Carteolol (original) (raw)

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Chemical compound

Carteolol
Clinical data
Trade names Ocupress
AHFS/Drugs.com Professional Drug Facts
MedlinePlus a601078
License data US DailyMed: Carteolol
Routes of administration Eye drops
ATC code C07AA15 (WHO) S01ED05 (WHO)
Legal status
Legal status US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 85%
Metabolism Liver, active with 8-hydrocarteolol
Elimination half-life 6–8 hours
Excretion Kidney (50–70%)
Identifiers
IUPAC name (RS)-5-[3-(tert_-butylamino)-2-hydroxypropoxy]-3,4-dihydroquinolin-2(1_H)-one
CAS Number 51781-06-7
PubChem CID 2583
IUPHAR/BPS 7142
DrugBank DB00521 checkY
ChemSpider 2485 checkY
UNII 8NF31401XG
KEGG D07624 checkY
ChEBI CHEBI:3437 checkY
ChEMBL ChEMBL839 checkY
CompTox Dashboard (EPA) DTXSID3022746 Edit this at Wikidata
Chemical and physical data
Formula C16H24N2O3
Molar mass 292.379 g·mol−1
3D model (JSmol) Interactive image
Chirality Racemic mixture
SMILES O=C2Nc1cccc(OCC(O)CNC(C)(C)C)c1CC2
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) checkYKey:LWAFSWPYPHEXKX-UHFFFAOYSA-N checkY
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Carteolol is a non-selective beta blocker used to treat glaucoma. It is administered in the form of eye drops.[_citation needed_]

Carteolol was patented in 1972 and approved for medical use in 1980.[1]

Carteolol is a beta blocker, or an antagonist of the β-adrenergic receptors.[2] It is selective for the β1-adrenergic receptor and has intrinsic sympathomimetic activity.[2] Carteolol has also been found to act as a serotonin 5-HT1A and 5-HT1B receptor antagonist in addition to being a beta blocker.[3]

Carteolol is classified as a beta blocker with low lipophilicity and hence lower potential for crossing the blood–brain barrier.[2] This in turn may result in fewer effects in the central nervous system as well as a lower risk of neuropsychiatric side effects.[2]

Society and culture

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Brand names of carteolol include Arteolol, Arteoptic, Calte, Cartéabak, Carteol, Cartéol, Cartrol, Elebloc, Endak, Glauteolol, Mikelan, Ocupress, Poenglaucol, Singlauc, and Teoptic.

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 460. ISBN 978-3-527-60749-5.
  2. ^ a b c d Cojocariu SA, Maștaleru A, Sascău RA, Stătescu C, Mitu F, Leon-Constantin MM (February 2021). "Neuropsychiatric Consequences of Lipophilic Beta-Blockers". Medicina (Kaunas). 57 (2): 155. doi:10.3390/medicina57020155. PMC 7914867. PMID 33572109.
  3. ^ Langlois M, Brémont B, Rousselle D, Gaudy F (January 1993). "Structural analysis by the comparative molecular field analysis method of the affinity of beta-adrenoreceptor blocking agents for 5-HT1A and 5-HT1B receptors". European Journal of Pharmacology. 244 (1): 77–87. doi:10.1016/0922-4106(93)90061-d. PMID 8093601.