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MedKoo Cat#: 571410 | Name: Gitoformate

Description:

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

Gitoformate, also known as pentaformylgitoxin, is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). Gitoformate is a derivative of the glycoside gitoxin, with five of the six free hydroxyl groups formylated, one on the aglycon and four on the sugar. Gitoxin, a cardiac glycoside from the woolly foxglove (Digitalis lanata), has an aglycon of the cardenolide type named gitoxigenin, which is also the aglycon of lanatoside B, another Digitalis lanata glycoside.

Chemical Structure

Gitoformate
Gitoformate
CAS#10176-39-3

Theoretical Analysis

MedKoo Cat#: 571410

Name: Gitoformate

CAS#: 10176-39-3

Chemical Formula: C46H64O19

Exact Mass: 920.4042

Molecular Weight: 921.00

Elemental Analysis: C, 59.99; H, 7.00; O, 33.01

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 #
No Data
Synonym
Gitoformate; Formiloxin; Pentaformylgitoxin; AC 2770
IUPAC/Chemical Name
(2R,3R,4S,6S)-6-(((2R,3R,4S,6S)-4-(formyloxy)-6-(((2R,3R,4S,6R)-4-(formyloxy)-6-(((3S,5R,8R,9S,10S,13R,14S,16S,17R)-16-(formyloxy)-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 diformate
InChi Key
DOMHWKQEPDYUQX-LJAQBGIBSA-N
InChi Code
InChI=1S/C46H64O19/c1-24-41(59-23-51)32(55-19-47)14-38(60-24)64-43-26(3)62-39(16-34(43)57-21-49)65-42-25(2)61-37(15-33(42)56-20-48)63-29-8-10-44(4)28(13-29)6-7-31-30(44)9-11-45(5)40(27-12-36(52)54-18-27)35(58-22-50)17-46(31,45)53/h12,19-26,28-35,37-43,53H,6-11,13-18H2,1-5H3/t24-,25-,26-,28-,29+,30+,31-,32+,33+,34+,35+,37+,38+,39+,40+,41-,42-,43-,44+,45-,46+/m1/s1
SMILES Code
C[C@@H]1[C@@H](OC=O)[C@@H](OC=O)C[C@H](O[C@@H]2[C@@H](C)O[C@@H](O[C@@H]3[C@@H](C)O[C@@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@@]7(C)[C@]6(O)C[C@H](OC=O)[C@@H]7C8=CC(OC8)=O)C4)C[C@@H]3OC=O)C[C@@H]2OC=O)O1
Appearance
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 921.00 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: Kubin S, Woodcock BG, Menke G, Rietbrock N. [Postprandial delay of drug absorption in a gitoformate model]. Arzneimittelforschung. 1987 Dec;37(12):1376-8. German. PubMed PMID: 3449065. 2: Reuter N, Meyer F. [Effects of pentaformylgitoxin (gitoformate) on the cardiovascular system of anesthetized cats]. Arzneimittelforschung. 1976;26(6):1201-5. German. PubMed PMID: 989416. 3: Dei Cas L, Manca C, Assanelli D, Vasini G, Pelagatti T, Buia E. [Pharmacokinetics and pharmacodynamics of gitoformate in subjects with atrial fibrillation]. Boll Soc Ital Cardiol. 1981;26(12):2383-4. Italian. PubMed PMID: 7185409. 4: Dei Cas L, Vasini G, Manca C, Buia E, Pelagatti T, Bernardini B. [Pharmacokinetics of gitoformate in subjects with renal insufficiency under dialysis treatment]. Boll Soc Ital Cardiol. 1981;26(12):2381-2. Italian. PubMed PMID: 7185408. 5: Lesne M, Cremers S, Carlier J. [Pharmacokinetic and biopharmaceutic parameters of gitoformate]. Therapie. 1978 Nov-Dec;33(6):723-34. French. PubMed PMID: 746519. 6: Rietbrock N, Woodcock BG, Hrazdil U. [Gitoformate and digitoxin as alternatives to kidney-dependent glycosides in the therapy of cardiac insufficiency]. Arzneimittelforschung. 1984;34(8):915-7. German. PubMed PMID: 6541927. 7: Dei Cas L, Vasini G, Bianchi G, Manca C, Ghinelli R, Mansour M. [Gitoformate in chronic renal insufficiency: pharmacokinetic aspects]. Boll Soc Ital Cardiol. 1979;24(2):209-12. Italian. PubMed PMID: 548097. 8: Dei Cas L, Biasucci LM, Buia E, Frustaci A, Manca C, Metra M, Rebuzzi AG. [Circadian aspects of the heart rate in atrial fibrillation patients: the comparative effect of digoxin and pentaformylgitoxin]. Cardiologia. 1983 Dec;28(12):1019-25. Italian. PubMed PMID: 6681261. 9: Kesteloot H, Brasseur L, Carlier J, Demanet JC, Andriange M, Bataille G, Collignon P, Cosyns J, Vancrombreucq JC, Van Durme JP, Willems J, Foucart G. Effect of digitalis on the left ventricular ejection time: a multicenter double-blind comparative study of digitoxin and pentaformylgitoxin in normal subjects. Acta Cardiol. 1969;24(4):409-25. PubMed PMID: 4928444. 10: Dei Cas L, Biasucci LM, Buia E, Frustaci A, Manca C, Metra M, Rebuzzi AG. [Circadian aspects of heart rate in patients with atrial fibrillation: comparative influence of digoxin and pentaformylgitoxin]. Cardiologia. 1983 Dec;28(12):1019-25. Italian. PubMed PMID: 6687204. 11: Dei Cas L, Affatato A, Buia E, Casciarri G, Faggiano P, Giunti G, Metra M, Pelagatti T, Quinzanini M. [Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate]. Cardiologia. 1984 May-Jun;29(5-6):291-300. Italian. PubMed PMID: 6542412. 12: Carlier J, de Landsheere C, Lesne M, Muisers A. [Effect of renal insufficiency on the pharmacokinetic parameters of gitoformate in man]. Therapie. 1979 Mar-Apr;34(2):255-8. French. PubMed PMID: 494149.