6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 6-甲氧基-2-[[(4-甲氧基-3,5-二甲基-2-吡啶基)甲基]亚磺酰基]-1H-苯并咪唑

CAS 73590-58-6 MFCD00083192

化学结构图

73590-58-6
SMILES: CC1C=NC(CS(=O)C2NC3C=CC(=CC=3N=2)OC)=C(C)C=1OC

化学属性

Mol. FormulaC17H19N3O3S
Mol. Weight345
Density1.422
Melting Point148-150
SolubilityH2O: 0.5 mg/mL
Appearance solid

别名和识别编码

Chemical Name6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
Synonym 2-[(4-METHOXY-3,5-DIMETHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]SULFINYL]-1H-BENZIMIDAZOLE 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole Antra Losec Omeprazole 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole Antra Losec 5-甲氧基-2-{[(4-甲氧基-3,5-二甲基-2-吡啶基)-甲基]-亚砜}-1H-苯并咪唑 6-methoxy-2-[(r)-(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-1h-benzoimidazole H 168/68 Losec MOPRAL OMEPRAL 亚砜咪唑 奥克 欧麦亚砜 艾美拉唑
CAS Number73590-58-6
PubChem Substance ID87560875
MDL NumberMFCD00083192
Reaxys-RN3628192
Merck Number6845
EC Number250-023-7
Beilstein Registry Number2384789
Chemical Name Translation6-甲氧基-2-[[(4-甲氧基-3,5-二甲基-2-吡啶基)甲基]亚磺酰基]-1H-苯并咪唑
LabNetwork Molecule IDLN00392890
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分类

  • Application Index, Approved Therapeutics/Drug Candidates, AstraZeneca, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience, Enzymes, Inhibitors, and Substrates, Inhibitors, Ion Channels, Ion Pump Inhibitors, Monovalent Ion Channels, O, Potassium Channel Modulators, Substrates, Voltage-gated Ion Channels, Xenobiotics an
  • {SNA} APIs & Metabolites, APIs (Active Pharmaceutical Ingredients) & Metabolites, All alphabetically sorted, Analytical Standards, Analytical/Chromatography, Chromatography,
  • {SNA} Application Index,

产品应用

  • 奥美拉唑是一种质子泵抑制剂,对动物和人胃酸分泌具有很强的和较长时间的抑制作用。临床上用于治疗消化性溃疡;反流性食管炎;Zollinger-Ellison综合症;根除幽门螺杆菌(HP),取得令人满意的疗效。

相关文献及参考

  • [2]. Jonkers D, et al. Omeprazole inhibits growth of gram-positive and gram-negative bacteria including Helicobacter pylori in vitro. J Antimicrob Chemother. 1996 Jan;37(1):145-50.
  • [3]. Huarui Zhang, et al. Advances in the discovery of exosome inhibitors in cancer. J Enzyme Inhib Med Chem. 2020 Dec;35(1):1322-1330.
  • Merck 14 ,6845
  • Morii, M., et al., Different biochemical modes of action of two irreversible H + K (+)-ATPase inhibitors omeprazole and E3810. J. Biol. Chem. 268 , 21553, (1993) 摘要
  • Ritter, M. et al., Effect of inhibitors of Na+/H+-exchange and gastric H + /K + ATPase on cell volume intracellular pH and migration of human polymorphonuclear leucocytes. Br. J. Pharmacol. 124 , 627-638, (1998) 摘要
  • [1]. Li XQ, et al. Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-

安全信息

GHS Symbol
WGK Germany2
Hazard Codes Xi
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H303 May be harmfully swallowed 吞食可能有害
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSDD9087000
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • 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。
  • P305+P351+P338
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
Signal word Warning
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • 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
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Storage condition 0-10 储存温度: 2-8°C 0-10°C 2-8°C
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >100 mg/kg
TOXIC EFFECTS :
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 36,369,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >100 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - ptosis
   Skin and Appendages - hair
   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: 36,369,1988

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >50 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - ptosis
   Gastrointestinal - hypermotility, diarrhea
   Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 36,3

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 4 mg/kg/2W-I
TOXIC EFFECTS :
   Musculoskeletal - joints
   Biochemical - Metabolism (Intermediary) - effect on inflammation or
   mediation of inflammation
REFERENCE :
   LANCAO Lancet.  (7 Adam St., London WC2N 6AD, UK)  V.1-    1823-

