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Identification
NameIcatibant
Accession NumberDB06196
TypeSmall Molecule
GroupsApproved
DescriptionIcatibant (Firazyr) is a synthetic peptidomimetic drug consisting of ten amino acids, and acts as 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 and FDA approved on August 25, 2011.
Structure
Thumb
Synonyms
HOE 140
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Firazyrinjection, solution30 mg/3mLsubcutaneousShire US Manufacturing Inc.2011-08-25Not applicableUs
Firazyrsolution10 mgsubcutaneousShire Orphan Therapies Inc2014-07-14Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Icatibant Acetate
Thumb
  • InChI Key: DKYJWPPYONLYTF-DZJWSCHMSA-N
  • Monoisotopic Mass: 1362.697908506
  • Average Mass: 1363.59
DBSALT000097
Categories
UNII7PG89G35Q7
CAS number130308-48-4
WeightAverage: 1304.522
Monoisotopic: 1303.660794719
Chemical FormulaC59H89N19O13S
InChI KeyInChIKey=QURWXBZNHXJZBE-MCDGZUPGSA-N
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
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
SMILES
[H][C@]12CC(N(C(=O)C3CC4=CC=CC=C4CN3C(=O)[[email protected]](CO)NC(=O)[[email protected]](CC3=CC=CS3)NC(=O)CNC(=O)C3C[C@@H](O)CN3C(=O)C3CCCN3C(=O)C(CCCN=C(N)N)NC(=O)[[email protected]](N)CCCN=C(N)N)[C@@]1([H])CCCC2)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • N-acyl-l-alpha-amino acid
  • Tetrahydroisoquinoline
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Indole or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Heteroaromatic compound
  • Thiophene
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationApproved for use in acute attacks of hereditary angioedema (HAE). Investigated for use/treatment in angioedema, liver disease, and burns and burn infections.
PharmacodynamicsIcatibant is a potent, specific, competitive, 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). If an IV dose of 0.4 and 0.8 mg/kg was infused over 4 hours, one may observe an inhibited response to bradykinin challenge for 6 - 8 hours following completion of infusion.
Mechanism of actionBradykinin is a peptide-based hormone that is formed locally in tissues, very often in response to a trauma. It increases vessel permeability, dilates blood vessels and causes smooth muscle cells to contract. Bradykinin plays an important role in the mediation of pain. Surplus bradykinin is responsible for the typical symptoms of inflammation, such as swelling, redness, overheating and pain. These symptoms are mediated by activation of bradykinin B2 receptors. In patients with HAE, they have an absent or dysfunctional C1-esterase inhibitor. This inhibitor is responsible for the production of bradykinin in which displacement of bradykinin from B2 receptors by icatibant has an inhibitory effect on the receptor for a relatively long time.
Related Articles
AbsorptionThe absolute bioavailability of icatibant following a 30 mg subcutaneous dose is approximately 97%. Maximum plasma concentrations (Cmax) of 974 ± 280 ng/mL was reached when a single subcutaneous dose of 30 mg was administered. The AUC was 2165 ± 568 ng∙hr/mL. Icatibant did not accumulate following multiple doses.
Volume of distribution

Vdss, subcutaneous injection = 29.0 ± 8.7 L.

Protein bindingNot Available
Metabolism

Icatibant is metabolized by proteolytic enzymes into inactive metabolites. The cytochrome P450 enzyme system is not involved with the metabolism of icatibant.

Route of eliminationUrine (<10% unchanged)
Half lifeAfter subcutaneous administration, mean elimination half-life was 1.4 ± 0.4 hours.
Clearance

Plasma clearance following subcutaneous administration was 245 ± 58 mL/min.

ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5123
Blood Brain Barrier-0.8713
Caco-2 permeable-0.8198
P-glycoprotein substrateSubstrate0.8421
P-glycoprotein inhibitor INon-inhibitor0.8961
P-glycoprotein inhibitor IINon-inhibitor0.9801
Renal organic cation transporterNon-inhibitor0.6176
CYP450 2C9 substrateNon-substrate0.7753
CYP450 2D6 substrateNon-substrate0.7828
CYP450 3A4 substrateNon-substrate0.5958
CYP450 1A2 substrateNon-inhibitor0.661
CYP450 2C9 inhibitorNon-inhibitor0.8477
CYP450 2D6 inhibitorNon-inhibitor0.876
CYP450 2C19 inhibitorNon-inhibitor0.796
CYP450 3A4 inhibitorNon-inhibitor0.729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.6483
CarcinogenicityNon-carcinogens0.8963
BiodegradationNot ready biodegradable0.898
Rat acute toxicity2.4262 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9506
hERG inhibition (predictor II)Inhibitor0.5187
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, solutionsubcutaneous30 mg/3mL
Solutionsubcutaneous10 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5648333 No1999-07-152019-07-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility1 mg/mL MSDS
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. 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 ]
  2. 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 ]
External Links
ATC CodesB06AC02
AHFS Codes
  • 92:32
PDB EntriesNot Available
FDA labelDownload (543 KB)
MSDSDownload (87.6 KB)
Interactions
Drug Interactions
Drug
AbciximabIcatibant may increase the anticoagulant activities of Abciximab.
AcebutololIcatibant may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Icatibant is combined with Aceclofenac.
AcenocoumarolIcatibant may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Icatibant.
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Icatibant.
Alendronic acidThe risk or severity of adverse effects can be increased when Icatibant is combined with Alendronic acid.
AliskirenIcatibant may decrease the antihypertensive activities of Aliskiren.
AlprenololIcatibant may decrease the antihypertensive activities of Alprenolol.
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Icatibant.
AmikacinIcatibant may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmilorideIcatibant may decrease the antihypertensive activities of Amiloride.
AncrodIcatibant may increase the anticoagulant activities of Ancrod.
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with Icatibant.
Antithrombin III humanIcatibant may increase the anticoagulant activities of Antithrombin III human.
ApixabanIcatibant may increase the anticoagulant activities of Apixaban.
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with Icatibant.
ArdeparinIcatibant may increase the anticoagulant activities of Ardeparin.
ArgatrobanIcatibant may increase the anticoagulant activities of Argatroban.
ArotinololIcatibant may decrease the antihypertensive activities of Arotinolol.
AtenololIcatibant may decrease the antihypertensive activities of Atenolol.
AzapropazoneThe risk or severity of adverse effects can be increased when Icatibant is combined with Azapropazone.
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Icatibant.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Icatibant.
BalsalazideIcatibant may increase the nephrotoxic activities of Balsalazide.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Icatibant.
BecaplerminIcatibant may increase the anticoagulant activities of Becaplermin.
BefunololIcatibant may decrease the antihypertensive activities of Befunolol.
BenazeprilIcatibant may decrease the antihypertensive activities of Benazepril.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Icatibant.
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Icatibant.
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Icatibant.
BetaxololIcatibant may decrease the antihypertensive activities of Betaxolol.
BevantololIcatibant may decrease the antihypertensive activities of Bevantolol.
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Icatibant.
BisoprololIcatibant may decrease the antihypertensive activities of Bisoprolol.
BivalirudinIcatibant may increase the anticoagulant activities of Bivalirudin.
BopindololIcatibant may decrease the antihypertensive activities of Bopindolol.
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Icatibant.
BufuralolIcatibant may decrease the antihypertensive activities of Bufuralol.
BumetanideIcatibant may decrease the diuretic activities of Bumetanide.
BupranololIcatibant may decrease the antihypertensive activities of Bupranolol.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Icatibant.
CandoxatrilIcatibant may decrease the antihypertensive activities of Candoxatril.
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Icatibant.
CaptoprilIcatibant may decrease the antihypertensive activities of Captopril.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Icatibant.
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Icatibant.
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with Icatibant.
CarteololIcatibant may decrease the antihypertensive activities of Carteolol.
CarvedilolIcatibant may decrease the antihypertensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with Icatibant.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Icatibant.
CeliprololIcatibant may decrease the antihypertensive activities of Celiprolol.
CertoparinIcatibant may increase the anticoagulant activities of Certoparin.
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Icatibant.
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Icatibant.
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Icatibant.
CholestyramineCholestyramine can cause a decrease in the absorption of Icatibant resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilazaprilIcatibant may decrease the antihypertensive activities of Cilazapril.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Icatibant.
Citric AcidIcatibant may increase the anticoagulant activities of Citric Acid.
ClodronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Clodronate.
ClonixinThe risk or severity of adverse effects can be increased when Icatibant is combined with Clonixin.
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Icatibant.
ColesevelamColesevelam can cause a decrease in the absorption of Icatibant resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Icatibant resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclosporineIcatibant may increase the nephrotoxic activities of Cyclosporine.
