Monatepil

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
CAS Number	103377-41-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	54798 ;
KEGG	D01171 ;
PubChem CID	60810;
UNII	N4MMI0J7PW ;
CompTox Dashboard (EPA)	DTXSID3048811 ;
	InChI 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) Key: WFNRNNUZFPVBSM-UHFFFAOYSA-N ;
	SMILES C1CN(CCN1CCCC(=O)NC2C3=CC=CC=C3CSC4=CC=CC=C24)C5=CC=C(C=C5)F;
Properties
Chemical formula	C28H30FN3OS
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). Infobox references

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 (4) to yield monatepil.^[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.

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[pmid7564365-1] 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.

[US4749703-2] US 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.

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[2]

[3]

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Beloxepin Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Perlapine Phenindamine Pimethixene Pirolate Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Anticholinergics	Darenzepine Dipitramine Nuvenzepine Pirenzepine Profenamine Rispenzepine Siltenzepine Telenzepine Tripitramine Tropatepine Zolenzepine
Others	Adosopine Aminopromazine Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole

Monatepil

Monatepil

Monatepil

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Monatepil

Synthesis

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