Icatibant (CED0006751)

Record Information

Version

1.0

Creation Date

2016-05-25 18:29:19 UTC

Update Date

2026-04-14 16:03:14 UTC

Accession Number

CHEM022348

Identification

Common Name

Icatibant

Class

Small Molecule

Description

Icatibant is an organic compound with the chemical formula C59H89N19O13S. Icatibant belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 1,305 g/mol, Icatibant is a heavy molecule. The compound is found in healthcare, pharmaceuticals, and veterinary products, specifically as a hematological agent, and is administered via subcutaneous exposure. In terms of biological activity, Icatibant acts as an antagonist/inhibitor of the B2 bradykinin receptor (BDKRB2) and Aminopeptidase N (ANPEP).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
JE049	HMDB
D-Arg(hyp(3)-thi(5)-D-tic(7)-oic(8))BK	HMDB
HOE 140	HMDB
HOE-140	HMDB
Hoechst 140	HMDB
Hoechst-140	HMDB
Icatibant acetate	HMDB
(2S)-2-({[(3as,7as)-1-{2-[(2S)-2-{[(2S)-2-{[2-({[(4R)-1-[1-(2-{[(2R)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxy-3-(thiophen-2-yl)propylidene]amino}-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl}-octahydro-1H-indol-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoate	HMDB
Icatibant	MeSH

Chemical Formula

C₅₉H₈₉N₁₉O₁₃S

Average Molecular Mass

1304.522 g/mol

Monoisotopic Mass

1303.661 g/mol

CAS Registry Number

130308-48-4

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

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

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-8	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	11.45	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	523.72 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	332.91 m³·mol⁻¹	ChemAxon
Polarizability	137.03 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00gr-0691030200-f4034e2b8591e5c7dc90	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-3950020400-0bec86946a9c590e3f8f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0259-6930010300-8cc169eccb32d7bc5778	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0hhc-0090000000-7ca39d623eee7b68641e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05nf-1190000000-f36973e3c45e2e9ff484	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6u-9520121111-b1ecb866c5afc970c045	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w2i-0389450124-22001e497de4663bdc45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fe0-2246112953-7f60b7d53a3cd6d03655	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9624300121-4f1f4dac936cc35dbda6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0iml-2064520901-1a989066076a73d93a86	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001u-1091010206-19bad718402ccc5ca425	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfv-2094110201-f25a407e15ff561a10c2	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
283	Hematological agents	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Icatibant Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	B2 bradykinin receptor	P25023	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	B2 bradykinin receptor	P30411	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	44.6855
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	59.4768
Click to view 3D structure	B2 bradykinin receptor	O70526	Cavia porcellus	Predicted (SEA)	0.0778492
Click to view 3D structure	B1 bradykinin receptor	P46663	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	B2 bradykinin receptor	Q28642	Oryctolagus cuniculus	Predicted (SEA)	0.233548
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	161.537
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	140.129
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	179.209
Click to view 3D structure	Substance-P receptor	P14600	Rattus norvegicus	Predicted (SEA)	77.9271
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	161.926
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	148.926
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	111.169
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	256.902
Click to view 3D structure	Neuropilin-1	Q9QWJ9	Rattus norvegicus	Predicted (SEA)	14.9471
Click to view 3D structure	Neurotensin receptor type 1	P30989	Humans	Predicted (SEA)	63.3693
Click to view 3D structure	Neurotensin receptor type 2	O95665	Humans	Predicted (SEA)	53.3267
Click to view 3D structure	Neurotensin receptor type 1	O88319	Mus musculus	Predicted (SEA)	60.1774
Click to view 3D structure	Neuropeptide FF receptor 2	Q9Y5X5	Humans	Predicted (SEA)	122.145
Click to view 3D structure	Substance-K receptor	P16610	Rattus norvegicus	Predicted (SEA)	101.438
Click to view 3D structure	G-protein coupled receptor 15	P49685	Humans	Predicted (SEA)	72.4776
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	145.967
Click to view 3D structure	Adapter molecule crk	P46108	Humans	Predicted (SEA)	78.2385
Click to view 3D structure	Plasminogen	P00747	Humans	Predicted (SEA)	165.274