Buserelin Acetate

Buserelin Acetate is an agonist of gonadotropin-releasing hormone receptor(GnRHR). Buserelin is a synthetic luteinizing hormone–releasing hormone (LHRH) analog.

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CAT#	10-101-07
CAS	57982-77-1 (net), 68630-75-1 (acetate)
Background	Buserelin is a synthetic analog of gonadotropin-releasing hormone (GnRH). It binds to and activates pituitary gonadotropin releasing hormone (GnRH) receptors. Prolonged administration of buserelin results in sustained inhibition of gonadotropin production, suppression of testicular and ovarian steroidogenesis, and reduced levels of circulating gonadotropin and gonadal steroids. Buserelin is more potent that GnRH.
Synonyms/Alias	(Des-Gly10,D-Ser(tBu)6,Pro-NHEt9)-LHRH; Bigonist; HOE-766; HOE766; HOE 766; Profact; Receptal; Suprecur; Suprefact; Tiloryth; Hoe-766 MP; Hoe766 MP; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-tert-butyl-D-seryl-L-leucyl-L-arginyl-L-proline ethylamide acetic acid
Chemical Name	acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
M.F/Formula	C62H90N16O15
M.W/Mr.	1299.48
Sequence	One Letter Code: XHWSYXLRP Three Letter Code: H-Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-NHEt.CH3CO2H
Labeling Target	Gonadotropin-releasing hormone (GNRH) receptor
Application	Buserelin may be used in the treatment of hormone-responsive cancers such as prostate cancer or breast cancer, estrogen-dependent conditions (such as endometriosis or uterine fibroids), and in assisted reproduction.
Appearance	Solid powder
Purity	>98% (or refer to the Certificate of Analysis)
Activity	Agonist
Biological Activity	Buserelin Acetate is a gonadotropin-releasing hormone agonist (GnRH agonist).
Areas of Interest	Cardiovascular System & Diseases Pituitary & Hypothalamic Hormones
Functions	Luteinizing hormone receptor activity
Target	GNRH Receptor

CAT#	Product Name	M.W	Molecular Formula	Inquiry
10-101-10	Deslorelin Acetate	1342.5	C66H87N17O14	Inquiry
10-101-17	Fertirelin Acetate	1166.56	C55H74N16O13	Inquiry
10-101-19	Gonadorelin Acetate	1242.36	C55H75N17O13.C2H4O2	Inquiry
10-101-61	Ganirelix	1570.4	C80H113ClN18O13	Inquiry

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Source#	Synthetic
Length	9
Solubility	Soluble in DMSO, not in water
Shipping Condition	Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions	Dry, dark and at 0 - 4 °C
Long-term Storage Conditions	-20 °C
Organism	Human
InChI	InChI=1S/C60H86N16O13.C2H4O2/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40;1-2(3)4/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65);1H3,(H,3,4)/t40-,41-,42-,43-,44-,45-,46-,47+,48-;/m0./s1
InChI Key	PYMDEDHDQYLBRT-DRIHCAFSSA-N
Canonical SMILES	CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(COC(C)(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
Isomeric SMILES	CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O
BoilingPoint	N/A
ShelfLife	>2 years if stored properly
References	Buserelin acetate appears to cause a progressive blockade of gonadotrophin secretion when administered to female rats for four, eight or 12 days, and an important rebound effect, with accentuated estrogen release already apparent in the first estrous cycle following treatment. Trindade C R, Camargos A F, Pereira F E L. The effect of buserelin acetate on the uterus of adult rats: morphological aspects[J]. Clin Exp Obstet Gynecol, 2008, 3: 198-201. A comparison has been established retrospectively between clomiphene citrate-human menopausal gonadotropin (CC-hMG) and buserelin acetate-hMG treatments in in vitro fertilization trials performed over a 3-year period. The analysis of 466 CC-hMG and 319 buserelin acetate-hMG trials shows that buserelin acetate-hMG stimulation generates a greater ovarian response resulting in higher numbers of oocytes being retrieved (6.2 + 3.8 versus 9.3 + 5.2) and fertilized (2.8 + 2.7 versus 4.3 + 3.8). More embryos are thus obtained, allowing a wider choice for intrauterine replacement and cryopreservation. Mean embryonic vitality scores do not differ (4.33 + 1.51 versus 4.44 + 1.54), implying that the embryonic quality remains similar in both treatments. A premature demise of the corpus luteum occurs in a large proportion of buserelin acetate-hMG cycles. However, when suppletive progesterone treatment is given, there is a trend toward a better implantation rate per embryo, and a significantly higher ongoing pregnancy rate is observed in relation to buserelin acetate-hMG treatment (20%) as compared with CC-hMG cycles (14%). Lejeune B, Barlow P, Puissant F, et al. Use of buserelin acetate in an in vitro fertilization program: a comparison with classical clomiphene citrate-human menopausal gonadotropin treatment[J]. Fertility and sterility, 1990, 54(3): 475-481.
Melting Point	N/A