D-LimoneneThe risk or severity of adverse effects can be increased when Icatibant is combined with D-Limonene.
Dabigatran etexilateIcatibant may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinIcatibant may increase the anticoagulant activities of Dalteparin.
DanaparoidIcatibant may increase the anticoagulant activities of Danaparoid.
DaunorubicinIcatibant may decrease the excretion rate of Daunorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DeferasiroxThe risk or severity of adverse effects can be increased when Icatibant is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Icatibant.
DesirudinIcatibant may increase the anticoagulant activities of Desirudin.
DesmopressinThe risk or severity of adverse effects can be increased when Icatibant is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Icatibant.
DextranIcatibant may increase the anticoagulant activities of Dextran.
Dextran 40Icatibant may increase the anticoagulant activities of Dextran 40.
Dextran 70Icatibant may increase the anticoagulant activities of Dextran 70.
Dextran 75Icatibant may increase the anticoagulant activities of Dextran 75.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Icatibant.
DicoumarolIcatibant may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Icatibant.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Icatibant.
DihydrostreptomycinIcatibant may decrease the excretion rate of Dihydrostreptomycin which could result in a lower serum level and potentially a reduction in efficacy.
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Icatibant.
DoxorubicinIcatibant may decrease the excretion rate of Doxorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DrospirenoneIcatibant may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Icatibant is combined with Droxicam.
Edetic AcidIcatibant may increase the anticoagulant activities of Edetic Acid.
EdoxabanIcatibant may increase the anticoagulant activities of Edoxaban.
EnalaprilIcatibant may decrease the antihypertensive activities of Enalapril.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Icatibant.
EnalaprilatIcatibant may decrease the antihypertensive activities of Enalaprilat.
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Icatibant.
EnoxaparinIcatibant may increase the anticoagulant activities of Enoxaparin.
EpirizoleThe risk or severity of adverse effects can be increased when Icatibant is combined with Epirizole.
EpirubicinIcatibant may decrease the excretion rate of Epirubicin which could result in a lower serum level and potentially a reduction in efficacy.
EplerenoneIcatibant may decrease the antihypertensive activities of Eplerenone.
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Icatibant.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Icatibant.
EsmololIcatibant may decrease the antihypertensive activities of Esmolol.
Etacrynic acidIcatibant may decrease the diuretic activities of Etacrynic acid.
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Icatibant.
Ethyl biscoumacetateIcatibant may increase the anticoagulant activities of Ethyl biscoumacetate.
Etidronic acidThe risk or severity of adverse effects can be increased when Icatibant is combined with Etidronic acid.
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Icatibant.
EtofenamateThe risk or severity of adverse effects can be increased when Icatibant is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with Icatibant.
Evening primrose oilThe risk or severity of adverse effects can be increased when Icatibant is combined with Evening primrose oil.
exisulindThe risk or severity of adverse effects can be increased when Icatibant is combined with exisulind.
FenbufenThe risk or severity of adverse effects can be increased when Icatibant is combined with Fenbufen.
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Icatibant.
FingolimodIcatibant may increase the immunosuppressive activities of Fingolimod.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Icatibant.
FlunixinThe risk or severity of adverse effects can be increased when Icatibant is combined with Flunixin.
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Icatibant.
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Icatibant.
Fondaparinux sodiumIcatibant may increase the anticoagulant activities of Fondaparinux sodium.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Icatibant.
FosinoprilIcatibant may decrease the antihypertensive activities of Fosinopril.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Icatibant.
FramycetinIcatibant may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FurosemideIcatibant may decrease the diuretic activities of Furosemide.
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Icatibant.
GentamicinIcatibant may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
HaloperidolThe risk or severity of adverse effects can be increased when Icatibant is combined with Haloperidol.
HeparinIcatibant may increase the anticoagulant activities of Heparin.
HirulogIcatibant may increase the anticoagulant activities of Hirulog.
HMPL-004The risk or severity of adverse effects can be increased when HMPL-004 is combined with Icatibant.
HydralazineIcatibant may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Icatibant.
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Icatibant.
Hygromycin BIcatibant may decrease the excretion rate of Hygromycin B which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Ibandronate.
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Icatibant.
IbuproxamThe risk or severity of adverse effects can be increased when Icatibant is combined with Ibuproxam.
IdarubicinIcatibant may decrease the excretion rate of Idarubicin which could result in a lower serum level and potentially a reduction in efficacy.
