ChemFOnt: Showing chemical card for Icatibant (CFc000009880)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:09 UTC

Chemfont ID

CFc000009880

Molecule Identification

Common Name

Icatibant

Definition

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

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 Weight

1304.522

Monoisotopic Molecular 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

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015624)
Membrane (HMDB: HMDB0015624)

Source

Exogenous

Exogenous (HMDB: HMDB0015624)

Process

Not Available

Role

Not Available

Physical Properties

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

External Links

HMDB ID

HMDB0015624

DrugBank ID

DB06196

Phenol Explorer Compound ID

Not Available

FooDB 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

METLIN ID

Not Available

PubChem Compound

71364

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Icatibant (CFc000009880)

MOL for CFc000009880 (Icatibant)

3D MOL for CFc000009880 (Icatibant)

3D SDF for CFc000009880 (Icatibant)

3D-SDF for CFc000009880 (Icatibant)

PDB for CFc000009880 (Icatibant)

3D PDB for CFc000009880 (Icatibant)

SMILES for CFc000009880 (Icatibant)

INCHI for CFc000009880 (Icatibant)

Structure for CFc000009880 (Icatibant)

3D Structure for CFc000009880 (Icatibant)