Abarelix

Abarelix

Systematic (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
Clinical data
Trade names	Plenaxis
AHFS/Drugs.com	monograph
Pregnancy category	US: X (Contraindicated)
Routes of administration	Intramuscular injection
Pharmacokinetic data
Protein binding	96–99%
Identifiers
CAS Number	183552-38-7
ATC code	L02BX01 (WHO)
PubChem	CID 16131215
IUPHAR/BPS	1188
DrugBank	DB00106
ChemSpider	10482301
UNII	W486SJ5824
KEGG	D02738
ChEBI	CHEBI:337298
ChEMBL	CHEMBL1252
Chemical data
Formula	C72H95ClN14O14
Molar mass	1416.06 g/mol
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.

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)