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20153-98-4

20153-98-4 structure
20153-98-4 structure
  • Name: Dilazep dihydrochloride
  • Chemical Name: Dilazep dihydrochloride
  • CAS Number: 20153-98-4
  • Molecular Formula: C31H46Cl2N2O10
  • Molecular Weight: 677.61000
  • Catalog: Research Areas Cardiovascular Disease
  • Create Date: 2016-07-21 02:07:09
  • Modify Date: 2025-08-27 18:26:03
  • Dilazep dihydrochloride is an inhibitor of adenosine uptake. Dilazep dihydrochloride has cerebral and coronary vasodilating action through enhancement of effect of adenosine. Dilazep dihydrochloride also inhibits the ischemic damage, platelet aggregation, and membrane transport of nucleosides[1][2].
Name Dilazep dihydrochloride
Synonyms 3-[4-[3-(3,4,5-trimethoxybenzoyl)oxypropyl]-1,4-diazepan-1-yl]propyl 3,4,5-trimethoxybenzoate,dihydrochloride
Description Dilazep dihydrochloride is an inhibitor of adenosine uptake. Dilazep dihydrochloride has cerebral and coronary vasodilating action through enhancement of effect of adenosine. Dilazep dihydrochloride also inhibits the ischemic damage, platelet aggregation, and membrane transport of nucleosides[1][2].
Related Catalog
Target

Adenosine uptake

In Vitro The uptake mechanism has been studied extensively in vitro and Dilazep, NBI and Dipyridamole have been reported to inhibit the uptake of adenosine into different cells. Of these compounds, Dilazep and NBI are almost 10 times more potent than Dipyridamole. In addition, only Dilazep is water soluble and no solubility aiding organic solvent is needed for preparing an aqueous solution[1].
In Vivo After administration of Dilazep, even low doses (0.04-0.1 mg/kg/min) of exogenous adenosine significantly increases superior mesenteric arterial conductance (SMAC) and elevates arterial plasma adenosine concentration. The increased adenosine levels were highly correlated with the increased percentage of change of SMAC and values for Rmax and EC50 were 193.4% change of SMAC and 2.8 μM, respectively. Administration of bolus doses of 8-phenyltheophylline abolishes the ability of Dilazep to potentiate vasodilation, but did not affect isoproterenol-induced relaxation[1]. Dilazep inhibits the phospholipase activation in reperfused heart mitochondria and also inhibits the lipid peroxidation caused by cerebral ischemia and reperfusion. Dilazep may prevent ischemic cerebral injury due to an increase in cerebral blood flow and/or its protective effects on vascular endothelial cell membrane[1].
References

[1]. Zhang Y, et al. Dilazep potentiation of adenosine-mediated superior mesenteric arterial vasodilation. J Pharmacol Exp Ther. 1991 Sep;258(3):767-71.

[2]. Kawagoe J, et al. Effect of dilazep dihydrochloride against ischemia and reperfusion-induced disruption of blood-brain barrier in rats: a quantitative study. Naunyn Schmiedebergs Arch Pharmacol. 1992 Apr;345(4):485-8.
Boiling Point 646ºC at 760 mmHg
Molecular Formula C31H46Cl2N2O10
Molecular Weight 677.61000
Flash Point 344.5ºC
Exact Mass 676.25300
PSA 114.46000
LogP 5.01970
Vapour Pressure 1.41E-16mmHg at 25°C
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DI0250000
CHEMICAL NAME :
Benzoic acid, 3,4,5-trimethoxy-, diester with tetrahydro-1H-1,4-diazepine-1,4(5H)dipropanol, dihydrochloride
CAS REGISTRY NUMBER :
20153-98-4
LAST UPDATED :
199506
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C31-H44-N2-O10.2Cl-H
MOLECULAR WEIGHT :
677.69
WISWESSER LINE NOTATION :
T7N DNTJ A3OVR CO1 DO1 EO1& D3OVR CO1 DO1 EO1 &GH 2

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 :
>2150 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,667,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
85200 ug/kg
TOXIC EFFECTS :
Behavioral - tremor Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,667,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
369 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2044,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
13700 ug/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2044,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2860 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2044,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
161 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,667,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
154 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,667,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16800 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2044,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>316 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP 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: 22,667,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
11200 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 22,667,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
156 gm/kg/26W-I
TOXIC EFFECTS :
Liver - other changes Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2062,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
30 gm/kg/30D-C
TOXIC EFFECTS :
Liver - changes in liver weight Endocrine - changes in adrenal weight Related to Chronic Data - changes in ovarian weight
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2050,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
336 mg/kg/28D-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - normocytic anemia Related to Chronic Data - death
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18(Suppl 12),S3091,199
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1456 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in bladder weight Endocrine - changes in adrenal weight Blood - normocytic anemia
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18(Suppl 12),S3155,199
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
84 mg/kg/7D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in sodium
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18(Suppl 12),S3141,199
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
728 mg/kg/26W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in platelet count Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18(Suppl 12),S3193,199 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1750 mg/kg
SEX/DURATION :
female 7-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,4368,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
672 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 18(Suppl 12),S3227,199
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2084,1974
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 gm/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 8,2084,1974
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS DI0250000
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