CAS 34661-75-1|Urapidil

Introduction：Basic information about CAS 34661-75-1|Urapidil, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Urapidil BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Synonyms

Common Name	Urapidil
CAS Number	34661-75-1	Molecular Weight	387.476
Density	1.3±0.1 g/cm3	Boiling Point	549.0±60.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₉N₅O₃	Melting Point	159 °C
MSDS	/	Flash Point	285.8±32.9 °C

Names

Name	6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione
Synonym	More Synonyms

Urapidil BiologicalActivity

Description	Urapidil is an α1 adrenoreceptor antagonist and a 5-HT1A receptor agonist.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT ReceptorSignaling Pathways >>GPCR/G Protein >>Adrenergic ReceptorResearch Areas >>Neurological Disease
Target	α1 adrenoreceptor, 5-HT1A receptor[1]
In Vitro	Urapidil is an α1 adrenoreceptor antagonist and a 5-HT1A receptor agonist. Urapidil does not affect vascular tone at concentrations up to 10-5 M. Urapidil (10-5 M) markedly inhibits the alpha 1-adrenergic agonist (phenylephrine)-induced concentration-dependent contractions in aortic rings without endothelium and also to some extent in those with endothelium. Moreover, the inhibitory effect of Urapidil is more pronounced in rings without endothelium than in those with endothelium. Urapidil (10-5 M) affects neither the vascular tone nor the concentration-dependent contraction to serotonin[1].
Cell Assay	The rat aorta is placed in Krebs solution and stripped of connective tissue, then subsequently cut into rings (2 to 3 mm in length). As indicated, the endothelium is removed by rubbing the intimal surface of rings with a pair of forceps. The rings are suspended in organ baths containing oxygenated (95% O2 and 5% CO2) Krebs bicarbonate solution. Following equilibration for 90 min under a resting tension of 2 g, the rings are contracted with KCl (80 mM) to assess their reactivity. After a 30-min washout period, the rings are contracted with the α1-adrenergic receptor agonist phenylephrine (10-6 M) to about 80% of the maximal contraction before addition of acetylcholine (10-6 M) to check for the presence of a functional endothelium. After a 30-min equilibration period, the rings with or without endothelium are exposed to Urapidil (10-5 M) for 25 min before inducing a concentration-contraction curve to phenylephrine[1].
References	[1]. Bopp C, et al. The effect of urapidil, an alpha-1 adrenoceptor antagonist and a 5-HT1A agonist, on the vascular tone of the porcine coronary and pulmonary arteries, the rat aorta and the human pulmonary artery. Eur J Pharmacol. 2016 May 15;779:53-8.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	549.0±60.0 °C at 760 mmHg
Melting Point	159 °C
Molecular Formula	C₂₀H₂₉N₅O₃
Molecular Weight	387.476
Flash Point	285.8±32.9 °C
Exact Mass	387.227051
PSA	71.74000
LogP	2.28
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.622
InChIKey	ICMGLRUYEQNHPF-UHFFFAOYSA-N
SMILES	COc1ccccc1N1CCN(CCCNc2cc(=O)n(C)c(=O)n2C)CC1

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YQ9862000

CHEMICAL NAME :: Uracil, 1,3-dimethyl-6-(3-(4-(o-methoxyphenyl)-1-piperazinyl) proppylamino)-

CAS REGISTRY NUMBER :: 34661-75-1

BEILSTEIN REFERENCE NO. :: 0725782

LAST UPDATED :: 199612

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C20-H29-N5-O3

MOLECULAR WEIGHT :: 387.54

WISWESSER LINE NOTATION :: T6NVNVJ A1 C1 EM3- AT6N DNTJ DR BO1

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 :: 520 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: 27,1919,1977

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 314 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2192 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 140 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: 27,1919,1977

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 508 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 327 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1847 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 203 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 357 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Cardiac - pulse rate Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 gm/kg/30D-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in adrenal weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 45500 mg/kg/52W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition Endocrine - changes in spleen weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,473,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2250 mg/kg/3W-I

TOXIC EFFECTS :: Endocrine - changes in thyroid weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in uterine weight

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 27,1919,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 20930 mg/kg/26W-C

TOXIC EFFECTS :: Endocrine - changes in adrenal weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in uterine weight

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 27,1919,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1728 mg/kg/4W-I

TOXIC EFFECTS :: Cardiac - pulse rate increase, without fall in BP

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 27,1919,1977 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8500 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating female 1-20 day(s) after conception

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 27,1919,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 286 mg/kg

SEX/DURATION :: female 15 day(s) pre-mating female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,501,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2160 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,535,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3750 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,453,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 224 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating female 1-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 27,1919,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 780 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,549,1987

Safety Information

Hazard Codes	Xn
Risk Phrases	22-36/37/38
Safety Phrases	26

Synonyms

Urapidilum [INN-Latin]

Urapidil

6-{3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-propylamino}-1,3-dimethyl-1H-pyrimidine-2,4-dione

EINECS 252-130-4

6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil

Eupressyl

6-[[3-[4-(o-Methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyluracil

Mediatensyl

Uraprene

6-[3-[4-(2-Methoxyphenyl)piperazinyl]propylamino]-1,3-dimethyluracil

2,4(1H,3H)-Pyrimidinedione, 6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]amino]-1,3-dimethyl-

6-({3-[4-(2-Methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

6-[[3-[4-(2-Methoxyphenyl)-1-piperazinyl)propyl]-amino]-1,3-dimethyluracil

6-({3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}amino)-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione

1,3-dimethyl-6-[[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]amino]-2,4(1H,3H)pyrimidine-dione

MFCD00133908

Ebrantil

6-({3-[4-(2-Methoxyphenyl)-1-piperazinyl]propyl}amino)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

urapidil(jan)

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