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    Chemistry

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    Also known as: 220810-26-4, Vantas, Histrelin (acetate), Schembl18715, Chembl1200509, Dtxsid30176580
    Molecular Formula
    C68H90N18O14
    Molecular Weight
    1383.6  g/mol
    InChI Key
    OWAUGAMNPZHEOJ-YKZVIGSYSA-N
    Histrelin Acetate
    Histrelin Acetate is the acetate salt form of histrelin, a long-acting, synthetic nonapeptide analog of gonadotropin-releasing hormone (GnRH) with potential anti-tumor activity. Upon administration, histrelin binds to and activates GnRH receptors; prolonged administration results in pituitary GnRH receptor desensitization and inhibition of follicle stimulating hormone (FSH) and luteinizing hormone (LH) secretion, leading to a significant decline in testosterone production in males and may inhibit androgen receptor-positive tumor progression; in females, prolonged administration results in decreased estradiol production.
    1 2D Structure

    Histrelin Acetate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(1-benzylimidazol-4-yl)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C66H86N18O12.C2H4O2/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47;1-2(3)4/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71);1H3,(H,3,4)/t47-,48-,49-,50-,51-,52-,53+,54-,55-;/m0./s1
    2.1.3 InChI Key
    OWAUGAMNPZHEOJ-YKZVIGSYSA-N
    2.1.4 Canonical SMILES
    CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC2=CN(C=N2)CC3=CC=CC=C3)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8.CC(=O)O
    2.1.5 Isomeric SMILES
    CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CN(C=N2)CC3=CC=CC=C3)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8.CC(=O)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. 220810-26-4

    2. Vantas

    3. Histrelin (acetate)

    4. Schembl18715

    5. Chembl1200509

    6. Dtxsid30176580

    7. Mfcd00918679

    8. 767h828

    9. (des-gly10,d-his(bzl)6,pro-nhet9)-lhrh Acetate

    2.3 Create Date
    2008-12-10
    3 Chemical and Physical Properties
    Molecular Weight 1383.6 g/mol
    Molecular Formula C68H90N18O14
    Hydrogen Bond Donor Count16
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count34
    Exact Mass1382.68838962 g/mol
    Monoisotopic Mass1382.68838962 g/mol
    Topological Polar Surface Area487 Ų
    Heavy Atom Count100
    Formal Charge0
    Complexity2690
    Isotope Atom Count0
    Defined Atom Stereocenter Count9
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameVantas
    PubMed Healthhistrelin
    Drug ClassesEndocrine-Metabolic Agent
    Active IngredientHistrelin acetate
    Dosage FormImplant
    RouteSubcutaneous
    Strength50mg
    Market StatusPrescription
    CompanyEndo Pharm

    2 of 2  
    Drug NameVantas
    PubMed Healthhistrelin
    Drug ClassesEndocrine-Metabolic Agent
    Active IngredientHistrelin acetate
    Dosage FormImplant
    RouteSubcutaneous
    Strength50mg
    Market StatusPrescription
    CompanyEndo Pharm

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Pharmacological Classes
    Gonadotropin Releasing Hormone Receptor Agonists [MoA]; Gonadotropin Releasing Hormone Receptor Agonist [EPC]

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