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Chemistry

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Also known as: Icatibant acetate [usan], Icatibant (acetate), Firazyr, 325o8467xk, 138614-30-9, (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)

Molecular Formula

C₆₁H₉₃N₁₉O₁₅S

Molecular Weight

1364.6 g/mol

InChI Key

HKMZRZUEADSZDQ-DZJWSCHMSA-N

FDA UNII

325O8467XK

Icatibant Acetate is the acetate salt form of icatibant, an antagonist of the human bradykinin B2 receptor (B2R), that can be used for the treatment of hereditary angioedema (HAE). Upon administration, icatibant targets and binds to B2R, thereby preventing bradykinin from binding to the B2R. This may prevent bradykinin/B2R-mediated vasodilation, the resulting increase in vascular permeability, and the swelling, inflammation, and pain associated with HAE. This may also prevent or improve pulmonary edema not associated with HAE and improve the associated decrease in blood oxygen levels.

1 2D Structure

Icatibant Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[[(2S)-2-[[2-[[(2S,4R)-1-[(2S)-1-[(2S)-2-[[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carbonyl]amino]acetyl]amino]-3-thiophen-2-ylpropanoyl]amino]-3-hydroxypropanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoic acid;acetic acid

2.1.2 InChI

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

2.1.3 InChI Key

HKMZRZUEADSZDQ-DZJWSCHMSA-N

2.1.4 Canonical SMILES

CC(=O)O.C1CCC2C(C1)CC(N2C(=O)C3CC4=CC=CC=C4CN3C(=O)C(CO)NC(=O)C(CC5=CC=CS5)NC(=O)CNC(=O)C6CC(CN6C(=O)C7CCCN7C(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)N)O)C(=O)NC(CCCN=C(N)N)C(=O)O

2.1.5 Isomeric SMILES

CC(=O)O.C1CC[C@H]2[C@@H](C1)C[C@H](N2C(=O)[C@H]3CC4=CC=CC=C4CN3C(=O)[C@H](CO)NC(=O)[C@H](CC5=CC=CS5)NC(=O)CNC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H]7CCCN7C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)N)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

325O8467XK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D-arg(hyp(3)-thi(5)-d-tic(7)-oic(8))bk

2. D-arg(hyp(3)-thi(5)-l-tic(7)-oic(8))bk

3. Firazyr

4. Hoe 140

5. Hoe-140

6. Hoe140

7. Hoechst 140

8. Hoechst-140

9. Icatibant

10. Je 049

11. Je-049

12. Win 65365

13. Win-65365

2.3.2 Depositor-Supplied Synonyms

1. Icatibant Acetate [usan]

2. Icatibant (acetate)

3. Firazyr

4. 325o8467xk

5. 138614-30-9

6. (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)

7. Hoe 140

8. Unii-325o8467xk

9. Icatibant Acetate [mi]

10. Icatibant Acetate [jan]

11. Chembl2028852

12. Icatibant Acetate [mart.]

13. Icatibant Acetate [who-dd]

14. Je-049

15. Icatibant Acetate [orange Book]

16. Hy-108896

17. Cs-0031296

18. Q27256146

19. 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

20. 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)

21. 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-(2alpha,3abeta,7abeta)-octahydro-1h-indole-2-carbonyl-, Acetate (salt)

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₆₁H₉₃N₁₉O₁₅S
Molecular Weight	1364.6 g/mol
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	30
Exact Mass	1363.68192451 g/mol
Monoisotopic Mass	1363.68192451 g/mol
Topological Polar Surface Area	589 Å²
Heavy Atom Count	96
Formal Charge	0
Complexity	2750
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Firazyr is indicated for symptomatic treatment of acute attacks of hereditary angioedema (HAE) in adults (with C1-esterase-inhibitor deficiency).

Treatment of hereditary angioedema

Icatibant Accord is indicated for symptomatic treatment of acute attacks of hereditary angioedema (HAE) in adults, adolescents and children aged 2 years and older, with C1 esterase inhibitor deficiency.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Bradykinin B2 Receptor Antagonists

Compounds and drugs that inhibit ligand binding or cellular signaling by BRADYKININ B2 RECEPTORS. (See all compounds classified as Bradykinin B2 Receptor Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Bradykinin B2 Receptor Antagonists [MoA]; Bradykinin B2 Receptor Antagonist [EPC]

5.3 ATC Code

B06AC02

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API Reference Price

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