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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 No: 10-101-07

CAS No: 57982-77-1 (net), 68630-75-1 (acetate)

Synonyms/Alias: Buserelin acetate;68630-75-1;Suprecur;Suprefact;Buserelin monoacetate;Buserelin (Acetate);Conceptal;Profact;HOE 766MP;HOE 766 MP;UNII-13U86G7YSP;NSC-725176;13U86G7YSP;HOE 766;HOE-766;Receptal;CHEBI:31324;DTXSID30218712;NSC 725176;BUSERELIN ACETATE (MART.);BUSERELIN ACETATE [MART.];Estomal;Acetate, Buserelin;Buserelin acetate [USAN:JAN];NSC725176;Suprefact Depot;Profact Depot;Suprefact Flakon;BSRL Acetate;Suprecur (TN);Hoe-766 MP;5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-tert-butyl-D-seryl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide monoacetate (salt);SCHEMBL167553;Buserelin acetate (JAN/USAN);BUSERELIN ACETATE [JAN];BUSERELIN ACETATE [USAN];CHEMBL2106198;DTXCID80141203;PYMDEDHDQYLBRT-DRIHCAFSSA-N;BUSERELIN MONOACETATE [MI];BUSERELIN ACETATE [WHO-DD];HY-13581A;MFCD01716229;AKOS032960353;AKOS040763961;AT41853;CS-5962;FP19363;DA-51475;TS-10343;NS00036669;Buserelin Acetate (57982-77-1 free base);D01831;D-Ser (Bu(t))(6) Pro(9) NEt LHRH Acetate;(Des-Gly10,D-Ser(tBu)6,Pro-NHEt9)-LHRH Acetate;Q27888490;(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(TERT-BUTOXY)-2-[(2S)-2-[(2S)-3-HYDROXY-2-[(2S)-2-[(2S)-3-(1H-IMIDAZOL-4-YL)-2-{[(2S)-5-OXOPYRROLIDIN-2-YL]FORMAMIDO}PROPANAMIDO]-3-(1H-INDOL-3-YL)PROPANAMIDO]PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANAMIDO]PROPANAMIDO]-4-METHYLPENTANAMIDO]-5-CARBAMIMIDAMIDOPENTANOYL]-N-ETHYLPYRROLIDINE-2-CARBOXAMIDE; ACETIC ACID;pGlu-His-Trp-Ser-Tyr-D-Ser(t-Bu)-Leu-Arg-Pro-NHEt acetate salt;Estomal;pGlu-His-Trp-Ser-Tyr-D-Ser(t-Bu)-Leu-Arg-Pro-NHEt acetate sal t;6-[O-(1,1-Dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)-1-9-luteinizing hormone-releasing factor monoacetate;

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

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC62H90N16O15
M.W/Mr.1299.5
SequenceOne Letter Code:XHWSYXLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-NHEt.CH3CO2H
Labeling TargetGonadotropin-releasing hormone (GNRH) receptor
ApplicationBuserelin 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.
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
ActivityAgonist
Biological ActivityBuserelin Acetate is a gonadotropin-releasing hormone agonist (GnRH agonist).
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
FunctionsLuteinizing hormone receptor activity
TargetGNRH Receptor
Source#Synthetic
Length9
Long-term Storage ConditionsSoluble in DMSO, not in water
Shipping ConditionShipped 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 ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismHuman
InChIInChI=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 KeyPYMDEDHDQYLBRT-DRIHCAFSSA-N
Canonical SMILESCCNC(=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 SMILESCCNC(=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
BoilingPointN/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 PointN/A

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3. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

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