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L5413

Sigma-Aldrich

Formyl-[D-Trp6]-LH-RH Fragment 2-10

>97% (HPLC)

Synonym(s):

Formyl-Triptorelin 2-10

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About This Item

Empirical Formula (Hill Notation):
C60H77N17O12
Molecular Weight:
1228.36
MDL number:
MFCD03093472
UNSPSC Code:
12352203
PubChem Substance ID:
329817624
NACRES:
NA.32

Quality Level

100

Assay

>97% (HPLC)

UniProt accession no.

P13562

storage temp.

−20°C

SMILES string

CC(C)C[C@H](NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CO)NC(=O)[C@H](Cc4c[nH]c5ccccc45)NC(=O)[C@H](Cc6c[nH]cn6)NC=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N7CCC[C@H]7C(=O)NCC(N)=O

InChI

1S/C60H77N17O12/c1-33(2)21-45(53(83)71-43(13-7-19-65-60(62)63)59(89)77-20-8-14-50(77)58(88)68-29-51(61)81)72-55(85)47(23-35-26-66-41-11-5-3-9-39(35)41)75-54(84)46(22-34-15-17-38(80)18-16-34)73-57(87)49(30-78)76-56(86)48(24-36-27-67-42-12-6-4-10-40(36)42)74-52(82)44(70-32-79)25-37-28-64-31-69-37/h3-6,9-12,15-18,26-28,31-33,43-50,66-67,78,80H,7-8,13-14,19-25,29-30H2,1-2H3,(H2,61,81)(H,64,69)(H,68,88)(H,70,79)(H,71,83)(H,72,85)(H,73,87)(H,74,82)(H,75,84)(H,76,86)(H4,62,63,65)/t43-,44-,45-,46-,47+,48-,49-,50-/m0/s1

InChI key

ZZPMMEBSDBNQDQ-NTXUYPKOSA-N

Gene Information

mouse ... Gnrh1(14714)

Amino Acid Sequence

Formyl-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2

Biochem/physiol Actions

Formyl-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2 (Formyl-[D-Trp6]-LH-RH Fragment 2-10) is a peptide from GnRH (gonadotropin-releasing hormone) agonist, triptorelin. GnRH (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. Application of triptorelin suppresses premature LH surge in IVF (in vitro fertilization). Additionally, triptorelin-mediated ovarian suppression in premenopausal women, undergoing chemotherapy for breast cancer, decreases chances of chemotherapy-associated early menopause.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P C Lindsay et al.
Fertility and sterility, 65(2), 342-348 (1996-02-01)
To assess whether tibolone can prevent the bone loss and symptomatic side effects normally associated with GnRH agonist (GnRH-a) use and whether tibolone modifies the effect of GnRH-a on endometriosis. Prospective, double-blind, placebo-controlled, group comparative study. Gynecological research unit in
R M Janssens et al.
Human reproduction (Oxford, England), 15(11), 2333-2340 (2000-11-01)
Gonadotrophin-releasing hormone agonists (GnRHa) are routinely used in IVF programmes to prevent an unwanted LH surge and consequent ovulation. Despite its widespread use in IVF, a convincing dose recommendation for GnRHa in IVF does not exist. In our opinion, the
Lucia Del Mastro et al.
JAMA, 306(3), 269-276 (2011-07-21)
Premenopausal patients with breast cancer are at high risk of premature ovarian failure induced by systemic treatments, but no standard strategies for preventing this adverse effect are yet available. To determine the effect of the temporary ovarian suppression obtained by
Indira Nederpelt et al.
British journal of pharmacology, 173(1), 128-141 (2015-09-24)
Drug-target residence time is an important, yet often overlooked, parameter in drug discovery. Multiple studies have proposed an increased residence time to be beneficial for improved drug efficacy and/or longer duration of action. Currently, there are many drugs on the
Luigi Maione et al.
PloS one, 8(7), e69616-e69616 (2013-08-13)
Normosmic congenital hypogonadotropic hypogonadism (nCHH) is a rare reproductive disease leading to lack of puberty and infertility. Loss-of-function mutations of GNRH1 gene are a very rare cause of autosomal recessive nCHH. R31C GNRH1 is the only missense mutation that affects
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