Cicloprolol

Cicloprolol
Clinical data
Other names	Cycloprolol; SL-75177
Identifiers
	IUPAC name 1-[4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol;
CAS Number	63659-12-1 ;
PubChem CID	146294;
IUPHAR/BPS	552;
ChemSpider	129044;
UNII	1K2ACH4U3R;
KEGG	D03490;
ChEBI	CHEBI:135377;
ChEMBL	ChEMBL2110772;
CompTox Dashboard (EPA)	DTXSID70867026 ;
Chemical and physical data
Formula	C18H29NO4
Molar mass	323.433 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)NCC(COC1=CC=C(C=C1)OCCOCC2CC2)O;
	InChI InChI=1S/C18H29NO4/c1-14(2)19-11-16(20)13-23-18-7-5-17(6-8-18)22-10-9-21-12-15-3-4-15/h5-8,14-16,19-20H,3-4,9-13H2,1-2H3; Key:JNDJPKHYZWRRIS-UHFFFAOYSA-N;

Cicloprolol (INNTooltip International Nonproprietary Name; developmental code name SL-75177), or cycloprolol (BANTooltip British Approved Name), is a β-adrenergic receptor antagonist (beta blocker) described as an antihypertensive agent which was never marketed.^[1]^[2]^[3]^[4]^[5] It has weak partial agonist or intrinsic sympathomimetic activity (30%) at the β-adrenergic receptors.^[4]^[2] This is higher than that of many other beta blockers but is lower than that of xamoterol (45%).^[4] The drug is selective for the β₁-adrenergic receptor.^[3] It has been studied in the treatment of heart failure.^[3]

Chemistry

The chemical structure of cicloprolol is very similar to that of betaxolol.

Cicloprolol can be synthesized starting from 4-benzyloxyphenol.^[6]^[7]

Cicloprolol synthesis

^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 272. ISBN 978-1-4757-2085-3. Retrieved 29 August 2024.
^ ^a ^b Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 88. ISBN 978-94-011-4439-1. Retrieved 2024-08-29.
^ ^a ^b ^c Persson H, Erhardt L (June 1991). "Beta receptor antagonists in the treatment of heart failure". Cardiovascular Drugs and Therapy. 5 (3): 589–604. doi:10.1007/BF03029728. PMID 1678962.
^ ^a ^b ^c Waller DG (August 1990). "Beta-adrenoceptor partial agonists: a renaissance in cardiovascular therapy?". British Journal of Clinical Pharmacology. 30 (2): 157–171. doi:10.1111/j.1365-2125.1990.tb03760.x. PMC 1368213. PMID 1976342.
^ Cocco G, Alfiero R, Pouleur H (January 1992). "An evaluation of the safety of the beta-modulator cicloprolol in chronic heart failure". Clinical Cardiology. 15 (1): 38–42. doi:10.1002/clc.4960150109. PMID 1347258.
^ DE 2649605, Manoury PM, Cavero IA, Majer H, Giudicelli DP, "Phenoläther, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimttel [Phenol ethers, processes for their preparation and medicinal products containing them]", published 1977-05-18, assigned to Synthelabo S.A.
^ P. M. J. Manouri, I. A. G. Carero, H. Majer, and P. R. L. Giudicelli, (1977) Chem. Abstr., 87:134,543j (1977). eidem U.S. patent 4,311,708