| Revision as of 01:59, 17 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validati← Previous edit |
Latest revision as of 20:53, 31 July 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits added Category:Cyclohexyl compounds using HotCat |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| verifiedrevid = 445252268 |
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| IUPAC_name = 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate |
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| image = Cetiedil_small.png |
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| image2 = Cetiedil-3D-balls.png |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| metabolism = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 14176-10-4 |
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| ATC_prefix = C04 |
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| ATC_suffix = AX26 |
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| PubChem = 66384 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 419380 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 621RT200TO |
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| UNII = 621RT200TO |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| verifiedrevid = 437151200 |
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| ChemSpiderID = 59759 |
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| IUPAC_name = 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate |
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| smiles = O=C(OCCN1CCCCCC1)C(c2ccsc2)C3CCCCC3 |
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| image = Cetiedil_small.png |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| CAS_number = 14176-10-4 |
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| 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 |
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| ATC_prefix = C04 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| ATC_suffix = AX26 |
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| StdInChIKey = MMNICIJVQJJHHF-UHFFFAOYSA-N |
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| PubChem = 66384 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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<!--Chemical data--> |
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| DrugBank = |
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| C=20|H=31|N=1|O=2|S=1 |
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| C=20 | H=31 | N=1 | O=2 | S=1 |
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| molecular_weight = 349.53064 |
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| bioavailability = |
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| protein_bound = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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}} |
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}} |
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'''Cetiedil''' is a ] 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> |
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'''Cetiedil''' is a ] and an anti-sickling agent. |
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==Synthesis== |
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Original patents:<ref>Pons, Robba, {{Cite patent|FR|1460571}} and Pons et al., {{Cite patent|FR|M5504}} (1966, 1967, both to ]), 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>]] |
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The Clemmensen reduction of 3-thienylcyclohexyl-glycolic acid, ('''1''') gives cyclohexyl(thiophen-3-yl)acetic acid ('''2'''). Esterification of the sodium salt of the resulting acid with 1-(2-chloroethyl)azepane ('''3''') produces ''cetiedil'' ('''4'''). |
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== References == |
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{{Reflist}} |
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{{Peripheral vasodilators}} |
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{{Peripheral vasodilators}} |
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