Leuprolide TFA

Names

[ Name ]:
Leuprolide TFA

[Synonym ]:
Enantone
Leuprorelin
L-Prolinamide, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-
Leuplin
Leuprolide
nghormone
des-Gly10 ethylamide]gonadotropin releasing hormone
MFCD00167544
LH-RH LEUPROLIDE
Carcinil
5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5
Lucrin
<D-Leu6,DesGly10> LHRH ethylamide
LEUPROPELIN
Leuprorelin Acetate
GLP-HIS-TRP-SER-TYR-DLEU-LEU-ARG-PRO-NHET: GLP-HWSY-DL-LRP-NHET

Biological Activity

[Description]:

Leuprolide is an agonist at pituitary GnRH receptors. Target: GnRH receptorLeuprorelin is a gonadotrophin-releasing hormone (GnRH) analogue used to treat a wide range of sex hormone-related disorders including advanced prostatic cancer, endometriosis and precocious puberty. Leuprorelin acts primarily on the anterior pituitary, inducing a transient early rise in gonadotrophin release. With continued use, Leuprorelin causes pituitary desensitisation and/or down-regulation, leading to suppressed circulating levels of gonadotrophins and sex hormones. [1] 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 and testosterone levels in both sexes. [2]

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> GNRH Receptor

Research Areas >> Neurological Disease

Peptides

[References]

[1]. Plosker GL, Leuprorelin. A review of its pharmacology and therapeutic use in prostatic cancer, endometriosis and other sex hormone-related disorders. Drugs.1994 Dec;48(6):930-967.

[2]. Leuprorelin

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Molecular Formula ]:
C₅₉H₈₄N₁₆O₁₂

[ Molecular Weight ]:
1209.40

[ PSA ]:
466.34000

[ LogP ]:
0.41

[ Index of Refraction ]:
1.682

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OK6700000

CHEMICAL NAME :: Luteinizing hormone-releasing hormone (pig), 6-D-leucine-9-(N-ethyl-L-prolinamide)- 10-deglycinamide-

CAS REGISTRY NUMBER :: 53714-56-0

LAST UPDATED :: 199201

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C59-H84-N16-O12

MOLECULAR WEIGHT :: 1209.59

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 5214 ug/kg

SEX/DURATION :: male 1 year(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 42,765,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 280 ug/kg

SEX/DURATION :: female 28 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - menstrual cycle changes or disorders

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 27,853,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 50 ug/kg

SEX/DURATION :: female 15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 152,29,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 25 ug/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 152,29,1976

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H360

[ Precautionary Statements ]:
P201-P280-P308 + P313

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
OH6390000

Synthetic Route

Click to get detail synthetic route

Articles

Estradiol, but not testosterone, heightens cortisol-mediated negative feedback on pulsatile ACTH secretion and ACTH approximate entropy in unstressed older men and women.

Am. J. Physiol. Regul. Integr. Comp. Physiol. 306(9) , R627-35, (2014)

How sex steroids modulate glucocorticoid feedback on the hypothalamic-pituitary-corticotrope (HPC) unit is controversial in humans. We postulated that testosterone (T) in men and estradiol (E2) in wom...

Two different formulations with equivalent effect? Comparison of serum estradiol suppression with monthly goserelin and trimonthly leuprolide in breast cancer patients.

Med. Oncol. 30(1) , 354, (2013)

Data comparing the efficacy of monthly and trimonthly formulations of LHRH agonists are lacking. The aim of this study was to compare the effects of monthly goserelin and trimonthly leuprolide on estr...

Novasure as a mechanical endometrial preparation agent in large uteri.

JSLS 16(4) , 537-41, (2012)

We evaluated Novasure ablation as a mechanical endometrial preparation agent before Roller Ball endometrial ablation in lieu of GnRH agonists in large uteri.A retrospective chart review of 20 consecut...