Acetyldigoxin

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MedKoo CAT#: 329407

CAS#: 5511-98-8

Description: 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

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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: 822.986
Elemental Analysis: C, 62.76; H, 8.08; O, 29.16

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Preparing Stock Solutions

The following data is based on the product molecular weight 822.986 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

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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.