Leuprorelin acetate

Base Information

• Chemical Name: Leuprorelin acetate
• CAS No.: 74381-53-6
• Molecular Formula: C59H84N16O12^.C2H4O2
• Molecular Weight: 1269.47
• Hs Code.: 29371900
• European Community (EC) Number: 686-285-8
• NSC Number: 746847
• Mol file: 74381-53-6.mol

Synonyms:74381-53-6;Leuprorelin Acetate;H-Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt.CH3CO2H;Lupron (TN);MFCD00072080;Fensolvi (TN);Eligard (TN);Lutrate (TN);Leuprolide acetate (USP);Leuprorelin acetate (JP17);SCHEMBL1651429;5-oxoPro-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-ProNHC2H5 dihydrate;AMY12301;NSC746847;NSC-746847;SY225936;FT-0627807;D00989;Leuprorelin acetate;Lupron;Leuprolide acetate

Chemical Property of Leuprorelin acetate

Chemical Property:

• Appearance/Colour: fluffy solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 150-155oC
• Boiling Point: 1720.5oC at 760 mmHg
• Flash Point: 994.3oC
• PSA: 466.34000
• LogP: 3.44730
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 16
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 32
• Exact Mass: 1268.66659154
• Heavy Atom Count: 91
• Complexity: 2420

Purity/Quality:

99% min ^*data from raw suppliers

Leuprolide, Human ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6.CC(=O)O
• Recent EU Clinical Trials: Short versus long-term androgen deprivation therapy combined with salvage radiotherapy in prostate cancer patients with biochemical recurrence after prostatectomy: a multicentre phase III randomised controlled trial
• Description: Leuprolide acetate is a potent analog of LH-RH useful in achieving a medical castration in the treatment of advanced prostate cancer. It has also been investigated for the treatment of advanced breast cancer.
• Uses: Leuprolide acetate USP (Leupron) is used to treat Prostatic carcinoma. In mice, leuprolide acetate salt has been used to check the need of estrogen receptor α in spermatogenic cells, for development or function in fertilization.
• Therapeutic Function: Antineoplastic
• Clinical Use: Leuprolide acetate, a synthetic nonapeptide analogue of GnRH that possesses greater potency than the natural hormone, is a superagonist that is commercially available. Note that leuprolide acetate contains substitutions that hinder enzymatic degradation, D-Leu and NH-Et in place of Gly6 and Gly10-NH2, respectively. Leuprolide acetate is reportedly 15-fold the potency of natural GnRH. When given continuously and in therapeutic doses, leuprolide acetate inhibits LH and FSH secretion by desensitizing/downregulating the GnRH receptors. After an initial stimulation, chronic administration of leuprolide acetate results in suppression of ovarian and testicular steroidogenesis. In premenopausal females, estrogens are reduced to postmenopausal levels; in males, testosterone is reduced to castrate levels.Leuprolide acetate is administered by daily injections or as depot injections every month, every 3 months, every 4 months, or every 6 months as a palliative treatment in advanced prostatic carcinoma (as an alternative to orchiectomy). An implant version (Viadur) also is available for long-term palliative therapy; after implantation of the device into the upper arm, leuprolide acetate is continuously released over a 12-month period. Because dihydrotestosterone, a metabolite of testosterone, is able to stimulate the growth of prostate cancer, the ability of leuprolide acetate to bring testosterone to near castrate levels is why this drug finds use as a palliative in the advanced disease. The addition of a nonpeptidyl antiandrogen, such as flutamide or bicalutamide, to the leuprolide acetate regimen inhibits adrenal and testicular synthesized androgens from binding to or being taken up by target prostate cancer tissue. This combination therapy helps to control the initial flare-up, by blocking all sources of androgen, and is referred to as maximal androgen blockade.Leuprolide acetate, in monthly and every-3-months depot formulations, is useful in treating women diagnosed with endometriosis, but not for longer than six months because of the chance of developing osteoporosis.Central precocious puberty that is idiopathic, or gonadotropin dependent, can cause the development of secondary sexual characteristics in girls before the age of 8 years and in boys before the age of 9 years. In addition to the psychological and physiological changes that occur because of entering puberty too early, there is the risk of the child failing to reach his or her full adult height. Therefore, leuprolide acetate's ability to suppress LH and sex steroid levels (testosterone and estradiol) to prepubertal levels is the reason that leuprolide acetate is approved for use in treating children with this disease. Use of this drug in a child with precocious puberty will slow or stop that child's secondary sexual development, slow linear growth and skeletal maturation, and in girls, will bring about the cessation of menstruation.
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Leuprorelin acetate

There total 1 articles about Leuprorelin acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 38.6%

Z-pGlu-His-Trp(Mtr)-Ser-Tyr-D-Leu-Leu-Arg(Mbs)-Pro-NH-C2H5 (82155-05-3) → 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide acetate (74381-53-6)

Guidance literature:

With methanesulfonic acid; methyl-phenyl-thioether; ethane-1,2-dithiol; for 1h; Ambient temperature;

Reference yield:

5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide acetate (74381-53-6) → leuprolide hydrochloride

Guidance literature:

With hydrogenchloride; In water;

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide acetate (74381-53-6) → leuprolide mesylate

Guidance literature:

In water;

upstream raw materials:

Z-pGlu-His-Trp(Mtr)-Ser-Tyr-D-Leu-Leu-Arg(Mbs)-Pro-NH-C₂H₅

Refernces