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

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 100 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 262,73,1991

TYPE OF TEST            : DNA damage
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 100 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 368,1,1996

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 3520 mg/kg
SEX/DURATION            : female 7-17 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: 36,189,1988

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 8320 mg/kg
SEX/DURATION            : female 17-20 day(s) after conception
                          lactating female 21 day(s) post-birth
TOXIC EFFECTS :
   Reproductive - Maternal Effects - other effects
   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: 36,189,1988

其他信息

  • 上游原料:三氯甲烷 --> 间氯过氧苯甲酸 --> 1,2-苯二胺 --> 4-甲氧基-3,5-二甲基-2-羟甲基吡啶 --> 乙基黄原酸钾 --> 苯并咪唑 --> 2-巯基-5-甲氧基苯并咪唑
  • 用途二:质子泵抑制剂,即壁细胞内H + -K + -ATP酶抑制剂。有强而持久的抑制基础胃酸及食物、五肽胃酸泌素所致的胃酸分泌的作用。显效快,可逆,且无H2受体拮抗剂诱发精神方面的副作用。用于胃及十二指肠溃疡、反流性或糜烂性食管炎、佐-埃二氏综合征等,对用H2受体拮抗剂无效的胃和十二指肠溃疡也有效。
  • Sigma Aldrich:73590-58-6(sigmaaldrich)
  • MSDS 信息:5-Methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3H-benzoimidazole(73590-58-6).msds
  • 抑制胃酸分泌药:奥美拉唑是一种能够有效抑制胃酸分泌的质子泵抑制剂,市面上流通的商品名称包括安胃哌唑、奥咪拉唑、亚枫咪唑、洛赛克、甲氧磺唑、沃必唑、渥米哌唑,属于抑酸类药物,常见的抑酸类药物还包括泮托拉唑、雷贝拉唑、埃索美拉唑,作用机制是选择性性地作用于胃粘膜壁细胞,抑制处于胃壁细胞顶端膜构成的分泌性微管和胞浆内的管状泡上的H+,K+-ATP酶的活性,从而有效地抑制胃酸的分泌,起效迅速,适用于治疗胃溃疡、十二指肠溃疡、反流性食管炎和胃泌素瘤(卓-艾综合征)。但需要注意过度使用奥美拉唑等抑酸类药物,可导致胃酸浓度降低,酸性减弱,那么进入胃里的病菌就可能不被杀死,进入肠道,使肠道感染病菌危险加倍,那么就可能腹泻。因胃酸降低影响消化,进而影响肠道对钙、铁等微量元素及维生素的吸收,导致机体缺钙,易发生骨折。
  • 外观性质:白色固体。
  • 用途一:适用于消化性溃疡、反流性食道炎等
  • TCI Shanghai:奥美拉唑 Omeprazole,>;98.0%(LC)(T)(73590-58-6)
  • MOL 文件:73590-58-6.mol
  • 用途三:奥美拉唑是一种质子泵抑制剂,对动物和人胃酸分泌具有很强的和较长时间的抑制作用。临床上用于治疗消化性溃疡、反流性食管炎、Zollinger-Ellison综合症、根除幽门螺杆菌(HP),取得令人满意的疗效。
  • color:white
  • 奥美拉唑价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 O0359 奥美拉唑 Omeprazole 5G 750元 2014/06/02 O0359 奥美拉唑 Omeprazole 25G 2450元
  • 用途四:奥美拉唑是一种质子泵抑制剂,对动物和人胃酸分泌具有很强的和较长时间的抑制作用。临床上用于治疗消化性溃疡;反流性食管炎;Zollinger-Ellison综合症;根除幽门螺杆菌(HP),取得令人满意的疗效。
  • 方法一:3,5-二甲基-2-羟甲基-4-甲氧基吡啶经氯化,生成2-氯甲基-3,5-二甲基-4-甲氧基吡啶。 4-甲氧基1,2-苯二胺和黄原酸钾反应,生成2-巯基-5-甲氧基苯并咪唑,再和上面得到的吡啶衍生物反应,生成2-[(3,5-二甲基-4-甲氧基-2-吡啶基)甲硫基]-5-甲氧基-1H-苯并咪唑,最后在氯仿中,5℃下,用间氯过苯甲酸氧化,得到奥美拉唑。粗品奥美拉唑可用乙腈重结晶。

系列性分类


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