5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-one

• ChemBase ID: 403
• Molecular Formular: C16H24N2O3
• Molecular Mass: 292.37336
• Monoisotopic Mass: 292.17869264
• SMILES: O(CC(O)CNC(C)(C)C)c1c2CCC(=O)Nc2ccc1
• Canonical SMILES: OC(COc1cccc2c1CCC(=O)N2)CNC(C)(C)C
• InChI: InChI=1S/C16H24N2O3/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20)
• InChIKey: LWAFSWPYPHEXKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-one
• IUPAC Traditional name: carteololum
• Brand Name: Cartrol; Endak Hydrochloride; Ocupress
• Synonyms: Carteololum [INN-Latin]; Carteolol Hydrochloride; Carteolol HCl; Carteolol

Database IDs

• CAS Number: 51781-06-7
• PubChem SID: 160963866; 46507513
• PubChem CID: 2583

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.408522
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.7840903
• LogD (pH = 7.4): -0.8902049
• Log P: 1.4181689
• Molar Refractivity: 83.1416 cm^3
• Polarizability: 32.03236 Å^3
• Polar Surface Area: 70.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.05
• LOG S: -2.84
• Solubility (Water): 4.21e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.1

DETAILS

DrugBank - DB00521

• Drug Groups: approved
• Description: A beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent. [PubChem]
• Indication: For the treatment of intraocular hypertension and chronic open-angle glaucoma
• Pharmacology: Carteolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Carteolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Carteolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.
• Toxicity: The most common effects expected with overdosage of a beta-adrenergic blocking agent are bradycardia, bronchospasm, congestive heart failure and hypotension.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• References: El-Kamel A, Al-Dosari H, Al-Jenoobi F: Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride. Drug Deliv. 2006 Jan-Feb;13(1):55-9. [Pubmed] ; Kuwahara K, Oizumi N, Fujisawa S, Tanito M, Ohira A: Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. Cornea. 2005 Mar;24(2):213-20. [Pubmed] ; Trinquand C, Romanet JP, Nordmann JP, Allaire C: [Efficacy and safety of long-acting carteolol 1% once daily. A double-masked, randomized study] J Fr Ophtalmol. 2003 Feb;26(2):131-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• El-Kamel A, Al-Dosari H, Al-Jenoobi F: Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride. Drug Deliv. 2006 Jan-Feb;13(1):55-9. Pubmed
• Kuwahara K, Oizumi N, Fujisawa S, Tanito M, Ohira A: Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. Cornea. 2005 Mar;24(2):213-20. Pubmed
• Trinquand C, Romanet JP, Nordmann JP, Allaire C: [Efficacy and safety of long-acting carteolol 1% once daily. A double-masked, randomized study] J Fr Ophtalmol. 2003 Feb;26(2):131-6. Pubmed