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L4788

Sigma-Aldrich

[D-Trp6]-LH-RH-Leu-Arg-Pro-Gly-NH2

≥80% (HPLC)

Synonym(s):

Triptorelin-Leu-Arg-Pro-Gly Amide

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About This Item

Empirical Formula (Hill Notation):
C83H115N25O17
Molecular Weight:
1734.96
MDL number:
MFCD03093474
UNSPSC Code:
12352200
PubChem Substance ID:
329817413

Quality Level

200

assay

≥80% (HPLC)

UniProt accession no.

P01148

storage temp.

−20°C

SMILES string

CC(C)C[C@H](NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc4ccc(O)cc4)NC(=O)[C@H](CO)NC(=O)[C@H](Cc5c[nH]c6ccccc56)NC(=O)[C@H](Cc7c[nH]cn7)NC(=O)[C@@H]8CCC(=O)N8)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N9CCC[C@H]9C(=O)NCC(N)=O

InChI

1S/C83H115N25O17/c1-44(2)31-58(71(115)99-56(17-9-27-90-82(85)86)80(124)107-29-11-19-65(107)78(122)94-40-67(84)111)98-69(113)41-95-79(123)66-20-12-30-108(66)81(125)57(18-10-28-91-83(87)88)100-72(116)59(32-45(3)4)101-74(118)61(34-47-37-92-53-15-7-5-13-51(47)53)103-73(117)60(33-46-21-23-50(110)24-22-46)102-77(121)64(42-109)106-75(119)62(35-48-38-93-54-16-8-6-14-52(48)54)104-76(120)63(36-49-39-89-43-96-49)105-70(114)55-25-26-68(112)97-55/h5-8,13-16,21-24,37-39,43-45,55-66,92-93,109-110H,9-12,17-20,25-36,40-42H2,1-4H3,(H2,84,111)(H,89,96)(H,94,122)(H,95,123)(H,97,112)(H,98,113)(H,99,115)(H,100,116)(H,101,118)(H,102,121)(H,103,117)(H,104,120)(H,105,114)(H,106,119)(H4,85,86,90)(H4,87,88,91)/t55-,56-,57-,58-,59-,60-,61+,62-,63-,64-,65-,66-/m0/s1

InChI key

PVYPXXICFOKNOB-NMBRWIPZSA-N

Gene Information

human ... CHRNA1(2796)

Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-Trp-Leu-Arg-Pro-Gly-Leu-Arg-Pro-Gly-NH2

Biochem/physiol Actions

Glp-His-Trp-Ser-Tyr-Trp-Leu-Arg-Pro-Gly-Leu-Arg-Pro-Gly-NH2 ([D-Trp6]-LH-RH-Leu-Arg-Pro-Gly-NH2) is a GnRH (gonadotropin-releasing hormone) agonist, triptorelin.[1] 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.[2][3][1] Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism.[3] Triptorelin is used for the treatment of hormone-associated prostate and breast cancers, endometriosis, uterine fibroids, central precocious puberty and in vitro fertilization.[4]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW9507
SLBB6821V
061M1150V
041M1166V
079K1016

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Amino Acids, Peptide and Proteins
Royal Society of Chemistry, 38 (2013)
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
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
Brooke Tata et al.
PLoS biology, 12(9), e1001952-e1001952 (2014-09-24)
Characterization of the genetic defects causing gonadotropic deficiency has made a major contribution to elucidation of the fundamental role of Kisspeptins and Neurokinin B in puberty onset and reproduction. The absence of puberty may also reveal neurodevelopmental disorders caused by

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