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166663-25-8 分子结构
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N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide

ChemBase编号:246
分子式:C58H73N7O17
平均质量:1140.23692
单一同位素质量:1139.50629391
SMILES和InChIs

SMILES:
O[C@H]1[C@H](CN2[C@@H]1C(=O)N[C@H](O)[C@H](O)C[C@H](NC(=O)c1ccc(cc1)c1ccc(cc1)c1ccc(OCCCCC)cc1)C(=O)N[C@H](C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)N[C@H](C(=O)N[C@H](C2=O)[C@H](O)C)[C@H](O)[C@@H](O)c1ccc(O)cc1)[C@H](O)C)C
Canonical SMILES:
CCCCCOc1ccc(cc1)c1ccc(cc1)c1ccc(cc1)C(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)[C@H](O)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@H](O)C)C
InChI:
InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42-,43+,44-,45-,46-,47-,48-,49-,50-,54+/m0/s1
InChIKey:
JHVAMHSQVVQIOT-MFAJLEFUSA-N

引用这个纪录

CBID:246 http://www.chembase.cn/molecule-246.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide
IUPAC传统名
eraxis
商标名
Eraxis
别名
anidulafungin
Anidulafungin
CAS号
166663-25-8
PubChem SID
46505616
160963709
PubChem CID
166548

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00362 external link
PubChem 166548 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 9.457179  质子受体 17 
质子供体 14  LogD (pH = 5.5) -1.4572647 
LogD (pH = 7.4) -1.4609743  Log P -1.4572171 
摩尔折射率 292.2932 cm3 极化性 116.85305 Å3
极化表面积 377.42 Å2 可自由旋转的化学键 14 
里宾斯基五规则 false 
Log P 1.87  LOG S -4.31 
溶解度 5.64e-02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Practically insoluble expand 查看数据来源
疏水性(logP)
2.9 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00362 external link
Item Information
Drug Groups approved; investigational
Description Anidulafungin or Eraxis is an anti-fungal drug manufactured by Pfizer that gained approval by the Food and Drug Administration (FDA) in February 21, 2006; it was previously known as LY303366. There is preliminary evidence that it has a similar safety profile to caspofungin. [Wikipedia]
Indication For use in the treatment of the following fungal infections: Candidemia and other forms of Candida infections (intra-abdominal abscess, and peritonitis), Aspergillus infections, and esophageal candidiasis. Also considered an alternative treatment for oropharyngeal canaidiasis.
Pharmacology Anidulafungin is a semi-synthetic lipopeptide synthesized from a fermentation product of Aspergillus nidulans. Anidulafungin is an echinocandin, a class of antifungal drugs that inhibits the synthesis of 1,3-β-D-glucan, an essential component of fungal cell walls. Anidulafungin is active in vitro against many Candida, as well as some Aspergillus. Like other echinocandins, anidulafungin is not active against Cryptococcus neoformans, Trichosporon, Fusarium, or zygomycetes.
Toxicity During clinical trials a single 400 mg dose of anidulafungin was inadvertently administered as a loading dose. No clinical adverse events were reported. The maximum non-lethal dose of anidulafungin in rats was 50 mg/kg, a dose which is equivalent to 10 times the recommended daily dose for esophageal candidiasis (50mg/day).
Affected Organisms
Aspergillis, Candida and other fungi
Biotransformation Hepatic metabolism of anidulafungin has not been observed. Anidulafungin is not a clinically relevant substrate, inducer, or inhibitor of cytochrome P450 (CYP450) isoenzymes. Anidulafungin undergoes slow chemical degradation at physiologic temperature and pH to a ring-opened peptide that lacks antifungal activity.
Half Life 40-50 hours
Protein Binding 84%
Elimination Less than 1% of the administered radioactive dose was excreted in the urine. Anidulafungin is not hepatically metabolized.
Distribution * 30 to 50 L
Clearance * 1 L/h
References
Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [Pubmed]
Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [Pubmed]
Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. [Pubmed]
Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [Pubmed]
Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [Pubmed]
Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [Pubmed]
Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. [Pubmed]
Morace G, Borghi E, Iatta R, Montagna MT: Anidulafungin, a new echinocandin: in vitro activity. Drugs. 2009;69 Suppl 1:91-4. doi: 10.2165/11315560-000000000-00000. [Pubmed]
External Links
Wikipedia
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. Pubmed
  • Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. Pubmed
  • Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. Pubmed
  • Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. Pubmed
  • Morace G, Borghi E, Iatta R, Montagna MT: Anidulafungin, a new echinocandin: in vitro activity. Drugs. 2009;69 Suppl 1:91-4. doi: 10.2165/11315560-000000000-00000. Pubmed
  • Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. Pubmed
  • Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. Pubmed
  • Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. Pubmed
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专利

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