Hexobendine
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444607795
| IUPAC_name = Ethane-1,2-diylbis[(methylimino)propane-3,1-diyl] bis(3,4,5-trimethoxybenzoate)
| image = Hexobendine.png
| width = 250
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| ATC_prefix = C01
| ATC_suffix = DX06
| PubChem = 5777
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B6X4SYR93B
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 54-03-5
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 5573
| C=30 | H=44 | N=2 | O=10
| smiles = COc1c(cc(cc1OC)C(=O)OCCCN(C)CCN(C)CCCOC(=O)c2cc(OC)c(OC)c(OC)c2)OC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KRQAMFQCSAJCRH-UHFFFAOYSA-N
}}
Hexobendine is a vasodilator that acts as an adenosine reuptake inhibitor.{{cite journal | vauthors = Kolassa N, Pfleger K | title = Adenosine uptake by erythrocytes of man, rat and guinea-pig and its inhibition by hexobendine and dipyridamole | journal = Biochemical Pharmacology | volume = 24 | issue = 1 | pages = 154–6 | date = January 1975 | pmid = 1168469 | doi = 10.1016/0006-2952(75)90331-7 | url = http://ukpmc.ac.uk/abstract/MED/1168469 }}
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).{{cite web | url = https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-08-0024 | title = Pharmaceutical Substances: Hexobendine | publisher = Thieme }}AT231432 idem Schlogl Karl, Kraupp Otto, {{US patent|3267103}} (1964 & 1966 to Chemie Linz Ag).
:File:Hexobendine synthesis.svg{{clear-left}}
==See also ==
References
{{Reflist}}
{{Vasodilators used in cardiac diseases}}
{{Purinergics}}
Category:Adenosine reuptake inhibitors
{{cardiovascular-drug-stub}}