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Monatepil

From Wikipedia, the free encyclopedia
Monatepil
Chemical structure of monatepil
Chemical structure of monatepil
Names
Preferred IUPAC name
N-(6,11-Dihydrodibenzo[b,e]thiepin-11-yl)-4-[4-(4-fluorophenyl)piperazin-1-yl]butanamide
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C28H30FN3OS/c29-22-11-13-23(14-12-22)32-18-16-31(17-19-32)15-5-10-27(33)30-28-24-7-2-1-6-21(24)20-34-26-9-4-3-8-25(26)28/h1-4,6-9,11-14,28H,5,10,15-20H2,(H,30,33) checkY
    Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N checkY
  • C1CN(CCN1CCCC(=O)NC2C3=CC=CC=C3CSC4=CC=CC=C24)C5=CC=C(C=C5)F
Properties
C28H30FN3OS
Molar mass475.63 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Monatepil is acalcium channel blocker andα1-adrenergic receptorantagonist used as anantihypertensive.[1]

Synthesis

[edit]

The synthesis of monatepil was first disclosed in patents filed by Dainippon Pharmaceutical.[2]

The amino group of the dihydrodibenzothiepin (1) is first reacted with theacid chloride of 4-chlorobutyric acid, to give theamide (3). This is then used toalkylatepara-fluorophenylpiperazine (4) to yield monatepil.[2][3]

References

[edit]
  1. ^Sugimoto T, Hosoki K, Karasawa T (July 1995)."Relative contribution of alpha 1-adrenoceptor blocking activity to the hypotensive effect of the novel calcium antagonist monatepil".Journal of Cardiovascular Pharmacology.26 (1):55–60.doi:10.1097/00005344-199507000-00009.PMID 7564365.S2CID 1548014.
  2. ^abUS patent 4749703, Hitoshi Uno, et al., "Calcium antagonist piperazine derivatives, and compositions therefor", issued 1988-06-07, assigned to Dainippon Pharmaceutical Co Ltd 
  3. ^Kurokawa, Mikio; Sato, Fuminori; Fujiwara, Iwao; et al. (1991). "A new class of calcium antagonists. 2. Synthesis and biological activity of 11-[4-[4-(4-fluorophenyl)-1-piperazinyl]butyryl]amino]-6,11-dihydrodibenzo[b,e]thiepin maleate and related compounds".Journal of Medicinal Chemistry.34 (3):927–934.doi:10.1021/jm00107a009.PMID 2002473.
Sympatholytic (and closely related)antihypertensives (C02)
Sympatholytics
(antagonizeα-adrenergic
vasoconstriction)
Central
α2-Adrenergic receptor agonists
Adrenergic release inhibitors
Imidazoline receptor agonists
Ganglion-blocking/nicotinic antagonists
Peripheral
Indirect
Monoamine oxidase inhibitors
VMAT inhibitors
Tyrosine hydroxylase inhibitors
Direct
α1-Adrenergic receptor blockers
Non-selective α-adrenergic receptor blockers
Otherantagonists
Serotonin receptor antagonists
Endothelin receptor antagonists (forPHTooltip Pulmonary hypertension)
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
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ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
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CFTRTooltip Cystic fibrosis transmembrane conductance regulator
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Unsorted
Blockers
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TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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α2
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Antagonists
β
Agonists
Antagonists
Classes
Antidepressants
(Tricyclic antidepressants(TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
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