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    Chemistry

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    Also known as: Zilucoplan [inn], Zilucoplan [usan], Yg391pk0cc, Ra101495, 1841136-73-9, Zilucoplan [usan:inn]
    Molecular Formula
    C172H278N24O55
    Molecular Weight
    3562  g/mol
    InChI Key
    JDXCOXKBIGBZSK-PSNKNOTQSA-N
    FDA UNII
    YG391PK0CC
    Zilucoplan Sodium
    Zilucoplan is a synthetic macrocyclic peptide inhibitor of the terminal complement protein C5, with potential anti-inflammatory and cell protective activities. Upon subcutaneous administration, complement zilucoplan binds to a unique site in terminal complement protein C5, which blocks C5 cleavage into C5a and C5b and prevents the C5b-dependent assembly of the membrane-attack complex (MAC). Zilucoplan also inhibits the interaction between C5b and C6, thereby further blocking MAC assembly. This prevents MAC-mediated lysis and destruction of red blood cells (RBCs) that occurs in complement-mediated diseases, such as paroxysmal nocturnal hemoglobinuria (PNH), generalized myasthenia gravis (gMG) and lupus nephritis (LN). C5, a complement pathway protein, is expressed at high levels by the liver.
    1 2D Structure

    Zilucoplan Sodium

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,5S,8S,11S,14S,22S)-22-acetamido-11-benzyl-8-(3-carbamimidamidopropyl)-5-(2-carboxyethyl)-3,6,9,12,16,23-hexaoxo-2-propan-2-yl-1,4,7,10,13,17-hexazacyclotricosane-14-carbonyl]-methylamino]-3-carboxypropanoyl]amino]-3,3-dimethylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-2-cyclohexylacetyl]amino]-6-[3-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[[(4S)-4-carboxy-4-(hexadecanoylamino)butanoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoylamino]hexanoic acid
    2.1.2 InChI
    InChI=1S/C172H278N24O55/c1-9-10-11-12-13-14-15-16-17-18-19-20-27-44-146(202)182-136(170(226)227)53-56-144(200)177-64-67-229-69-71-231-73-75-233-77-79-235-81-83-237-85-87-239-89-91-241-93-95-243-97-99-245-101-103-247-105-107-249-109-111-251-113-112-250-110-108-248-106-104-246-102-100-244-98-96-242-94-92-240-90-88-238-86-84-236-82-80-234-78-76-232-74-72-230-70-68-228-66-59-145(201)175-60-31-29-41-135(169(224)225)186-165(220)152(126-37-25-22-26-38-126)193-162(217)142-43-34-65-196(142)168(223)140(116-125-47-51-129(199)52-48-125)190-157(212)133(54-57-148(204)205)184-161(216)139(117-127-120-180-154-130(127)39-32-62-178-154)188-159(214)138(115-124-45-49-128(198)50-46-124)189-166(221)153(172(5,6)7)194-163(218)143(119-150(208)209)195(8)167(222)141-118-147(203)176-61-30-28-40-131(181-122(4)197)158(213)192-151(121(2)3)164(219)185-134(55-58-149(206)207)156(211)183-132(42-33-63-179-171(173)174)155(210)187-137(160(215)191-141)114-123-35-23-21-24-36-123/h21,23-24,32,35-36,39,45-52,62,120-121,126,131-143,151-153,198-199H,9-20,22,25-31,33-34,37-38,40-44,53-61,63-119H2,1-8H3,(H,175,201)(H,176,203)(H,177,200)(H,178,180)(H,181,197)(H,182,202)(H,183,211)(H,184,216)(H,185,219)(H,186,220)(H,187,210)(H,188,214)(H,189,221)(H,190,212)(H,191,215)(H,192,213)(H,193,217)(H,194,218)(H,204,205)(H,206,207)(H,208,209)(H,224,225)(H,226,227)(H4,173,174,179)/t131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,151-,152-,153+/m0/s1
    2.1.3 InChI Key
    JDXCOXKBIGBZSK-PSNKNOTQSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCC(=O)NC(CCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)NCCCCC(C(=O)O)NC(=O)C(C1CCCCC1)NC(=O)C2CCCN2C(=O)C(CC3=CC=C(C=C3)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC4=CNC5=C4C=CC=N5)NC(=O)C(CC6=CC=C(C=C6)O)NC(=O)C(C(C)(C)C)NC(=O)C(CC(=O)O)N(C)C(=O)C7CC(=O)NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N7)CC8=CC=CC=C8)CCCNC(=N)N)CCC(=O)O)C(C)C)NC(=O)C)C(=O)O
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCCCCCC(=O)N[C@@H](CCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)[C@H](C1CCCCC1)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC4=CNC5=C4C=CC=N5)NC(=O)[C@H](CC6=CC=C(C=C6)O)NC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(=O)O)N(C)C(=O)[C@@H]7CC(=O)NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N7)CC8=CC=CC=C8)CCCNC(=N)N)CCC(=O)O)C(C)C)NC(=O)C)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    YG391PK0CC
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Zilucoplan [inn]

    2. Zilucoplan [usan]

    3. Yg391pk0cc

    4. Ra101495

    5. 1841136-73-9

    6. Zilucoplan [usan:inn]

    7. Unii-yg391pk0cc

    8. Zilucoplan [who-dd]

    9. Gtpl10404

    10. Dtxsid301336930

    11. Who 10602

    2.4 Create Date
    2018-05-16
    3 Chemical and Physical Properties
    Molecular Weight 3562 g/mol
    Molecular Formula C172H278N24O55
    XLogP34.8
    Hydrogen Bond Donor Count28
    Hydrogen Bond Acceptor Count57
    Rotatable Bond Count142
    Exact Mass3560.9727939 g/mol
    Monoisotopic Mass3559.9694390 g/mol
    Topological Polar Surface Area1070 Ų
    Heavy Atom Count251
    Formal Charge0
    Complexity6980
    Isotope Atom Count0
    Defined Atom Stereocenter Count16
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of myasthenia gravis

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