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{{Short description|Chemical compound}}
{{drugbox
{{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
| image2 = Cetiedil-3D-balls.png

<!--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_Ref = {{fdacite|correct|FDA}}
| UNII = 621RT200TO | UNII = 621RT200TO
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | verifiedrevid = 437151200
| ChemSpiderID = 59759
⚫ | IUPAC_name = 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate
| smiles = O=C(OCCN1CCCCCC1)C(c2ccsc2)C3CCCCC3
⚫ | image = Cetiedil_small.png
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫ | CAS_number = 14176-10-4
| 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
⚫ | ATC_prefix = C04
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | ATC_suffix = AX26
| StdInChIKey = MMNICIJVQJJHHF-UHFFFAOYSA-N
⚫ | PubChem = 66384

⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
<!--Chemical data-->
⚫ | DrugBank =
| C=20|H=31|N=1|O=2|S=1 | C=20 | H=31 | N=1 | O=2 | S=1
| molecular_weight = 349.53064
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | 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 =
}} }}
'''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>
'''Cetiedil''' is a ] and an anti-sickling agent.
==Synthesis==
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>]]
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''').
== References ==
{{Reflist}}


{{Peripheral vasodilators}} {{Peripheral vasodilators}}
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Latest revision as of 20:53, 31 July 2024

Chemical compound Pharmaceutical compound
Cetiedil
Clinical data
ATC code
Identifiers
IUPAC name
  • 2-(azepan-1-yl)ethyl 2-cyclohexyl-2-(thiophen-3-yl)acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.034.556 Edit this at Wikidata
Chemical and physical data
FormulaC20H31NO2S
Molar mass349.53 g·mol
3D model (JSmol)
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
  • Key:MMNICIJVQJJHHF-UHFFFAOYSA-N
  (what is this?)  (verify)

Cetiedil is a vasodilator and an anti-sickling agent.

Synthesis

Thieme Original patents: Prepn and activity: Revised synthesis: Analogues:

The Clemmensen reduction of 3-thienylcyclohexyl-glycolic acid, CID:11064522 (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).

References

  1. 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.
  2. Pons, Robba, FR 1460571  and Pons et al., FR M5504  (1966, 1967, both to Innothera), C.A. 68, 59429d (1968); 71, 91286c (1969).
  3. Robba, LeGuen, Chim. Ther. 2, 120 (1967).
  4. 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.
  5. Charles Pigerol, et al. U.S. patent 4,108,865 (1978 to Labaz SA).
  6. 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.
Peripheral vasodilators (C04)
Phenylethanolamine derivatives
Alpha blockers
Nicotinic acid and derivatives
Purine derivatives
Ergot alkaloids
Other peripheral vasodilators


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