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    Glycinamide, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolyl-

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    2D Structure
    Also known as: Lhrh, Lh-rh, Gonadoliberin, luliberin, Gnrh, 9034-40-6, 71447-49-9
    Molecular Formula
    C55H75N17O13
    Molecular Weight
    1182.3  g/mol
    InChI Key
    XLXSAKCOAKORKW-UHFFFAOYSA-N
    A decapeptide that stimulates the synthesis and secretion of both pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE. GnRH is produced by neurons in the septum PREOPTIC AREA of the HYPOTHALAMUS and released into the pituitary portal blood, leading to stimulation of GONADOTROPHS in the ANTERIOR PITUITARY GLAND.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[1-[[1-[[1-[[1-[[2-[[1-[[1-[2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]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/C55H75N17O13/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60)
    2.1.3 InChI Key
    XLXSAKCOAKORKW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Cystorelin

    2. Dirigestran

    3. Factrel

    4. Fsh Releasing Hormone

    5. Fsh-releasing Hormone

    6. Gn-rh

    7. Gnrh

    8. Gonadoliberin

    9. Gonadorelin

    10. Gonadorelin Acetate

    11. Gonadorelin Hydrochloride

    12. Gonadotropin Releasing Hormone

    13. Gonadotropin-releasing Hormone

    14. Kryptocur

    15. Lfrh

    16. Lh Fsh Releasing Hormone

    17. Lh Releasing Hormone

    18. Lh-fsh Releasing Hormone

    19. Lh-releasing Hormone

    20. Lh-rh

    21. Lhfsh Releasing Hormone

    22. Lhfshrh

    23. Lhrh

    24. Luliberin

    25. Luteinizing Hormone Releasing Hormone

    26. Luteinizing Hormone-releasing Hormone

    27. Releasing Hormone, Lhfsh

    2.2.2 Depositor-Supplied Synonyms

    1. Lhrh

    2. Lh-rh

    3. Gonadoliberin, Luliberin

    4. Gnrh

    5. 9034-40-6

    6. 71447-49-9

    7. Lhrh, Human

    8. Ncgc00182043-01

    9. 6918-09-8

    10. Chembl1981292

    11. Luteinizing Hormone Releasingfactor

    12. Bcp12609

    13. Bcp12654

    14. Luteinizing Hormone Releasing Factor

    15. Syntheticgonadotropin-releasinghormone

    16. Db00644

    17. Ncgc00389662-01

    18. Luteinizing Hormone Releasing Hormone Human

    19. Db-057197

    20. Ft-0628048

    21. C07607

    22. A821811

    23. L000690

    24. Luteinizing Hormone Releasing Hormone Human Acetate Salt;lhrh

    25. Lhrh;lh-releasing Factor;gonadorelina;glp-his-trp-ser-tyr-gly-leu-ser-pro-gly-nh2

    26. N-[1-[[1-[[1-[[1-[[2-[[1-[[1-[2-[(2-azanyl-2-oxidanylidene-ethyl)carbamoyl]pyrrolidin-1-yl]-5-[bis(azanyl)methylideneamino]-1-oxidanylidene-pentan-2-yl]amino]-4-methyl-1-oxidanylidene-pentan-2-yl]amino]-2-oxidanylidene-ethyl]amino]-3-(4-hydroxyphenyl)-1-o

    27. N-[1-[[1-[[1-[[1-[[2-[[1-[[1-[2-[[(2-amino-2-oxoethyl)amino]-oxomethyl]-1-pyrrolidinyl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropa

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 1182.3 g/mol
    Molecular Formula C55H75N17O13
    XLogP3-2.4
    Hydrogen Bond Donor Count16
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count31
    Exact Mass1181.57302551 g/mol
    Monoisotopic Mass1181.57302551 g/mol
    Topological Polar Surface Area475 Ų
    Heavy Atom Count85
    Formal Charge0
    Complexity2390
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count8
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For evaluating the functional capacity and response of the gonadotropes of the anterior pituitary also for evaluating residual gonadotropic function of the pituitary following removal of a pituitary tumor by surgery and/or irradiation.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Gonadorelin is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pitutitary. In the pituitary GnRH stimulates synthesis and release of FSH and LH, a process that is controlled by the frequency and amplitude of GnRH pulses, as well as the feedback of androgens and estrogens. The pulsatility of GnRH secretion has been seen in all vertebrates, and it is necessary to ensure a correct reproductive function. Thus a single hormone, GnRH, controls a complex process of follicular growth, ovulation, and corpus luteum maintenance in the female, and spermatogenesis in the male. Its short half life requires infusion pumps for its clinical use

    5.2 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed when injected

    5.3 Metabolism/Metabolites

    Rapidly hydrolyzed to inactive peptide components

    5.4 Biological Half-Life

    Very short, initial, 2 to 10 minutes; terminal, 10 to 40 minutes

    5.5 Mechanism of Action

    Systemic - Like naturally occurring gonadotropin-releasing hormone (GnRH), gonadorelin primarily stimulates the synthesis and release of luteinizing hormone (LH) from the anterior pituitary gland. Follicle-stimulating hormone (FSH) production and release is also increased by gonadorelin, but to a lesser degree. In prepubertal females and some gonadal function disorders, the FSH response may be greater than the LH response. For the treatment of amenorrhea, delayed puberty, and infertility the administration of gonadorelin is used to simulate the physiologic release of GnRH from the hypothalamus in treatment of delayed puberty, treatment of infertility caused by hypogonadotropic hypogonadism, and induction of ovulation in those women with hypothalamic amenorrhea. This results in increased levels of pituitary gonadotropins LH and FSH, which subsequently stimulate the gonads to produce reproductive steroids.