阿拉普利

阿拉普利 基本信息
CAS号 74258-86-9 分子式 C20H26N2O5S
分子量 406.49600 精确质量 　406.15600
PSA 　129.08000 LogP 　2.03410
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目录
基本信息 制备方法与用途 物化性质 安全信息 合成路线 毒性 结构与计算数据 上下游

基本信息 展开↓

CAS号：
74258-86-9
3D弹球模型：
立即前往扯扯看
分子式：
C20H26N2O5S
分子量：
406.49600
中文名称：
阿拉普利
英文名称：
Alacepril
中文别名：
阿拉普利;
2-[[1-(3-乙酰硫基-2-甲基丙酰基)吡咯烷-2-甲酰]氨基]-3-苯丙酸;
阿拉普拉;
(S)-N-[1-[3-(乙酰基硫代)-2-甲基-1-氧丙基]-L-脯氨酰]-L-苯丙氨酸
英文别名：
Alacepril;
Cetapfil;
1-[(S)-3-Acetylthio-2-methylpropanoyl]-L-Pro-L-Phe-OH;
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine;
(S)-N-[1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-L-phenylalanil;
(s)-l-phenylalanin;
du1219;
L-Phenylalanine,1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl;
cetapril;
1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine;
1-((S)-3-acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine;
N-[(S)-3-Acetylthio-2-methylpropanoyl]-L-Pro-L-Phe-OH
精确分子量/精确质量：
406.15600
极性分子表面积/PSA：
129.08000
油水分配系数/LogP：

LogP值指的是某物质在正辛醇/水两相体系中的分配系数的对数值，反映了物质在油水两相中的分配情况。其中、LogP值越大，说明该物质越亲油；反之，LogP值越小，则说明该物质越亲水。
InChI：
InChI=1/C20H26N2O5S/c1-13(12-28-14(2)23)19(25)22-10-6-9-17(22)18(24)21-16(20(26)27)11-15-7-4-3-5-8-15/h3-5,7-8,13,16-17H,6,9-12H2,1-2H3,(H,21,24)(H,26,27)/t13-,16+,17+/m1/s1

生产制备方法及用途展开↓

制备方法

1.0g化合物(I)溶于含有N-甲基吗啉的二氯甲烷中，加入0.57g化合物(Ⅱ)，反应1h，得化合物(Ⅲ)。2.5g化合物(Ⅲ)在三氟乙酸-苯甲醚中反应1h，得1.8g阿拉普利。

合成制备方法

1.0g化合物(I)溶于含有N-甲基吗啉的二氯甲烷中，加入0.57g化合物(Ⅱ)，反应1h，得化合物(Ⅲ)。2.5g化合物(Ⅲ)在三氟乙酸-苯甲醚中反应1h，得1.8g阿拉普利。

用途简介

血管紧张素转化酶抑制剂，是前体药物，口服后转化为脱乙酰基阿拉普利和卡托普利。用于原发性和肾性高血压。

用途

血管紧张素转化酶抑制剂，是前体药物，口服后转化为脱乙酰基阿拉普利和卡托普利。用于原发性和肾性高血压。

物化性质展开↓

密度：
1.281g/cm3
沸点：
679.1ºC at 760 mmHg
闪点：
364.5ºC
折射率：
1.581
其它信息：

1.性状：从乙醇-n-己烷结晶，白色结晶或结晶性粉末，无气味或略有异味，味微苦。

2.熔点（℃）：155-156。

3.比旋光度（C=1.02，乙醇)）：-81.3°。

4.溶解度：易溶于氯仿或甲醇，较易溶于乙醇，较难溶于丙酮，难溶于水，极难溶于乙醚

安全信息展开↓

WGK_Germany：
3
德国有关水污染物质的分类清单
危险类别码：
R22:Harmful if swallowed.
RTECS号：
UO3516500
危险标志：
Xn

合成路线查看所有的合成路线

  • 74258-85-8

    1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine tert-butyl ester

  • →

    ~99%

  • 74258-86-9

    阿拉普利

  • 74345-73-6

    3-乙酰硫基-2-甲基丙酰氯

  • +

  • 13589-02-1

    H-PRO-PHE-OH

  • →

    ~65%

  • 74258-86-9

    阿拉普利

  • 147-85-3

    L-脯氨酸

  • →

  • 74258-86-9

    阿拉普利

毒理性展开↓

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SQ7325700
CHEMICAL NAME :
L-Phenylalanine, N-(1-(3-(acetylthio)-2-methyl-1-oxopropyl)-L-prolyl)- , (S)-
CAS REGISTRY NUMBER :
74258-86-9
LAST UPDATED :
199612
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C20-H26-N2-O5-S
MOLECULAR WEIGHT :
406.54

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 :
>5 gm/kg
TOXIC EFFECTS :
Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea
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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1872 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - hypermotility, diarrhea 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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Skin and Appendages - hair
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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)
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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2921 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - hypermotility, diarrhea 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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Skin and Appendages - hair
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: 13,7033,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #7477
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,64,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
54600 mg/kg/26W-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Nutritional and Gross Metabolic - weight loss or decreased weight gain 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: 13,7097,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9 gm/kg/30D-I
TOXIC EFFECTS :
Cardiac - changes in heart weight Blood - normocytic anemia Blood - other changes
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: 13,7041,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
18 gm/kg/30D-C
TOXIC EFFECTS :
Gastrointestinal - other changes Liver - other changes 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: 13,7061,1985 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
26 gm/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced 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: 13,5711,1985
毒理学数据：

急性毒性LD50大鼠，小鼠(mg／kg)：＞5000，＞5000口服；＞3000，＞3000皮下注射；约2000，约3000腹腔注射。

分子结构与计算化学数据展开↓

分子结构数据

1、  摩尔折射率：105.81

2、  摩尔体积（cm3/mol）：317.3

3、  等张比容（90.2K）：873.6

4、  表面张力（dyne/cm）：57.4

5、  极化率（10-24cm3）：41.94

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