Cetrorelix

Title: Cetrorelix
CAS Registry Number: 120287-85-6
CAS 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
Additional Names: Ac-D-Nal(2)1-D-Phe(4Cl)2-D-Pal(3)3-D-Cit6-D-Ala10-LH-RH
Manufacturers' Codes: SB-75
Molecular Formula: C70H92ClN17O14
Molecular Weight: 1431.04
Percent Composition: C 58.75%, H 6.48%, Cl 2.48%, N 16.64%, O 15.65%
Literature References: Decapeptide LH-RH antagonist. Prepn: A. V. Schally, S. Bajusz, EP 299402 (1989 to Asta); eidem, US 4800191 (1989); S. Bajusz et al., Int. J. Pept. Protein Res. 32, 425 (1988). Structural study: A. Müller et al., ibid. 43, 264 (1994). HPLC determn in plasma: H. H. Raffel et al., J. Chromatogr. B 653, 102 (1994). Pharmacology: T. Reissmann et al., Eur. J. Cancer 32A, 1574 (1996). Clinical evaluation in prostatic cancer: D. Gonzalez-Barcena et al., Urology 45, 275 (1995); in assisted fertilization: C. Albano et al., Fertil. Steril. 67, 917 (1997).
Derivative Type: Acetate
CAS Registry Number: 145672-81-7
Manufacturers' Codes: D-20761
Trademarks: Cetrotide (Serono)
Properties: Sol in water.
Therap-Cat: Antineoplastic (hormonal). In treatment of infertility.
Keywords: Antineoplastic (Hormonal); LH-RH Analogs; LH-RH Antagonist.
Cetuximab Cetyl Lactate Cetyl Palmitate Cetyldimethylethylammonium Bromide Cetylpyridinium Chloride

Cetrorelix
Cetrorelix.svg
Cetrorelix ball-and-stick.png
Systematic (IUPAC) name
Acetyl-D-3-(2´-naphtyl)-alanine- D-4-chlorophenylalanine-D-3-(3´-pyridyl)- alanine-L-serine-L-tyrosine-D-citrulline-L- leucine-L-arginine-L-proline-D- alanine-amide
Clinical data
Trade names Cetrotide
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. X (US)
Legal status -only (US)
Routes Subcutaneous injection
Pharmacokinetic data
Bioavailability 85%
Protein binding 86%
Half-life 62.8 hours / 3mg single dose; 5 hours / 0.25 mg single dose; 20.6 hours / 0.25mg multiple doses
Excretion feces (5% to 10% as unchanged drug and metabolites); urine (2% to 4% as unchanged drug)
Identifiers
CAS number 120287-85-6 YesY
ATC code H01CC02
PubChem CID 16130924
DrugBank DB00050
ChemSpider 10482082 YesY
UNII OON1HFZ4BA YesY
KEGG D07665 YesY
ChEBI CHEBI:59224 YesY
ChEMBL CHEMBL1200490 N
Chemical data
Formula C70H92ClN17O14 
Mol. mass 1431.06 g/mol
 N (what is this?)  (verify)

Cetrorelix acetate (trade name Cetrotide) is an injectable gonadotropin-releasing hormone antagonist (GnRH antagonist). A synthetic decapeptide, it is used to treat hormone-sensitive cancers of the prostate and breast (in pre-/perimenopausal women) and some benign gynaecological disorders (endometriosis, uterine fibroids and endometrial thinning). In addition, cetrorelix is used in assisted reproduction to inhibit premature luteinizing hormone surges. The drug works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of LH and FSH. It is administered as either multiple 0.25 mg daily subcutaneous injections or as a single-dose 3 mg subcutaneous injection. The duration of the 3 mg single dose is four days; if hCG is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.