Anti-cancer drugs
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Leuprorelin acetate

Anti-cancer drugs
Product Name
Leuprorelin acetate
CAS No.
74381-53-6
Chemical Name
Leuprorelin acetate
Synonyms
LEUPROLIDE;Leuprolide acetate;lupron;Leuprolide acetate (Leuprorelin acetate);6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamideluteinizing Hormone-Releasing Factor Acetate(Pig);tap-144;Prostap;Procrin;TPA-144;DC-2-269
CBNumber
CB7174300
Molecular Formula
C61H88N16O14
Formula Weight
1269.47
MOL File
74381-53-6.mol
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Leuprorelin acetate Property

Melting point:
150-155°C
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
color 
White to Off-White
Merck 
14,5457
InChIKey
RGLRXNKKBLIBQS-XNHQSDQCSA-N
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Safety

Safety Statements 
22-24/25
WGK Germany 
2
RTECS 
OH6390000
HS Code 
29371900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L0399
Product name
Leuprolide acetate salt
Purity
≥98% (HPLC)
Packaging
1mg
Price
$78.6
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3193
Product name
Leuprolide Acetate
Purity
pharmaceutical secondary standard, certified reference material
Packaging
5MG
Price
$668
Updated
2024/03/01
Cayman Chemical
Product number
22275
Product name
Leuprorelin (acetate)
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
22275
Product name
Leuprorelin (acetate)
Purity
≥98%
Packaging
5mg
Price
$93
Updated
2024/03/01
Sigma-Aldrich
Product number
L0399
Product name
Leuprolide acetate salt
Purity
≥98% (HPLC)
Packaging
5mg
Price
$448
Updated
2024/03/01
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Leuprorelin acetate Chemical Properties,Usage,Production

Anti-cancer drugs

Leuprolide acetate is a commonly used hormone anti-cancer drug, , it is a acetate of leuprolide which is a nonapeptide synthetic analogue of LHRH( one kind decapeptide), it is a LH-RH antagonist, LHRH is produced by the hypothalamus, it can promote pituitary for the release of gonadotropins and follicle-stimulating hormone (FSH) and luteinizing hormone (LH). This product’s structure is similar to LHRH, its acting on the anterior pituitary which prompts FSH, LH release function, increases serum concentrations of testosterone and dihydro testosterone. It is used as maintenance therapy for advanced prostate cancer clinically, but in about one week after use of the product, the number of active receptors will be reduced, and gonadotropin secretion will be reduced.After 2 to 4 weeks, the concentration of testosterone and dihydro testosterone can be reduced to castration levels. After the withdrawal, gonadotropin and androgen concentrations can be recovered to normal.
Note that this product is not effective when administered orally, subcutaneous or intramuscular administration has good absorption. T1/2 of parenteral administration is 3 h. There is no accumulation in the body, unchanged drugs and its metabolites in urine excretion rates are2.9% and 1.5%, respectively. Ethanol can enhance the role of this product, the course of treatment should not drink, in case it is difficult to control the incidence of adverse reactions. In the first week of the course of treatment ,patients should try to be hospitalized for monitoring, choose an experienced physician to guide treatment to prevent severe neurological complications, urinary tract obstruction. Injection site should often vary.
The above information is edited by the chemicalbook of Tian Ye.

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.

Chemical Properties

Fluffy Solid

Originator

Takeda (Japan)

Uses

Leuprolide acetate USP (Leupron) is used to treat Prostatic carcinoma.

Uses

Synthetic nonapeptide agonist analog of LH-RH. Antineoplastic (hormonal).

Uses

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.

Definition

ChEBI: An acetate salt obtained by combining the nonapeptide leuprolide with acetic acid. A long lasting GnRH analog, LH-Rh agonist. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant for the t eatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.

Manufacturing Process

5-Oxo-L-prolyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-Larginyl-L-prolylethylamideacetate was prepared by using of Boc strategy on a 2%-crosslinking chloromethylated divinylbenzene-styrene copolymer in a the Merrifield automatic sintesizer apparatus. 4.6 g of this resin/aminoacid material is used for the synthesis of the desired nonapeptide. Each N-blocked aminoacid is added in a three-fold access and allowed to couple to them, existing aminoacid-resin ester in the usual coupling cycle. Ordinarily the solvent used for the coupling reaction is dichloromethane or, when the solubility of the blocked aminoacid is low, a mixture of dichloromethane and DMF. Coupling is effected by the addition of a solution of dicyclohexylcarbodiimide in dichloromethane at a 2.9 fold excess. The sequence used for deprotection, neutralization and coupling of the next aminoacid is done in a fully automatic system. In this manner, the peptide is assembled using in turn Boc-Arg(Tos), Boc-Leu, Boc-D-Leu, Boc-Tyr(Cl2Bzl), Boc-Ser(Bzl), Boc-Trp, Boc-His(DNP), and pGlu wherein all aminoacids are in the L-form except in the leucine so designated. A 250 mg sample of the above is placed in a hydrogen fluoride reaction with 250 mg vessel of anisole and about 5 ml of anhydrous hydrogen fluoride is distilled into it. After 1 hour at 0°C, the hydrogen fluoride is removed with a stream of dry nitrogen and the residue is taken up in 1% acetic acid. This solution is extracted with ether, and the aqueous phase applied to a 1 time 30 cm column of a highly basic ion exchange resin (marketed by Bio-Rad as AGl resin) in the acetate form. The product is eluted with 0.1 N acetic acid and localized using thin-layer chromatography (CHCl3/MeOH/32% HOAc: 120/90/40, silica gel G, Cl2/tolidine). The product bearing solution is lyophilized, rechromatographed on a Sephadex G-25 (marketed by Pharmacia of Uppsala, Sweden) column. The product eluted is collected and lyophilized to yield a fluffy white solid. An aminoacid analysis shows the expected ratio of all desired aminoacids assembled in the above fashion.

brand name

Eligard (QLT); Lupron(TAP); Viadur (ALZA);CARCINIL.

