Alprostadil (11α,13E,15S)-11,15-二羟基-9-酮前列-13-烯-1-酸

CAS 745-65-3 MFCD00077860

化学结构图

745-65-3
SMILES: CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(=O)O

化学属性

Mol. FormulaC20H34O5
Mol. Weight354
Melting Point115-116 ºC
SolubilityDMSO 71 mg/mL Water <1 mg/mL Ethanol 71 mg/mL
Appearance powder

别名和识别编码

Chemical Name(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid
CAS Number745-65-3
Synonym ######## (-)-Protaglandin E1 (11Α, 13E, 15S)-11, (11α,13E,15S)-11,15-二羟基-9-氧代前列-13-烯-1-酸 (11α,13E,15S)-11,15-二羟基-9-氧代前列-13-烯-1-酸 PGE1 前列地尔 (11α,13E,15S)-11,15-二羟基-9-氧代前列-13-烯-1-酸 PGE1 前列地尔 前列腺素 E1 11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid; PGE1 11,15-dihydroxy-9-oxo-,(11-alpha,13e,15s)-prost-13-en-1-oicaci ALPROSTADIL Alprostadil Caverject Edex Lipo PGE1 Lipo-PGE1 Minprog Muse PGE1 PGE1alpha PROSTAGLANDIN E1 PROSTAGLANDIN E1 GAMMA-IRRADIATED*CELL C ULTURE TEST Prostaglandin E1 Prostaglandin E1alpha Prostavasin Prostin VR Prostine VR Sugiran Vasaprostan Viridal {} {} {} {} {
PubChem Substance ID5280723
EC Number212-017-2
Beilstein Registry Number5294062
MDL NumberMFCD00077860
Chemical Name Translation(11α,13E,15S)-11,15-二羟基-9-酮前列-13-烯-1-酸
Merck Number13,7968
Wiswesser Line NotationL5VTJ B6VQ C1U1YQ5 DQ
LabNetwork Molecule IDLN01309089
InChIInChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
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分类

  • {SNA} Eicosanoids (Prostaglandins, Leukotrienes), Fatty Acyls, Miscellaneous Reagents and Supplements, Prostaglandins, 生化试剂, 细胞培养, 脂类, 试剂和添加剂
  • {SNA} Allium sativum (Garlic), Arachidonic Acid Cascade, Bioactive Small Molecule Alphabetical Index, Eicosanoids (Prostaglandins, Leukotrienes),

产品应用

  • A primary Prostaglandin; easily crystallized from purified biological extracts. Vasodilator (peripheral).

相关文献及参考

  • [2]. Cattaneo MG, et, al. Alprostadil suppresses angiogenesis in vitro and in vivo in the murine Matrigel plug assay. Br J Pharmacol. 2003 Jan;138(2):377-85.
  • [3]. Hauck EW, et, al. Prostaglandin E1 long-term self-injection programme for treatment of erectile dysfunction--a follow-up of at least 5 years. Andrologia. 1999;31 Suppl 1:99-103.
  • Anggard, S., et al.: J. Biol. Chem., 239, 4097 (1964),
  • Fang WT, Li HJ, Zhou LS., Protective effects of prostaglandin E1 on human umbilical vein endothelial cell injury induced by hydrogen peroxide. Acta Pharmacol. Sin. 31 , 485-492, (2010) 摘要
  • Herrler T, Leicht SF, Huber S, Hermann PC, et. al., Prostaglandin E positively modulates endothelial progenitor cell homeostasis: an advanced treatment modality for autologous cell therapy. J. Vasc. Res. 46 , 333-346, (2009) 摘要
  • Linet, O.I., et al.: N. Engl. J. Med., 334, 873 (1996),
  • Merck 14 ,7876
  • Wooster, D.L., et al.: J. Am. Med. Assoc., 245, 1

安全信息

GHS Symbol
WGK Germany3
Hazard Codes Xn Xn,Xi
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSGY4569800
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P203
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P310
  • P301+P316
  • P308+P313
  • P318
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
Risk Statements
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
UN Number UN 2811 6.1/PG 3 2811
Storage condition -20°C 储存温度-20°C 
{hazard_c

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 26400 ug/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: 6,47,1982

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 21 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: 6,47,1982

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 19800 ug/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: 6,47,1982

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraarterial
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 21 mg/kg
TOXIC EFFECTS :
   Behavioral - altered sleep time (including change in righting reflex)
   Lungs, Thorax, or Respiration - dyspnea
   Gastrointestinal - hypermotility, diarrhea
REFERENCE :
   YAKUD5 Gekkan Yakuji.  Pharmaceuticals Monthly.  (Yakugyo Jihosha, Inaoka
   Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan)  V.1-   1959-
   Volume(issue)/page/year: 25,499,1983

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 1 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   43,3514,1983

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 100 nmol/L
REFERENCE :
   JIDEAE Journal of Investigative Dermatology.  (Williams & Wilkins Co., 428
   E. Preston St., Baltimore, MD 21202)  V.1-    1938- Volume(issue)/page/year:
   66,313,1976

