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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
    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 Weight 1364.6 g/mol
    Molecular Formula C61H93N19O15S
    Hydrogen Bond Donor Count16
    Hydrogen Bond Acceptor Count20
    Rotatable Bond Count30
    Exact Mass1363.68192451 g/mol
    Monoisotopic Mass1363.68192451 g/mol
    Topological Polar Surface Area589 Ų
    Heavy Atom Count96
    Formal Charge0
    Complexity2750
    Isotope Atom Count0
    Defined Atom Stereocenter Count12
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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

    B06AC02

    API Reference Price

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    01-Mar-2021
    12-Aug-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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