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Compound guide

What is gonadorelin?

Gonadorelin is the synthetic form of gonadotropin-releasing hormone, GnRH, a decapeptide made in the hypothalamus. It was one of the first hypothalamic hormones to be sequenced, in 1971, and it is the parent of a whole family of analogues. Here is its structure, where it came from, how the analogues differ from it and the identifiers that confirm what is in a vial.

At a glance

Gonadorelin in one table.

SequencepGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2
Length10 amino acids; N-terminal pyroglutamate, C-terminal amide
FormulaC55H75N17O13
Molecular weight1182.3 g/mol
Other namesGnRH, LHRH, luteinizing-hormone-releasing hormone, LH-RH
CAS number33515-09-2
PubChem CID638793
OriginHypothalamus; identical sequence in all mammals
StatusApproved as a prescription drug in some formulations; also supplied as a research compound
Discovery

Two groups, one Nobel.

The sequence of GnRH was worked out in 1971 by the groups of Andrew Schally and Roger Guillemin, who isolated it from the hypothalami of hundreds of thousands of pigs and sheep, an effort that shared the 1977 Nobel Prize in Physiology or Medicine. The porcine and ovine sequences turned out to be identical to the human one, and the synthetic decapeptide, named gonadorelin, was being made within months of the structure being published.

Structure

A ring-free decapeptide with two caps.

Gonadorelin is a linear chain of ten residues. Its first residue is pyroglutamate, a glutamic acid whose side chain has cyclized onto its own amino group, which removes the free N-terminus and the water that the calculator would otherwise count: C55H77N17O14 for the open chain becomes C55H75N17O13, 1182.3 g/mol, for the hormone. The C-terminus is an amide. Glycine at position 6 and the Pro-Gly-NH2 ending are the two places the analogues change. How to read a peptide sequence explains the pGlu and -NH2 notation.

The analogues

Position 6 and position 10.

Nearly every GnRH analogue swaps the glycine at position 6 for a D-amino acid, which protects the chain from cleavage, and many replace the final glycinamide with an ethylamide. Leuprolide uses D-leucine at 6 and the ethylamide; triptorelin uses D-tryptophan at 6 and keeps the glycinamide; buserelin uses D-serine with a tert-butyl group at 6 and the ethylamide. Each is a different molecule with its own mass, so a catalog entry has to say which one it is. Gonadorelin itself is the unchanged hormone.

Status

A drug and a research compound.

Gonadorelin has been approved as a prescription drug in several formulations, including a human diagnostic product and veterinary products that remain on the US market, and its analogues are widely used medicines. The research compound is the same decapeptide supplied lyophilized as a laboratory reference material, labeled research use only; it is not a drug product. What research use only means covers the distinction.

Reading a COA

The mass to expect.

Identity by mass spectrometry should find the neutral mass 1182.3, or a charge-state peak such as [M+2H]2+ near 592.2. The pyroglutamate is easy to miss on a label: a supplier who lists glutamic acid at position 1, or a mass near 1200, is describing a different molecule. Mass spectrometry for peptide identity explains the charge states and how to read a peptide COA the rest of the report.

At Helion

Not currently supplied.

Helion does not currently supply gonadorelin. The research library covers it as a reference page alongside kisspeptin-10, the peptide upstream of it in the same hormonal axis, and peptide hormones explained places it among the other hypothalamic peptides.

Questions and sources
Questions (6)

What is gonadorelin?
The synthetic form of gonadotropin-releasing hormone (GnRH), a ten-residue hypothalamic peptide, pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2.

Is gonadorelin the same as GnRH and LHRH?
Yes. GnRH and LHRH are two names for the natural hormone; gonadorelin is the name of its synthetic form.

What is the molecular weight of gonadorelin?
1182.3 g/mol, formula C55H75N17O13, with the N-terminal pyroglutamate counted.

What is the difference between gonadorelin and leuprolide?
Leuprolide replaces glycine at position 6 with D-leucine and the final glycinamide with an ethylamide; gonadorelin is the unchanged hormone.

What does pGlu mean in the sequence?
Pyroglutamate: a glutamic acid whose side chain has cyclized onto its own amino group, so the peptide has no free N-terminus.

Does Helion sell gonadorelin?
Not currently. It is covered in the research library as a reference page.

Published studies (1)

Citations from PubMed for reference. They describe the compound in the literature, not any Helion lot, and nothing here is guidance on use.

Helion Research supplies reference compounds for laboratory and in-vitro research only. Nothing on this page is medical advice, and no statement here has been evaluated by the FDA. Not for human or veterinary use. 21+.