Icatibant | Reverse transcriptase reverse-transcriptase.com

Common Name

Icatibant 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. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source JE049HMDB D-Arg(hyp(3)-thi(5)-D-tic(7)-oic(8))BKMeSH HOE 140MeSH HOE-140MeSH Hoechst 140MeSH Hoechst-140MeSH Icatibant acetateMeSH

Chemical Formlia

C₅₉H₈₉N₁₉O₁₃S Average Molecliar Weight

1304.522 Monoisotopic Molecliar Weight

1303.660794719 IUPAC Name

(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 Traditional Name

icatibant CAS Registry Number

130308-48-4 SMILES

[H][C@]12CC(N(C(=O)C3CC4=CC=CC=C4CN3C(=O)[C@H](CO)NC(=O)[C@H](CC3=CC=CS3)NC(=O)CNC(=O)C3C[C@@H](O)CN3C(=O)C3CCCN3C(=O)C(CCCN=C(N)N)NC(=O)[C@H](N)CCCN=C(N)N)[C@@]1([H])CCCC2)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O

InChI Identifier

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

InChI Key

QURWXBZNHXJZBE-MCDGZUPGSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Oligopeptides Alternative Parents

N-acyl-L-alpha-amino acids

Proline and derivatives

Alpha amino acid amides

Tetrahydroisoquinolines

Indoles and derivatives

N-acylpyrrolidines

Pyrrolidinecarboxamides

Benzenoids

N-acyl amines

Thiophenes

Tertiary carboxylic acid amides

Heteroaromatic compounds

Secondary alcohols

Secondary carboxylic acid amides

Amino acids

Guanidines

Propargyl-type 1,3-dipolar organic compounds

Azacyclic compounds

Monocarboxylic acids and derivatives

Carboximidamides

Carboxylic acids

Hydrocarbon derivatives

Carbonyl compounds

Monoalkylamines

Organic oxides

Primary alcohols

Organopnictogen compounds

Substituents

Alpha-oligopeptide

Proline or derivatives

N-acyl-alpha-amino acid

N-acyl-alpha amino acid or derivatives

N-acyl-l-alpha-amino acid

Alpha-amino acid amide

N-substituted-alpha-amino acid

Alpha-amino acid or derivatives

Tetrahydroisoquinoline

Indole or derivatives

N-acylpyrrolidine

Pyrrolidine carboxylic acid or derivatives

Pyrrolidine-2-carboxamide

Fatty acyl

Fatty amide

Benzenoid

N-acyl-amine

Thiophene

Heteroaromatic compound

Tertiary carboxylic acid amide

Pyrrolidine

Amino acid or derivatives

Carboxamide group

Guanidine

Amino acid

Secondary carboxylic acid amide

Secondary alcohol

Azacycle

Organic 1,3-dipolar compound

Carboxylic acid

Propargyl-type 1,3-dipolar organic compound

Organoheterocyclic compound

Monocarboxylic acid or derivatives

Carboximidamide

Primary aliphatic amine

Organic oxide

Primary amine

Organic nitrogen compound

Organic oxygen compound

Amine

Carbonyl group

Primary alcohol

Organopnictogen compound

Hydrocarbon derivative

Alcohol

Organonitrogen compound

Organooxygen compound

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Adrenergic beta-Antagonists

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility5.70e-02 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.057 mg/mLALOGPS logP-2.3ALOGPS logP-8ChemAxon logS-4.4ALOGPS pKa (Strongest Acidic)3.46ChemAxon pKa (Strongest Basic)11.45ChemAxon Physiological Charge3ChemAxon Hydrogen Acceptor Count23ChemAxon Hydrogen Donor Count15ChemAxon Polar Surface Area523.72 Å²ChemAxon Rotatable Bond Count30ChemAxon Refractivity332.91 m³·mol^-1ChemAxon Polarizability137.03 Å³ChemAxon Number of Rings7ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06196

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06196

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB06196 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

64461 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Icatibant NuGOwiki Link

HMDB15624 Metagene Link

HMDB15624 METLIN ID

Not Available PubChem Compound

71364 PDB ID

Not Available ChEBI ID

Not Available

Product: Nadifloxacin

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General 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:7833220 ]
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:17418383 ]

Enzymes

General function:: Involved in proteolysis
Specific function:: Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and IV, neuropeptides, and chemokines. Found to cleave antigen peptides bound to major histocompatibility complex class II molecules of presenting cells and to degrade neurotransmitters at synaptic junctions. Is also implicated as a regulator of IL-8 bioavailability in the endometrium, and therefore may contribute to the regulation of angiogenesis. Is used as a marker for acute myeloid leukemia and plays a role in tumor invasion. In case of human coronavirus 229E (HCoV-229E) infection, serves as receptor for HCoV-229E spike glycoprotein. Mediates as well human cytomegalovirus (HCMV) infection.
Gene Name:: ANPEP
Uniprot ID:: P15144
Molecular weight:: Not Available

References

Bawolak MT, Fortin JP, Vogel LK, Adam A, Marceau F: The bradykinin B2 receptor antagonist icatibant (Hoe 140) blocks aminopeptidase N at micromolar concentrations: off-target alterations of signaling mediated by the bradykinin B1 and angiotensin receptors. Eur J Pharmacol. 2006 Dec 3;551(1-3):108-11. Epub 2006 Sep 8. [PubMed:17026984 ]

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for bradykinin. It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: BDKRB2
Uniprot ID:: P30411
Molecular weight:: 44460.2

References

Privitera PJ, Beckstead RM, Yates P, Walgren R: Autoradiographic localization of [125I-Tyr0]bradykinin binding sites in brains of Wistar-Kyoto and spontaneously hypertensive rats. Cell Mol Neurobiol. 2003 Oct;23(4-5):805-15. [PubMed:14514033 ]

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

PMID: 17585751

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Structure for HMDB15624 (Icatibant)

Enzymes

References

References