A synthetic peptide GnRHR antagonist
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Cetrorelix (acetate)

Item No. 23910

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide, acetate
CAS Number
145672-81-7
Synonyms
  • SB-75
Molecular Formula
C70H92ClN17O14 • XC2H4O2
Formula Weight
1431.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly SolubleMethanol: Slightly Soluble
SMILES
O=C(C)N[C@@H](C(N[C@H](CC1=CC=C(Cl)C=C1)C(N[C@H](CC2=CC=CN=C2)C(N[C@@H](CO)C(N[C@@H](CC3=CC=C(O)C=C3)C(N[C@H](CCCNC(N)=O)C(N[C@@H](CC(C)C)C(N[C@@H](CCCNC(N)=N)C(N4C(C(N[C@H](C)C(N)=O)=O)CCC4)=O)=O)=O)=O)=O)=O)=O)=O)CC5=CC6=CC=CC=C6C=C5.OC(C)=O
InChi Code
InChI=1S/C70H92ClN17O14.C2H4O2/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44;1-2(3)4/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102);1H3,(H,3,4)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58?;/m1./s1
InChi Key
KFEFLCOCAHJBEA-PNZHXRLMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Cetrorelix is a synthetic peptide antagonist of the gonadotropin-releasing hormone receptor (GnRHR) with a Kd value of 0.2 nM for radioligand binding to murine LTK- cells expressing human GnRHR.1 It inhibits the activation of hGnRHR and a downstream luciferase reporter gene in murine LTK- cells by the GnRHR agonist [D-Trp6]GnRH (IC50 = 1.2 nM). In vivo, cetrorelix (60 μg per day) reduces tumor volume to 35% of control and decreases serum luteinizing hormone levels by 50% in a human epithelial ovarian cancer mouse xenograft model.2 Centrorelix (0.5 mg/kg) protects the primordial follicles (PMF) in mouse ovaries from damage induced by cyclophosphamide (Item No. 13849) with 65% to 86% PMF survival compared to 46% PMF survival with a saline control.3 Formulations containing cetrorelix have been used to prevent ovulation during in vitro fertilization.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beckers, T., Reiländer, H., and Hilgard, P. Characterization of gonadotropin-releasing hormone analogs based on a sensitive cellular luciferase reporter gene assay. Anal. Biochem. 251(1), 17-23 (1997).

    2. Yano, T., Pinski, J., Halmos, G., et al. Inhibition of growth of OV-1063 human epithelial ovarian cancer xenografts in nude mice by treatment with luteinizing hormone-releasing hormone antagonist SB-75. Proc. Natl. Acad. Sci. USA 91(15), 7090-7094 (1994).

    3. Meirow, D., Assad, G., Dor, J., et al. The GnRH antagonist cetrorelix reduces cyclophosphamide-induced ovarian follicular destruction in mice. Hum. Reprod. 19(6), 1294-1299 (2004).