Deslorelin Chemical Properties

Melting point:

>189oC

alpha 

D24 -61° (c = 0.37 in 0.1M acetic acid)

Density 

1.48±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

Acetic acid (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.82±0.15(Predicted)

color 

White to Off-White

Sequence

Pyr-His-Trp-Ser-Tyr-DTrp-Leu-Arg-Pro-NHEt

InChI

InChI=1/C64H83N17O12/c1-4-68-62(92)53-16-10-24-81(53)63(93)46(15-9-23-69-64(65)66)74-56(86)47(25-35(2)3)75-58(88)49(27-37-30-70-43-13-7-5-11-41(37)43)77-57(87)48(26-36-17-19-40(83)20-18-36)76-61(91)52(33-82)80-59(89)50(28-38-31-71-44-14-8-6-12-42(38)44)78-60(90)51(29-39-32-67-34-72-39)79-55(85)45-21-22-54(84)73-45/h5-8,11-14,17-20,30-32,34-35,45-53,70-71,82-83H,4,9-10,15-16,21-29,33H2,1-3H3,(H,67,72)(H,68,92)(H,73,84)(H,74,86)(H,75,88)(H,76,91)(H,77,87)(H,78,90)(H,79,85)(H,80,89)(H4,65,66,69)/t45-,46-,47-,48-,49+,50-,51-,52-,53-/s3

InChIKey

GJKXGJCSJWBJEZ-QCOVUDKBNA-N

SMILES

C(C1=CNC2C=CC=CC1=2)[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(N1CCC[C@H]1C(=O)NCC)=O)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](NC([C@@H]1CCC(=O)N1)=O)CC1N=CNC=1)CC1=CNC2C=CC=CC1=2)CC1C=CC(O)=CC=1 |&1:10,14,22,35,45,49,55,59,62,r|

CAS DataBase Reference

57773-65-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

60

Safety Statements 

53-22-36/37/39-45

WGK Germany 

3

RTECS 

OK6755000

HS Code 

3504009000

MSDS

• Language:English Provider:SigmaAldrich

Deslorelin Usage And Synthesis

Description

Deslorelin is an injectable gonadotropin releasing hormone super-agonist also known as an LHRH agonist. It stops the production of sex hormones with potential antineoplastic activity. Deslorelin binds to and activates pituitary gonadotropin releasing hormone (GnRH) receptors. Continuous, prolonged administration of goserelin 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.

Chemical Properties

White powder, tens of times more biologically active than natural LH-RH, is synthesized by solid-phase or liquid-phase synthesis method using the corresponding protected amino acid monomers as raw materials.

Uses

Induction of ovulation in estrous mares Reproduction control in dogs

Definition

ChEBI: Deslorelin is an oligopeptide.

brand name

Somagard [as acetate] (Roberts Pharmaceutical).

General Description

Deslorelin (brand names: SucroMate, Suprelorin F, Suprelorin 12, Suprelorin-6) is a synthetic hormone used to induce ovulation and manage artificial insemination programs in horses, modulate reproduction in dogs, or manage adrenal disease in ferrets. In the U.S., deslorelin is only FDA approved for use in mares and ferrets, and 'off label' or 'extra-label' use is prohibited at this time.

Side effects

The most common side effects include swelling, sensitivity, and redness or warmth at the injection site. Rarely reported side effects in dogs include prolonged estrus and uterine infections.

Veterinary Drugs and Treatments

Deslorelin is approved for inducing ovulation in estrual mares. There is also interest in developing dosages and dosage forms as a long-term, reversible contraceptive in a variety of animal species, as a treatment for prostatic disease in male dogs, and incontinence in ovariectomized dogs. At the time of writing, deslorelin in not available in the USA, but is marketed in Canada.
In humans, deslorelin has been investigated for treating children with precocious puberty, and in adults for prostate carcinoma, dysmenorrhea, fibroids, and endometriosis.

References

[1] CLAIRE GROSSET. Contraceptive effect and potential side-effects of deslorelin acetate implants in rats (Rattus norvegicus): preliminary observations.[J]. Canadian journal of veterinary research = Revue canadienne de recherche veterinaire, 2012, 76 3: 209-214.
[2] STEFANO ROMAGNOLI. Chronic Use of Deslorelin in Dogs: Six Cases (2005-2022).[J]. Animals, 2023, 13 2. DOI:10.3390/ani13020265.
[3] K E OERTER. Adult height in precocious puberty after long-term treatment with deslorelin.[J]. Journal of Clinical Endocrinology & Metabolism, 1991, 73 6: 1235-1240. DOI:10.1210/jcem-73-6-1235.

Deslorelin(57773-65-6)Related Product Information

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