NAV

Leuprolide

Identification

Summary

Leuprolideis a peptide-based GnRH receptor superagonist used for the palliative treatment of prostate cancer, uterine leiomyomata, endometriosis, and central precocious puberty.

Brand Names
Camcevi, Eligard, Fensolvi, Lupaneta Pack 1-month, Lupron, Lupron Depot-ped, Viadur, Zeulide Depot
Generic Name
Leuprolide
DrugBank Accession Number
DB00007
Background

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.4As 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.11Since this initial approval, various long-acting intramuscular and subcutaneous products have been developed such that patients can be dosed once every six months.6,9Leuprolide remains frontline therapy in all conditions for which it is indicated for use.

Type
Small Molecule
Groups
Approved, Investigational
Structure
MOL SDF PDB SMILES InChI
Similar Structures
Weight
Average: 1209.3983
Monoisotopic: 1208.645462232
Chemical Formula
C59H84N16O12
Synonyms
  • Leuprorelin
  • Leuprorelina
  • Leuproreline
  • Leuprorelinum
External IDs
  • CKD-841

Pharmacology

Indication

Leuprolide is indicated for the treatment of advanced prostate cancer6,12and as palliative treatment of advanced prostate cancer.9

It is also used for the treatment of pediatric patients with central precocious puberty (CPP).7,8

In combination with oralnorethisterone(also known as norethindrone), leuprolide is also indicated for the initial treatment of the symptoms of endometriosis.5Finally, in combination with iron supplementation, leuprolide is indicated for the preoperative hematological improvement of anemic patients with uterine leiomyomata (uterine fibroids).10

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Leuprolide is a gonadotropin-releasing hormone (GnRH) analogue that functions as a GnRH receptor superagonist.3,4After an initial spike in GnRH-mediated steroidal production, including testosterone and estradiol, prolonged use results in a significant drop in circulating steroid levels, in line with those produced through other forms of androgen-deprivation therapy (ADT).1,2,3The corresponding hormonal/steroidal changes produce specific adverse effects in different patient populations.

In women undergoing treatment for endometriosis or uterine leiomyomata, careful consideration regarding pregnancy status is advised. The initial increase in estradiol levels may worsen symptoms such as pain and bleeding. Long-term use of leuprolide is associated with loss of bone mineral density. Patients co-administered withnorethisteronemay experience sudden vision loss, proptosis, diplopia, migraine, thrombophlebitis, and pulmonary embolism and may also be at higher risk of cardiovascular disease. Patients with a history of depression may experience severe recurrence of depressive symptoms.5,10

In men undergoing palliative treatment for advanced/metastatic prostate cancer, short-term spikes in testosterone levels may cause tumour flare and associated symptoms such as bone pain, hematuria, neuropathy, bladder and/or ureteral obstruction, and spinal cord compression. In addition, patients are at increased risk of developing hyperglycemia, diabetes, and cardiovascular disease, which may manifest through myocardial infarction, stroke, cardiac death, or prolonged QT/QTc interval. In addition, Leuprolide may cause convulsions and embryo-fetal toxicity.6,9

In pediatric patients undergoing treatment for central precocious puberty (CPP), the initial steroidal spike may be associated with increased clinical signs of puberty within 2-4 weeks of treatment initiation. In addition, leuprolide may cause convulsions and psychiatric symptoms, including irritability, impatience, aggression, anger, and crying.7,8

Mechanism of action

Gonadotropin-releasing hormone (GnRH) is a naturally occurring decapeptide that modulates the hypothalamic-pituitary-gonadal (HPG) axis. GnRH binds to corresponding receptors (GnRHRs) on the anterior pituitary gonadotropes, which in turn release luteinizing hormone (LH) and follicle-stimulating hormone (FSH); these, in turn, affect the downstream synthesis and release of the sex hormones testosterone, dihydrotestosterone, estrone, and estradiol.1,3

