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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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Chemistry

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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

Gonadorelin

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 Formula	C₅₅H₇₅N₁₇O₁₃
Molecular Weight	1182.3 g/mol
XLogP3	-2.4
Hydrogen Bond Donor Count	16
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	31
Exact Mass	1181.57302551 g/mol
Monoisotopic Mass	1181.57302551 g/mol
Topological Polar Surface Area	475 Å²
Heavy Atom Count	85
Formal Charge	0
Complexity	2390
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	8
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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