{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 445252268 | IUPAC_name = 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate | image = Cetiedil_small.png | image_class = skin-invert-image | image2 = Cetiedil-3D-balls.png | image_class2 = bg-transparent
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 14176-10-4 | ATC_prefix = C04 | ATC_suffix = AX26 | PubChem = 66384 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 419380 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 621RT200TO | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 59759 | smiles = O=C(OCCN1CCCCCC1)C(c2ccsc2)C3CCCCC3 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C20H31NO2S/c22-20(23-14-13-21-11-6-1-2-7-12-21)19(18-10-15-24-16-18)17-8-4-3-5-9-17/h10,15-17,19H,1-9,11-14H2 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = MMNICIJVQJJHHF-UHFFFAOYSA-N
<!--Chemical data--> | C=20 | H=31 | N=1 | O=2 | S=1 }} '''Cetiedil''' is a vasodilator and an anti-sickling agent.<ref name="Alavi_1984">{{cite journal | vauthors = Alavi JB | title = Sickle cell anemia. Pathophysiology and treatment | journal = The Medical Clinics of North America | volume = 68 | issue = 3 | pages = 545–56 | date = May 1984 | pmid = 6205230 | doi = 10.1016/s0025-7125(16)31115-4 }}</ref> ==Synthesis== [[File:Cetiedil synthesis.svg|thumb|center|550px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0095 Thieme] Original patents:<ref>Pons, Robba, {{Cite patent|FR|1460571}} and Pons et al., {{Cite patent|FR|M5504}} (1966, 1967, both to Innothera), C.A. 68, 59429d (1968); 71, 91286c (1969).</ref> Prepn and activity:<ref>Robba, LeGuen, Chim. Ther. 2, 120 (1967).</ref> Revised synthesis:<ref>Roxburgh, Craig J.; Ganellin, C. Robin; Shiner, Mark A. R.; Benton, David C. H.; Dunn, Philip M.; Ayalew, Yeshi; Jenkinson, Donald H. (1996). "The Synthesis and Some Pharmacological Actions of the Enantiomers of the K+-Channel Blocker Cetiedil". Journal of Pharmacy and Pharmacology. 48 (8): 851–859. doi:10.1111/j.2042-7158.1996.tb03986.x.</ref><ref>Charles Pigerol, et al. {{US patent|4108865}} (1978 to Labaz SA).</ref> Analogues:<ref>Roxburgh, Craig J.; Ganellin, C. Robin; Athmani, Salah; Bisi, Alessandra; Quaglia, Wilma; Benton, David C. H.; Shiner, Mark A. R.; Malik-Hall, Misbah; Haylett, Dennis G.; Jenkinson, Donald H. (2001). "Synthesis and Structure−Activity Relationships of Cetiedil Analogues as Blockers of the Ca2+-Activated K+Permeability of Erythrocytes†". Journal of Medicinal Chemistry. 44 (20): 3244–3253. doi:10.1021/jm001113w.</ref>]] The Clemmensen reduction of 3-thienylcyclohexyl-glycolic acid, [https://pubchem.ncbi.nlm.nih.gov/compound/11064522 CID:11064522] ('''1''') gives cyclohexyl(thiophen-3-yl)acetic acid [16199-74-9] ('''2'''). Esterification of the sodium salt of the resulting acid with 1-(2-chloroethyl)azepane [2205-31-4] ('''3''') produces ''cetiedil'' ('''4'''). == References == {{Reflist}}
{{Peripheral vasodilators}}
Category:Thiophenes Category:Carboxylate esters Category:Azepanes Category:Cyclohexyl compounds
{{cardiovascular-drug-stub}}