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Monatepil
Names
Preferred IUPAC name
N -(6,11-Dihydrodibenzo[b ,e ]thiepin-11-yl)-4-[4-(4-fluorophenyl)piperazin-1-yl]butanamide
Identifiers
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)
Y Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N
Y
C1CN(CCN1CCCC(=O)NC2C3=CC=CC=C3CSC4=CC=CC=C24)C5=CC=C(C=C5)F
Properties
C 28 H 30 F N 3 O S
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Monatepil is a calcium channel blocker and α1 -adrenergic receptor antagonist used as an antihypertensive .[ 1]
Synthesis
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 the acid chloride of 4-chlorobutyric acid, to give the amide (3). This is then used to alkylate para -fluorophenylpiperazine[ 2] [ 3]
References
^ 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 . ^ a b US patent 4749703 , Hitoshi Uno, et al., "Calcium antagonist piperazine derivatives, and compositions therefor", issued 1988-06-07, assigned to Dainippon Pharmaceutical Co Ltd ^ 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 .
Calcium
VDCCs Tooltip Voltage-dependent calcium channels
Potassium
VGKCs Tooltip Voltage-gated potassium channels
IRKs Tooltip Inwardly rectifying potassium channel
KCa Tooltip Calcium-activated potassium channel
K2Ps Tooltip Tandem pore domain potassium channel
Sodium
VGSCs Tooltip Voltage-gated sodium channels
ENaC Tooltip Epithelial sodium channel
ASICs Tooltip Acid-sensing ion channel
Chloride
CaCCs Tooltip Calcium-activated chloride channel
CFTR Tooltip Cystic fibrosis transmembrane conductance regulator
Unsorted
Others
TRPs Tooltip Transient receptor potential channels LGICs Tooltip Ligand gated ion channels
α1
Agonists Antagonists
Abanoquil Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g., brexpiprazole , clozapine , olanzapine , quetiapine , risperidone )Benoxathian Beta blockers (e.g., adimolol , amosulalol , arotinolol , carvedilol , eugenodilol , labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine , ergotamine , dihydroergotamine , lisuride , nicergoline , terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin )Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , imipramine , trimipramine )Trimazosin Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Urapidil WB-4101 Zolertine
α2
Agonists Antagonists
1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine , brexpiprazole , clozapine , lurasidone , olanzapine , paliperidone , quetiapine , risperidone , zotepine )Azapirones (e.g., buspirone , gepirone , ipsapirone , tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Yohimbine
β
