Abarelix

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.[2][3]

Abarelix

Clinical data
Trade names	Plenaxis
AHFS/Drugs.com	Monograph
Pregnancy category	US: X (Contraindicated)
Routes of administration	Intramuscular injection
Drug class	GnRH analogue; GnRH antagonist; Antigonadotropin
ATC code	L02BX01 (WHO)
Pharmacokinetic data
Protein binding	96–99%
Identifiers
IUPAC name N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-N-methyl-L-tyrosyl-D-asparagyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide[1]
CAS Number	183552-38-7^N
PubChem CID	16131215
IUPHAR/BPS	1188
DrugBank	DB00106^Y
ChemSpider	10482301^Y
UNII	W486SJ5824
KEGG	D02738^Y
ChEBI	CHEBI:337298^Y
ChEMBL	ChEMBL1252^Y
CompTox Dashboard (EPA)	DTXSID20171443
Chemical and physical data
Formula	C72H95ClN14O14
Molar mass	1416.09 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(C)C[C@H](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](NCc5ccc4ccccc4c5)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N6CCC[C@H]6C(=O)N[C@H](C)C(N)=O
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^Y Key:AIWRTTMUVOZGPW-HSPKUQOVSA-N^Y
^NY (what is this?)  (verify)

It was originally marketed by Praecis Pharmaceuticals as Plenaxis,[2] and is now marketed by Speciality European Pharma in Germany[4] 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.[5] It remains marketed in Germany and the Netherlands however.[6]

See also

• Gonadotropin-releasing hormone receptor § Antagonists

References

1. "Abarelix". PubChem. 2017-07-29.
2. "Abarelix". Drugs.com.
3. Boccon-Gibod L, van der Meulen E, Persson BE (June 2011). "An update on the use of gonadotropin-releasing hormone antagonists in prostate cancer". Therapeutic Advances in Urology. 3 (3): 127–40. doi:10.1177/1756287211414457. PMC 3159401. PMID 21904569.
4. Pharmazeutische Zeitung online: Abarelix (in German)
5. Minev B (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.
6. "Abarelix". Drugs.com.