cetrorelix

Also known as SB-075

Chemical data

Formula: C70H92ClN17O14
Molecular weight: 1431 g/mol
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
SMILES: C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCNC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(=O)C
InChIKey: SBNPWPIBESPSIF-MHWMIDJBSA-N
XLogP: 1.9
Polar surface area: 498 Å²
H-bond donors: 16
H-bond acceptors: 16
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 1999
Admin. routes: parenteral
Indications: benign prostatic hyperplasia, infertility, rheumatoid arthritis, endometriosis

via ChEMBL · EBI

Research

791 papers

Cetrorelix in the treatment of female infertility and endometriosis.Expert opinion on pharmacotherapy · 2006
GnRH antagonist, cetrorelix, for pituitary suppression in modern, patient-friendly assisted reproductive technology.Expert opinion on drug metabolism & toxicology · 2009
The LHRH antagonist cetrorelix: a review.Human reproduction update · 2000
Effect of Cetrorelix administration on ovarian stimulation in aged mice.Experimental animals · 2021
Effects of Cetrorelix on Ovary and Endometrium Prior to Anti-PD-L1 Antibody in Murine Model.Tissue engineering and regenerative medicine · 2024

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 1429.669818
Has use: medication

Show 6 more facts

chemical formula: C₇₀H₉₂ClN₁₇O₁₄
isomeric SMILES: C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCNC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(=O)C
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
World Health Organisation international non-proprietary name: cetrorelix
defined daily dose: 0.25
Commons category: Cetrorelix

Sources (3)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Medical uses
Contraindications
Research
References
External links

Cetrorelix (, ), or cetrorelix acetate (, ), sold under the brand name Cetrotide, is an injectable gonadotropin-releasing hormone (GnRH) antagonist. A synthetic decapeptide, it 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 luteinizing hormone (LH) and follicle-stimulating hormone (FSH). In addition, cetrorelix can be 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). 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 human chorionic gonadotropin (hCG) is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.

It is available as a generic medication.

Excerpted from Wikipedia’s “cetrorelix” article, available under the CC BY-SA 4.0 licence.

Available in 16 languages

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