Hexobendine

Hexobendine
Clinical data
ATC code	C01DX06 (WHO) ;
Identifiers
	IUPAC name Ethane-1,2-diylbis[(methylimino)propane-3,1-diyl] bis(3,4,5-trimethoxybenzoate);
CAS Number	54-03-5 ;
PubChem CID	5777;
ChemSpider	5573 ;
UNII	B6X4SYR93B;
CompTox Dashboard (EPA)	DTXSID20202302 ;
ECHA InfoCard	100.000.173
Chemical and physical data
Formula	C30H44N2O10
Molar mass	592.686 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1c(cc(cc1OC)C(=O)OCCCN(C)CCN(C)CCCOC(=O)c2cc(OC)c(OC)c(OC)c2)OC;
	InChI InChI=1S/C30H44N2O10/c1-31(11-9-15-41-29(33)21-17-23(35-3)27(39-7)24(18-21)36-4)13-14-32(2)12-10-16-42-30(34)22-19-25(37-5)28(40-8)26(20-22)38-6/h17-20H,9-16H2,1-8H3 ; Key:KRQAMFQCSAJCRH-UHFFFAOYSA-N ;
	(what is this?) (verify)

Hexobendine is a vasodilator that acts as an adenosine reuptake inhibitor.^[1]

Synthesis

Hexobendine can be synthesized starting with a reaction between 3,4,5-trimethoxybenzoyl chloride (1) and 3-chloropropanol (2) to give the corresponding ester, 3-chloropropyl 3,4,5-trimethoxybenzoate (3). The last step involves the reaction between two molar equivalents of 3 with one molar equivalent of 1,2-dimethylethylenediamine (4) completing the synthesis of hexobendine (5).^[2]^[3]

References

^ Kolassa N, Pfleger K (January 1975). "Adenosine uptake by erythrocytes of man, rat and guinea-pig and its inhibition by hexobendine and dipyridamole". Biochemical Pharmacology. 24 (1): 154–6. doi:10.1016/0006-2952(75)90331-7. PMID 1168469.
^ "Pharmaceutical Substances: Hexobendine". Thieme.
^ AT231432 idem Schlogl Karl, Kraupp Otto, U.S. patent 3,267,103 (1964 & 1966 to Chemie Linz Ag).

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[1] Kolassa N, Pfleger K (January 1975). "Adenosine uptake by erythrocytes of man, rat and guinea-pig and its inhibition by hexobendine and dipyridamole". Biochemical Pharmacology. 24 (1): 154–6. doi:10.1016/0006-2952(75)90331-7. PMID 1168469.

[2] "Pharmaceutical Substances: Hexobendine". Thieme.

[3] AT231432 idem Schlogl Karl, Kraupp Otto, U.S. patent 3,267,103 (1964 & 1966 to Chemie Linz Ag).

[1]

[2]

[3]

v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Synthesis

See also

References