Fostedil
From Wikipedia, the free encyclopedia
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Clinical data | |
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Routes of administration |
Oral |
ATC code | none |
Legal status | |
Legal status |
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Identifiers | |
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CAS Number | 75889-62-2 |
PubChem (CID) | 53421 |
ChemSpider | 48253 |
UNII | D41WS786UL ![]() |
KEGG | D04260 |
ChEMBL | CHEMBL39516 |
Chemical and physical data | |
Formula | C18NO3PS |
Molar mass | 361.40 g/mol |
3D model (Jmol) | Interactive image |
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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.[1][2][3][4] It has antihypertensive and antiarrhythmic effects.[5][6][7]
Synthesis[edit]
![](http://web.archive.org./web/20161216154422im_/https://upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Fostedil_synthesis.png/700px-Fostedil_synthesis.png)
Fostedil synthesis:[8]
- Treatment of benzanilide with phosphorus pentasulfide or Lawesson's reagent gives thioamide.
- Oxidative ring formation by reaction with potassium ferricyanide and base (presumably involving a free radical intermediate) constructs the benzothiazole ring.
- Bromination of this compound with N-bromosuccinimide produces bromomethyl intermediate.
- The synthesis of fostedil concludes with a Michaelis-Arbuzov reaction with triethyl phosphite.
See also[edit]
References[edit]
- ^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
- ^ 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.
- ^ Morita T, Yoshino K, Kanazawa T, Ito K, Nose T (1982). "Vasodilator action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1037–42. PMID 6890822.
- ^ Morita T, Kanazawa T, Ito K, Nose T (1982). "Vasodilator mechanism of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1043–6. PMID 6890823.
- ^ 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): 1047–52. PMID 6890824.
- ^ Morita T, Ito K, Nose T (1982). "Cardiac action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1053–5. PMID 6890825.
- ^ 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): 1056–9. PMID 6890826.
- ^ Yoshino, K.; Kohno, T.; Uno, T.; Morita, T.; Tsukamoto, G. (1986). "Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator". Journal of Medicinal Chemistry. 29 (5): 820. doi:10.1021/jm00155a037.