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    Chemistry

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    Also known as: 129311-55-3, Ganirelix acetate [usan], Ganirelix acetate injection, Antagon, 56u7906fqw, Orgalutran
    Molecular Formula
    C84H121ClN18O17
    Molecular Weight
    1690.4  g/mol
    InChI Key
    OVBICQMTCPFEBS-SATRDZAXSA-N
    FDA UNII
    56U7906FQW
    Ganirelix
    Ganirelix Acetate is the acetate salt form of ganirelix, a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix directly competes with the GnRH for receptor binding in the anterior pituitary gland, thus induces a rapid and reversible suppression of the release of follicle stimulating hormone (FSH) and luteinizing hormone (LH). This agent is used for the inhibition of premature LH surges in women undergoing controlled ovarian hyperstimulation, and in combination with other hormones for retrieval of the mature follicles for in-vitro fertilization.
    1 2D Structure

    Ganirelix

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-1-[(2S)-2-[[(2S)-2-[[(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]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]amino]-4-methylpentanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;acetic acid
    2.1.2 InChI
    InChI=1S/C80H113ClN18O13.2C2H4O2/c1-9-84-79(85-10-2)88-38-17-15-24-60(70(104)94-62(41-49(5)6)71(105)93-61(25-16-18-39-89-80(86-11-3)87-12-4)78(112)99-40-20-26-68(99)77(111)90-50(7)69(82)103)92-73(107)64(44-53-30-35-59(102)36-31-53)97-76(110)67(48-100)98-75(109)66(46-55-21-19-37-83-47-55)96-74(108)65(43-52-28-33-58(81)34-29-52)95-72(106)63(91-51(8)101)45-54-27-32-56-22-13-14-23-57(56)42-54;2*1-2(3)4/h13-14,19,21-23,27-37,42,47,49-50,60-68,100,102H,9-12,15-18,20,24-26,38-41,43-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,107)(H,93,105)(H,94,104)(H,95,106)(H,96,108)(H,97,110)(H,98,109)(H2,84,85,88)(H2,86,87,89);2*1H3,(H,3,4)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+;;/m1../s1
    2.1.3 InChI Key
    OVBICQMTCPFEBS-SATRDZAXSA-N
    2.1.4 Canonical SMILES
    CCNC(=NCCCCC(C(=O)NC(CC(C)C)C(=O)NC(CCCCN=C(NCC)NCC)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=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)NCC.CC(=O)O.CC(=O)O
    2.1.5 Isomeric SMILES
    CCNC(=NCCCC[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=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)NCC.CC(=O)O.CC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    56U7906FQW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Antagon

    2. Ganirelix

    3. Ganirelix Diacetate

    4. Gnrh, N-ac-2-nal(1)-4-cl-phe(2)-3-pal(3)-et2-harg(6,8)-alanh2(10)-

    5. Lhrh, N-acetyl-2-naphthylalanyl(1)-(4-chlorophenylalanyl)(2)-3-pyrdinylalanyl(3)-diethylhomoarginyl(6,8)-alaninamide(10)-

    6. Lhrh,n-ac-2-nal(1)-4-cl-phe(2)-3-pal(3)-et2-harg(6,8)-alanh2(10)-

    7. N-ac-(2-naphthyl)ala-2-(4-cl-phe)-3-(3-pyridinyl-ala)-6,8-et2-harg-10-alanh2-lhrh

    8. N-acetyl-3-(2-naphthyl)-d-alanyl-p-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-(n,n'-diethylamidino)-d-lysyl-l-leucyl-n(sup 6)-(n,n'-diethylamidino)-l-lysyl-l-prolyl-d-alaninamide Diacetate (salt)

    9. Orgalutran

    10. Rs 26306

    11. Rs-26306

    12. Rs-26306-298

    2.3.2 Depositor-Supplied Synonyms

    1. 129311-55-3

    2. Ganirelix Acetate [usan]

    3. Ganirelix Acetate Injection

    4. Antagon

    5. 56u7906fqw

    6. Orgalutran

    7. Rs-26306

    8. Ganirelix (acetate)

    9. Ganirest

    10. D-alaninamide,n-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-[bis(ethylamino)methylene]-d-lysyl-l-leucyl-n6-[bis(ethylamino)methylene]-l-lysyl-l-prolyl-, Diacetate (salt)

    11. N-acetyl-3-(2-naphthyl)-d-alanyl-p-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-(n,n'-diethylamidino)-d-lysyl-l-leucyl-n(sup 6)-(n,n'-diethylamidino)-l-lysyl-l-prolyl-d-alaninamide Diacetate (salt)

    12. Rs-26306-298

    13. Unii-56u7906fqw

    14. Ganirest (tn)

    15. Orgalutran Tfa Salt

    16. Ganirelix Acetate [mi]

    17. Ganirelix Acetate (jan/usan)

    18. Ganirelix Acetate [jan]

    19. Org-37462

    20. Ganirelix Acetate [vandf]

    21. Ganirelix Acetate Injection (tn)

    22. Ganirelix Acetate [mart.]

    23. Ganirelix Acetate [who-dd]

    24. Akos025394292

    25. Ganirelix Acetate [orange Book]

    26. Hy-109532

    27. D04302

    28. 311g553

    29. J-005666

    30. Q27261435

    31. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-((ethylamino)(ethylimino)methyl)-d-lysyl-l-leucyl-n(sup 6)-((ethylamino)(ethylimino)methyl)-l-lysyl-l-prolyl-, Diacetate (salt)

    2.4 Create Date
    2008-02-08
    3 Chemical and Physical Properties
    Molecular Weight 1690.4 g/mol
    Molecular Formula C84H121ClN18O17
    Hydrogen Bond Donor Count18
    Hydrogen Bond Acceptor Count20
    Rotatable Bond Count48
    Exact Mass1688.8845622 g/mol
    Monoisotopic Mass1688.8845622 g/mol
    Topological Polar Surface Area526 Ų
    Heavy Atom Count120
    Formal Charge0
    Complexity3060
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameGanirelix acetate
    Drug LabelGanirelix Acetate Injection is a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix Acetate is derived from native GnRH with substitutions of amino acids at positions 1,...
    Active IngredientGanirelix acetate
    Dosage FormInjectable
    RouteInjection
    Strengtheq 250mcg base/0.5ml
    Market StatusPrescription
    CompanyOrganon Usa

    2 of 2  
    Drug NameGanirelix acetate
    Drug LabelGanirelix Acetate Injection is a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix Acetate is derived from native GnRH with substitutions of amino acids at positions 1,...
    Active IngredientGanirelix acetate
    Dosage FormInjectable
    RouteInjection
    Strengtheq 250mcg base/0.5ml
    Market StatusPrescription
    CompanyOrganon Usa

    4.2 Drug Indication

    The prevention of premature luteinising-hormone surges in women undergoing controlled ovarian hyperstimulation for assisted reproduction techniques.

    In clinical studies, Orgalutran was used with recombinant human follicle-stimulating hormone or corifollitropin alfa, the sustained follicle stimulant.

    Prevention of premature luteinising hormone (LH) surges in women undergoing controlled ovarian hyperstimulation (COH) for assisted reproduction techniques (ART).

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Gonadotropin Releasing Hormone Receptor Antagonist [EPC]; Gonadotropin Releasing Hormone Receptor Antagonists [MoA]; Decreased GnRH Secretion [PE]
    5.3 ATC Code

    H01CC01

    H01CC01

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