Leuprolide acetateProduct ingredient for Leuprolide
- Name
- Leuprolide acetate
- Drug Entry
- Leuprolide
Leuprolide is a synthetic 9-residue peptide analogue of gonadotropin-releasing hormone (GnRH). Unlike the endogenous decapeptide GnRH, leuprolide contains a single D-amino acid (D-leucyl) residue, which helps to increase its circulating half-life from three to four minutes to approximately three hours.4 As a GnRH mimic, leuprolide is capable of binding to the GnRH receptor (GnRHR) and inducing downstream modulation of both gonadotropin hormone and sex steroid levels. Prolonged activation of GnRHR results in significant downregulation of sex steroid levels, which is primarily responsible for the clinical efficacy of leuprolide in diverse conditions, including advanced prostate cancer, endometriosis, and central precocious puberty.1,3
Leuprolide was first approved in 1985 as a daily subcutaneous injection under the tradename Lupron™ by Abbvie Endocrine Inc.11 Since this initial approval, various long-acting intramuscular and subcutaneous products have been developed such that patients can be dosed once every six months.6,9 Leuprolide remains frontline therapy in all conditions for which it is indicated for use.
- Accession Number
- DBSALT000105
- Structure
Structure for Leuprolide acetate (DBSALT000105)
- Synonyms
- Leuprolide acetate / Leuprorelin acetate
- External IDs
- TAP-144-SR
- UNII
- 37JNS02E7V
- CAS Number
- 74381-53-6
- Weight
- Average: 1269.473
Monoisotopic: 1268.666591578 - Chemical Formula
- C61H88N16O14
- InChI Key
- YFDMUNOZURYOCP-XNHQSDQCSA-N
- InChI
- InChI=1S/C59H84N16O12.C2H4O2/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-38(77)18-16-34)71-56(85)47(30-76)74-55(84)45(27-36-26-35-11-7-8-12-39(35)66-36)73-54(83)46(28-37-29-62-31-65-37)72-50(79)40-19-20-49(78)67-40;1-2(3)4/h7-8,11-12,15-18,26,29,31-33,40-48,66,76-77H,6,9-10,13-14,19-25,27-28,30H2,1-5H3,(H,62,65)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,79)(H,73,83)(H,74,84)(H4,60,61,64);1H3,(H,3,4)/t40-,41-,42-,43+,44-,45-,46-,47-,48-;/m0./s1
- IUPAC Name
- (2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-2-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-4-methylpentanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide; acetic acid
- SMILES
- CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC2=C(N1)C=CC=C2)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@@H]1CCC(=O)N1
- External Links
- PubChem Compound
- 657180
- ChemSpider
- 32702058
- ChEBI
- 63597
- ChEMBL
- CHEMBL1200775
- Wikipedia
- Leuprorelin
- Predicted Properties
Property Value Source Water Solubility 0.0354 mg/mL ALOGPS logP 1.07 ALOGPS logP -2.7 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 9.49 Chemaxon pKa (Strongest Basic) 11.9 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 16 Chemaxon Polar Surface Area 429.04 Å2 Chemaxon Rotatable Bond Count 32 Chemaxon Refractivity 327.23 m3·mol-1 Chemaxon Polarizability 127.77 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon