. 1981 Oct;30(4):518-27. PubMed PMID: 7285486. 15: Rameis H, Woodcock B, Bonelli J, Waginger H. Changes in metildigoxin pharmacokinetics in cirrhosis of the liver: a comparison with beta-acetyldigoxin. Int J Clin Pharmacol Ther Toxicol. 1984 Mar;22(3):145-51. PubMed PMID: 6715083. 16: Rietbrock N, Vöhringer HF, Kuhlmann J, Maertin K. [Isomerisation and bioavailability of beta- and alpha-acetyldigoxin (author's transl)]. Klin Wochenschr. 1977 Jul 1;55(13):641-6. German. PubMed PMID: 895002.