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74381-53-6 (Leuprolide (Acetate))

1

Identification

Leuprolide (Acetate) Leuprolide (Acetate)
Name Leuprolide (Acetate)
Formula C61H88N16O14
MW 1269.45
CAS No. 74381-53-6
EINECS
Smiles O=C(N[[email protected]](C(N[[email protected]@H](CC1=CC=C(O)C=C1)C(N[[email protected]](C(C)(C)C)C(N[[email protected]@H](C(C)(C)C)C(N[[email protected]@H](CCCNC(N)=N)C(N2CCC[[email protected]]2C(NCC)=O)=O)=O)=O)=O)=O)CO)[[email protected]@H](NC([[email protected]](CC3=CN=CN3)NC([[email protected]]4NC(CC4)=O)=O)=O)CC5=CNC6=CC=CC=C65.CC(O)=O
Synonyms Leuprorelin acetate;Lupron; (S)-1-((3S,6S,9S,12S,15R,18S,21S)-3-((1H-imidazol-5-yl)methyl)-6-((1H-indol-3-yl)methyl)-15,18-di-tert-butyl-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-1,4,7,10,13,16,19-heptaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-N-ethylpyrrolidine-2-carboxamide acetate
InChI InChI=1S/C59H84N16O12.C2H4O2/c1-8-63-53(84)44-16-12-24-75(44)56(87)39(15-11-23-64-57(60)61)68-54(85)46(58(2,3)4)74-55(86)47(59(5,6)7)73-51(82)40(25-32-17-19-35(77)20-18-32)69-52(83)43(30-76)72-49(80)41(26-33-28-65-37-14-10-9-13-36(33)37)70-50(81)42(27-34-29-62-31-66-34)71-48(79)38-21-22-45(78)67-38;1-2(3)4/h9-10,13-14,17-20,28-29,31,38-44,46-47,65,76-77H,8,11-12,15-16,21-27,30H2,1-7H3,(H,62,66)(H,63,84)(H,67,78)(H,68,85)(H,69,83)(H,70,81)(H,71,79)(H,72,80)(H,73,82)(H,74,86)(H4,60,61,64);1H3,(H,3,4)/t38-,39-,40-,41-,42-,43-,44-,46+,47-;/m0./s1
2

Introduction

Leuprolide acetate (Leuprorelin) is a GnRH analog; leuprolide acetate acts as an agonist at pituitary GnRH receptors. IC50 Value: Target: GnRH receptor By interrupting the normal pulsatile stimulation of, and thus desensitizing, the GnRH receptors, it indirectly downregulates the secretion of gonadotropins luteinizing hormone (LH) and follicle-stimulating hormone (FSH), leading to hypogonadism and thus a dramatic reduction in estradiol andtestosterone levels in both sexes. in vitro: The number of DNA 3'-end-labeled cells/cm2 in leiomyomas of control patients and in leiomyomas at the 2nd, 8th, 12th, and 16th weeks of Leuprolide Acetate treatment were at low levels [1].

Background Information

Leuprolide Acetate is a potent LHRH (GnRH) agonist. After a transient increase, continuous administration of leuprolide results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis. Studies with female Alzheimer patients indicate that application of leuprolide acetate in combination with an acetylcholinesterase inhibitor stabilizes the cognitive functions in mild-to-moderate cases. ......by Affix Scientific
leuprolide acetate is the acetate salt of a synthetic nonapeptide analogue of gonadotropin-releasing hormone. Leuprolide binds to and activates gonadotropin-releasing hormone (GnRH) receptors. Continuous, prolonged administration of leuprolide in males results in pituitary GnRH receptor desensitization and inhibition of pituitary secretion of follicle stimulating hormone (FSH) and luteinizing hormone (LH), leading to a significant decline in testosterone production; in females, prolonged administration results in a decrease in estradiol production. This agent reduces testosterone production to castration levels and may inhibit androgen receptor-positive tumor progression. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus) Shelf life: >2 years if stored properly Drug formulation: ......by MedKoo Biosciences, Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000016196

Storage condition

Up to one week at 4°C or six months at -20°C. by Affix Scientific

Solubility

DMSO by MedChemexpress Co., Ltd.
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Leuprolide (Acetate) Ipsen Prostate tumor 2012/8/31 2014/9/30 Phase 4 Clinical
Leuprolide (Acetate) HanAll Biopharma Co Ltd Metastatic prostate cancer 2011/1/31 2013/12/31 Phase 4 Clinical
Leuprolide (Acetate) Abbott Laboratories Prostate tumor 2011/6/30 2017/5/31 Phase 4 Clinical
Leuprolide (Acetate) Actavis Inc Hormone dependent prostate cancer 2010/7/31 2011/4/30 Phase 4 Clinical
Leuprolide (Acetate) Chesapeake Urology Research Associates Prostate tumor 2003/10/31 2009/6/30 Phase 4 Clinical
Leuprolide (Acetate) - Launched
7