Despite the variety of conditions indicated for treatment with leuprolide, the mechanism of action underlying efficacy is the same in all cases. As a GnRHR agonist, leuprolide binds to and initially activates downstream LH and FSH release; this initial spike in gonadotropin levels is responsible for some of the adverse effects associated with treatment. After 2-4 weeks of treatment, continuous stimulation of GnRHR results in feedback inhibition and significant downregulation of LH, FSH, and their corresponding downstream effects, producing a therapeutic benefit. These effects are reversible upon treatment discontinuation.1,2,3,4,5,6,7,8,9,10

Target Actions Organism
AGonadotropin-releasing hormone receptor
agonist
 Humans
Absorption

Leuprolide is typically administered as a single-dose long-acting formulation employing either microsphere or biodegradable solid depot technologies.1Regardless of the exact formulation and initial dose strength, the Cmaxis typically achieved by 4-5 hours post-injection and displays large variability in the range of 4.6 - 212 ng/mL. Eventual steady-state kinetics are typically achieved by four weeks, with a narrower range of 0.1 - 2 ng/mL. No studies on the effects of food on absorption have been carried out.5,6,7,8,9,10,12

Volume of distribution

Leuprolide has an apparent steady-state volume of distribution of 27 L following intravenous bolus administration to healthy males. The volume of distribution for indicated routes of subcutaneous or intramuscular injection has not been reported.5,6,7,8,9,10,12

Protein binding

Leuprolide displaysin vitrobinding to human plasma proteins between 43% and 49%.5,6,7,8,9,10,12

Metabolism

Radiolabeling studies suggest that leuprolide is primarily metabolized to inactive penta-, tri-, and dipeptide entities, which are likely further metabolized. It is expected that various peptidases encountered throughout systemic circulation are responsible for leuprolide metabolism.5,6,7,8,9,10,12

Route of elimination

Following administration of 3.75 mg leuprolide depot suspension to three patients, less than 5% of the initial dose was recovered as unchanged or pentapeptide metabolite in the urine.5,6,7,10

Half-life

Leuprolide终端的消除半衰期approximately three hours.5,6,7,8,9,10,12

Clearance

Leuprolide administered as a 1 mg intravenous bolus in healthy males has a mean systemic clearance between 7.6 and 8.3 L/h.5,6,7,8,9,10,12

Adverse Effects
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Toxicity

Leuprolide is considered extremely safe, with low dose-related toxicity and comparatively mild adverse effects.1Prostate cancer patients treated with leuprolide at doses as high as 20 mg/day for two years showed no additional adverse effects compared to those receiving 1 mg/day.10

Pathways
Not Available
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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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Abacavir Leuprolide may decrease the excretion rate of Abacavir which could result in a higher serum level.
Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Leuprolide.
Aceclofenac Aceclofenac may decrease the excretion rate of Leuprolide which could result in a higher serum level.
Acemetacin Acemetacin may decrease the excretion rate of Leuprolide which could result in a higher serum level.
Acetaminophen Leuprolide may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetazolamide Acetazolamide may increase the excretion rate of Leuprolide which could result in a lower serum level and potentially a reduction in efficacy.
Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Leuprolide.
Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Leuprolide which could result in a higher serum level.
Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Leuprolide is combined with Acipimox.
Aclidinium Leuprolide may decrease the excretion rate of Aclidinium which could result in a higher serum level.
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Food Interactions
No interactions found.

