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(Des-Gly10,D-Tyr5,D-Leu6,Pro-NHEt9)-LHRH

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(Des-Gly10,D-Tyr5,D-Leu6,Pro-NHEt9)-LHRH is an impurity of Leuprolide, which is a synthetic nonapeptide analog of gonadotropin-releasing hormone used as an antineoplastic agent, a gonadotropin-releasing hormone agonist, and an anti-estrogen.

Category

Others

Catalog number

BAT-015074

CAS number

112710-57-3

Molecular Formula

C59H84N16O12

Molecular Weight

1209.40

(Des-Gly10,D-Tyr5,D-Leu6,Pro-NHEt9)-LHRH

Specification
Reference Reading

IUPAC Name

(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2R)-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]-4-methyl-1-oxopentan-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

Synonyms

(D-Tyr5)-Leuprorelin; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-D-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamide; H-Pyr-His-Trp-Ser-D-Tyr-D-Leu-Leu-Arg-Pro-NHEt; 5-D-Tyrosine-6-D-leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide-luteinizing hormone-releasing Factor (swine); Luteinizing hormone-releasing factor (pig), 5-D-tyrosine-6-D-leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamide-; Leuprolide Acetate EP Impurity G; 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-D-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide

Appearance

White to Off-white Solid

Purity

≥95%

Density

1.44±0.1 g/cm3

Sequence

Pyr-HWSylLRP-NHEt

Storage

Store at -20°C

Solubility

Soluble in DMSO (Slightly), Methanol (Very Slightly), Water (Slightly)

InChI

InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44+,45-,46-,47-,48-/m0/s1

InChI Key

GFIJNRVAKGFPGQ-KWJSFHMPSA-N

Canonical SMILES

CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=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

1. Biological properties of chicken luteinizing hormone-releasing hormone: gonadotropin release from rat and chicken cultured anterior pituitary cells and radioligand analysis

S Sakakibara, N Chino, M Igarashi, K Miyamoto, Y Hasegawa Endocrinology . 1984 Apr;114(4):1441-7. doi: 10.1210/endo-114-4-1441.

We have examined the biological properties of chicken LHRH, which has been isolated and characterized in our laboratory, using primary monolayer cultures of rat and chicken anterior pituitary cells. The radioligand receptor analysis using rat pituitary LHRH receptor was also performed. Biological activities of mammalian LHRH and a more potent analog, [D-Leu6]des-Gly10-LHRH N-ethylamide ([D-Leu6] LHRH analog), were compared with those of chicken LHRH. The ED50 values for [D-Leu6]LHRH analog, mammalian LHRH, and chicken LHRH were, respectively, 0.0166, 0.455, and 18.2 nM for LH secretion and 0.0089, 0.263, and 8.28 nM for FSH secretion from rat pituitary cells. Relative potencies of chicken LHRH were 2.5% that of mammalian LHRH for LH and 3.2% that for FSH. On the other hand, the ED50 for chicken LHRH for LH release from chicken anterior pituitary cells was 1.03 nM, indicating that the biological potency of chicken LHRH acting on chicken pituitary cells was higher than that of chicken LHRH acting on mammalian pituitary cells. The ID50 of chicken LHRH to inhibit the binding of 125I-labeled [D-Leu6]LHRH analog to rat anterior pituitary membrane was 708.5 nM, and was 200 times that of mammalian LHRH (3.39 nM). These results suggest that the substitution of arginine residue of mammalian LHRH for glutamine residue of chicken LHRH causes a decrease in the binding affinity of the hormone for the mammalian LHRH receptor and that the mammalian LHRH receptor has a binding site for the cationic center of the arginine residue of LHRH. On the other hand, chicken pituitary LHRH receptor seems to have more broad specificity than mammalian LHRH receptor.

2. Gonadotropin release during repeated administration of d-Leu6 des Gly10-LH-RH-EA at different stages of the menstrual cycle and in functional amenorrhea

J P Hanker, D H Coy, H P Schneider, J Knippenberg, E J Wickings, A V Schally, A J Kastin Int J Fertil . 1980;25(1):7-17.

A highly potent analogue of OH-RH, d-Leu6 des GLY10 LH-RH-ethyl-amide was, used to study gonadotropin release after three repeated injections of a 25-microgram dose at 3-hourly intervals. Nine volunteers at different stages of the menstrual cycle and 14 patients with functional hypothalamic amenorrhea were investigated. LH secretion varied greatly according to the functional state of the gonadostats, whereas FSH release did not show such differences. After repeated stimulation with the analogue, a tendency for diminished release of both gonadotropins was observed. Significant incremental changes of estradiol-17 beta levels occurred only after a decrease of pituitary responsiveness to further d-Leu6 des Gly10 LH-RH-EA stimuli was already evident. Therefore, it appears unlikely that estradiol-17 beta itself exerted a substantial negative feedback action on LH and FSH release in our experimental model. It is suggested that repeated administration of d-Leu6 des Gly 10 LH-RH-EA leads to changes of pituitary receptor sensitivity.

3. Effects of ionizing radiation and pretreatment with [D-Leu6,des-Gly10] luteinizing hormone-releasing hormone ethylamide on developing rat ovarian follicles

L Belbeck, A McMahon, J Jarrell, G O'Connell, E V YoungLai, R Barr Cancer Res . 1987 Oct 1;47(19):5005-8.

To assess the effects of a gonadotropin-releasing hormone agonist, [D-Leu6,des-Gly10] luteinizing hormone-releasing hormone ethylamide, in ameliorating the damage caused by ionizing radiation, gonadotropin-releasing hormone agonist was administered to rats from day 22 to 37 of age in doses of 0.1, 0.4, and 1.0 microgram/day or vehicle and the rats were sacrificed on day 44 of age. There were no effects on estradiol, progesterone, luteinizing, or follicle-stimulating hormone, nor an effect on ovarian follicle numbers or development. In separate experiments, rats treated with gonadotropin-releasing hormone agonist in doses of 0.04, 0.1, 0.4, or 1.0 microgram/day were either irradiated or sham irradiated on day 30 and all groups sacrificed on day 44 of age. Irradiation produced a reduction in ovarian weight and an increase in ovarian follicular atresia. Pretreatment with the agonist prevented the reduction in ovarian weight and numbers of primordial and preantral follicles but not healthy or atretic antral follicles. Such putative radioprotection should be tested on actual reproductive performance.