Safety Data of Leuprolide (Acetate)

Safety Statements : 22-24/25
RTECS : OH6390000
WGKGermany : 2
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
Affix Scientific USA
Alfa Chemistry USA
BOC Sciences
CHEMSCENE, LLC 5mg/USD84();10mg/USD108() USA
Carbosynth Limited 5mg/USD140()
Clearsynth Labs Limited 25mg/USD800() India
Hubei Research Institute of Chemistry China
Lancrix Chemicals. 25mg/USD236() China
MedChemexpress Co., Ltd. 5mg/USD84();10mg/USD108() USA
MedKoo Biosciences, Inc. 10mg/USD150() USA
Santa Cruz Biotechnology, Inc. 1mg/USD80() USA
Shanghai Haoyuan Chemexpress Co., Ltd. 5mg/USD84();10mg/USD108() China
Sinoway Industrial Co., Ltd. China
Tokyo Chemical Industry Co., Ltd. 25mg/USD176() Japan
Xiangfan Goto Chemical Co., Ltd CHINA
10

Related Products

Other Forms of 74381-53-6

Name CAS No Formula MW

Recommended Compounds in GNRH Receptor

Name CAS No Formula MW
Goserelin Acetate 65807-02-5 C59H79D5N18O14 1274.44
Degarelix 214766-78-6 C82H103ClN18O16 1632.26
Abarelix 183552-38-7 C72H95ClN14O14 1416.06
Alarelin (Acetate) 79561-22-1 C60H86N16O16 1287.42
Relugolix 737789-87-6 C29H27F2N7O5S 623.6304
Elagolix 834153-87-6 C32H30F5N3O5 631.59
Goserelin 65807-02-5 C59H84N18O14 1269.41046
Nafarelin 76932-56-4 C66H83N17O13 1322.47
Lecirelin 61012-19-9 C59H84N16O12 1209.4
Gonadorelin 33515-09-2 C55H75N17O13 1182.29
Cetrorelix (Acetate) 145672-81-7 C72H96ClN17O16 1491.09
Buserelin (Acetate) 68630-75-1 C64H93N15O15 1312.52
Deslorelin 57773-65-6 C64H83N17O12 1282.45
Gonadorelin (acetate) 34973-08-5 C57H79N17O15 1242.34
Leuprorelin 53714-56-0 C59H84N16O12 1209.4
Triptorelin 57773-63-4 C64H82N18O13 1311.45
Goserelin (acetate) 145781-92-6 C61H88N18O16 1329.46242
Leuprolide Acetate 74381-53-6 C61H88N16O14 1269.45022
Alarelin (Acetate) 79561-22-1 C60H86N16O16 1287.422
Buserelin (Acetate) 68630-75-1 C62H90N16O15 1299.4762

Recommended Compounds in Same Indication

Name CAS No Formula MW
AT-101 90141-22-3 C30H30O8 518.55
Bicalutamide 90357-06-5 C18H14F4N2O4S 430.37
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Tivozanib 475108-18-0 C22H19ClN4O5 454.86
Orteronel 566939-85-3 C18H17N3O2 307.35
Fenretinide 65646-68-6 C26H33NO2 391.55
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
Ganetespib 888216-25-9 C20H20N4O3 364.4
Tasquinimod 254964-60-8 C20H17F3N2O4 406.36
Orteronel (racemate) 426219-18-3 C18H17N3O2 307.3465
TAK-700 (salt) 426219-53-6 C28H28N4O7 532.54
RO4929097 847925-91-1 C22H20F5N3O3 469.4
Zibotentan 186497-07-4 C19H16N6O4S 424.43
Genistein 446-72-0 C15H10O5 270.24
Calcifediol (monohydrate) 63283-36-3 C27H44O2 400.64
Abiraterone (acetate) 154229-18-2 C26H33NO2 391.55
Abiraterone 154229-19-3 C24H31NO 349.51
Dutasteride 164656-23-9 C27H30F6N2O2 528.53
Indoximod 110117-83-4 C12H14N2O2 218.25
Cabazitaxel 183133-96-2 C45H57NO14 835.93
11

Route of Synthesis

12

References

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More Information

Leuprolide (Acetate)

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