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Cetrorelix Acetate

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Cetrorelix Acetate is the acetate salt of cetrorelix, which is a potent and synthetic peptide antagonist of gonadotropin-releasing hormone (GnRH) receptor antagonist with IC50 value of 1.21 nM. It binds to radioligand murine LTK- cells with Kd value of 0.2 nM. It inhibits the activation of hGnRHR and a downstream luciferase reporter gene in murine LTK- cells by the GnRHR agonist [D-Trp6]GnRH. It suppresses production of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the pituitary gland. It prevents ovulation during in vitro fertilization. It causes prepubertal reduction in bone density, bone strength and bone modeling. It was used as a therapeutic agent for the treatment of blood cancers such as multiple myeloma (MM). It is also used to treat hormone-sensitive cancers of the breast and prostate. It also has antidepressant and anxiolytic activity in vivo.

Category

Peptide Inhibitors

Catalog number

BAT-010247

CAS number

145672-81-7

Molecular Formula

C70H92ClN17O14.xC2H4O2

Molecular Weight

1431.06 (free base)

Specification
Reference Reading

IUPAC Name

acetic acid; (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-(carbamoylamino)pentanoyl]amino]-4-methylpentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

Synonyms

D-Alaninamide, 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-, acetate (1:x); D-Alaninamide, 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-, acetate (salt); Cetrotid; Cetrotide; D 20761; NS 75A; Ovurelix; SB 075 acetate; Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Tyr-D-Cit-Leu-Arg-Pro-D-Ala-NH2.CH3CO2H

Related CAS

120287-85-6 (free base) 130143-01-0 (diacetate salt) 1631741-31-5 (monoacetate salt)

Appearance

White to Off-white Solid

Purity

>98%

Melting Point

>259°C (dec.)

Sequence

Ac-D-2Nal-D-F(4-Cl)-D-3Pal-SY-D-Cit-LRP-D-A-NH2.CH3CO2H

Storage

Store at -20°C

Solubility

Soluble in water

InChI

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-ANRVCLKPSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CCCNC(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CN=CC=C3)NC(=O)C(CC4=CC=C(C=C4)Cl)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)NC(=O)C.CC(=O)O

1.Expression of cytochrome P450 2C and 3A in female rat liver after long-term administration of gonadoliberin analogs.

Skowronek R1, Czekaj P2, Suszka-Świtek A3, Czech E3, Wiaderkiewicz A3, Plewka D1, Bryzek A1. Int J Occup Med Environ Health. 2016;29(2):293-314. doi: 10.13075/ijomeh.1896.00528.

OBJECTIVES: Gonadoliberin (GnRH) analogs may be expected to indirectly modify growth hormone (GH) total concentration and its 24-h secretion profile. As a consequence, changes in the levels of GH may modify the mechanism of sex-dependent cytochromes P450 (CYP450) synthesis, including the expression of transcriptional factors. The aim of the study has been to evaluate the effect of long-term administration of a low dose of GnRH analogs on hepatic expression of CYP2C and CYP3A isoforms, and the transcription factors: pregnane X receptor (PXR), hepatocyte nuclear factor 4α (HNF4α), HNF6 and signal transducers and activators of transcription 5b (STAT5b).

2.GnRH Agonist Triggering Modulates PEDF to VEGF Ratio Inversely to hCG in Granulosa Cells.

Miller I1, Chuderland D1, Ron-El R1, Shalgi R1, Ben-Ami I1. J Clin Endocrinol Metab. 2015 Nov;100(11):E1428-36. doi: 10.1210/jc.2015-2312. Epub 2015 Aug 26.

CONTEXT: GnRH agonist (GnRH-a) triggering is associated with a reduced risk of ovarian hyperstimulation syndrome (OHSS) compared with human chorionic gonadotropin (hCG) in assisted reproduction technology cycles. We have shown that ovarian pigment epithelium derived factor (PEDF), a potent antiangiogenic factor, counteracts vascular endothelial growth factor (VEGF) expression and that OHSS is correlated with hCG-induced impaired PEDF to VEGF ratio.

3.Triptorelin and cetrorelix induce immune responses and affect uterine development and expressions of genes and proteins of ESR1, LHR, and FSHR of mice.

Wei S1,2, Guo H3, Gong Z4, Zhang F2, Ma Z1. Immunopharmacol Immunotoxicol. 2016 Apr 14:1-8. [Epub ahead of print]

CONTEXT: GnRH immunity can reduce the expression of pituitary GnRH levels, and cause the changes in reproductive behaviors. It is unclear whether triptorelin (TRI) and cetrorelix (CET) immunity influences uterine development and expression of follicle-stimulating hormone receptor (FSHR), luteinizing hormone receptor (LHR), and estradiol receptor 1 (ERS1) in the uterus.