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Histrelin acetate is a synthetic nonapeptide agonist of the gonadotropin-releasing hormone receptor (GnRHR). It is derived from the native GnRH scaffold but contains several structural changes designed to alter receptor affinity, peptide stability and signaling duration.
A defining feature of Histrelin is the benzyl-substituted D-histidine at position 6, together with removal of Gly10 and conversion of the C-terminal Pro residue to an N-ethylamide.
Product Information
| Property | Specification |
|---|---|
| Product Name | Histrelin Acetate |
| CAS No. | 76712-82-8 |
| Condensed Sequence | pGlu-His-Trp-Ser-Tyr-D-His(Bzl)-Leu-Arg-Pro-NHEt |
| Peptide Length | 9 amino-acid residues |
| Peptide Formula | C66H86N18O12 |
| Peptide Moiety Molecular Weight | Approximately 1323.5 Da |
| Key Modification | D-His(Bzl) at position 6 |
| C-Terminus | Pro-NHEt |
| Primary Target | GnRH receptor / GNRHR |
| Pharmacological Role | GnRH receptor agonist |
D-His(Bzl)6 Defines the Histrelin Scaffold
Native GnRH contains Gly at position 6. Histrelin replaces this flexible residue with D-His(Bzl), introducing both D-stereochemistry and a bulky benzyl-substituted imidazole side chain.
The modification changes the conformational and hydrophobic environment presented to GnRHR while also reducing susceptibility to peptide degradation pathways associated with the native hormone.
This makes Histrelin useful for structure–activity studies examining how position 6 controls GnRH analog potency, receptor interaction and duration of signaling.
Agonism Followed by Receptor Desensitization
GnRHR is primarily coupled to Gq/11-dependent signaling in pituitary gonadotrope cells. Acute agonist exposure can activate phospholipase C pathways, intracellular calcium signaling and gonadotropin release.
Sustained exposure to a potent GnRH agonist produces a different experimental state. Repeated receptor stimulation can lead to reduced gonadotrope responsiveness and suppression of downstream LH and FSH secretion.
We recommend distinguishing acute receptor activation from long-duration desensitization when designing experiments with Histrelin, because the biological endpoint depends strongly on exposure time.
Histrelin Versus Leuprorelin
| Feature | Histrelin | Leuprorelin |
|---|---|---|
| Position 6 | D-His(Bzl) | D-Leu |
| Length | 9 residues | 9 residues |
| C-Terminus | Pro-NHEt | Pro-NHEt |
| Research Role | GnRHR agonist | GnRHR agonist |
The two analogs preserve a similar overall GnRH-derived framework but use different residue-6 chemistry. This makes them useful as a paired system for studying how a localized substitution alters ligand behavior.
Researchers can compare this material with Leuprorelin Acetate.
Salt Form and Molecular Weight
The molecular formula C66H86N18O12 and molecular weight of approximately 1323.5 Da refer to the Histrelin peptide moiety.
Acetate-containing material can include additional counterion mass. For precise molar preparation, we recommend using lot-specific peptide content and counterion information rather than calculating concentration from nominal dry mass alone.
Quality Considerations
For quantitative GnRHR experiments, identity of the D-His(Bzl) residue, terminal N-ethylamide and overall molecular mass should be confirmed together with chromatographic purity.
Our Peptide Quality Control capabilities support analytical HPLC and mass spectrometry according to the selected specification.
Frequently Asked Questions
Is Histrelin an agonist or antagonist?
Histrelin is a GnRH receptor agonist.
What distinguishes Histrelin from native GnRH?
Important changes include D-His(Bzl) at position 6, removal of Gly10 and conversion of the C-terminal Pro residue to an N-ethylamide.
Can modified GnRH agonists be synthesized?
D-amino-acid substitutions, terminal modifications and other GnRH analog designs can be evaluated through Chemical Peptide Synthesis.