Name | Buserelin |
Synonyms | Buserilin Buserelin 261-061-9 BUSERELIN BUSERELIN PH. EUR. (d-ser(tbu)(sup6)-ea(sup10))-lhrh (d-ser(bu(supt)(sup6)))-lh-rh(1-9)nonapeptide-ethylamide (d-ser(tbu)(sup6)-ea(sup10))-luteinizinghormone-releasinghormon (d-ser(tbu)(sup6)-ea(sup10))-luteinizinghormone-releasinghormone 1-9-Luteinizing hormone-releasing factor (swine), 6-[O-(1,1-dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)- 5-oxoprolylhistidyltryptophylseryltyrosyl-O-tert-butylserylleucyl-N~5~-(diaminomethylidene)ornithyl-N-ethylprolinamide 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-tert-butyl-D-seryl-L-leucyl-N~5~-(diaminomethylidene)-L-ornithyl-N-ethyl-L-prolinamide |
CAS | 57982-77-1 |
EINECS | 261-061-9 |
InChI | InChI=1/C60H86N16O13/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/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)/t40-,41-,42-,43-,44-,45-,46-,47+,48-/m0/s1 |
Molecular Formula | C60H86N16O13 |
Molar Mass | 1239.42 |
Density | 1.0711 (rough estimate) |
Boling Point | 845.19°C (rough estimate) |
Specific Rotation(α) | D20 -40.4° (c = 1 in dimethylacetamide) |
Solubility | Sparingly soluble in water and in dilute acids. |
pKa | 9.82±0.15(Predicted) |
Refractive Index | 1.6200 (estimate) |
Introduction | Buserelin (Buserelin) was developed by West Germany (Hoechst AG, now incorporated into Sanofi) and was first listed in West Germany in 1984. Buserelin is a polypeptide drug modified according to gonadotropin-releasing hormone (GnRH). |
mechanism of action | buserelin can increase the secretion of luteinizing hormone (Luteinizing Hormone,LH), follicle stimulating hormone (Follicle Stimulating Hormone,FSH) and sex hormone, and its effect on promoting the release of LH and FSH is 19 times and 26 times that of natural gonadotropin releasing hormone respectively, long-term use causes down-regulation of pituitary function, resulting in decreased secretion of LH and FSH. |
adverse reactions | may include facial fever, nausea, vomiting, headache, rash, weakness, bone pain, decreased libido, dysuria, etc. |
clinical application | buserelin is a GnRH analog. Early use can prompt I. H, FSH and sex hormone secretion increased, after 1~2 weeks began to produce the opposite effect, sex hormone secretion can be reduced to the level of castration. Clinically, it is mainly used for prostate cancer, breast cancer, etc. At the beginning, subcutaneous injection (flutamide is used in combination with men), and nasal spray is used for maintenance treatment. |
synthetic route | adopts the polypeptide synthesis method combining solid phase and liquid phase, adopts 2-chloro-triphenyl chloride resin (2-CTC resin) that is unstable to acid, and uses N,N-diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBT) as the condensing agent, gradually condensation to obtain Buserelin intermediate peptide resin, cleave with low concentration of acid to obtain fully protected Buserelin intermediate, and then add ethylamine in the liquid phase to realize N - end modification, and then catalytically hydrogenate to remove the nitro of arginine side chain and the benzyl of tyrosine side chain, select the appropriate concentration of acid to remove the trityl protecting group and retain the tert-butyl of D-serine to obtain crude peptide, finally, after semi-preparation and purification, high-purity Buserelin was obtained by freeze-drying. |