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Leuprolide acetate 37JNS02E7V 74381-53-6 YFDMUNOZURYOCP-XNHQSDQCSA-N
Leuprolide mesylate 8E3C3C493W 944347-41-5 MBIDSOMXPLCOHS-XNHQSDQCSA-N
International/Other Brands
Camcevi (Foresee Pharmaceuticals)/Leuplin (Takeda)/LeuProMaxx (Baxter/Teva)/Memryte (Curaxis)/Prostap 3 (Takeda UK)/Prostap SR (Takeda UK)
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Camcevi Injection, emulsion 42 mg/1mL Subcutaneous Foresee Pharmaceuticals Co., Ltd. 2022-12-30 Not applicable US flag
Camcevi 42 mg / syr Subcutaneous Accord Healthcare Inc Not applicable Not applicable Canada flag
Camcevi Injection, emulsion 42 mg/0.37g Subcutaneous 协议生物制药公司。 2022-04-05 Not applicable US flag
Camcevi 42 mg Subcutaneous Accord Healthcare S.L.U. 2022-06-21 Not applicable EU flag
Eligard Kit 45 mg/0.375mL Subcutaneous TOLMAR Inc. 2005-01-07 Not applicable US flag
Eligard Kit 7.5 mg/0.25mL Subcutaneous TOLMAR Inc. 2002-05-15 Not applicable US flag
Eligard Kit 30 mg/0.5mL Subcutaneous TOLMAR PHARMACEUTICALS INC. 2002-01-23 2015-05-08 US flag
Eligard Kit 22.5 mg/0.375mL Subcutaneous Sanofi Aventis 2002-01-23 2016-05-31 US flag
Eligard Injection, powder, for suspension, extended release 45 mg / syr Subcutaneous Tolmar International Ltd. 2005-08-15 Not applicable Canada flag
Eligard Kit 30 mg/0.5mL Subcutaneous TOLMAR Inc. 2003-02-26 Not applicable US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Leuprolide Acetate Injection, solution 1 mg/.2mL Subcutaneous Eon Labs, Inc. 1998-08-04 Not applicable US flag
Leuprolide Acetate Kit 1 mg/0.2mL Subcutaneous; Topical Teva Parenteral Medicines, Inc. 2000-11-06 2011-03-31 US flag
Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Leuprolide Acetate Leuprolide acetate(1 mg/0.2mL)+Isopropyl alcohol(0.7 mL/1mL) Injection, solution; Kit Subcutaneous; Topical AuroMedics Pharma LLC 2022-06-06 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(5 mg/1mL)+Isopropyl alcohol(0.7 mL/1mL) Injection, solution; Kit Subcutaneous; Topical Sun Pharmaceutical Industries, Inc. 2014-12-15 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(5 mg/1mL)+Isopropyl alcohol(0.7 mL/1mL) Kit Subcutaneous; Topical Sun Pharma Global Inc. 2014-12-15 2015-08-31 US flag
Leuprolide Acetate Leuprolide acetate(5 mg/1mL)+Isopropyl alcohol(0.7 mL/1mL) Kit Subcutaneous Amneal Pharmaceuticals LLC 2022-11-07 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(1 mg/0.2mL)+Isopropyl alcohol(0.7 mg/1mL) Kit Subcutaneous; Topical bryant ranch prepack 1998-08-04 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(1 mg/0.2mL)+Isopropyl alcohol(0.7 mL/1) Kit Subcutaneous; Topical Genzyme Corporation 2001-11-29 2010-03-31 US flag
Leuprolide Acetate Leuprolide acetate(5 mg/1mL)+Isopropyl alcohol(0.7 mL/1mL) Injection, solution; Kit; Swab Subcutaneous; Topical Northstar RxLLC 2022-08-01 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(1 mg/0.2mL)+Isopropyl alcohol(1 mL/1mL) Kit Subcutaneous; Topical VGYAAN Pharmaceuticals LLC 2021-10-01 Not applicable US flag
Leuprolide Acetate Leuprolide acetate(1 mg/0.2mL)+Isopropyl alcohol(0.7 mL/1mL) Kit Subcutaneous; Topical Sandoz Inc 1998-08-04 Not applicable US flag
Leuprolide Acetate Leuprolide acetate+Isopropyl alcohol Kit Subcutaneous; Topical Genzyme Corporation 2006-05-31 2006-05-31 US flag

Categories

ATC Codes
L02AE51 — Leuprorelin and bicalutamide L02AE02 — Leuprorelin
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
EFY6W0M8TG
CAS number
53714-56-0
InChI Key
GFIJNRVAKGFPGQ-LIJARHBVSA-N
InChI
InChI=1S/C59H84N16O12/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(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/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-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-4-methylpentanamido]-4-methylpentanamido]pentanoyl]-N-ethylpyrrolidine-2-carboxamide
SMILES
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=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@@H]1CCC(=O)N1

参考文献

Synthesis Reference

Daniel Kadzimirzs, Gerhard Jas, Volker Autze, "Solution-Phase Synthesis of Leuprolide and Its Intermediates." U.S. Patent US20090005535, issued January 01, 2009.

 US20090005535
一般引用
  1. Hoda MR, Kramer MW, Merseburger AS, Cronauer MV: Androgen deprivation therapy with Leuprolide acetate for treatment of advanced prostate cancer. Expert Opin Pharmacother. 2017 Jan;18(1):105-113. doi: 10.1080/14656566.2016.1258058. Epub 2016 Nov 28. [Article]
  2. Ali M, Chaudhry ZT, Al-Hendy A: Successes and failures of uterine leiomyoma drug discovery. Expert Opin Drug Discov. 2018 Feb;13(2):169-177. doi: 10.1080/17460441.2018.1417381. Epub 2017 Dec 18. [Article]
  3. Wilson AC, Meethal SV, Bowen RL, Atwood CS: Leuprolide acetate: a drug of diverse clinical applications. Expert Opin Investig Drugs. 2007 Nov;16(11):1851-63. doi: 10.1517/13543784.16.11.1851. [Article]
  4. Conn PM, Crowley WF Jr: Gonadotropin-releasing hormone and its analogues. N Engl J Med. 1991 Jan 10;324(2):93-103. doi: 10.1056/NEJM199101103240205. [Article]
  5. FDA Approved Drug Products: Lupaneta Pack for intramuscular and oral use [Link]
  6. FDA Approved Drug Products: Lupron Depot (leuprolide acetate) depot suspension, for intramuscular injection [Link]
  7. FDA Approved Drug Products: Lupron Depot-Ped (leuprolide acetate) depot suspension [Link]
  8. FDA Approved Drug Products: Fensolvi (leuprolide acetate) suspension [Link]
  9. FDA Approved Drug Products: ELIGARD (leuprolide acetate) for injectable suspension, for subcutaneous use [Link]
  10. FDA Approved Drug Products: Lupron Depot 3.75mg (leuprolide acetate) depot suspension [Link]
  11. FDA Approved Drug Products: Lupron (leuprolide) injection; discontinued [Link]
  12. FDA Approved Drug Products: CAMCEVI (leuprolide) injectable emulsion, for subcutaneous use [Link]
Human Metabolome Database
HMDB0041916
KEGG Drug
D08113
KEGG Compound
C07612
PubChem Substance
46507635
ChemSpider
571356
BindingDB
50369395
RxNav
42375
ChEBI
6427
ChEMBL
CHEMBL1201199
Therapeutic Targets Database
DAP000020
PharmGKB
PA450203
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Leuprorelin
FDA label
Download (477 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Not Available Effect of Two Protocols of Ovarian Stimulation on Oocyte Quality 1
4 Completed Not Available Endometriosis 1
4 Completed Not Available 前列腺Cancer 1
4 Completed Basic Science Contraception/Fertility 1
4 Completed Basic Science Depression/Hot Flashes/Menopause 1
4 Completed Basic Science Hot Flashes 1
4 Completed Basic Science Menopause 1
4 Completed Prevention Ovarian Hyper Stimulation Syndrome (OHSS) 1
4 Completed Treatment Central Precocious Puberty (CPP) 4
4 Completed Treatment Egg Donation 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Cardinal Health
  • Eon Labs
  • Hospira Inc.
  • Oso Biopharmaceuticals Manufacturing LLC
  • Physicians Total Care Inc.
  • Sanofi-Aventis Inc.
  • Sun Pharmaceutical Industries Ltd.
  • Takeda Pharmaceutical Co. Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Tolmar Inc.
Dosage Forms
Form Route Strength
Injection, emulsion Subcutaneous 42 mg/1mL
Injection, emulsion Subcutaneous 42 mg/0.37g
Injection, powder, for solution Parenteral 22.5 MG
Injection, powder, for solution Parenteral 45 MG
Injection, powder, for solution Parenteral 7.5 MG
Injection, powder, for solution Subcutaneous
Injection, powder, for suspension, extended release Subcutaneous 22.5 mg / syr
Injection, powder, for suspension, extended release Subcutaneous 30 mg / syr
Injection, powder, for suspension, extended release Subcutaneous 45 mg / syr
Injection, powder, for suspension, extended release Subcutaneous 7.5 mg / syr
Injection, suspension, extended release Subcutaneous 45 mg/0.375mL
Kit Subcutaneous 22.5 mg/0.375mL
Kit Subcutaneous 30 mg/0.5mL
Kit Subcutaneous 45 mg/0.375mL
Kit Subcutaneous 7.5 mg/0.25mL
Injection, powder, lyophilized, for suspension, extended release Subcutaneous 22.5 mg
Injection, powder, lyophilized, for suspension, extended release Subcutaneous 45 mg
Injection, powder, lyophilized, for suspension, extended release Subcutaneous 7.5 mg
Injection, powder, for suspension Subcutaneous 45 mg
Powder Intramuscular 22.5 mg/1vial
Injection Intramuscular 22.5 mg
Injection, powder, for solution Subcutaneous 22.5 MG
Powder Intramuscular 45 mg/1vial
Injection, solution Intramuscular 45 mg
Injection, solution Subcutaneous 45 mg
Injection, powder, for solution Subcutaneous 45 MG
Injection, solution Intramuscular
Injection, solution Subcutaneous 7.5 mg
Powder Intramuscular 7.5 mg/1vial
Injection, powder, for solution Subcutaneous 7.5 mg
Injection, powder, for solution Parenteral
Injection, powder, for suspension Subcutaneous 22.5 mg
Injection, powder, lyophilized, for solution Subcutaneous 22.5 mg
Injection, powder, for suspension Subcutaneous 7.5 mg
Injection, powder, lyophilized, for solution Subcutaneous 7.5 mg
Injection, powder, for suspension Parenteral 7.5 mg
Injection Intramuscular 3.75 MG
Injection, powder, for suspension Intramuscular; Subcutaneous 11.25 MG/ML
Injection, powder, for suspension Intramuscular; Subcutaneous 3.75 MG/ML
Injection, powder, for suspension, extended release Intramuscular 11.25 MG/2ML
Injection, powder, for suspension, extended release Intramuscular 3.75 MG/2ML
Injection, solution Subcutaneous 1 MG/0.2ML
Powder Intramuscular 11.25 mg/1vial
Injection, powder, for suspension Subcutaneous 3.75 mg
Injection, suspension, extended release; kit Subcutaneous 45 mg/0.375mL
Injection, powder, for suspension Intramuscular 11.25 mg
Injection, powder, for suspension Intramuscular 3.75 mg
Powder Intramuscular 22.5 mg
Powder Intramuscular 7.5 mg
Implant Parenteral 3.6 MG
Implant Parenteral 5 MG
Implant Subcutaneous 3.6 MG
Injection, solution Subcutaneous 1 mg/.2mL
Injection, solution; kit Subcutaneous; Topical
Injection, solution; kit; swab Subcutaneous; Topical
Kit Subcutaneous
Kit Subcutaneous; Topical 1 mg/0.2mL
Injection, powder, lyophilized, for suspension, extended release; kit Intramuscular 22.5毫克/ 2毫升
Liquid Subcutaneous 5 mg / mL
Implant Parenteral
Implant Subcutaneous
Implant Subcutaneous 5 mg
Suspension Intramuscular
Injection, solution Subcutaneous 5 mg/ml
Injection, powder, lyophilized, for solution Intramuscular; Subcutaneous 3.75 mg
Injection, powder, lyophilized, for solution Intramuscular; Subcutaneous 11.25 mg
Injection Intramuscular
Injection, powder, for solution Intramuscular; Subcutaneous 11.25 mg
Injection, powder, for solution Intramuscular; Subcutaneous 3.75 mg
Injection Subcutaneous
Injection, powder, for solution Subcutaneous 30 mg
Injection, powder, lyophilized, for solution Intramuscular; Subcutaneous
Injection Subcutaneous 5 mg/ml
Injection, powder, lyophilized, for suspension; kit; tablet Intramuscular; Oral; Topical
Kit Subcutaneous; Topical 5 mg/1mL
Solution Subcutaneous 5 mg / mL
Injection, powder, for suspension Intramuscular; Subcutaneous 11.25 mg
Solution Subcutaneous 5 mg
Injection, powder, for suspension, extended release Intramuscular 11.25 mg / vial
Injection, powder, for suspension, extended release Intramuscular 11.25 mg / syr
Injection, powder, for suspension, extended release Intramuscular 15 mg / vial
Injection, powder, for suspension, extended release Intramuscular 22.5 mg / syr
Injection, powder, for suspension, extended release Intramuscular 3.75 mg / syr
Injection, powder, for suspension, extended release Intramuscular 30 mg / syr
Injection, powder, for suspension, extended release Intramuscular 7.5 mg / syr
Injection, powder, lyophilized, for suspension Intramuscular 3.75 mg/1mL
Injection, powder, lyophilized, for suspension Intramuscular 30 mg/1.5mL
Injection, powder, lyophilized, for suspension; kit Intramuscular 11.25 mg/1.5mL
Injection, powder, lyophilized, for suspension; kit Intramuscular; Topical
Kit Intramuscular 22.5 mg/1.5mL
Kit Intramuscular 30 mg/1.5mL
Kit Intramuscular 45毫克/ 1.5毫升
Kit Intramuscular 7.5 mg/1mL
Kit Intramuscular; Topical 3.75 mg/1mL
Injection, powder, lyophilized, for suspension Intramuscular 11.25 mg/1mL
Injection, powder, lyophilized, for suspension Intramuscular 15 mg/1mL
Injection, powder, lyophilized, for suspension Intramuscular 7.5 mg/1mL
Kit Intramuscular 11.25 mg/1mL
Kit Intramuscular 11.25 mg/1.5mL
Kit Intramuscular 15 mg/1mL
Kit Intramuscular; Topical 11.25 mg/1mL
Injection, powder, for suspension Intramuscular; Subcutaneous 30 mg
Injection, powder, for suspension Parenteral
Injection, powder, for suspension, extended release Intramuscular 22.5 MG
Solution Parenteral 5 mg
Injection, powder, for suspension Subcutaneous 30 mg
Injection, powder, for solution
Injection, powder, for solution Parenteral 3.75 MG
Injection, powder, for solution Parenteral 11.25 mg
Injection, powder, for suspension Subcutaneous 11.25 mg
Kit Subcutaneous; Topical
Injection, powder, for suspension, extended release; kit Intramuscular 22.5 mg / vial
Injection, powder, for suspension, extended release; kit Intramuscular 3.75 mg / vial
Powder Intramuscular 1.88 mg/1vial
Powder Intramuscular 3.75 mg/1vial
Prices
单元描述 Cost Unit
Eligard 45 mg syringe 2959.2USD syringe
Eligard 30 mg syringe 1972.8USD syringe
Eligard 22.5 mg syringe 1479.6USD syringe
Lupron 2-wk 1 mg/0.2 ml kit 594.37USD kit
Eligard 7.5 mg syringe 493.2USD syringe
Leuprolide Acetate 1 mg/0.2ml Kit 2.8ml 2-Week Kit 400.74USD box
Leuprolide 2wk 1 mg/0.2 ml kit 385.33USD kit
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
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US8840916 No 2014-09-23 2020-11-13 US flag
US8470359 No 2013-06-25 2023-10-15 US flag
US9539333 No 2017-01-10 2020-11-13 US flag
US9914802 No 2018-03-13 2020-11-13 US flag
US10646572 No 2020-05-12 2027-01-16 US flag
US9572857 No 2017-02-21 2027-01-16 US flag
US9744207 No 2017-08-29 2027-01-16 US flag
US9789064 No 2017-10-17 2020-12-15 US flag

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 150-155 https://www.trc-canada.com/product-detail/?L330600
pKa 9.6 http://products.sanofi.ca/en/eligard.pdf
Predicted Properties
Property Value Source
Water Solubility 0.0338 mg/mL ALOGPS
logP 1.04 ALOGPS
logP -2.4 Chemaxon
logS -4.6 ALOGPS
pKa (Strongest Acidic) 9.49 Chemaxon
pKa (Strongest Basic) 11.92 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 327.24 m3·mol-1 Chemaxon
Polarizability 125.24 Å3 Chemaxon
Number of Rings 6 Chemaxon
Bioavailability 0 Chemaxon
Rule of Five No Chemaxon
Ghose Filter No Chemaxon
Veber's Rule No Chemaxon
医学博士DR-like Rule Yes Chemaxon
Predicted ADMET Features
Not Available

Spectra

质量规范(NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
预测MS / MS谱- 20 v -(注释d) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Details 1.Gonadotropin-releasing hormone receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Peptide binding
Specific Function
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
分子量
37730.355 Da
参考文献
  1. Castellon E, Clementi M, Hitschfeld C, Sanchez C, Benitez D, Saenz L, Contreras H, Huidobro C: Effect of leuprolide and cetrorelix on cell growth, apoptosis, and GnRH receptor expression in primary cell cultures from human prostate carcinoma. Cancer Invest. 2006 Apr-May;24(3):261-8. [Article]
  2. Borroni R, Di Blasio AM, Gaffuri B, Santorsola R, Busacca M, Vigano P, Vignali M: Expression of GnRH receptor gene in human ectopic endometrial cells and inhibition of their proliferation by leuprolide acetate. Mol Cell Endocrinol. 2000 Jan 25;159(1-2):37-43. [Article]
  3. Imai A, Takagi A, Horibe S, Takagi H, Tamaya T: Fas and Fas ligand system may mediate antiproliferative activity of gonadotropin-releasing hormone receptor in endometrial cancer cells. Int J Oncol. 1998 Jul;13(1):97-100. [Article]
  4. Murase M, Uemura T, Gao M, Inada M, Funabashi T, Hirahara F: GnRH antagonist-induced down-regulation of the mRNA expression of pituitary receptors: comparisons with GnRH agonist effects. Endocr J. 2005 Feb;52(1):131-7. [Article]
  5. Khurana KK, Singh SB, Tatum AH, Schulz V, Badawy SZ: Maintenance of increased Bcl-2 expression in uterine leiomyomas after GnRH agonist therapy. J Reprod Med. 1999 Jun;44(6):487-92. [Article]
  6. FDA Approved Drug Products: Lupaneta Pack for intramuscular and oral use [Link]
  7. FDA Approved Drug Products: Lupron Depot (leuprolide acetate) depot suspension, for intramuscular injection [Link]
  8. FDA Approved Drug Products: Lupron Depot-Ped (leuprolide acetate) depot suspension [Link]
  9. FDA Approved Drug Products: Fensolvi (leuprolide acetate) suspension [Link]
  10. FDA Approved Drug Products: ELIGARD (leuprolide acetate) for injectable suspension, for subcutaneous use [Link]
  11. FDA Approved Drug Products: Lupron Depot 3.75mg (leuprolide acetate) depot suspension [Link]

Drug created at June 13, 2005 13:24 / Updated at April 15, 2023 12:42