From Wikipedia, the free encyclopedia
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)
N Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N
N InChI=1/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)
Key: WFNRNNUZFPVBSM-UHFFFAOYAJ
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
475.63 g·mol−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
Synthesis:[ 2] Patent:[ 3]
Acylation of [1745-53-5] (1 ) with 4-chlorobutyryl chloride [4635-59-0] (2 ) then leads to the corresponding amide 4-Chloro-N-(5,11-dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-butyramide [103379-37-9] (3 ). Alkylation with para-Fluorophenylpiperazine [2252-63-3] (4 ) then completed the synthesis of monatepil (5 ).
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 .
^ Kurokawa, M., Sato, F., Fujiwara, I., Hatano, N., Honda, Y., Yoshida, T., Naruto, S., Mastumoto, J., Uno, H. (March 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 .
^ Hitoshi Uno, et al. U.S. patent 4,749,703 (1988 to Dainippon Pharmaceutical Co Ltd).
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