Fostedil

In this article, we are going to thoroughly explore the topic of Fostedil and all aspects related to it. From its historical origin to its influence on current society, through its impact on different areas of study and its relevance in the contemporary world. We will also analyze different perspectives and opinions about Fostedil, with the aim of providing a broad and complete vision that allows the reader to thoroughly understand this topic and form their own opinion about it. Additionally, we will examine case studies and concrete examples that illustrate the importance of Fostedil in various contexts, as well as its evolution over time. Get ready to immerse yourself in an informative and enriching journey that will allow you to gain in-depth knowledge about Fostedil!

Fostedil
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • diethyl phosphonate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18NO3PS
Molar mass341.24 g·mol−1
3D model (JSmol)
  • O=P(OCC)(OCC)Cc3ccc(c1nc2ccccc2s1)cc3

Fostedil (A-53,986, KB-944) is a vasodilator acting as a calcium channel blocker which was under development for the treatment of heart conditions such as angina pectoris but was never marketed. It has antihypertensive and antiarrhythmic effects.

Synthesis

Fostedil synthesis:
  1. Treatment of benzanilide with phosphorus pentasulfide or Lawesson's reagent gives thioamide.
  2. Oxidative ring formation by reaction with potassium ferricyanide and base (presumably involving a free radical intermediate) constructs the benzothiazole ring.
  3. Bromination of this compound with N-bromosuccinimide produces bromomethyl intermediate.
  4. The synthesis of fostedil concludes with a Michaelis-Arbuzov reaction with triethyl phosphite.

See also

References

  1. ^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
  2. ^ Khurmi NS, Bowles MJ, O'Hara MJ, Lahiri A, Raftery EB (November 1985). "Ambulatory monitoring and exercise testing in the evaluation of a new long-acting calcium ion antagonist KB-944 (Fostedil) for the treatment of exertional angina pectoris". International Journal of Cardiology. 9 (3): 289–302. doi:10.1016/0167-5273(85)90027-0. PMID 3902675.
  3. ^ Morita T, Yoshino K, Kanazawa T, Ito K, Nose T (1982). "Vasodilator action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1037–1042. PMID 6890822.
  4. ^ Morita T, Kanazawa T, Ito K, Nose T (1982). "Vasodilator mechanism of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1043–1046. PMID 6890823.
  5. ^ Morita T, Kanazawa T, Ito K, Nose T (1982). "Antihypertensive effect of KB-944, a new calcium antagonist, in conscious normotensive and hypertensive rats". Arzneimittel-Forschung. 32 (9): 1047–1052. PMID 6890824.
  6. ^ Morita T, Ito K, Nose T (1982). "Cardiac action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1053–1055. PMID 6890825.
  7. ^ Yoshidomi M, Sukamoto T, Morita T, Ito K, Nose T (1982). "Antiarrhythmic effect of KB-944, a new calcium antagonist. A comparison with verapamil and diltiazem". Arzneimittel-Forschung. 32 (9): 1056–1059. PMID 6890826.
  8. ^ Yoshino K, Kohno T, Uno T, Morita T, Tsukamoto G (May 1986). "Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator". Journal of Medicinal Chemistry. 29 (5): 820–825. doi:10.1021/jm00155a037. PMID 3701791.
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