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Icatibant.
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Icatibant.
IndenololIcatibant may decrease the antihypertensive activities of Indenolol.
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Icatibant.
IndoprofenThe risk or severity of adverse effects can be increased when Icatibant is combined with Indoprofen.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Icatibant.
IsoxicamThe risk or severity of adverse effects can be increased when Icatibant is combined with Isoxicam.
KanamycinIcatibant may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneThe risk or severity of adverse effects can be increased when Icatibant is combined with Kebuzone.
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Icatibant.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Icatibant.
LabetalolIcatibant may decrease the antihypertensive activities of Labetalol.
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with Icatibant.
LepirudinIcatibant may increase the anticoagulant activities of Lepirudin.
LevobunololIcatibant may decrease the antihypertensive activities of Levobunolol.
LisinoprilIcatibant may decrease the antihypertensive activities of Lisinopril.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Icatibant.
LithiumThe serum concentration of Lithium can be increased when it is combined with Icatibant.
LornoxicamThe risk or severity of adverse effects can be increased when Icatibant is combined with Lornoxicam.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Icatibant.
LoxoprofenThe risk or severity of adverse effects can be increased when Icatibant is combined with Loxoprofen.
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Icatibant.
LumiracoxibThe risk or severity of adverse effects can be increased when Lumiracoxib is combined with Icatibant.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Icatibant.
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Icatibant.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Icatibant.
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Icatibant.
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Icatibant.
MesalazineIcatibant may increase the nephrotoxic activities of Mesalazine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Icatibant.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Icatibant.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Icatibant.
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Icatibant.
MetipranololIcatibant may decrease the antihypertensive activities of Metipranolol.
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Icatibant.
MetoprololIcatibant may decrease the antihypertensive activities of Metoprolol.
MetrizamideIcatibant may decrease the excretion rate of Metrizamide which could result in a lower serum level and potentially a reduction in efficacy.
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Icatibant.
MoexiprilIcatibant may decrease the antihypertensive activities of Moexipril.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Icatibant.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Icatibant.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Icatibant.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Icatibant.
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Icatibant.
NadololIcatibant may decrease the antihypertensive activities of Nadolol.
NadroparinIcatibant may increase the anticoagulant activities of Nadroparin.
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Icatibant.
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Icatibant.
NatalizumabThe risk or severity of adverse effects can be increased when Icatibant is combined with Natalizumab.
NCX 4016The risk or severity of adverse effects can be increased when NCX 4016 is combined with Icatibant.
NeomycinIcatibant may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacThe risk or severity of adverse effects can be increased when Icatibant is combined with Nepafenac.
NetilmicinIcatibant may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with Icatibant.
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Icatibant.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Icatibant.
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Icatibant.
OlsalazineIcatibant may increase the nephrotoxic activities of Olsalazine.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Icatibant.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Icatibant is combined with Omacetaxine mepesuccinate.
OmapatrilatIcatibant may decrease the antihypertensive activities of Omapatrilat.
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Icatibant.
OrgoteinThe risk or severity of adverse effects can be increased when Icatibant is combined with Orgotein.
OtamixabanIcatibant may increase the anticoagulant activities of Otamixaban.
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Icatibant.
OxprenololIcatibant may decrease the antihypertensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Icatibant.
PamidronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Pamidronate.
ParecoxibThe risk or severity of adverse effects can be increased when Icatibant is combined with Parecoxib.
ParomomycinIcatibant may decrease the excretion rate of Paromomycin which could result in a lower serum level and potentially a reduction in efficacy.
PenbutololIcatibant may decrease the antihypertensive activities of Penbutolol.
Pentosan PolysulfateIcatibant may increase the anticoagulant activities of Pentosan Polysulfate.
PerindoprilIcatibant may decrease the antihypertensive activities of Perindopril.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Icatibant.
PhenindioneIcatibant may increase the anticoagulant activities of Phenindione.
PhenprocoumonIcatibant may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Icatibant.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Icatibant.
PindololIcatibant may decrease the antihypertensive activities of Pindolol.
PiretanideIcatibant may decrease the diuretic activities of Piretanide.
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with Icatibant.
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Icatibant.
PlicamycinIcatibant may decrease the excretion rate of Plicamycin which could result in a lower serum level and potentially a reduction in efficacy.
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Icatibant.
PractololIcatibant may decrease the antihypertensive activities of Practolol.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Icatibant.