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - mouse Cells - not otherwise specified
DOSE/DURATION           : 19 mg/L
REFERENCE :
   JRPFA4 Journal of Reproduction and Fertility.  (Biochemical Soc. Book Depot,
   POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1960-
   Volume(issue)/page/year: 47,1,1976

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 200 ug/kg
REFERENCE :
   JDGRAX Journal of Drug Research.  (National Organization for Drug Research
   and Control, POB 29, Cairo, Egypt)  V.2-    1969-  Volume(issue)/page/year:
   13(1-2),1,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 2500 ug/kg
SEX/DURATION            : female 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   BIREBV Biology of Reproduction.  (Soc. for the Study of Reproduction, 309 W.
   Clark St., Champaign, IL 61820)  V.1-    1969-  Volume(issue)/page/year:
   7,106,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE                    : 360 ng/kg
SEX/DURATION            : female 20 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
   AJOGAH American Journal of Obstetrics and Gynecology.  (C.V. Mosby Co.,
   11830 Westline Industrial Dr., St. Louis, MO 63146)  V.1-    1920-
   Volume(issue)/page/year: 102,317,1968

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE                    : 64 ug/kg
SEX/DURATION            : female 20 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - abortion
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   2,258,1970

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - guinea pig
DOSE                    : 1200 ug/kg
SEX/DURATION            : female 23-24 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - abortion
REFERENCE :
   ACEDAB Acta Endocrinologica, Supplementum (Copenhagen).  (Periodica,
   Skolegade 12 E, DK-2500 Valby, Denmark)  No.1-    194

其他信息

  • 所属类别一:生物化学品: 脂类: 固醇及类固醇类
  • 列腺素 E1价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 235020100 列腺素 E1 Prostaglandin E1 98+% 10 MG 5397元
  • MOL 文件:745-65-3.mol
  • 前列地尔
  • 生产方法:以羊精囊为原料 PGE粗品的制备 以羊精囊为原料，经酶制备、孵育、有机溶剂提取、硅胶柱分离制得。 绵羊精囊[KCl, EDTANa 2 , Ph8]→酶混悬液[氢醌，谷胱甘肽]→[花生四烯酸，O 2 ]反应液[丙酮，乙醚，二氯甲烷]→PGS粗品[分离]→[硅胶柱]PGE粗品 PGE 1 成品的制备 每1g PGE粗品用20g硅胶，取200-250目10倍PGE质量的活化硝酸银硅胶混悬于V 乙酸乙酯 ：V 冰醋酸 ：V 石油醚 ：V 水 =220：22.5：125：5(石油醚的bp 90-120℃)的展开剂中，湿法装柱。将粗品用少量的同一展开剂溶解，上柱，洗脱。分别收集PGE 1 和PGE 2 部分。将PGE 1 部分于35℃以下充氮浓缩至无醋酸味，加乙酸乙酯溶解，加水洗酸，pH4-5，加生理盐水除银。乙酸乙酯溶液置冰箱过夜，得PGE 1 成品。 PGE粗品[硝酸银硅胶柱]→PGE 1 梁涌涛、魏凤萍等以γ-亚麻酸甲酯为起始原料，采用化学-酶促合成技术，经两条不同路线合成前列腺素E 1 ，总收率分别为13%和16%。
  • 所属类别二:药物: 激素及其有关药物: 前列腺素
  • 比旋光度:-64 ° (c=1.0, C2H5OH)
  • 用途:治疗肝炎肝硬变、脑梗塞、糖尿病、阳痿、呼吸系统疾病。对肝功能损害不严重的childA、B级患者，尤其是childA级患者有抗纤维华作用。用于引产、催产、肾功能不全，治疗腮腺炎、胰腺炎等。注射用前列腺素E 1 主要适用于心肌梗死、心力衰竭、血栓性脉管炎、慢性动脉闭塞症、视网膜中央静脉血栓，用于体外循环保护血小板、动脉造影、血管重建手术等。
  • F:8-10
  • PackingGroup:III
  • HazardClass:6.1(b)
  • RTECS号:GY4569800

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Fatty Acyls - Lipids
  5. Eicosanoids (Prostaglandins, Leukotrienes) - Fatty Acyls
  6. Prostaglandins - Eicosanoids (Prostaglandins, Leukotrienes)
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Lipids - Biochemicals and Reagents
  4. Fatty Acyls - Lipids
  5. Eicosanoids (Prostaglandins, Leukotrienes) - Fatty Acyls
  6. Prostaglandins - Eicosanoids (Prostaglandins, Leukotrienes)
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Leukotrienes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Fatty Acids
  5. Enzyme Substrate
  6. Chromogen
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Lipids
  4. Lipids in Cell Signaling
  5. Arachidonic Acid Cascade
  6. Leukotrienes
  1. Medical Research Areas
  2. GPCR & G Protein
  3. Prostaglandin Receptor  (前列腺素受体)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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