Icatibant Acetate

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C59H89N19O13S.C2H4O2
Molecular Weight	1364.574
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.N[C@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N2C[C@H](O)C[C@H]2C(=O)NCC(=O)N[C@@H](CC3=CC=CS3)C(=O)N[C@@H](CO)C(=O)N4CC5=CC=CC=C5C[C@@H]4C(=O)N6[C@H]7CCCC[C@H]7C[C@H]6C(=O)N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=HKMZRZUEADSZDQ-DZJWSCHMSA-N

InChI=1S/C59H89N19O13S.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t33-,35+,37+,38-,39-,40-,41-,42-,43-,44-,45-,46+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C59H89N19O13S
Molecular Weight	1304.522
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf
Curator's Comment: http://www.drugbank.ca/drugs/DB06196

Icatibant (trade name 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. Icatibant inhibits bradykinin from binding the B2 receptor and thereby treats the clinical symptoms of an acute, episodic attack of HAE.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bradykinin B2 receptor 3 Target ID: CHEMBL2501 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf	Antagonist 2849		1.07 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hereditary angioedema 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf	Primary		Approved 8583	FIRAZYR Approved Use Indicated for the treatment of acute attacks of hereditary angioedema (HAE) in adults 18 years of age and older. Launch Date 2011

C_max

Value	Dose	Analyte	Population
1190 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02045264	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: healthy age: Adults sex: food status:
405 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03888755	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: unhealthy age: sex: food status:
974 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022150s012s013lbl.pdf	30 mg single, subcutaneous dose: 30 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	ICATIBANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2320 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02045264	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: healthy age: Adults sex: food status:
2320 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02045264	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: healthy age: Adults sex: food status:
611 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03888755	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: unhealthy age: sex: food status:
1198 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03888755	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: unhealthy age: sex: food status:
1506 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03888755	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:	ICATIBANT plasma	Homo sapiens population: unhealthy age: sex: food status:
2165 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022150s012s013lbl.pdf	30 mg single, subcutaneous dose: 30 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	ICATIBANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.77 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT02045264	30 mg single, subcutaneous dose: 30 mg route of administration: subcutaneous experiment type: single co-administered:		ICATIBANT plasma	Homo sapiens population: healthy age: Adults sex: food status:
1.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022150s012s013lbl.pdf	30 mg single, subcutaneous dose: 30 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		ICATIBANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
56% REVIEW https://pubmed.ncbi.nlm.nih.gov/20030426/	30 mg 1 times / day unknown, subcutaneous dose: 30 mg route of administration: Subcutaneous experiment type: UNKNOWN co-administered:		ICATIBANT plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
90 mg single, subcutaneous Highest studied dose Dose: 90 mg Route: subcutaneous Route: single Dose: 90 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27128215	healthy, 18–50 Health Status: healthy Age Group: 18–50 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27128215	Sources: https://pubmed.ncbi.nlm.nih.gov/27128215
0.15 mg/kg multiple, intravenous Highest studied dose Dose: 0.15 mg/kg Route: intravenous Route: multiple Dose: 0.15 mg/kg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf	healthy Health Status: healthy Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf
3.2 mg/kg single, intravenous Highest studied dose Dose: 3.2 mg/kg Route: intravenous Route: single Dose: 3.2 mg/kg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf	healthy Health Status: healthy Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf
30 mg 2 times / day multiple, subcutaneous Recommended Dose: 30 mg, 2 times / day Route: subcutaneous Route: multiple Dose: 30 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf	Disc. AE: Laryngeal disorder... AEs leading to discontinuation/dose reduction: Laryngeal disorder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf

AEs

AE	Significance	Dose	Population
Laryngeal disorder	Disc. AE	30 mg 2 times / day multiple, subcutaneous Recommended Dose: 30 mg, 2 times / day Route: subcutaneous Route: multiple Dose: 30 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022150s000lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060	CYP 303	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=174, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 130, 166, 174, 176, (ClinPharm) 49	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=174, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 130, 166, 174, 176, (ClinPharm) 49	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=173, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000ClinPharmR.pdf#page=49 Page: 173-174, (ClinPharm) 49	no

