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Cetiedil

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Chemical compound

Pharmaceutical compound

Cetiedil
Clinical data


ATC code	C04AX26 (WHO)
Identifiers
IUPAC name 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate
CAS Number	14176-10-4^Y
PubChemCID	66384
ChemSpider	59759^N
UNII	621RT200TO
ChEMBL	ChEMBL419380^N
CompTox Dashboard(EPA)	DTXSID70864474
ECHA InfoCard	100.034.556
Chemical and physical data
Formula	C₂₀H₃₁NO₂S
Molar mass	349.53 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OCCN1CCCCCC1)C(c2ccsc2)C3CCCCC3
InChI InChI=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^N Key:MMNICIJVQJJHHF-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Cetiedil is avasodilator and an anti-sickling agent.^[1]

Synthesis

[edit]

The Clemmensen reduction of 3-thienylcyclohexyl-glycolic acid,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) producescetiedil (4).

References

[edit]

^Alavi JB (May 1984). "Sickle cell anemia. Pathophysiology and treatment".The Medical Clinics of North America.68 (3):545–56.doi:10.1016/s0025-7125(16)31115-4.PMID 6205230.
^Pons, Robba,FR 1460571 and Pons et al.,FR M5504 (1966, 1967, both toInnothera), C.A. 68, 59429d (1968); 71, 91286c (1969).
^Robba, LeGuen, Chim. Ther. 2, 120 (1967).
^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.
^Charles Pigerol, et al.U.S. patent 4,108,865 (1978 to Labaz SA).
^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.

v t e Peripheral vasodilators (C04)
Phenylethanolamine derivatives	Isoxsuprine Buphenine Bamethan
Alpha blockers	Non-selective Buflomedil Phentolamine Phenoxybenzamine Tolazoline Selectiveα₁-blockers Alfuzosin Doxazosin Prazosin Silodosin Tamsulosin Terazosin
Nicotinic acid and derivatives	Nicotinic acid Nicotinyl alcohol Inositol nicotinate Ciclonicate
Purine derivatives	Pentifylline Xantinol nicotinate Pentoxifylline Etofylline nicotinate
Ergot alkaloids	Ergoloid Nicergoline Dihydroergocristine
Other peripheral vasodilators	Cyclandelate Vincamine Moxisylyte Bencyclane Vinburnine Sulcotidil Naftidrofuryl Butalamine Visnadine Cetiedil Cinepazide Ifenprodil Azapetine Fasudil

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