abarelix

Also known as Plenaxis®, PPI 149, R 3827

Abarelix, sold under the brand name Plenaxis, is an injectable gonadotropin-releasing hormone antagonist (GnRH antagonist) which is marketed in Germany and the Netherlands. It is primarily used in oncology to reduce the amount of testosterone made in patients with advanced symptomatic prostate cancer for which no other treatment options are available.

Chemical data

Formula: C72H95ClN14O14
Molecular weight: 1416.1 g/mol
IUPAC name: (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]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]butanediamide
SMILES: C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)N(C)C(=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: AIWRTTMUVOZGPW-HSPKUQOVSA-N
XLogP: 3.7
Polar surface area: 425 Å²
H-bond donors: 13
H-bond acceptors: 16
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2003
Admin. routes: parenteral
Indications: neoplasm, prostate cancer

via ChEMBL · EBI

Research

64 papers

Abarelix: abarelix-depot-F, abarelix-depot-M, abarelix-L, PPI 149, R 3827.Drugs in R&D · 2003
Abarelix: the first gonadotrophin-releasing hormone antagonist for the treatment of prostate cancer.Expert opinion on pharmacotherapy · 2004
Abarelix for injectable suspension: first-in-class gonadotropin-releasing hormone antagonist for prostate cancer.Future oncology (London, England) · 2006
Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer.BJU international · 2009
Abarelix (Plenaxis): a gonadotropin-releasing hormone antagonist for medical castration in patients with advanced prostate cancer.Clinical prostate cancer · 2004

via PubMed

Wikidata facts

Mass: 1414.684071
Has use: medication

Show 6 more facts

chemical formula: C₇₂H₉₅ClN₁₄O₁₄
isomeric SMILES: C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)N(C)C(=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(CCCCNC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)N(C)C(=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: abarelix
defined daily dose: 3.6
has characteristic: biopharmaceutical

Sources (2)

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Encyclopedic overview

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Contents

See also
References

It was originally marketed by Praecis Pharmaceuticals as Plenaxis, and is now marketed by Speciality European Pharma in Germany after receiving a marketing authorization in 2005. The drug was introduced in the United States in 2003, but was discontinued in this country in May 2005 due to poor sales and a higher-than-expected incidence of severe allergic reactions. It remains marketed in Germany and the Netherlands however.

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

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