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130308-48-4 分子结构
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(2S)-2-{[(3aS,7aS)-1-{2-[(2S)-2-[(2S)-2-(2-{[(4R)-1-(1-{2-[(2R)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-5-[(diaminomethylidene)amino]pentanoyl}pyrrolidine-2-carbonyl)-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl}-octahydro-1H-indol-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid

ChemBase编号:4420
分子式:C59H89N19O13S
平均质量:1304.52246
单一同位素质量:1303.660795
SMILES和InChIs

SMILES:
s1c(C[C@H](NC(=O)CNC(=O)C2N(C[C@H](O)C2)C(=O)C2N(CCC2)C(=O)C(NC(=O)[C@H](N)CCCN=C(N)N)CCCN=C(N)N)C(=O)N[C@H](C(=O)N2C(C(=O)N3[C@@H]4[C@H](CC3C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)CCCC4)Cc3c(C2)cccc3)CO)ccc1
Canonical SMILES:
OC[C@@H](C(=O)N1Cc2ccccc2CC1C(=O)N1[C@H]2CCCC[C@H]2CC1C(=O)N[C@H](C(=O)O)CCCN=C(N)N)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)C1C[C@H](CN1C(=O)C1CCCN1C(=O)C(NC(=O)[C@@H](CCCN=C(N)N)N)CCCN=C(N)N)O
InChI:
InChI=1S/C59H89N19O13S/c60-37(14-5-19-67-57(61)62)48(82)72-38(15-6-20-68-58(63)64)52(86)75-22-8-18-43(75)54(88)77-30-35(80)26-44(77)50(84)70-28-47(81)71-40(27-36-13-9-23-92-36)49(83)74-41(31-79)53(87)76-29-34-12-2-1-10-32(34)24-46(76)55(89)78-42-17-4-3-11-33(42)25-45(78)51(85)73-39(56(90)91)16-7-21-69-59(65)66/h1-2,9-10,12-13,23,33,35,37-46,79-80H,3-8,11,14-22,24-31,60H2,(H,70,84)(H,71,81)(H,72,82)(H,73,85)(H,74,83)(H,90,91)(H4,61,62,67)(H4,63,64,68)(H4,65,66,69)/t33-,35+,37+,38?,39-,40-,41-,42-,43?,44?,45?,46?/m0/s1
InChIKey:
QURWXBZNHXJZBE-MCDGZUPGSA-N

引用这个纪录

CBID:4420 http://www.chembase.cn/molecule-4420.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
(2S)-2-{[(3aS,7aS)-1-{2-[(2S)-2-[(2S)-2-(2-{[(4R)-1-(1-{2-[(2R)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-5-[(diaminomethylidene)amino]pentanoyl}pyrrolidine-2-carbonyl)-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl}-octahydro-1H-indol-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid
IUPAC传统名
icatibant
(2S)-2-{[(3aS,7aS)-1-{2-[(2S)-2-[(2S)-2-(2-{[(4R)-1-(1-{2-[(2R)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-5-[(diaminomethylidene)amino]pentanoyl}pyrrolidine-2-carbonyl)-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl}-octahydroindol-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanoic acid
商标名
Firazyr
别名
JE049
icatibant
Icatibant
CAS号
130308-48-4
PubChem SID
99443237
160967852
PubChem CID
71364
CHEBI ID
68556
ATC码
B06AC02
CHEMBL
1743581
Chemspider ID
16736634
DrugBank ID
DB06196
IUPHAR配体索引
667
美国药典/FDA物质标识码
7PG89G35Q7
维基百科标题
Icatibant

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 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.4622498  质子受体 23 
质子供体 15  LogD (pH = 5.5) -14.416425 
LogD (pH = 7.4) -12.670704  Log P -7.9869075 
摩尔折射率 332.9107 cm3 极化性 128.73781 Å3
极化表面积 523.72 Å2 可自由旋转的化学键 30 
里宾斯基五规则 false 
Log P -2.32  LOG S -4.36 
溶解度 5.70e-02 g/l 

分子性质

分子性质

药理学性质 生物活性(PubChem)
给药途径
subcutaneous expand 查看数据来源
法定药品分级
Rx-only (US) expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源
美国(FDA)药品许可证
Icatibant expand 查看数据来源
欧盟(EMEA)药品许可证
Firazyr expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB06196 external link
Item Information
Drug Groups approved; investigational
Description Icatibant (Firazyr) is a peptidomimetic drug consisting of ten amino acids, which is an effective and specific antagonist of bradykinin B2 receptors. It has been approved in the EU for use in hereditary angioedema, and is under investigation for a number of other conditions in which bradykinin is thought to play a significant role. Icatibant currently has orphan drug status in the United States.
Indication Approved for use in hereditary angioedema. Investigated for use/treatment in angioedema, liver disease, and burns and burn infections.
Pharmacology Icatibant is a potent, specific and selective peptidomimetic bradykinin beta2-receptor antagonist (pA2 = 9.04). It has a modified peptide structure, and is the first bradykinin receptor antagonist to act on the guinea-pig trachea without demonstrating agonist effects. It also inhibits aminopeptidase N (Ki = 9.1 μM).
Affected Organisms
Humans and other mammals
Half Life Elimination half-lives calculated from linear regression of the mean data were 25, 27 and 29 min after 20, 50 and 100 micrograms kg-1 doses respectively.
References
Cockcroft JR, Chowienczyk PJ, Brett SE, Bender N, Ritter JM: Inhibition of bradykinin-induced vasodilation in human forearm vasculature by icatibant, a potent B2-receptor antagonist. Br J Clin Pharmacol. 1994 Oct;38(4):317-21. [Pubmed]
Bork K, Frank J, Grundt B, Schlattmann P, Nussberger J, Kreuz W: Treatment of acute edema attacks in hereditary angioedema with a bradykinin receptor-2 antagonist (Icatibant). J Allergy Clin Immunol. 2007 Jun;119(6):1497-503. Epub 2007 Apr 5. [Pubmed]
External Links
Wikipedia

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Cockcroft JR, Chowienczyk PJ, Brett SE, Bender N, Ritter JM: Inhibition of bradykinin-induced vasodilation in human forearm vasculature by icatibant, a potent B2-receptor antagonist. Br J Clin Pharmacol. 1994 Oct;38(4):317-21. Pubmed
  • Bork K, Frank J, Grundt B, Schlattmann P, Nussberger J, Kreuz W: Treatment of acute edema attacks in hereditary angioedema with a bradykinin receptor-2 antagonist (Icatibant). J Allergy Clin Immunol. 2007 Jun;119(6):1497-503. Epub 2007 Apr 5. Pubmed
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专利

专利

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