5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine 甲氧苄啶

CAS 738-70-5 MFCD00036761

化学结构图

738-70-5
SMILES: COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC

化学属性

Mol. FormulaC14
Mol. Weight290
Melting Point199-205
SolubilitySoluble in water (0.4 mg/ml), ethanol (2.6 mg/ml at 20 °C), methanol (12.1 mg/ml), chloroform (22.2 mg/ml at 20 °C), and DMSO (50 mg/ml).
TSCANo
Appearance 白色结晶性粉末,无臭,味苦。熔点199-203℃。难溶于水、乙醚、苯、微溶于氯仿、甲醇,溶于醋酸。 white powder
Stability对光线和湿度敏感

别名和识别编码

Chemical Name5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine
CAS Number738-70-5
Alfabeta NameTRIMETHOXYBENZYLPYRIMIDINEDIAMINE 534524()----,,,
MDL NumberMFCD00036761
Synonym 2,4-DIAMINO-5-(3,4,5-TRIMETHOXYBENZYL)PYRIMIDE 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine; 5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine; 5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine; Abaprim 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)- 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidin 5-((3,4,5-trimethoxyphenyl)-methyl)-4-pyrimidinediamine 5-(3,4,5-TRIMETHOXYBENZYL)PYRIMIDINE-2,4-DIYLAMINE 5-[(3,4,5-Trimethoxyphenyl)methyl]- Bactramin Monoprim NSC-106568 Proloprim Syraprim TMP Trimethoprim Trimopan Trimpex WR 5949 Wellcoprim 三甲氧苄氨嘧啶 三甲氧苄胺嘧啶 甲氧苄啶 甲氧苄定 甲氧苄氨嘧啶
PubChem Substance ID5578
Beilstein Registry Number625127
EC Number212-006-2
Merck Number9709
Reaxys-RN625127
Chemical Name Translation甲氧苄啶
Wiswesser Line NotationT6N CNJ BZ DZ E1R CO1 DO1 EO1
LabNetwork Molecule IDLN00159058
InChIInChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
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分类

  • Pharmaceuticals
  • {SNA} Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Chemical Structure Class, Core Bioreagents, Folic Acid Metabolism, Inhibits an Enzyme, Interferes with DNA Synthesis, L - Z, Mechanism of Action, Metabolic Pathways, Metabolomics, Pyridines and Pyrimidines,
  • {SNA} 1694 Pharmaceuticals & Personal Care Products, APIs & Metabolites, APIs (Active Pharmaceutical Ingredients) & Metabolites, Alphabetical Index of Analytical Standards, Analytical Standards, Analytical/Chromatography, Antibacterial,
  • {SNA

产品应用

  • An antibacterial agent which selectively inhibits dihydrofolate reductase.

相关文献及参考

  • Manius, G.J., et al.: Anal. Profiles Drug Subs., 7, 445 (1978),
  • Roth, B., et al.: J. Med. Chem., 23, 379 (1980),
  • Brogden, R.N., et al.: Drugs, 23, 405 (1982),

安全信息

Warnings IRRITANT
WGK Germany3
RTECSUV8225000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Packing GroupIII
Hazard Class6.1(b)
GHS Symbol
Safety Statements
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
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P263 Avoid contact during pregnancy/while nursing. 怀孕/哺乳期间避免接触。
  • 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。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • 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+P312
  • P301+P316
  • P301+P317
  • P308+P313
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P318
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Storage condition 储存温度 2-8°C ,充氩储存 2-8°C
UN Number 3249
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 60 mg/kg/10D-I
TOXIC EFFECTS :
   Blood - thrombocytopenia
REFERENCE :
   NZMJAX New Zealand Medical Journal.  (New Zealand Medical Assoc., P.O. Box
   156, Wellington, New Zealand)  V.1-    1900-  Volume(issue)/page/year:
   106,251,1993