Drug as victim

Target	Modality	Activity	Metabolite
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=174 Page: 174, 176, 261	no
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=174 Page: 174, 176, 261	no	M1 18
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=174 Page: 174, 176, 261	no	M2 12

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022150Orig1s000PharmR.pdf#page=129 Page: 129, 164, 260, 475, 575

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:68556	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68556
ChemicalBook	CB1318492	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1318492
eMolecules	31216553	https://www.emolecules.com/cgi-bin/more?vid=31216553
MolPort	MolPort-039-139-674	https://www.molport.com/shop/molecule-link/MolPort-039-139-674

PubMed

Title	Date	PubMed
Inhibition of bradykinin-induced vasodilation in human forearm vasculature by icatibant, a potent B2-receptor antagonist.	1994-10	7833220

Patents

Sample Use Guides

In Vivo Use Guide

30 mg administered by subcutaneous (SC) injection in the abdominal area. Additional doses may be administered at intervals of at least 6 hours if response is inadequate or if symptoms recur. No more than 3 doses may be administered in any 24 hour period.

Route of Administration: Other

In Vitro Use Guide

In vitro studies indicated Hoe 140 as a highly potent bradykinin antagonist. In isolated organ preparations Hoe 140 inhibited bradykinin-induced contractions concentration dependently, with IC50-values in the guinea-pig ileum preparation of 11 mM. In the rat uterus preparation the IC50 value for Hoe 140 was 4.9 nM. In the guinea-pig isolated pulmonary artery IC50 was 5.4 nM. In cultured bovine endothelial cells, Hoe 140 antagonized (IC50 = 100 nM) bradykinin-induced endothelium-derived relaxing factor (EDRF) release and the bradykinin-induced increase in cytosolic free calcium (IC50 = 1 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:07 GMT 2025`
Record UNII	325O8467XK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FIRAZYR

Preferred Name

English

Icatibant Acetate

Official Name

English

ICATIBANT ACETATE [ORANGE BOOK]

Common Name

English

ICATIBANT ACETATE [USAN]

Common Name

English

HOE-140

Code

English

Icatibant acetate [WHO-DD]

Common Name

English

ICATIBANT ACETATE [MI]

Common Name

English

L-ARGININE, D-ARGINYL-L-ARGINYL-L-PROLYL-(4R)-4-HYDROXY-L-PROLYLGLYCYL-3-(2-THIENYL)-L-ALANYL-L-SERYL-(3R)-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBONYL-(2S,3AS,7AS)-OCTAHYDRO-1H-INDOLE-2-CARBONYL-, ACETATE

Common Name

English

L-ARGININE, D-ARGINYL-L-ARGINYL-L-PROLYL-TRANS-4-HYDROXY-L-PROLYLGLYCYL-3-(2-THIENYL)-L-ALANYL-L-SERYL-D-1,2,3,4-TETRAHYDRO-3-ISOQUINOLINECARBONYL-L-(2.ALPHA.,3A.BETA.,7A.BETA.)-OCTAHYDRO-1H-INDOLE-2-CARBONYL-, ACETATE (SALT)

Common Name

English

(R)-Arginyl-(S)-arginyl-(S)-prolyl-(2S,4R)-(4-hydroxyprolyl)glycyl-(S)-[3-(2-thienyl)alanyl]-(S)-seryl-(R)-[(1,2,3,4-tetrahydro-3-isoquinolyl)carbonyl]-(2S,3aS,7aS)-[(hexahydro-2-indolinyl)carbonyl]-(S)-arginine acetate (salt)

Common Name

English

ICATIBANT ACETATE [MART.]

Common Name

English

ICATIBANT ACETATE [JAN]

Common Name

English

HOE 140

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C257