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Icatibant

CAT: 0926-FI45882-03Size: 5 gDry Ice: NoHazardous: No
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CAT#:0926-FI45882-03Size:5 g
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CAS Number
130308-48-4
Synonyms
HOE 140; D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-Tic-Oic-Arg
Smiles
C1CC[C@H]2[C@@H] (C1) C[C@H] (N2C (=O) [C@H]3CC4=CC=CC=C4CN3C (=O) [C@H] (CO) NC (=O) [C@H] (CC5=CC=CS5) NC (=O) CNC (=O) [C@@H]6C[C@H] (CN6C (=O) [C@@H]7CCCN7C (=O) [C@H] (CCCN=C (N) N) NC (=O) [C@@H] (CCCN=C (N) N) N) O) C (=O) N[C@@H] (CCCN=C (N) N) C (=O) O
Molecular Formula
C59H89N19O13S
Molecular Weight
1,304.52 g/mol
Shipping Conditions
Cool Pack
Controlled
No

Chemical Information

Icatibant

Icatibant is a synthetic decapeptide with 5 nonproteinogenic amino acid antagonist targeting the B2 receptors with a similar affinity to bradykinin. It is resistant to bradykinin-cleaving enzyme degradation and has a potency of 2-3 times higher than earlier B2 receptors antagonists, thus representing a new class of medication. It was investigated as a potential treatment of hereditary angioedema (HAE) as bradykinin was implicated in HAE swelling; specifically, mice lacking B2 receptors showed reduced swelling, thus demonstrating bradykinin involvement in the disease pathophysiology. Icatibant was approved by the FDA on August 25, 2011, and by the EMA in 2008 as a treatment for hereditary angioedema. The FDA approval was based on positive results obtained from 3 double-blind, randomized, controlled clinical trials known as FAST 1, 2, and 3, where a median time to almost complete symptom relief was observed to be 8 hours compared to 36 hours for the placebo treatment.

CAS Number130308-48-4
PubChem CID6918173
IUPAC Name(2S)-2-[[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[[(2S)-2-[[2-[[(2S,4R)-1-[(2S)-1-[(2S)-2-[[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-3-thiophen-2-ylpropanoyl]amino]-3-hydroxypropanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid
Molecular FormulaC59H89N19O13S
Molecular Weight1304.5
XLogP-6.4
Topological Polar Surface Area552
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count18
Rotatable Bond Count30
Heavy Atom Count92
Formal Charge0
Complexity2720
SMILES
C1CC[C@H]2[C@@H](C1)C[C@H](N2C(=O)[C@H]3CC4=CC=CC=C4CN3C(=O)[C@H](CO)NC(=O)[C@H](CC5=CC=CS5)NC(=O)CNC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H]7CCCN7C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)N)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)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-SKXRKSCCSA-N
Chemical Structure
2D Structure
2D structure of Icatibant
CAS: 130308-48-4
CID: 6918173
Formula: C59H89N19O13S
MW: 1304.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1304.5
XLogP3-6.4
Hydrogen Bond Donor Count15
Hydrogen Bond Acceptor Count18
Rotatable Bond Count30
Exact Mass1303.66079514
Monoisotopic Mass1303.66079514
Topological Polar Surface Area552 Ų
Heavy Atom Count92
Formal Charge0
Complexity2720
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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