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Fostedil

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Fostedil
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate
CAS Number
PubChemCID
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 avasodilator acting as acalcium channel blocker which was under development for the treatment ofheart conditions such asangina pectoris but was never marketed.[1][2][3][4] It hasantihypertensive andantiarrhythmic effects.[5][6][7]

Synthesis

[edit]
Fostedil synthesis:[8]
  1. Treatment of benzanilide withphosphorus pentasulfide orLawesson's reagent givesthioamide.
  2. Oxidative ring formation by reaction withpotassium ferricyanide and base (presumably involving a free radical intermediate) constructs the benzothiazole ring.
  3. Bromination of this compound withN-bromosuccinimide produces bromomethyl intermediate.
  4. The synthesis of fostedil concludes with aMichaelis-Arbuzov reaction withtriethyl phosphite.

See also

[edit]

References

[edit]
  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.
Medications used in the management ofpulmonary arterial hypertension (B01,C02)
Prostacyclin analogues
Endothelin receptor antagonists
PDE5 inhibitors
sGC stimulators
Adjunctive therapy
Channel blockers
class I
(Na+ channel blockers)
class Ia (Phase 0→ andPhase 3→)
class Ib (Phase 3←)
class Ic (Phase 0→)
class III
(Phase 3→,K+ channel blockers)
class IV
(Phase 4→,Ca2+ channel blockers)
Receptoragonists
andantagonists
class II
(Phase 4→,β blockers)
A1 agonist
M2
α receptors
Ion transporters
Na+/ K+-ATPase
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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