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Cetrorelix diacetate

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

Cetrorelix is a gonadotropin-releasing hormone (GnRH) antagonist. Under the trade name Cetrotide, It is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian stimulation.

Category

Peptide Inhibitors

Catalog number

BAT-010074

CAS number

130143-01-0

Molecular Formula

C74H100ClN17O18

Molecular Weight

1551.16

Size	Price	Stock	Quantity
50 mg	$499	In stock

Specification
Reference Reading

IUPAC Name

(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;acetic acid

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-, diacetate (salt); Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Tyr-D-Cit-Leu-Arg-Pro-D-Ala-NH2.CH3CO2H; N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-L-tyrosyl-D-citrullyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide diacetate salt

Related CAS

120287-85-6 (free base) 145672-81-7 (x-acetate salt) 1631741-31-5 (monoacetate salt)

Appearance

White to Off-white Powder

Purity

≥95%

Boiling Point

1768.4°C at 760 mmHg

Sequence

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

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C70H92ClN17O14.2C2H4O2/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;2*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);2*1H3,(H,3,4)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;;/m1../s1

InChI Key

DTPVYWHLQLAXFT-SMCUOGPFSA-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.CC(=O)O

1.Rapid Anti-Inflammatory Effects of Gonadotropin-Releasing Hormone Antagonism in Rheumatoid Arthritis Patients with High Gonadotropin Levels in the AGRA Trial.

Kåss A1, Hollan I2, Fagerland MW3, Gulseth HC4, Torjesen PA5, Førre ØT6. PLoS One. 2015 Oct 13;10(10):e0139439. doi: 10.1371/journal.pone.0139439. eCollection 2015.

OBJECTIVES: Gonadotropin-releasing hormone (GnRH) and pituitary gonadotropins, which appear to be proinflammatory, undergo profound secretory changes during events associated with rheumatoid arthritis (RA) onset, flares, or improvement e.g. menopausal transition, postpartum, or pregnancy. Potential anti-inflammatory effects of GnRH-antagonists may be most pronounced in patients with high GnRH and gonadotropin levels. Therefore, we investigated the efficacy and safety of a GnRH-antagonist, cetrorelix, in RA patients with high gonadotropin levels.

2.c-Jun NH2-terminal kinase inhibitor bentamapimod reduces induced endometriosis in baboons: an assessor-blind placebo-controlled randomized study.

Hussein M1, Chai DC2, Kyama CM2, Mwenda JM2, Palmer SS3, Gotteland JP4, D'Hooghe TM5. Fertil Steril. 2016 Mar;105(3):815-824.e5. doi: 10.1016/j.fertnstert.2015.11.022. Epub 2015 Dec 2.

OBJECTIVE: To test the hypothesis that the c-Jun NH2-terminal kinase (JNK) inhibitor (JNKI) bentamapimod (AS602801/PGL5001) can reduce induced endometriosis in baboons.

3.Intracellular mechanisms involved in copper-gonadotropin-releasing hormone (Cu-GnRH) complex-induced cAMP/PKA signaling in female rat anterior pituitary cells in vitro.

Gajewska A1, Zielinska-Gorska M2, Wolinska-Witort E3, Siawrys G4, Baran M2, Kotarba G2, Biernacka K2. Brain Res Bull. 2016 Jan;120:75-82. doi: 10.1016/j.brainresbull.2015.11.002. Epub 2015 Nov 10.

The copper-gonadotropin-releasing hormone molecule (Cu-GnRH) is a GnRH analog, which preserves its amino acid sequence, but which contains a Cu(2+) ion stably bound to the nitrogen atoms including that of the imidazole ring of Histidine(2). A previous report indicated that Cu-GnRH was able to activate cAMP/PKA signaling in anterior pituitary cells in vitro, but raised the question of which intracellular mechanism(s) mediated the Cu-GnRH-induced cAMP synthesis in gonadotropes. To investigate this mechanism, in the present study, female rat anterior pituitary cells in vitro were pretreated with 0.1μM antide, a GnRH antagonist; 0.1μM cetrorelix, a GnRH receptor antagonist; 0.1μM PACAP6-38, a PAC-1 receptor antagonist; 2μM GF109203X, a protein kinase C inhibitor; 50mM PMA, a protein kinase C activator; the protein kinase A inhibitors H89 (30μM) and KT5720 (60nM); factors affecting intracellular calcium activity: 2.5mM EGTA; 2μM thapsigargin; 5μM A23187, a Ca(2+) ionophore; or 10μg/ml cycloheximide, a protein synthesis inhibitor.

4.Follicular fluid levels of vascular endothelial growth factor and its receptors and pregnancy outcome of women participating in intracytoplasmic sperm injection cycles.

Ntala V, Asimakopoulos B, Veletza S, Alexandris E, Karachaiou V, Nikolettos N. Clin Exp Obstet Gynecol. 2015;42(4):437-41.

PURPOSE: The intracytoplasmic sperm injection (ICSI) outcome is depended mainly on oocyte quality. Cytokines and their receptors play a critical role in oocyte maturation, fertilization, and embryo implantation. The purpose of the study was to study the levels of vascular endothelial growth factors (VEGFA, VEGFR1, VEGFA) in follicular fluids (FF) women participating in ICSI-in vitro fertilization (IVF) cycles in relation to cycle's outcome.