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Merck

L4513

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate

≥97% (HPLC), LH-RH agonist, powder

Synonym(s):

Ethylamide Acetate, Ethylamide Acetate Salt, des-Gly¹⁰ LH-RH

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About This Item

Empirical Formula (Hill Notation):
C56H78N16O12 · xC2H4O2 · yH2O
Molecular Weight:
1167.32 (anhydrous free base basis)
UNSPSC Code:
12352209
PubChem Substance ID:
329817410
NACRES:
NA.32
MDL number:
MFCD11046043

Key Documents

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Product Name

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate, ≥97% (HPLC), powder

SMILES string

O.CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@@H]6CCC(=O)N6

InChI

1S/C56H78N16O12.C2H4O2.H2O/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38;1-2(3)4;/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61);1H3,(H,3,4);1H2/t31-,38+,39+,40+,41+,42+,43+,44+,45+;;/m1../s1

InChI key

YEEHIOYEWOESQR-PFHUABGLSA-N

assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01148
P13562
P30968
Q01776

storage temp.

−20°C

Quality Level

100

Gene Information

mouse ... GNRH1(2796), GNRHR(2798)
rat ... GNRH1(14714), GNRHR(14715)

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Application

[des-Gly10, D-Ala6]-LH-RH ethylamide acetate salt hydrate has been used:
  • as an luteinizing hormone-releasing hormone (LHRH) agonist to synchronize a cohort of females rats
  • to synchronize naturally cycling rats
  • to induce ovulation as a gonadotropin-releasing hormone (GnRH) analogue and as a supplement in Galap extender to dilute qualified ejaculate

Biochem/physiol Actions

Potent LH-RH agonist in rats and mice; reversibly delays sexual maturation in rats, stimulates spawning activity in fish. GnRH ( gonadotropin-releasing hormone, Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2), which is also referred as LHRH (luteinizing hormone-releasing hormone) or gonadorelin, is crucial for mammalian reproduction and is released from hypothalamic neurons. It is responsible for the secretion of gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH), from the pituitary glands. Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9124
BCCM2085
BCCK4962
BCCH1267
BCCH5398

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E L Mumford et al.
Journal of animal science, 72(1), 174-177 (1994-01-01)
A lack of pituitary LH stores has been implicated as the cause of seasonal anestrus and failure to ovulate during the spring transition period in mares. In this experiment, 40 mares were used to study the effects of GnRH, estrogen
Motility, mitochondrial membrane potential and ATP content of rabbit spermatozoa stored in extender supplemented with GnRH analogue [des-Gly10, D-Ala6]-LH-RH ethylamide
Gogol P, et al.
Polish Journal of Veterinary Sciences, 17(4), 571-575 (2014)
Kari L Chesney et al.
Journal of the American Association for Laboratory Animal Science : JAALAS, 59(3), 282-287 (2020-04-04)
Vaginal cytology is the most common method of monitoring the estrous cycle in rats; however, this test requires specific technical training and can be subject to interpretation. Vaginal impedance offers a quicker and less technically challenging alternative and has been
Ovulation induction in rabbit does by intravaginal administration of the GnRH analogue [des-Gly10, D-Ala6]-LHRH ethylamide: field trial
Reproduction in domestic animals = Zuchthygiene (2008)
Ashley Michelle Watt et al.
Zoo biology, 39(1), 23-28 (2019-10-17)
The objective of this study was to investigate variation in sperm quality metrics (motility, velocity, and concentration) in the critically endangered Mississippi gopher frog (Lithobates sevosus) over three sampling time points after a luteinizing hormone-releasing hormone analog (LHRHa) induction injection.
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