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34661-75-1

34661-75-1 structure
34661-75-1 structure
  • Name: Urapidil
  • Chemical Name: 6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione
  • CAS Number: 34661-75-1
  • Molecular Formula: C20H29N5O3
  • Molecular Weight: 387.476
  • Catalog: API Circulatory system medication Prevention and treatment of angina pectoris
  • Create Date: 2018-06-01 08:00:00
  • Modify Date: 2024-01-02 13:11:00
  • Urapidil is an α1 adrenoreceptor antagonist and a 5-HT1A receptor agonist.
Name 6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione
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)
Description Urapidil is an α1 adrenoreceptor antagonist and a 5-HT1A receptor agonist.
Related Catalog
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.
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

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

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