Histrelin Chemical Properties

alpha 

D20 -33.9° (c = 1 in acetic acid)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

powder

pka

9.82±0.15(Predicted)

Sequence

{Pyr}-His-Trp-Ser-Tyr-D-His(Bzl)-Leu-Arg-Pro-NHEt

Stability:

Hygroscopic

InChIKey

HHXHVIJIIXKSOE-HMGGNIPDNA-N

Safety Information

Hazard Codes 

T

Risk Statements 

60

Safety Statements 

53-22-36/37/39-45

WGK Germany 

3

RTECS 

OK6370800

HS Code 

3504009000

Hazardous Substances Data

76712-82-8(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Histrelin Usage And Synthesis

Description

Histrelin, a synthetic gonadotrophin-releasing hormone (GnRH) agonist, was introduced as a first-line therapy for the treatment of central precocious puberty. When administered over a prolonged period, it suppresses the release of gonadotrophin, inhibits ovarian and testicular steroidogenesis, and prevents sexual maturation. Superior to the traditional therapy with progestational agents, histrelin appears to have decelerating effects on skeletal maturation allowing more statural growth and significantly increased final adult height. Histrelin has also been used to treat other disorders including endometriosis, polycystic ovarian disease, uterine leiomyomas, severe premenstrual syndrome and to prevent acute intermittent porphyria.

Chemical Properties

[α]_D²⁰-33.9°(C=1, acetic acid).

Originator

Johnson & Johnson (U.S.A.)

Uses

LHRH agonist.

Uses

[des-Gly¹⁰, D-His(Bzl)⁶]-LH-RH ethylamide has been used:

• for inducing Batrachoseps gravid females to oviposit
• for comparing the effect of LHRH (luteinizing hormone-releasing hormone) agonists and dopamine antagonists in Lithobates pipiens
• for inducing oviposition in females of Taricha granulosa and Ensatina eschscoltzii
• to induce spawning in Spea hammondii adults

Definition

ChEBI: An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, 1-benzyl-D-histidyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotro in-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the diacetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.

brand name

Supprelin (Roberts Pharmaceutical).

Biochem/physiol Actions

Glp-His-Trp-Ser-Tyr-His(Bzl)-Leu-Arg-Pro-NHEt ([des-Gly10, D-His(Bzl)6]-LH-RH) is a GnRH (gonadotropin-releasing hormone) agonist, histerelin. 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. Histerelin is used for the treatment of central precocious puberty in children. It inhibits actions of sex steroids on the male and female reproductive organs.

Description

Histrelin has a molecular formula of C66H86N18O12, a.a. sequence of Pyr-His-Trp-Ser-Tyr-D-His(Bzl)-Leu-Arg-Pro-NHEt and having a Mw of 1323.32 Dalton.

Background

Histrelin is a hormone similar to one normally released from the hypothalamus gland in the brain. Histrelin works by decreasing the amount of estrogen and testosterone in the blood. Suppressing estrogen can cause thinning of the bones or slowing of their growth. Histrelin acetate is a potent LHRH agonist which stimulates LH and FSH release and inhibits the actions of sex steroids on the male and female reproductive tracts. After a transient increase, continuous administration results in down regulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis. Histrelin potency in vivo and in vitro is similar to that of the D-Trp6-containing analog. Especially because of its high water solubility and greater lipophilic character, it appears promising for clinical application.

Histrelin(76712-82-8)Related Product Information

• Benzyl acetate
• Butyl acetate
• Cellulose acetate
• Ammonium acetate
• Goserelin acetate
• Vinyl acetate
• Sodium acetate
• Taltirelin
• Alarelin Acetate
• Ethyl acetate
• Magnesium acetate
• ACETATE
• LHRH (1-6) AMIDE
• FERTIRELIN
• Histamine
• L-Prolinamide
• (D-LEU7)-HISTRELIN
• Fertirelin acetate