TYPE OF TEST            : LD50 - Lethal dose

{

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 90 mg/kg
TOXIC EFFECTS :
   Vascular - BP lowering not characterized in autonomic section
REFERENCE :
   CHTHBK Chemotherapy (Basel).  (S. Karger Pub., Inc., 79 Fifth Ave., New
   York, NY 10003) V.13-    1968-  Volume(issue)/page/year: 14,37,1969

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1460 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Lungs, Thorax, or Respiration - acute pulmonary edema
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   NKRZAZ Chemotherapy (Tokyo).  (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki,
   Shinagawa-Ku, Tokyo 141, Japan)  V.1-    1953- Volume(issue)/page/year:
   21,175,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 132 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JCHEEU Journal of Chemotherapy.  (Edizioni Riviste Scientifiche, via R.
   Giuliani, 419, 50141 Florence, Italy)  V.1-    1989-
   Volume(issue)/page/year: 5,400,1993

TYPE OF TEST

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 50 ug/plate
REFERENCE :
   AMACCQ Antimicrobial Agents and Chemotherapy.  (American Soc. for
   Microbiology, 1913 I St., NW, Washington, DC 20006)  V.1-    1972-
   Volume(issue)/page/year: 12,84,1977

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 10 umol/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1958-  Volume(issue)/page/year:
   26,1593,1977

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 15 ug/plate
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 188,197,1987

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 50 umol/L
REFERENCE :
   BCPCA6 Biochemical Pharmacology.  (Pergamon Press Inc., Maxwell House,
   Fairview Par

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 10 ug/plate
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   43,2819,1983

TYPE OF TEST            : Sperm Morphology
ROUTE OF EXPOSURE       : Unreported
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 800 mg/kg/8D
REFERENCE :
   JOURAA Journal of Urology.  (Williams & Wilkins Co., 428 E. Preston St.,
   Baltimore, MD  21202) V.1-    1917-  Volume(issue)/page/year: 112,348,1974

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 2250 mg/kg
SEX/DURATION            : female 11-13 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   ANANAU Anatomischer Anzeiger.  (VEB Gustav Fischer Verlag, Postfach 176,
   Jena DDR-6900, Ger. Dem. Rep.)  V.1-    1886-  Volume(issue)/page/year:
   149,151,1981

Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • 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
  • H372 Causes damage to organs through prolonged or repeated exposure 长期或频繁接触会损伤器官
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。

