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 acetate, also known as Cetrotide, is a synthetic decapeptide analog of luteinizing hormone-releasing hormone (LH-RH) with structural modifications in positions 1, 2, 3, 6, and 10. It is a potent and long-acting gonadotrophin-releasing hormone (GnRH) antagonist that blocks gonadotrophins and sex steroid secretion immediately after administration. Cetrorelix acetate has a low histamine-releasing potency and is the first LH-RH antagonist approved worldwide.

Uses

Used in Oncology:
Cetrorelix acetate is used as a hormone-sensitive cancer treatment for prostate and breast cancers. It functions as a GnRH antagonist, helping to control the growth of hormone-sensitive tumors.
Used in Infertility Treatment:
Cetrorelix acetate is used as a controlled ovulation agent in female infertility treatment. It helps in avoiding premature LH-surge, thus improving the success rate of in-vitro fertilization (IVF) treatments without complications associated with controlled ovarian hyperstimulation protocols.
Used in Gynecological Disorders:
Cetrorelix acetate is currently under clinical investigation for the treatment of various sex hormone-dependent disorders, including benign prostate hypertrophy, breast, ovarian, or prostate cancers, and diverse gynecological disorders. Its role as a GnRH antagonist makes it a potential candidate for managing these conditions.

Originator

Asta Medica (Germany)

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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