120287-85-6

Basic information

• Product Name: Cetrorelix acetate
• Synonyms: AC-(D-ALA[3-(2-NAPHTHYL)])-[D-PHE(4-CL)]-(D-ALA[3-(3-PYRIDYL)])-SER-TYR-(D-CIT)-LEU-ARG-PRO-D-ALA-OH;CETRORELIX;CETRORELIX ACID;Cetrorelix acetate;CETRIZINEDIHYDROCHLORIDE;N-Acetyl-3-(2-naphthalenyl)-D-Ala-4-chloro-D-Phe-3-(3-pyridyl)-D-Ala-L-Ser-L-Tyr-N5-(aminocarbonyl)-D-Orn-L-Leu-L-Arg-L-Pro-D-Ala-NH2;Cetrorelixum;Cetrorelixum [inn-latin]
• CAS NO: 120287-85-6
• Molecular Formula: C₇₀H₉₂ClN₁₇O₁₄
• Molecular Weight: 1431.04
• EINECS: 1592732-453-0
• Product Categories: Peptide
• Mol File: 120287-85-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.42 g/cm³
• Refractive Index: 1.667
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Methanol (Very Slightly)
• PKA: 9.82±0.15(Predicted)
• CAS DataBase Reference: Cetrorelix acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Cetrorelix acetate(120287-85-6)
• EPA Substance Registry System: Cetrorelix acetate(120287-85-6)

Safety Data

• Hazardous Substances Data: 120287-85-6(Hazardous Substances Data)

Usage

Description

Cetrorelix was launched in Germany for the treatment of female infertility. It is a decapeptidic analog of luteinizing hormone-releasing hormone (LH-RH) bearing structural modifications in the crucial positions 1, 2, 3, 6 and 10 : [Ac-D-Nal1, D-4-CI Phe-2, D-Pal3, D-Cit6, D-Alal0]-GnRH. Cetrorelix is an extremely potent and long acting gonadotrophin releasing hormone (GnRH) antagonist and thus blocks gonadotrophins and sex steroid secretion immediately after administration. Moreover, it has a low histamine-releasing potency. Cetrorelix will be the first LH-RH antagonist approved worldwide. In several Phase III clinical trials, female patients receiving Cetrorelix had a successful controlled ovulation thus avoiding a premature LH-surge. Cetrorelix could be a first-choice in-vitro fertilization (IVF) treatment without the complications of current controlled ovarian hyperstimulation protocols. Cetrorelix is currently under clinical investigation for the treatment of diverse sex hormone dependent disorders such as benign prostate hypertrophy, breast, ovarian or prostate cancers and diverse gynaecological disorders.

Originator

Asta Medica (Germany)

Uses

Cetrorelix Acetate is an gonadotropin-releasing hormone antagonist and is used to treat hormone-sensitive cancers of the prostate and breast.

Definition

ChEBI: A synthetic ten-membered oligopeptide comprising N-acetyl-3-(naphthalen-2-yl)-D-alanyl, 4-chloro-D-phenylalanyl, 3-(pyridin-3-yl)-D-alanyl, L-seryl, L-t rosyl, N5-carbamoyl-D-ornithyl, L-leucyl, L-arginyl, L-prolyl, and D-alaninamide residues coupled in sequence. A gonadotrophin-releasing hormone (GnRH antagonist, it is used for treatment of infertility and of hormone-sensitive cancers of the prostate and breast.

Brand name

Cetrotide (Serono).

InChI:InChI=1/C70H92ClN17O14/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/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)/t40-,50-,51+,52+,53-,54-,55+,56-,57-,58?/m1/s1

Synthetic route

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + N-tert-butoxycarbonyl-L-leucine (13139-15-6) + Boc-(R)-Ala (3744-87-4, 7764-95-6, 15761-38-3) + Boc-Arg(Tos)-OH (13836-37-8) + Boc-DCit, Boc-Tyr(O-2Br-Cbz), Boc-Ser(OBzl), Boc-D3Pal, Boc-D4ClPhe, Boc-D2Nal, AcOH → cetrorelix (120287-85-6)

Conditions	Yield
Multistep reaction;

Ac-D-Nal-D-Cpa-D-Pal-Ser(tBu)-Tyr(tBu)-D-Cit-Leu-Arg(Pbf)-Pro-D-Ala-NH2 → cetrorelix (120287-85-6)

Conditions	Yield
With chlorotriisopropylsilane; ethane-1,2-dithiol; trifluoroacetic acid at 20℃; for 2h;

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 3744-87-4 Boc-(R)-Ala 
• 13836-37-8 Boc-Arg(Tos)-OH 

Relevant articles and documents

The effect of NMeTyr5 substitution in luteinizing hormone-releasing hormone antagonists.

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