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Details

Stereochemistry ABSOLUTE
Molecular Formula C72H95ClN14O14
Molecular Weight 1416.0658
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ABARELIX

SMILES

CC(C)C[C@H](NN[C@H](CC(N)=O)C(=O)C(=O)[C@H](CC1=CC=C(O)C=C1)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC2=CC=CN=C2)NC(=O)[C@@H](CC3=CC=C(Cl)C=C3)NC(=O)[C@@H](CC4=CC=C5C=CC=CC5=C4)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

InChIKey=LNNDRFNNTDYHIO-OMYILHBOSA-N
InChI=1S/C72H95ClN14O14/c1-41(2)32-58(69(98)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)70(99)78-43(5)65(75)94)85-84-54(38-62(74)91)63(92)64(93)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)83-68(97)57(36-48-14-12-29-76-39-48)82-67(96)56(34-45-20-25-51(73)26-21-45)81-66(95)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,84-85,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,94)(H,78,99)(H,79,89)(H,80,98)(H,81,95)(H,82,96)(H,83,97)/t43-,53+,54-,55-,56-,57-,58+,59+,60+,61+/m1/s1

HIDE SMILES / InChI
Molecular Formula C72H95ClN14O14
Molecular Weight 1416.0658
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-320_Plenaxis_Prntlbl.pdf

Abarelix is a synthetic decapeptide antagonist to gonadotropin releasing hormone (GnRH). It is marketed by Praecis Pharmaceuticals as Plenaxis. Used in the palliative treatment of advanced prostate cancer. Abarelix is a luteinizing hormone agonist that results in suppression of testicular or follicular steroidogenesis. Abarelix binds to the gonadotropin releasing hormone receptor and acts as a a potent inhibitor of gonadotropin secretion. Praecis announced in June 2006 that it was voluntarily withdrawing the drug from the market.

Originator

Approval Year

2003
181
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 3.5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Plenaxis

Approved Use

For palliative treatment of advanced prostate cancer.

Launch Date

2003
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
43.4 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21320_plenaxis_lbl.pdf
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ABARELIX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
500 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21320_plenaxis_lbl.pdf
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ABARELIX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.2 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21320_plenaxis_lbl.pdf
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ABARELIX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21320_plenaxis_lbl.pdf
100 mg single, intramuscular
dose: 100 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
ABARELIX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 ug/kg 1 times / 3 weeks multiple, intramuscular
Dose: 15 ug/kg, 1 times / 3 weeks
Route: intramuscular
Route: multiple
Dose: 15 ug/kg, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
healthy, 50 - 75 years
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
Other AEs: Libido decreased...
Other AEs:
Libido decreased (11 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
15 ug/kg single, intramuscular
Dose: 15 ug/kg
Route: intramuscular
Route: single
Dose: 15 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
healthy, 50 - 75 years
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
Other AEs: Libido decreased...
Other AEs:
Libido decreased (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
AEs

AEs

AESignificanceDosePopulation
Libido decreased 11 patient
15 ug/kg 1 times / 3 weeks multiple, intramuscular
Dose: 15 ug/kg, 1 times / 3 weeks
Route: intramuscular
Route: multiple
Dose: 15 ug/kg, 1 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
healthy, 50 - 75 years
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
Libido decreased 2 patients
15 ug/kg single, intramuscular
Dose: 15 ug/kg
Route: intramuscular
Route: single
Dose: 15 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
healthy, 50 - 75 years
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/15102870/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:337298
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:337298
ChemicalBook
CB11117588
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB11117588
MolPort
MolPort-006-167-469
https://www.molport.com/shop/molecule-link/MolPort-006-167-469
PubMed

