Abarelix

Abarelix

Clinical data
Trade names	Plenaxis
AHFS/Drugs.com	Monograph
Pregnancy category	US: X (Contraindicated)
Routes of administration	Intramuscular injection
ATC code	L02BX01 (WHO)
Pharmacokinetic data
Protein binding	96–99%
Identifiers
IUPAC name acetyl-D-β-naphthylalanyl- D-4-chlorophenylalanyl-D-3-pyridylalanyl-L-seryl-L- N-methyl- tyrosyl-D-asparagyl-L-leucyl-L-N(e )-isopropyl-lysyl-L-prolyl-D-alanyl-amide
CAS Number	183552-38-7
PubChem (CID)	16131215
IUPHAR/BPS	1188
DrugBank	DB00106
ChemSpider	10482301
UNII	W486SJ5824
KEGG	D02738
ChEBI	CHEBI:337298
ChEMBL	CHEMBL1252
Chemical and physical data
Formula	C72H95ClN14O14
Molar mass	1416.06 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N[C@H](C)C(N)=O)[C@@H]6CCCN6C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](Cc1ccc(O)cc1)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](Cc2cccnc2)NC(=O)[C@@H](Cc3ccc(Cl)cc3)NC(=O)[C@@H](\nCc4ccc5ccccc5c4)NC(=O)C
InChI InChI=1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1 Key:AIWRTTMUVOZGPW-HSPKUQOVSA-N
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Abarelix (trade name Plenaxis) is an injectable gonadotropin-releasing hormone antagonist (GnRH antagonist). 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.^[1][2]

It was originally marketed by Praecis Pharmaceuticals as Plenaxis,^[1] and is now marketed by Speciality European Pharma in Germany^[3] after receiving a marketing authorisation 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.^[4]

References

1. Drugs.com: Abarelix
2. Boccon-Gibod, L.; Van Der Meulen, E.; Persson, B. -E. (2011). "An update on the use of gonadotropin-releasing hormone antagonists in prostate cancer". Therapeutic Advances in Urology. 3 (3): 127–140. doi:10.1177/1756287211414457. PMC 3159401. PMID 21904569.
3. Pharmazeutische Zeitung online: Abarelix (German)
4. Boris Minev (13 January 2011). Cancer Management in Man: Chemotherapy, Biological Therapy, Hyperthermia and Supporting Measures. Springer Science & Business Media. pp. 182–. ISBN 978-90-481-9704-0.