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Carteolol HCl (OPC1085; Arteoptic; Cartrol; Mikelan; Abbott-43326), the hydrochloride salt of Carteolol, is a potent and non-selective β-adrenoceptor antagonist that was approved for the treatment of glaucoma. Carteolol was discovered to be a nonconventional partial agonist that interacts with the low-affinity propranolol-resistant site of β1-adrenoceptors to produce agonistic effects and the high-affinity site of the same receptors to produce antagonistic actions.
Physicochemical Properties
| Molecular Formula | C16H25CLN2O3 | |
| Molecular Weight | 328.83 | |
| Exact Mass | 328.155 | |
| Elemental Analysis | C, 58.44; H, 7.66; Cl, 10.78; N, 8.52; O, 14.60 | |
| CAS # | 51781-21-6 | |
| Related CAS # | Carteolol-d9 hydrochloride; 1346602-13-8; Carteolol; 51781-06-7 | |
| PubChem CID | 40127 | |
| Appearance | White to off-white solid powder | |
| Density | 1.13g/cm3 | |
| Boiling Point | 518.6ºC at 760mmHg | |
| Melting Point | 278ºC | |
| Flash Point | 267.4ºC | |
| LogP | 3.03 | |
| Hydrogen Bond Donor Count | 4 | |
| Hydrogen Bond Acceptor Count | 4 | |
| Rotatable Bond Count | 6 | |
| Heavy Atom Count | 22 | |
| Complexity | 354 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | O=C1NC2=C(C(OCC(O)CNC(C)(C)C)=CC=C2)CC1.Cl |
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| InChi Key | FYBXRCFPOTXTJF-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C16H24N2O3.ClH/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);1H | |
| Chemical Name | 5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one;hydrochloride | |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Beta adrenergic Receptor | ||
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation No data are available for the use of carteolol during breastfeeding. Because its excretion into breastmilk is probably extensive, other beta-adrenergic blocking drugs are preferred to oral carteolol while breastfeeding a neonate. Infants over 2 months of age have more mature kidney function and are less likely to be affected. Ophthalmic use of carteolol by the mother should pose little risk to the breastfed infant, although some guidelines state that gel formulations are preferred over solutions. substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue. ◉ Effects in Breastfed Infants A study of mothers taking beta-blockers during nursing found a numerically, but not statistically significant increased number of adverse reactions in those taking any beta-blocker. Although the ages of infants were matched to control infants, the ages of the affected infants were not stated. None of the mothers were taking carteolol. Beta-adrenergic blocking drugs with similar breastmilk excretion characteristics have caused adverse effects in breastfed newborns. ◉ Effects on Lactation and Breastmilk A study in 6 patients with hyperprolactinemia and galactorrhea found no changes in serum prolactin levels following beta-adrenergic blockade with propranolol. There are no reports on the effects of beta-blockade or carteolol use during normal lactation. |
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| References |
[1]. Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. Cornea, 2005. 24(2): p. 213-20. [2]. [Efficacy and safety of long-acting carteolol 1% once daily. A double-masked, randomized study]. J Fr Ophtalmol, 2003. 26(2): p. 131-6. |
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| Additional Infomation |
Carteolol Hydrochloride is a synthetic quinolinone derivative, antihypertensive Carteolol Hydrochloride is a nonselective beta-adrenoceptor blocking agent for beta-1 and beta-2 receptors with no membrane-stabilizing activity but moderate intrinsic sympathomimetic effects. It is used for treatment of hypertension and certain arrhythmias, and as an anti-angina and antiglaucoma agent. (NCI04) A beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent. See also: Carteolol (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (9.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3 mg/mL (9.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 3 mg/mL (9.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0411 mL | 15.2054 mL | 30.4109 mL | |
| 5 mM | 0.6082 mL | 3.0411 mL | 6.0822 mL | |
| 10 mM | 0.3041 mL | 1.5205 mL | 3.0411 mL |