Cicloprolol Explained
| Width: | 250px |
| Cas Number: | 63659-12-1 |
| Pubchem: | 146294 |
| Iuphar Ligand: | 552 |
| Chemspiderid: | 129044 |
| Unii: | 1K2ACH4U3R |
| Kegg: | D03490 |
| Chebi: | 135377 |
| Chembl: | 2110772 |
| Synonyms: | Cycloprolol; SL-75177 |
| Iupac Name: | 1-[4-[2-(cyclopropylmethoxy)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol |
| C: | 18 |
| H: | 29 |
| N: | 1 |
| O: | 4 |
| Smiles: | CC(C)NCC(COC1=CC=C(C=C1)OCCOCC2CC2)O |
| Stdinchi: | 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 |
| Stdinchikey: | JNDJPKHYZWRRIS-UHFFFAOYSA-N |
Cicloprolol (; developmental code name SL-75177), or cycloprolol, 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. This is higher than that of many other beta blockers but is lower than that of xamoterol (45%). The drug is selective for the β1-adrenergic receptor. It has been studied in the treatment of heart failure.
Chemistry
The chemical structure of cicloprolol is very similar to that of betaxolol.
Synthesis
Cicloprolol can be synthesized starting from 4-benzyloxyphenol.[6] [7]
Notes and References
- Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer US . 2014 . 978-1-4757-2085-3 . 29 August 2024 . 272.
- Book: Morton IK, Hall JM . Concise Dictionary of Pharmacological Agents: Properties and Synonyms . Springer Netherlands . 2012 . 978-94-011-4439-1 . 2024-08-29 . 88.
- Persson H, Erhardt L . Beta receptor antagonists in the treatment of heart failure . Cardiovascular Drugs and Therapy . 5 . 3 . 589–604 . June 1991 . 1678962 . 10.1007/BF03029728 .
- Waller DG . Beta-adrenoceptor partial agonists: a renaissance in cardiovascular therapy? . British Journal of Clinical Pharmacology . 30 . 2 . 157–171 . August 1990 . 1976342 . 1368213 . 10.1111/j.1365-2125.1990.tb03760.x .
- Cocco G, Alfiero R, Pouleur H . An evaluation of the safety of the beta-modulator cicloprolol in chronic heart failure . Clinical Cardiology . 15 . 1 . 38–42 . January 1992 . 1347258 . 10.1002/clc.4960150109 . free .
- DE . 2649605 . 1977-05-18 . Phenoläther, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimttel [Phenol ethers, processes for their preparation and medicinal products containing them]. . Manoury PM, Cavero IA, Majer H, Giudicelli DP.
- P. M. J. Manouri, I. A. G. Carero, H. Majer, and P. R. L. Giudicelli, (1977) Chem. Abstr., 87:134,543j (1977). eidem
