icatibant

Also known as HOE-140, HOE 140

Icatibant, sold under the brand name Firazyr, is a medication for the symptomatic treatment of acute attacks of hereditary angioedema (HAE) in adults with C1-esterase-inhibitor deficiency. It is not effective in angioedema caused by medication from the ACE inhibitor class.

Chemical data

Formula: C59H89N19O13S
Molecular weight: 1304.5 g/mol
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
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
InChIKey: QURWXBZNHXJZBE-SKXRKSCCSA-N
XLogP: -6.4
Polar surface area: 552 Å²
H-bond donors: 15
H-bond acceptors: 18
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2008
Admin. routes: parenteral
Indications: heart failure, angioedema, joint disease, severe acute respiratory syndrome

via ChEMBL · EBI

Research

1,542 papers

Is Icatibant Safe for the Treatment of Hereditary Angioedema During Pregnancy?Current allergy and asthma reports · 2022
Icatibant for hereditary angioedema.Drugs of today (Barcelona, Spain : 1998) · 2009
Icatibant in viral infections.Infectious diseases (London, England) · 2023
The Icatibant Outcome Survey: 10 years of experience with icatibant for patients with hereditary angioedema.Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology · 2022
Icatibant for the treatment of hereditary angioedema.The Annals of pharmacotherapy · 2013

via PubMed

Wikidata facts

Subclass of: chemical compound
Has part: carbon
Mass: 1303.661
Has use: medication

Show 5 more facts

chemical formula: C₅₉H₈₉N₁₉O₁₃S
World Health Organisation international non-proprietary name: icatibant
isomeric 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
canonical SMILES: C1CCC2C(C1)CC(N2C(=O)C3CC4=CC=CC=C4CN3C(=O)C(CO)NC(=O)C(CC5=CC=CS5)NC(=O)CNC(=O)C6CC(CN6C(=O)C7CCCN7C(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)N)O)C(=O)NC(CCCN=C(N)N)C(=O)O
defined daily dose: 30

Sources (3)

via Wikidata · CC0

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