Therapeutic Function

Antineoplastic

Biochem/physiol Actions

Glp-His-Trp-Ser-Tyr-Leu-Leu-Arg-Pro-NHEt (des-Gly10-[D-Leu6]-LH-RH) is a GnRH (gonadotropin-releasing hormone) agonist, leuprolide. GnRH (Glp-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2), which is also referred as LHRH (luteinizing hormone-releasing hormone) or gonadorelin, is crucial for mammalian reproduction and is released from hypothalamic neurons. It is responsible for the secretion of gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH), from the pituitary glands. Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism. Low concentration of leuprolide can be used for the treatment of endometriosis, uterine fibroids, central precocious puberty and advanced prostate cancer.

Pharmacology

Leuprolide, 5-oxo-L-prolyl-L-histadyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucil-L-leucil-L-arginyl-N-ethyl-L-prolinamide (30.5.9), is made synthetically.
pyroGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt
The nonapeptide leuprolide is a synthetic analog of the decapeptide, gonadotropin releasing hormone, and it exceeds the activity of the natural hormone and significantly elevates the level of testosterone and dihydrotestosterone in men, and estrogen in women. It also inhibits follicle-stimulating hormone and leutenizing hormone.
Leuprolide is used for prostate cancer, when orchiectomy or estrogen therapy is counterproductive to the patient. A synonym of this drug is lupron.

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.

Side effects

Side effects: allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue; breathing problems; chest pain; depression or memory disorders; pain in your legs or groin; pain at site where injected or implanted; seizures; severe headache; signs and symptoms of high blood sugar such as being more thirsty or hungry or having to urinate more than normal. You may also feel very tired or have blurry vision; swelling of the feet and legs; suicidal thoughts or other mood changes; visual changes; vomiting

Drug interactions

Leuprorelin acetate can not take with mang drugs, such as chasteberry, cisapride, dronedarone, pimozide, or thioridazine. This medicine may also interact with the following medications: herbal or dietary supplements, like black cohosh or DHEA; female hormones, like estrogens or progestins and birth control pills, patches, rings, or injections; male hormones, like testosterone; other medicines that prolong the QT interval (abnormal heart rhythm).

Leuprorelin acetate Preparation Products And Raw materials

Raw materials

Preparation Products

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Leuprorelin acetate Suppliers

Chinese Peptide Company
Tel
0571-86737118-8680 15988144796
Email
sales@chinesepeptide.com
Country
China
ProdList
12
Advantage
58
Hangzhou Peptide Biochem Co.,Ltd
Tel
0571-89197072; 18668118770
Fax
0571-89197072
Email
linda@peptide-china.com
Country
China
ProdList
248
Advantage
56
Hangzhou Peptidego Biotech Co.,Ltd.
Tel
0571-87213919
Fax
0571-87213919
Email
eric@peptidego.com
Country
China
ProdList
6119
Advantage
58
Sichuan Jisheng Biopharmaceutical Co.,Ltd.
Tel
+86-0833-2598983 +86-18086877136
Fax
+86-833-2598903
Email
Nyx-peptide@jsjpharm.cn
Country
China
ProdList
306
Advantage
58
Hangzhou Xinhai Pharmaceutical Technology Co., Ltd.
Tel
0571-86758863 13867485072
Fax
0571-86758863
Email
lulu@thinheal.com
Country
China
ProdList
300
Advantage
58
Twochem Co.Ltd.
Tel
021-58111628 15800915896
Fax
QQ 3285589261
Country
China
ProdList
1988
Advantage
58
Nanjing Yuanpeptide Biotech Co.,Ltd.
Tel
18168071971
Email
support@yuan-peptide.com
Country
China
ProdList
2977
Advantage
58
Zhongke Huayao (Jiangsu) Biotechnology Co., Ltd
Tel
18014456767 18014456767
Email
wenxi@jszkhy.com
Country
China
ProdList
1349
Advantage
58
Shanghai Aladdin Biochemical Technology Co.,Ltd.
Tel
+86-18521732826
Email
market@aladdin-e.com
Country
China
ProdList
33048
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
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View Lastest Price from Leuprorelin acetate manufacturers

Wuhan Cell Pharmaceutical Co., Ltd
Product
Leuprorelin acetate 74381-53-6
Price
US $9.90/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2023-04-07
hebei hongtan Biotechnology Co., Ltd
Product
Leuprorelin 74381-53-6
Price
US $30.00/box
Min. Order
1box
Purity
98%
Supply Ability
5000box
Release date
2024-03-20
Nantong Guangyuan Chemicl Co,Ltd
Product
Leuprolide acetate 74381-53-6
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2023-11-15

74381-53-6, Leuprorelin acetateRelated Search:


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