Natamycin (1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-氨基-3,5-二羟基-6-甲基四氢-2H-吡喃-2-基)氧基)-1,3,26-三羟基-12-甲基-10-氧代-6,11,28-三氧三环[22.3.1.05,7 ] 二十八烷-8,14,16,18,20-戊烯-25-羧酸

CAS 7681-93-8 MFCD00135085

化学结构图

7681-93-8
SMILES: C[C@@H]1C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@H]2O[C@](O)(C[C@@H](O)C[C@H]3O[C@@H]3/C=C/C(=O)O1)C[C@H](O)[C@H]2C(=O)O

化学属性

Mol. FormulaC33H47NO13
Mol. Weight666
Density1.0 g/mL at 20 °C(lit.)

别名和识别编码

Chemical NameNatamycin
CAS Number7681-93-8
Synonym Antibiotic A 5283 CL 12,625 Delvocid Delvolan Delvopos Mycophyt Myprozine Natacyn Natamycin Pimafucin Pimaricin Pimarizin Synogil Tennecetin 匹马霉素 游霉素 那他霉素
MDL NumberMFCD00135085
PubChem Substance ID5284447
EC Number231-683-5
Beilstein Registry Number1614878
Chemical Name Translation(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-氨基-3,5-二羟基-6-甲基四氢-2H-吡喃-2-基)氧基)-1,3,26-三羟基-12-甲基-10-氧代-6,11,28-三氧三环[22.3.1.05,7 ] 二十八烷-8,14,16,18,20-戊烯-25-羧酸
Wiswesser Line NotationT3-25- BO DV SOV IU KU MU OU UUTJ EVQ FQ R1 C&YQ1QC&Q HO- BT5OTJ CQ DZ EYQ1
LabNetwork Molecule IDLN01327049
InChIInChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
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分类

  • {SNA} Analytical Standards, Analytical/Chromatography, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antifungal, Biochemicals and Reagents, Chemical Structure Class, Chromatography, Environmental Standards, Fungicides, Interferes with Cell Membrane Permeability (Ionophores), Macrolides, Mechanism of Action, Pesticides, Pesticides & Metabolites, Spectrum of Activity
  • {SNA} Antibiotics A to Z, Antibiotics N-S, Antifungal, Interferes with Cell Membrane Permeability (Ionophores), Mechanism of Action, Spectrum of Activity, 抗生素, 生化试剂
  • {SNA} A

产品应用

  • 一种抗真菌的多烯类抗生素,靠特异性地结合麦角甾醇,抑制真菌生长。 不像制霉菌素和菲律宾霉素, 纳他霉素不改变细胞膜的通透性。

相关文献及参考

  • [2]. Yvonne Maria te Welscher, et al. Polyene antibiotic that inhibits membrane transport proteins. Proc Natl Acad Sci U S A. 2012 Jul 10;109(28):11156-9.
  • Brik, H., et al.: Anal. Profiles Drug Subs. Excip., 23, 399 (1994),
  • Levinskas, G.J., et al.: Toxicol. Appl. Pharmacol., 8, 97 (1966),
  • Merck: 14,6427
  • Pandey, R.C., et al.: J. Antibiot., 29, 1035 (1976),
  • [1]. Wu H, et al. SlnM gene overexpression with different promoters on natamycin production in Streptomyces lydicus A02. J Ind Microbiol Biotechnol. 2014 Jan;41(1):163-72.
  • [1]. Wu H, et al. SlnM gene overexpression with different promoters on natamycin production in Streptomyces lydicus A02. J Ind Microbiol Biotechnol. 2014 Jan;41(1):163-72.
  • [2]. Yvonne Maria te Welscher, et al. Polyene antibiotic that inhibits membrane transport proteins. Proc Natl Acad Sci U S A. 2012 Jul 10;109(28):11156-9.

安全信息

Personal Protective Equipment Eyeshields, Gloves Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSTK3325000
WGK Germany3
GHS Symbol
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Precautionary statements
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
Storage condition 储存温度 2-8°C
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150,

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 450 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ABANAE Antibiotics Annual.  (New York, NY)  1953-60.  For publisher
   information, see AMACCQ.  Volume(issue)/page/year: 5,878,1957/1958

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 190 mg/kg
TOXIC EFFECTS :
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   ANTCAO Antibiotics and Chemotherapy (Washington, DC).  (Washington, DC)
   V.1-12, 1951-62.  For publisher information, see CLMEA3.
   Volume(issue)/page/year: 9,406,1959

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 128 mg

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 40 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   QJDRAZ Quarterly Journal of Crude Drug Research.  (Lisse, Netherlands)
   V.1-19, 1961-81.  For publisher information, see IJCREE.
   Volume(issue)/page/year: 8,1274,1968

TYPE OF

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Mold - Aspergillus nidulans
DOSE/DURATION           : 30 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 79,169,1980

其他信息

  • 几乎无臭无味,可含3mol的水,几乎不溶于水,高级醇、醚、酯,微溶于甲醇,溶于冰醋酸和二甲苯亚 砜。对氧化剂和紫外线较为敏感。

系列性分类


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