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    Abarelix

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Plenaxis, 183552-38-7, Ppi-149, Ppi 149, R 3827, R3827
    Molecular Formula
    C72H95ClN14O14
    Molecular Weight
    1416.1  g/mol
    InChI Key
    AIWRTTMUVOZGPW-HSPKUQOVSA-N
    Abarelix is a synthetic decapeptide and antagonist of naturally occurring gonadotropin-releasing hormone (GnRH). Abarelix directly and competitively binds to and blocks the gonadotropin releasing hormone receptor in the anterior pituitary gland, thereby inhibiting the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. As a result, this may relieve symptoms associated with prostate hypertrophy or prostate cancer, since testosterone is required to sustain prostate growth.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-2-[[(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]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(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]butanediamide
    2.1.2 InChI
    InChI=1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1
    2.1.3 InChI Key
    AIWRTTMUVOZGPW-HSPKUQOVSA-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(CC(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)N(C)C(=O)C(CO)NC(=O)C(CC3=CN=CC=C3)NC(=O)C(CC4=CC=C(C=C4)Cl)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)NC(=O)C
    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](CC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(=O)C
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Plenaxis

    2. Ppi-149

    2.2.2 Depositor-Supplied Synonyms

    1. Plenaxis

    2. 183552-38-7

    3. Ppi-149

    4. Ppi 149

    5. R 3827

    6. R3827

    7. R-3827

    8. Chembl1252

    9. Plenaxis Depot

    10. Chebi:337298

    11. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparaginyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-

    12. Abarelix-depot-m

    13. Plenaxis (tn)

    14. Abarelix (usan/inn)

    15. Abarelix [usan:inn]

    16. Unii-w486sj5824

    17. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparginyl-l-leucyl-n6-isopropyl-l-lysyl-l-prolyl-d-alaninamide

    18. Schembl9533

    19. Gtpl1188

    20. Ppi149

    21. Schembl19712245

    22. Dtxsid20171443

    23. Bdbm50102442

    24. Ppi 149r3827

    25. R3827;ppi 149

    26. Cs-5873

    27. Db00106

    28. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparaginyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl- 10

    29. Hy-13534

    30. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(pyridin-3-yl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparginyl-l-leucyl-n(6)-isopropyl-l-lysyl-l-prolyl-d-alaninamide

    31. A12613

    32. D02738

    33. 552a387

    34. Q305555

    35. Ac-d-nal-[d-(pcl)phe]-d-pal-ser-[nalpha-me-tyr]-d-asn-leu-ilys-pro-dala-nh2

    36. N-acetyl-3-(2-naphthyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-n-methyl-l-tyrosyl-d-asparagyl-l-leucyl-n6-isopropyl-l-lysyl-l-prolyl-d-alaninamide

    2.3 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 1416.1 g/mol
    Molecular Formula C72H95ClN14O14
    XLogP33.7
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count38
    Exact Mass1414.6840715 g/mol
    Monoisotopic Mass1414.6840715 g/mol
    Topological Polar Surface Area425 Ų
    Heavy Atom Count101
    Formal Charge0
    Complexity2770
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    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

    For palliative treatment of advanced prostate cancer.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Used in the palliative treatment of advanced prostate cancer. Abarelix is a luteinizing hormone agonist that results in suppression of testicular or follicular steroidogenesis.

    5.2 MeSH Pharmacological Classification

    Hormone Antagonists

    Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. (See all compounds classified as Hormone Antagonists.)

    5.3 ATC Code

    L - Antineoplastic and immunomodulating agents

    L02 - Endocrine therapy

    L02B - Hormone antagonists and related agents

    L02BX - Other hormone antagonists and related agents

    L02BX01 - Abarelix

    5.4 Absorption, Distribution and Excretion

    Absorption

    Following IM administration of 100 mg, abarelix is absorbed slowly with a mean peak concentration of 43.4 ng/mL observed approximately 3 days after the injection.

    5.5 Metabolism/Metabolites

    In vitro hepatocyte (rat, monkey, human) studies and in vivo studies in rats and monkeys showed that the major metabolites of abarelix were formed via hydrolysis of peptide bonds. No significant oxidative or conjugated metabolites of abarelix were found either in vitro or in vivo. There is no evidence of cytochrome P-450 involvement in the metabolism of abarelix.

    5.6 Biological Half-Life

    13.2 ± 3.2 days

    5.7 Mechanism of Action

    Abarelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion.