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    Chemistry

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    Also known as: 934016-19-0, Gonax, Firmagon, Ext215f4zu, Degarelix (as acetate), Degarelix acetate hydrate
    Molecular Formula
    C84H107ClN18O18
    Molecular Weight
    1692.3  g/mol
    InChI Key
    AUTFSFUMNFDPLH-KYMMNHPFSA-N
    FDA UNII
    EXT215F4ZU
    Degarelix Acetate
    Degarelix Acetate is the acetate form of a long-acting, synthetic peptide with gonadotrophin-releasing hormone (GnRH) antagonistic properties. Degarelix targets and blocks GnRH receptors located on the surfaces of gonadotroph cells in the anterior pituitary, thereby reducing secretion of luteinizing hormone (LH) by pituitary gonadotroph cells and so decreasing testosterone production by interstitial (Leydig) cells in the testes.
    1 2D Structure

    Degarelix Acetate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S)-N-[4-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[4-(carbamoylamino)phenyl]-1-oxopropan-2-yl]amino]-3-oxopropyl]phenyl]-2,6-dioxo-1,3-diazinane-4-carboxamide;acetic acid
    2.1.2 InChI
    InChI=1S/C82H103ClN18O16.C2H4O2/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52;1-2(3)4/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117);1H3,(H,3,4)/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+;/m1./s1
    2.1.3 InChI Key
    AUTFSFUMNFDPLH-KYMMNHPFSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(=O)NC(CCCCNC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)NC(=O)N)NC(=O)C(CC3=CC=C(C=C3)NC(=O)C4CC(=O)NC(=O)N4)NC(=O)C(CO)NC(=O)C(CC5=CN=CC=C5)NC(=O)C(CC6=CC=C(C=C6)Cl)NC(=O)C(CC7=CC8=CC=CC=C8C=C7)NC(=O)C.CC(=O)O
    2.1.5 Isomeric SMILES
    C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=C(C=C2)NC(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)NC(=O)[C@@H]4CC(=O)NC(=O)N4)NC(=O)[C@H](CO)NC(=O)[C@@H](CC5=CN=CC=C5)NC(=O)[C@@H](CC6=CC=C(C=C6)Cl)NC(=O)[C@@H](CC7=CC8=CC=CC=C8C=C7)NC(=O)C.CC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    EXT215F4ZU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ac-2nal-4cpa-3pal-ser-4aph(hydroorotyl)-4aph(carbamoyl)-leu-ilys-pro-ala-nh2

    2. Acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ilys-prolyl-alaninamide

    3. Degarelix

    4. Fe 200486

    5. Fe-200486

    6. Fe200486

    7. Firmagon

    8. Gonax

    9. Uglypeptide1

    2.3.2 Depositor-Supplied Synonyms

    1. 934016-19-0

    2. Gonax

    3. Firmagon

    4. Ext215f4zu

    5. Degarelix (as Acetate)

    6. Degarelix Acetate Hydrate

    7. Fe-200486

    8. Degarelix Acetate (jan)

    9. N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-4-[[[(4s)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-l-phenylalanyl-4-[(aminocarbonyl)amino]-d-phenylalanyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-d-alaninamide,monoacetate

    10. Asp3550

    11. Fe200486

    12. Unii-ext215f4zu

    13. Fe200486 (free Base)

    14. Firmagon (tn)

    15. Degarelix Monoacetate

    16. Chembl2028987

    17. Degarelix Acetate Anhydrous

    18. Dtxsid201027699

    19. Asp-3550

    20. Mfcd16879085

    21. Degarelix Monoacetate Anhydrous

    22. Degarelix (acetate) Pound>>fe 200486

    23. Degarelix Acetate(214766-78-6 Free Base)

    24. D09400

    25. Q27277419

    26. D-alaninamide, N-acetyl-3-(naphtalen-2-yl)-d-alanyl-4-chloro-d-phenylalanyl-3-(pyridin-3-yl)-d-alanyl-l-seryl-4-((((4s)-2,6-dioxohexahydropyrimidin-4-yl)carbonyl)amino)-l-phenylalanyl-4-(carbamoylamino)-d-phenylalanyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-, Acetate (1:1)

    2.4 Create Date
    2007-07-04
    3 Chemical and Physical Properties
    Molecular Weight 1692.3 g/mol
    Molecular Formula C84H107ClN18O18
    Hydrogen Bond Donor Count18
    Hydrogen Bond Acceptor Count20
    Rotatable Bond Count41
    Exact Mass1690.7699263 g/mol
    Monoisotopic Mass1690.7699263 g/mol
    Topological Polar Surface Area550 Ų
    Heavy Atom Count121
    Formal Charge0
    Complexity3420
    Isotope Atom Count0
    Defined Atom Stereocenter Count11
    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

    FIRMAGON is a gonadotrophin releasing hormone (GnRH) antagonist indicated:

    - for treatment of adult male patients with advanced hormone-dependent prostate cancer .

    - for treatment of high-risk localised and locally advanced hormone dependent prostate cancer in combination with radiotherapy.

    - as neo-adjuvant treatment prior to radiotherapy in patients with high-risk localised or locally advanced hormone dependent prostate cancer .

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L02BX02

    API Reference Price

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