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Leuprorelin acetate, also known as leuprolide acetate, is a synthetic nonapeptide GnRH receptor agonist. It is derived from the native GnRH sequence through modification of position 6 and the C-terminal region to produce a receptor-active peptide with different stability and pharmacological behavior from endogenous GnRH.
The key sequence features are D-Leu at position 6 and a C-terminal Pro-NHEt residue in place of the native Pro-Gly-NH₂ terminus.
Product Information
| Property | Specification |
|---|---|
| Product Name | Leuprorelin Acetate |
| Synonym | Leuprolide Acetate |
| CAS No. | 74381-53-6 |
| Condensed Sequence | pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt |
| Peptide Length | 9 amino-acid residues |
| Acetate Reference Formula | C61H88N16O14 |
| Acetate Reference Molecular Weight | Approximately 1269.4 Da |
| Peptide Moiety Molecular Weight | Approximately 1209.4 Da |
| Key Substitution | Gly6 → D-Leu |
| C-Terminus | Pro-NHEt |
| Primary Target | GnRH receptor / GNRHR |
D-Leu6 and C-Terminal Engineering
Native mammalian GnRH is a decapeptide ending in Pro-Gly-NH₂ and contains Gly6. Leuprorelin introduces two major structural changes.
First, Gly6 is replaced by D-Leu. The D-amino-acid substitution alters peptide conformation and helps stabilize the receptor-active sequence against enzymatic degradation.
Second, the terminal Gly10 is removed and the remaining Pro9 is converted to an N-ethylamide. Together, these changes produce a compact nonapeptide agonist that preserves strong GnRHR activity.
Time-Dependent GnRH Receptor Biology
Short exposure to Leuprorelin activates GnRHR signaling and can stimulate pituitary gonadotrope responses. Prolonged or repeated exposure produces receptor-system desensitization and reduced gonadotropin output.
The same molecule can therefore generate very different experimental outcomes depending on exposure schedule.
We recommend recording concentration, pulse duration, pretreatment period and washout conditions when Leuprorelin is used in receptor or pituitary-cell studies.
Native GnRH Versus Leuprorelin
| Feature | Native GnRH | Leuprorelin |
|---|---|---|
| Length | 10 residues | 9 residues |
| Position 6 | Gly | D-Leu |
| C-Terminus | Pro-Gly-NH₂ | Pro-NHEt |
| Exposure Behavior | Physiological pulsatile ligand | Potent synthetic agonist |
This sequence comparison makes Leuprorelin useful for experiments examining how stereochemistry and terminal engineering affect a short GPCR-active peptide.
Research Applications
Applications include GnRHR activation assays, calcium and downstream signaling studies, gonadotrope desensitization, receptor pharmacology and comparison of synthetic GnRH agonists.
Other receptor agonists and antagonists can be explored in our GnRH Analogues & Antagonists collection.
Analytical Considerations
The acetate form and free peptide should not be assigned the same molecular mass. The Leuprorelin peptide moiety is approximately 1209.4 Da, while the commonly referenced monoacetate composition is approximately 1269.4 Da.
For quantitative experiments, peptide content and counterion specification should be included when preparing molar solutions.
Frequently Asked Questions
Is Leuprorelin a GnRH agonist?
Yes. It directly activates GnRH receptors, although sustained exposure can subsequently produce receptor-system desensitization.
What residue distinguishes Leuprorelin from native GnRH at position 6?
Leuprorelin contains D-Leu instead of Gly.
Is Leuprorelin Acetate the same as Leuprolide Acetate?
Yes. Leuprorelin and leuprolide are commonly used names for the same peptide active moiety.