Celiprolol HCl

Names

[ Name ]:
Celiprolol HCl

[Synonym ]:
MFCD00941500
3-{3-Acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl}-1,1-diethylurea hydrochloride (1:1)
Urea, N'-[3-acetyl-4-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenyl]-N,N-diethyl-, hydrochloride (1:1)
(+)-3-(3-Acetyl-4-(3-(tert-butylamino)-2-hydroxypropoxy)phenyl)-1,1-diethylurea hydrochloride
Celiprolol Hydrochloride
UNII:G1M3398594
3-(3-Acetyl-4-{2-hydroxy-3-[(2-methyl-2-propanyl)amino]propoxy}phenyl)-1,1-diethylurea hydrochloride (1:1)
EINECS 260-752-2
Celiprolol HCl
3-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1,1-diethylurea,hydrochloride

Biological Activity

[Description]:

Celiprolol hydrochloride is a potent, selective and orally active antagonist of β1-andrenoceptor with partial β2 agonist activity, therefore it is a selective adrenoreceptor modulator (SAM). Celiprolol hydrochloride demonstrates antihypertensive and antianginal activity[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

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

[Target]

β1-andrenoceptor[1]

[In Vivo]

Celiprolol (5 or 50 mg/kg; p.o. every day for 12 weeks) has a moderate antihypertensive action at the dose of 50 mg/kg, and significantly reduces media smooth muscle hypertrophy of the mesenteric artery in SHR[2]. Animal Model: Male spontaneously hypertensive rats (SHR) and age-matched Wistar-Kyoto (WKY) rats (8 weeks old)[2] Dosage: 5, 50 mg/kg Administration: P.o. every day (administered in drinking water) for 12 weeks Result: Attenuated the rise in blood pressure significantly at the dose of 50 mg/kg in SHR. Did not significantly affect absolute heart or body weights. Reduced the average medial thickness of the mesenteric artery in SHR.

[References]

[1]. Nawarskas JJ, et, al. Celiprolol: A Unique Selective Adrenoceptor Modulator. Cardiol Rev. Sep/Oct 2017; 25(5): 247-253.

[2]. Tolvanen JP, et, al. Effect of celiprolol therapy on arterial dilatation in experimental hypertension. Br J Pharmacol. 1996 Nov; 119(6): 1137-44.

Chemical & Physical Properties

[ Density]:
1.114g/cm3

[ Boiling Point ]:
586.5ºC at 760 mmHg

[ Melting Point ]:
197-200ºC (dec.)

[ Molecular Formula ]:
C₂₀H₃₄ClN₃O₄

[ Molecular Weight ]:
415.955

[ Flash Point ]:
308.5ºC

[ Exact Mass ]:
415.223785

[ PSA ]:
94.39000

[ LogP ]:
4.09720

[ Storage condition ]:
Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YR6560000

CHEMICAL NAME :: Urea, 3-(3-acetyl-4-(3-((1,1-dimethylethyl)amino)-2-hydroxy propoxy)phenyl)-1,1-d iethyl-, monohydrochloride

CAS REGISTRY NUMBER :: 57470-78-7

LAST UPDATED :: 199709

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C20-H33-N3-O4.Cl-H

MOLECULAR WEIGHT :: 416.02

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 40 mg/kg/2W-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: APHRER Annals of Pharmacotherpy. (Harvey Whitney Books Co., POB 42696, Cincinnati, OH 45242) V. 26- 1992- Volume(issue)/page/year: 26,842,1992

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2157 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 754 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68300 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,41,1983

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1362 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 310 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 42300 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 512 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) 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: 38,443,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - nausea or vomiting

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 33,41,1983

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

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The analysis is described for separating seven beta-adrenergic blocking agents (atenolol, celiprolol, clorprenaline, fenoterol, metoprolol, propranolol, terbutaline) and clenbuterol (sympathomimetic b...

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