其他信息

  • F:8-10-21
  • Sigma Aldrich:738-70-5(sigmaaldrich)
  • 参考质量标准:参见《中国兽药典》1990年版 含量(干基)/% ≥99.0 PH 7.5~8.5 干燥失重/% ≤0.5 灼烧残渣/% ≤0.5
  • 方法二:三甲氧基苯甲醛经缩合、环合而得。
  • 不良反应:甲氧苄啶(简称TMP)毒性较低,常用剂量不良反应少见。由于本品可干扰叶酸代谢,患者可能会出现贫血、白细胞减少及血小板减少等血液系统的反应,多见于剂量过大、疗程过长的情况。故用药期间应勤查血象。本品每日最大用量不应超过0.5g,连续用药时间不应超过1周,血液系统不良反应明显时,可口服叶酸制剂给予纠正。本品不宜与抗肿瘤药物、抗癫痫药物及其他叶酸拮抗剂同时使用;TMP与SMZ或SD合用时偶可致结晶尿。其他不良反应有皮疹及轻度胃肠道反应等。
  • MOL 文件:738-70-5.mol
  • 乙胺嘧啶类抑菌剂:甲氧苄啶是一种亲脂弱碱性乙胺嘧啶类抑菌剂,又称磺胺增效剂、甲氧苄氨嘧啶、抗菌增效剂、甲氧苄胺嘧啶、甲氧苄嘧啶、三甲氧苄胺嘧啶、三甲氧苄啶,常温下为白色或类白色结晶性粉末,无臭,味苦,在氯仿中略溶,在乙醇或丙酮中微溶,在水中几乎不溶,在冰醋酸中易溶。抗菌谱和磺胺药相似,但抗菌作用较强,对大肠杆菌、奇异变形杆菌、肺炎杆菌、腐生葡萄球菌、多种革兰阳性和阴性细菌有效,但对绿脓杆菌感染无效,最低抑菌浓度常低于10mg/L,单用易引起细菌耐药性,故一般不单独使用,主要与磺胺药组成复方制剂,临床上用于治疗尿路感染、肠道感染、呼吸道感染、菌痢、肠炎、伤寒、脑膜炎、中耳炎、流脑、败血症及软组织感染等。对伤寒、副伤寒疗效不低于氨苄西林,也可与长效磺胺药合用于耐药恶性疟的防治。 甲氧苄啶的抗菌原理是干扰细菌的叶酸代谢。主要作用机制是选择性抑制细菌的二氢叶酸还原酶的活性,使二氢叶酸不能还原为四氢叶酸,而合成叶酸是核酸生物合成的主要组成部分,因此本品阻止了细菌核酸和蛋白质的合成,且甲氧卡啶(TMP)与细菌的二氢叶酸还原酶的结合较之对哺乳类动物酶的结合紧密 5~6万倍。与磺胺药的合用可使细菌的叶酸合成代谢遭到双重阻断,有协同作用,使磺胺药抗菌活性增强,并可使抑菌作用转为杀菌作用,减少耐药菌株。另外本品还可增强多种抗生素(如四环素、庆大霉素等)的抗菌作用。
  • 上游原料:乙醇 --> 乙酸乙酯 --> 乙酸 --> 甲醇钠 --> 丙烯腈 --> 硝酸胍 --> 赤血盐 --> 2,3,4—三甲氧基苯甲醛
  • 方法一:以三甲氧基苯甲醛为原料,先与甲氧基丙腈缩合生成3'4'5'-三甲氧基-2氰基-3甲氧基丙烯,然后在甲醇/甲醇钠中与硝酸胍环合而得。
  • 甲氧苄啶价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 T2286 甲氧苄氨嘧啶 Trimethoprim 25G 649元
  • 用途三:新型口服广谱抗菌药物。抗菌谱与磺胺药物相似而效力较强,对多种革兰氏阳性和阴性细菌有效。由于细菌对本品将易产生耐药性,故不宜单独作为抗菌药使用。甲氧苄啶与磺胺药合用可使抗菌作用增强数倍至数十倍。该品主要作磺安类药的增效药。一般按1:5的比例使用。也可作为兽药,治疗禽率大肠肝菌引起的败血症,鸡白痢,禽伤寒,霍乱,呼吸系统继发性细菌感染等。还可用于球虫病的治疗。
  • 用途四:新型口服光谱抗菌药物。抗菌谱与磺胺药物相似而效力较强,对多种革兰氏阳性和阴性细菌有效。由于细菌对本品将易产生耐药性,故不宜单独作为抗菌药使用。甲氧苄啶与磺胺药合用可使抗菌作用增强数倍至十倍。该品主要做磺胺类药的增效药。也可作为兽药,治疗禽率大肠杆菌引起的败血症,鸡白痢,禽伤寒,霍乱,呼吸系统继发性细菌感染等。还可用于球虫病的治疗。
  • 用途一:抗菌增效药,单独用于呼吸道感染、泌尿道感染、肠道感染等病症
  • TCI Shanghai:甲氧苄氨嘧啶 Trimethoprim,>;98.0%(LC)(T)(738-70-5)
  • MSDS 信息:Trimethoprim(738-70-5).msds
  • 用途二:作为抗菌增效药,也可以治疗家禽细菌感染和球虫病。
  • Trimethoprim 是一种抑制细菌的抗生素,主要用于预防和治疗

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