Carteolol (hydrochloride)

Names

[ Name ]:
Carteolol (hydrochloride)

[Synonym ]:
5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril monohydrochloride
5-{2-Hydroxy-3-[(2-methyl-2-propanyl)amino]propoxy}-3,4-dihydro-2(1H)-quinolinone hydrochloride (1:1)
UNII:4797W6I0T4
2(1H)-Quinolinone, 5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-, hydrochloride (1:1)
5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydrochinolin-2(1H)-onhydrochlorid
5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydroquinolin-2(1H)-one hydrochloride (1:1)
5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1H-quinolin-2-one,hydrochloride
Carteolol monohydrochloride
2(1H)-QUINOLINONE, 5-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-3,4-DIHYDRO-, MONOHYDROCHLORIDE
Carteolol Hydrochloride
5-{3-[(1,1-diméthyléthyl)amino]-2-hydroxypropoxy}-3,4-dihydroquinoléin-2(1H)-one chlorhydrate
Carteolol (hydrochloride)

Biological Activity

[Description]:

Carteolol HCl is a non-selective beta blocker used to treat glaucoma.Target: Beta adrenergic ReceptorCarteolol HCl is a beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent. Carteolol hydrochloride at 1 mmol/L (P<0.05) significantly inhibited H2O2-induced cell damage and was able to scavenge O2 (EC50 value: 48 mmol/L). carteolol hydrochloride has a protective action against UVB-induced HCEC damage, and its radical scavenging ability may be an important basis for this effect [1]. The new alginate formulation of long-acting carteolol 1% given once daily is as effective as standard 1% carteolol given twice daily, with no meaningful differences regarding safety. This efficacy wasy was verified at 9 AM (24 hours after the last drop of long-acting carteolol or 12 hours after that of standard carteolol) and at 11 AM (2 hours after the morning drop). The new alginate formulation of long-acting carteolol 1% given once a day is effective and well tolerated by glaucoma patients who require chronic treatment [2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Research Areas >> Cardiovascular Disease

[References]

[1]. Kuwahara, K., et al., Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. Cornea, 2005. 24(2): p. 213-20.

[2]. Trinquand, C., et al., [Efficacy and safety of long-acting carteolol 1% once daily. A double-masked, randomized study]. J Fr Ophtalmol, 2003. 26(2): p. 131-6.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.13g/cm3

[ Boiling Point ]:
518.6ºC at 760mmHg

[ Melting Point ]:
278ºC

[ Molecular Formula ]:
C₁₆H₂₅ClN₂O₃

[ Molecular Weight ]:
328.834

[ Flash Point ]:
267.4ºC

[ Exact Mass ]:
328.155365

[ PSA ]:
70.59000

[ LogP ]:
3.03000

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
Soluble in water, sparingly soluble in methanol, slightly soluble in ethanol 96 per cent, practically insoluble in methylene chloride.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC8282000

CHEMICAL NAME :: 2(1H)-Quinolinone, 5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4 -dihydro-, monohydrochloride

CAS REGISTRY NUMBER :: 51781-21-6

LAST UPDATED :: 199803

DATA ITEMS CITED :: 25

MOLECULAR FORMULA :: C16-H24-N2-O3.Cl-H

MOLECULAR WEIGHT :: 328.88

WISWESSER LINE NOTATION :: T66 BMVT&J GO1YQ1MX1&1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1330 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - ataxia

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,159,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 390 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,159,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1950 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,159,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4535079

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 810 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - sympathomimetic Vascular - measurement of regional blood flow

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,290,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 375 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - sympathomimetic Vascular - measurement of regional blood flow

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,290,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 12,668,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 54500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 12,668,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 830 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,290,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 740 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Cardiac - pulse rate Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,165,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 112 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Cardiac - pulse rate Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,165,1976 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12600 mg/kg/4W-C

TOXIC EFFECTS :: Liver - other changes Endocrine - other changes Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,173,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12600 mg/kg/12W-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - changes in lung weight Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,173,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 102 gm/kg/26W-C

TOXIC EFFECTS :: Cardiac - other changes Lungs, Thorax, or Respiration - other changes Related to Chronic Data - changes in testicular weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 12,703,1976 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 21 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,221,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 700 ug/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,197,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 7 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,197,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4350 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 4,59,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 4,59,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 525 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,211,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6975 mg/kg

SEX/DURATION :: male 73 day(s) pre-mating female 2 week(s) pre-mating - 6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 4,47,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 700 ug/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,197,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 175 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - sex ratio

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,197,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 36 mg/kg

SEX/DURATION :: female 7-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 11,231,1976

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
VC8282000

Precursor & DownStream

Precursor

DownStream

Articles

Allergic contact dermatitis due to carteolol, with good tolerance to betaxolol.

Dermatitis 22(4) , 232-3, (2011)

Spectroscopic studies on the interaction of carteolol hydrochloride and urea-induced bovine serum albumin.

Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 113 , 447-51, (2013)

The interaction of carteolol hydrochloride, to 0.2 mol L(-1) urea-induced bovine serum albumin in aqueous solution has been first investigated by fluorescence spectra and ultraviolet-visible (UV-vis) ...

Time course of changes in ocular aberrations after instillation of carteolol long-acting solution and timolol gel-forming solution.

J. Ocul. Pharmacol. Ther. 27(2) , 179-85, (2011)

To investigate the influence of 2% carteolol long-acting solution (long-acting carteolol) and 0.5% timolol gel-forming solution (timolol gel) on ocular wavefront aberrations.Ocular aberrations were as...