SML2856

Sigma-Aldrich

Degarelix acetate

≥98% (HPLC)

Synonym(s):
FE 200486, ASP3550 acetate, FE200486, N-Acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-[[[(4S)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-L-phenylalanyl-4-[(aminocarbonyl)amino]-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-D-alaninamide acetate salt, Ac-D2Nal-D4Cpa-D3Pal-Ser-4Aph(L-hydroorotyl)-D4Aph(carbamoyl)-Leu-ILys-Pro-DAla-NH2 acetate salt
Empirical Formula (Hill Notation):
C82H103ClN18O16 · xC2H4O2
CAS Number:
Molecular Weight:
1632.26 (free base basis)

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

storage temp.

−20°C

Inchi Code

1S/C82H103ClN18O16.CH4/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52;/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117);1H4/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+;/m1./s1

InChI key

XTTPORRNVGBDFF-KYMMNHPFSA-N

Biochem/physiol Actions

Degarelix acetate (FE200486) is a gonadotropin-/luteinizing hormone-/follicle-stimulating hormone-releasing hormone (GnRH, LHRH, FSH-RH) receptor antagonist that inhibits plasma testosterone for more than 40 days following a single s.c. dosage of 2 mg/kg in rats and monkeys, showing longer in vivo duration than abarelix, ganirelix, cetrorelix, azaline B or D-Trp6-LHRH, and exhibiting only weak histamine-releasing potency in isolated rat mast cells. Bi-weekly s.c. dosing (2 mg/kg) is efficacious in suppressing the growth of human prostate cancer PAC120 xenograft-derived tumors in mice in vivo.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

G Jiang et al.
Journal of medicinal chemistry, 44(3), 453-467 (2001-07-21)
A series of antagonists of gonadotropin-releasing hormone (GnRH) of the general formula Ac-D2Nal-D4Cpa-D3Pal-Ser-4Aph/4Amf(P)-D4Aph/D4Amf(Q)-Leu-ILys-Pro-DAla-NH2 was synthesized, characterized, and screened for duration of inhibition of luteinizing hormone release in a castrated male rat assay. Selected analogues were tested in a reporter gene...
Pierre Broqua et al.
The Journal of pharmacology and experimental therapeutics, 301(1), 95-102 (2002-03-22)
We describe the pharmacological profile in rats and monkeys of degarelix (FE200486), a member of a new class of long-acting gonadotropin-releasing hormone (GnRH) antagonists. At single subcutaneous injections of 0.3 to 10 microg/kg in rats, degarelix produced a dose-dependent suppression...
Wolfgang Koechling et al.
British journal of clinical pharmacology, 70(4), 580-587 (2010-09-16)
Early studies on gonadotrophin-releasing hormone (GnRH) antagonists pointed out histamine-mediated anaphylactic reactions as a potential adverse effect of these drug candidates. In this study we have compared the histamine-releasing potential of four approved and marketed antagonists, degarelix, cetrorelix, abarelix and...

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