ProbenecidThe serum concentration of Icatibant can be increased when it is combined with Probenecid.
PropacetamolThe risk or severity of adverse effects can be increased when Icatibant is combined with Propacetamol.
PropranololIcatibant may decrease the antihypertensive activities of Propranolol.
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Icatibant.
Protein CIcatibant may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeIcatibant may increase the anticoagulant activities of Protocatechualdehyde.
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with Icatibant.
PuromycinIcatibant may decrease the excretion rate of Puromycin which could result in a lower serum level and potentially a reduction in efficacy.
QuinaprilIcatibant may decrease the antihypertensive activities of Quinapril.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Icatibant.
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Icatibant.
Rabies vaccineThe risk or severity of adverse effects can be increased when Icatibant is combined with Rabies vaccine.
RamiprilIcatibant may decrease the antihypertensive activities of Ramipril.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Icatibant.
RescinnamineIcatibant may decrease the antihypertensive activities of Rescinnamine.
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Icatibant.
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Icatibant.
ReviparinIcatibant may increase the anticoagulant activities of Reviparin.
RibostamycinIcatibant may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Risedronate.
RivaroxabanIcatibant may increase the anticoagulant activities of Rivaroxaban.
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Icatibant.
RoflumilastRoflumilast may increase the immunosuppressive activities of Icatibant.
SalicylamideThe risk or severity of adverse effects can be increased when Icatibant is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Icatibant.
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Icatibant.
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Icatibant.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Icatibant.
SeratrodastThe risk or severity of adverse effects can be increased when Icatibant is combined with Seratrodast.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Icatibant.
SotalolIcatibant may decrease the antihypertensive activities of Sotalol.
SpectinomycinIcatibant may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
SpiraprilIcatibant may decrease the antihypertensive activities of Spirapril.
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Icatibant.
SpironolactoneIcatibant may decrease the antihypertensive activities of Spironolactone.
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Icatibant.
StreptomycinIcatibant may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptozocinIcatibant may decrease the excretion rate of Streptozocin which could result in a lower serum level and potentially a reduction in efficacy.
SulfasalazineIcatibant may increase the nephrotoxic activities of Sulfasalazine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Icatibant.
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Icatibant.
SulodexideIcatibant may increase the anticoagulant activities of Sulodexide.
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with Icatibant.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Icatibant.
TacrolimusIcatibant may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Icatibant.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Icatibant.
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Technetium Tc-99m Medronate.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Icatibant.
TemocaprilIcatibant may decrease the antihypertensive activities of Temocapril.
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Icatibant.
TenofovirThe risk or severity of adverse effects can be increased when Icatibant is combined with Tenofovir.
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Icatibant.
TepoxalinThe risk or severity of adverse effects can be increased when Icatibant is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Icatibant is combined with Teriflunomide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Icatibant.
TiludronateThe risk or severity of adverse effects can be increased when Icatibant is combined with Tiludronate.
TimololIcatibant may decrease the antihypertensive activities of Timolol.
TobramycinIcatibant may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TofacitinibIcatibant may increase the immunosuppressive activities of Tofacitinib.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Icatibant is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Icatibant.
TorasemideIcatibant may decrease the diuretic activities of Torasemide.
TrandolaprilIcatibant may decrease the antihypertensive activities of Trandolapril.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Icatibant.
TranilastThe risk or severity of adverse effects can be increased when Icatibant is combined with Tranilast.
TrastuzumabTrastuzumab may increase the neutropenic activities of Icatibant.
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Icatibant.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Icatibant.
TriamtereneIcatibant may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Icatibant.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Trisalicylate-choline is combined with Icatibant.
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Icatibant.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Icatibant.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Icatibant.
WarfarinIcatibant may increase the anticoagulant activities of Warfarin.
XimelagatranIcatibant may increase the anticoagulant activities of Ximelagatran.
ZaltoprofenThe risk or severity of adverse effects can be increased when Icatibant is combined with Zaltoprofen.
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Icatibant.
Zoledronic acidThe risk or severity of adverse effects can be increased when Icatibant is combined with Zoledronic acid.
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with Icatibant.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Type 1 angiotensin receptor binding
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:
44460.15 Da
References
  1. 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 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
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 I...
Gene Name:
ANPEP
Uniprot ID:
P15144
Molecular Weight:
109538.68 Da
References
  1. 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 ]
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Drug created on March 19, 2008 10:16 / Updated on September 27, 2016 02:25