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
Thumb
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
PubChem Compound
657180
ChemSpider
32702058
ChEBI
63597
ChEMBL
CHEMBL1200775
Wikipedia
Leuprorelin
Predicted Properties
PropertyValueSource
Water Solubility0.0354 mg/mLALOGPS
logP1.07ALOGPS
logP-2.7ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.49ChemAxon
pKa (Strongest Basic)11.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area429.04 Å2ChemAxon
Rotatable Bond Count32ChemAxon
Refractivity327.23 m3·mol-1ChemAxon
Polarizability127.77 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon