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MedKoo Cat#: 598688 | Name: Leuprorelin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Leuprorelin is a potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.

Chemical Structure

Leuprorelin
CAS#53714-56-0

Theoretical Analysis

MedKoo Cat#: 598688

Name: Leuprorelin

CAS#: 53714-56-0

Chemical Formula: C59H84N16O12

Exact Mass: 1208.6455

Molecular Weight: 1209.42

Elemental Analysis: C, 58.59; H, 7.00; N, 18.53; O, 15.87

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Synonym
Leuprorelin; NSC 377526; NSC-377526; NSC377526; Leuprorelinum; Eligard; A-43818; A 43818; A43818;
IUPAC/Chemical Name
(S)-N-ethyl-1-(((S)-5-oxopyrrolidine-2-carbonyl)-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl)pyrrolidine-2-carboxamide
InChi Key
GFIJNRVAKGFPGQ-LIJARHBVSA-N
InChi Code
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
SMILES Code
CCNC([C@@H]1CCCN1C([C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H]2CCC(N2)=O)=O)Cc3nc[nH]c3)=O)Cc4c5ccccc5[nH]c4)=O)CO)=O)Cc6ccc(O)cc6)=O)CC(C)C)=O)CC(C)C)=O)CCCNC(N)=N)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Leuprorelin is a potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE that regulates the synthesis and release of pituitary gonadotropins, LUTEINIZING HORMONE and FOLLICLE STIMULATING HORMONE.
In vitro activity:
DU145 cells treated with leuprolide (10(-9) and 10(-7) M) showed significant growth inhibition compared with control-treated DU145 cells. Reference: J Int Med Res. 2011;39(3):729-39. https://pubmed.ncbi.nlm.nih.gov/21819703/
In vivo activity:
Leuprolide--a luteinizing hormone-releasing hormone (LHRH) agonist, dose dependently (100, 200 and 300 microg/kg, s.c.) inhibited marble-burying behavior in mice, which was comparable to that of fluoxetine (10 and 15 mg/kg, i.p.)--a drug used in the treatment of obsessive-compulsive disorder. Reference: Eur J Pharmacol. 2007 Jun 1;563(1-3):155-9. https://pubmed.ncbi.nlm.nih.gov/17368614/

Preparing Stock Solutions

The following data is based on the product molecular weight 1,209.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ko YH, Ha YR, Kim JW, Kang SG, Jang HA, Kang SH, Park HS, Cheon J. Silencing of the GnRH type 1 receptor blocks the antiproliferative effect of the GnRH agonist, leuprolide, on the androgen-independent prostate cancer cell line DU145. J Int Med Res. 2011;39(3):729-39. doi: 10.1177/147323001103900304. PMID: 21819703. 2. Lama G, Papi M, Angelucci C, Maulucci G, Sica G, De Spirito M. Leuprorelin acetate long-lasting effects on GnRH receptors of prostate cancer cells: an atomic force microscopy study of agonist/receptor interaction. PLoS One. 2013;8(1):e52530. doi: 10.1371/journal.pone.0052530. Epub 2013 Jan 9. PMID: 23326338; PMCID: PMC3541369. 3. Palacios JL, Luquin S, Quintanar JL, Munoz A. Continuous administration of leuprolide acetate improves urinary function in male rats with severe thoracic spinal cord injury. Life Sci. 2022 Dec 1;310:121113. doi: 10.1016/j.lfs.2022.121113. Epub 2022 Oct 20. PMID: 36273627. 4. Uday G, Pravinkumar B, Manish W, Sudhir U. LHRH antagonist attenuates the effect of fluoxetine on marble-burying behavior in mice. Eur J Pharmacol. 2007 Jun 1;563(1-3):155-9. doi: 10.1016/j.ejphar.2007.02.016. Epub 2007 Feb 17. PMID: 17368614.
In vitro protocol:
1. Ko YH, Ha YR, Kim JW, Kang SG, Jang HA, Kang SH, Park HS, Cheon J. Silencing of the GnRH type 1 receptor blocks the antiproliferative effect of the GnRH agonist, leuprolide, on the androgen-independent prostate cancer cell line DU145. J Int Med Res. 2011;39(3):729-39. doi: 10.1177/147323001103900304. PMID: 21819703. 2. Lama G, Papi M, Angelucci C, Maulucci G, Sica G, De Spirito M. Leuprorelin acetate long-lasting effects on GnRH receptors of prostate cancer cells: an atomic force microscopy study of agonist/receptor interaction. PLoS One. 2013;8(1):e52530. doi: 10.1371/journal.pone.0052530. Epub 2013 Jan 9. PMID: 23326338; PMCID: PMC3541369.
In vivo protocol:
1. Palacios JL, Luquin S, Quintanar JL, Munoz A. Continuous administration of leuprolide acetate improves urinary function in male rats with severe thoracic spinal cord injury. Life Sci. 2022 Dec 1;310:121113. doi: 10.1016/j.lfs.2022.121113. Epub 2022 Oct 20. PMID: 36273627. 2. Uday G, Pravinkumar B, Manish W, Sudhir U. LHRH antagonist attenuates the effect of fluoxetine on marble-burying behavior in mice. Eur J Pharmacol. 2007 Jun 1;563(1-3):155-9. doi: 10.1016/j.ejphar.2007.02.016. Epub 2007 Feb 17. PMID: 17368614.
1: Li Z, Zhang HY, Zhu YJ, Hu YJ, Qu PP. A randomized study comparing the side effects and hormonal status of triptorelin and leuprorelin following conservative laparoscopic surgery for ovarian endometriosis in Chinese women. Eur J Obstet Gynecol Reprod Biol. 2014 Dec;183:164-8. doi: 10.1016/j.ejogrb.2014.10.022. Epub 2014 Nov 4. PubMed PMID: 25461372. 2: Mangoni M, Sottili M, Gerini C, Fucci R, Pini A, Calosi L, Bonomo P, Detti B, Greto D, Meattini I, Simontacchi G, Loi M, Scartoni D, Furfaro I, Pallotta S, Livi L. Protective Effect of Leuprorelin on Radiation-induced Intestinal Toxicity. Anticancer Res. 2015 Jul;35(7):3875-84. PubMed PMID: 26124333. 3: Lee SH, Lee HM, Kim SW, Lee ES, Hong SJ, Kim CS, Kang TW, Chung BH. Is high-dose leuprorelin acetate effective and safe in asian men with prostate cancer? An open-label, non-comparative, multi-center clinical trial. Yonsei Med J. 2014 Mar;55(2):310-5. doi: 10.3349/ymj.2014.55.2.310. PubMed PMID: 24532497; PubMed Central PMCID: PMC3936644. 4: Takenaka M, Yano R, Hiraku Y, Shibata M, Hatano K, Yamamoto S, Sato K, Yamamoto K, Morishige K. Exploratory study of pre-surgical medications with dienogest or leuprorelin in laparoscopic cystectomy of endometrial cysts. J Obstet Gynaecol Res. 2015 Aug;41(8):1234-9. doi: 10.1111/jog.12701. Epub 2015 Apr 1. PubMed PMID: 25833348. 5: Li WJ, Gong CX, Guo MJ, Xing J, Li T, Song WH, Luo XP, Wu D, Liang JP, Cao BY, Gu Y, Su C, Liang XJ, Liu M, Wang R, Li FT. Efficacy and safety of domestic leuprorelin in girls with idiopathic central precocious puberty: a multicenter, randomized, parallel, controlled trial. Chin Med J (Engl). 2015 May 20;128(10):1314-20. doi: 10.4103/0366-6999.156773. PubMed PMID: 25963350; PubMed Central PMCID: PMC4830309. 6: Suzuki K, Namiki M, Fujimoto T, Takabayashi N, Kudou K, Akaza H. Efficacy and safety of leuprorelin acetate 6-month depot in prostate cancer patients: a Phase III, randomized, open-label, parallel-group, comparative study in Japan. Jpn J Clin Oncol. 2015 Dec;45(12):1168-74. doi: 10.1093/jjco/hyv149. Epub 2015 Oct 20. PubMed PMID: 26486824; PubMed Central PMCID: PMC4653047. 7: Fukui S, Nakai Y, Matsumoto Y, Kagebayashi Y, Samma S. [Investigation of incidence and risk factors of subcutaneous granulomas induced by injection of leuprorelin acetate]. Hinyokika Kiyo. 2015 Feb;61(2):55-9. Japanese. PubMed PMID: 25812594. 8: Malinovskaja K, Laaksonen T, Hirvonen J. Controlled transdermal delivery of leuprorelin by pulsed iontophoresis and ion-exchange fiber. Eur J Pharm Biopharm. 2014 Nov;88(3):594-601. doi: 10.1016/j.ejpb.2014.08.010. Epub 2014 Aug 27. PubMed PMID: 25173088. 9: Merseburger AS, Björk T, Whitehouse J, Meani D. Treatment costs for advanced prostate cancer using luteinizing hormone-releasing hormone agonists: a solid biodegradable leuprorelin implant versus other formulations. J Comp Eff Res. 2015 Sep;4(5):447-53. doi: 10.2217/cer.14.82. Epub 2014 Dec 18. PubMed PMID: 25521079. 10: Periti P, Mazzei T, Mini E. Clinical pharmacokinetics of depot leuprorelin. Clin Pharmacokinet. 2002;41(7):485-504. Review. PubMed PMID: 12083977. 11: Hintzen F, Perera G, Hauptstein S, Müller C, Laffleur F, Bernkop-Schnürch A. In vivo evaluation of an oral self-microemulsifying drug delivery system (SMEDDS) for leuprorelin. Int J Pharm. 2014 Sep 10;472(1-2):20-6. doi: 10.1016/j.ijpharm.2014.05.047. Epub 2014 May 29. PubMed PMID: 24879935. 12: Gravel P, Samland D, Löffler M, Maier S, Panozzo M, Muenzberg M. Two innovative pharmaceutical forms of leuprorelin: results from 818 patients with advanced prostate cancer. Adv Ther. 2013 Mar;30(3):271-85. doi: 10.1007/s12325-013-0010-y. Epub 2013 Mar 1. PubMed PMID: 23460040. 13: Shiba E, Yamashita H, Kurebayashi J, Noguchi S, Iwase H, Ohashi Y, Sasai K, Fujimoto T. A randomized controlled study evaluating safety and efficacy of leuprorelin acetate every-3-months depot for 2 versus 3 or more years with tamoxifen for 5 years as adjuvant treatment in premenopausal patients with endocrine-responsive breast cancer. Breast Cancer. 2016 May;23(3):499-509. doi: 10.1007/s12282-015-0593-z. Epub 2015 Feb 6. PubMed PMID: 25655898; PubMed Central PMCID: PMC4839052. 14: Papadimitriou DT, Dermitzaki E, Papagianni M, Papaioannou G, Papaevangelou V, Papadimitriou A. Anastrozole plus leuprorelin in early maturing girls with compromised growth: the "GAIL" study. J Endocrinol Invest. 2016 Apr;39(4):439-46. doi: 10.1007/s40618-015-0399-z. Epub 2015 Oct 27. PubMed PMID: 26507391; PubMed Central PMCID: PMC4799269. 15: Zhou LM, Zheng J, Sun YT, Zhao YY, Xia AL. [Study on leuprorelin acetate in treatment of uterine adenomyosis with infertility]. Zhonghua Fu Chan Ke Za Zhi. 2013 May;48(5):334-7. Chinese. PubMed PMID: 24016474. 16: Tunn UW, Gruca D, Bacher P. Six-month leuprorelin acetate depot formulations in advanced prostate cancer: a clinical evaluation. Clin Interv Aging. 2013;8:457-64. doi: 10.2147/CIA.S27931. Epub 2013 Apr 26. Review. PubMed PMID: 23637525; PubMed Central PMCID: PMC3639016. 17: Kawai M, Ikoma N, Yamada A, Ota T, Manabe Y, Kato M, Mabuchi T, Ozawa A, Higure T, Terachi T. A case of foreign body granuloma induced by subcutaneous injection of leuprorelin acetate─clinical analysis for 335 cases in our hospital─. Tokai J Exp Clin Med. 2014 Sep 20;39(3):106-10. PubMed PMID: 25248424. 18: de Salins CA, Kupfer-Bessaguet I, Fleuret C, Staroz F, Plantin P. [Fixed drug eruption induced by leuprorelin]. Ann Dermatol Venereol. 2015 Dec;142(12):780-1. doi: 10.1016/j.annder.2015.06.016. Epub 2015 Aug 4. French. PubMed PMID: 26249532. 19: Wang L, Zhang WX, Jiang H. [Clinical applications of different doses of leuprorelin acetate in in vitro fertilization-embryo transfer]. Zhonghua Fu Chan Ke Za Zhi. 2012 Dec;47(12):910-4. Chinese. PubMed PMID: 23324190. 20: Park WS, Kim KM, Jung YW, Lim MH. A case of mental retardation with paraphilia treated with depot leuprorelin. J Korean Med Sci. 2014 Sep;29(9):1320-4. doi: 10.3346/jkms.2014.29.9.1320. Epub 2014 Sep 2. PubMed PMID: 25246754; PubMed Central PMCID: PMC4168189.