PubMed

TitleDatePubMed
Degarelix, a novel GnRH antagonist, causes minimal histamine release compared with cetrorelix, abarelix and ganirelix in an ex vivo model of human skin samples.
2010-10
GnRH antagonists in the treatment of advanced prostate cancer.
2010-04
Retraction statement: Reconstitution of Plenaxis® (Abarelix) 100 mg for injection is more effective with a vortex-like mixer than when performed manually.
2010-02
Evaluation of degarelix in the management of prostate cancer.
2010-01-25
Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer.
2009-12
[GnRH antagonists--a new therapy option for advanced prostate cancer].
2009-05
Will GnRH antagonists improve prostate cancer treatment?
2009-01
Six-month depot formulation of leuprorelin acetate in the treatment of prostate cancer.
2009
Degarelix and its therapeutic potential in the treatment of prostate cancer.
2009
Distinguishing compounds with anticancer activity by ANN using inductive QSAR descriptors.
2008-07-30
Leuprorelin depot injection: patient considerations in the management of prostatic cancer.
2008-04
Hormone ablation therapy: lightening the load for today's prostate cancer patient.
2007-02
Pharmacological characterization of a novel nonpeptide antagonist of the human gonadotropin-releasing hormone receptor, NBI-42902.
2007-02
Abarelix for injectable suspension: first-in-class gonadotropin-releasing hormone antagonist for prostate cancer.
2006-12
Dose-escalated abarelix in androgen-independent prostate cancer: a phase I study.
2006-10
Proprietary Rel-Ease drug delivery technology: opportunity for sustained delivery of peptides, proteins and small molecules.
2006-09
The effect of androgen deprivation therapy on fasting serum lipid and glucose parameters.
2006-08
Discovery of a pituitary adenoma following a gonadotropin-releasing hormone agonist in a patient with prostate cancer.
2006-03
Discovery of a pituitary adenoma following treatment with a gonadotropin-releasing hormone agonist in a patient with prostate cancer.
2006-01
[GnRH antagonists: present and future].
2005-10
Prostate-specific antigen decline after gonadotropin-releasing hormone antagonist withdrawal in androgen-independent prostate cancer.
2005-04
Innovations in antineoplastic therapy.
2005-03
Abarelix (plenaxis).
2004-12
Abarelix: the first gonadotrophin-releasing hormone antagonist for the treatment of prostate cancer.
2004-10
Hormone therapy in prostate cancer: LHRH antagonists versus LHRH analogues.
2004-09
Pharmacokinetics and pharmacodynamics of a novel depot formulation of abarelix, a gonadotropin-releasing hormone (GnRH) antagonist, in healthy men ages 50 to 75.
2004-05
New treatment for advanced prostate cancer.
2004-04-23
Abarelix (Plenaxis) for advanced prostate cancer.
2004-03-15
Abarelix (Plenaxis): a gonadotropin-releasing hormone antagonist for medical castration in patients with advanced prostate cancer.
2004-03
Plenaxis.
2004-02
Targeting FSH in androgen-independent prostate cancer: abarelix for prostate cancer progressing after orchiectomy.
2004-02
Experimental use of GnRH antagonists as second-line hormonal therapy.
2004
Gonadotropin-releasing hormone antagonist in the management of prostate cancer.
2004
Luteinizing hormone-releasing hormone agonists in the treatment of men with prostate cancer: timing, alternatives, and the 1-year implant.
2003-12-22
Gateways to clinical trials.
2003-11
An open-label study of abarelix in men with symptomatic prostate cancer at risk of treatment with LHRH agonists.
2003-11
Phase II study of abarelix depot for androgen independent prostate cancer progression during gonadotropin-releasing hormone agonist therapy.
2003-05
Encouraging results for Plenaxis in prostate cancer trial.
2003-04
Pharmacokinetics and pharmacodynamics of abarelix, a gonadotropin-releasing hormone antagonist, after subcutaneous continuous infusion in patients with prostate cancer.
2003-04
Abarelix: abarelix-depot-F, abarelix-depot-M, abarelix-L, PPI 149, R 3827.
2003
Gateways to clinical trials.
2002-11
Hormonal therapy of prostate cancer.
2002-08
Gateways to Clinical Trials. June 2002.
2002-06
Gateways to clinical trials.
2002-05
New single-isomer compounds on the horizon.
2002-04
A phase 3, multicenter, open label, randomized study of abarelix versus leuprolide plus daily antiandrogen in men with prostate cancer.
2002-04
Pharmacological profile of a new, potent, and long-acting gonadotropin-releasing hormone antagonist: degarelix.
2002-04
Emerging pharmacologic therapies for prostate cancer.
2001
The evolution of hormonal therapy for prostatic carcinoma.
2001
Androgen deprivation and other treatments for advanced prostate cancer.
2001
Patents

Patents

JP2006265244A
8
JP2006524634A
46
JP2007504265A
10
JP2007525429A
28
JP2009513567A
66
JP2010526091A
24
JP2011506455A
52
JP2011528275A
456
JP4701159B2
91

Sample Use Guides

In Vivo Use Guide
Adults Prostate Cancer IM 100 mg on days 1, 15, and 29 (week 4), and then every 4 weeks thereafter. Administer by IM injection into the buttock.
Route of Administration: Intramuscular
In Vitro Use Guide
At 30 and 300 ug/ml concentrations abarelix (143 ± 29% and 362 ± 58%, respectively, P < 0.05) caused significantly increased histamine release.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:07:21 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:21 GMT 2025
Record UNII
W486SJ5824
Record Status FAILED
Record Version
  • Download
Name Type Language
ABARELIX
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
PLENAXIS
Preferred Name English
ABARELIX [ORANGE BOOK]
Common Name English
ABARELIX [VANDF]
Common Name English
R-3827
Code English
PPI-149
Code English
R-382
Code English
R382
Code English
abarelix [INN]
Common Name English
N-ACETYL-3-(2-NAPHTHYL)-D-ALANYL-4-CHLORO-D-PHENYLALANYL-3-(3-PYRIDYL)-D-ALANYL-L-SERYL-N-METHYL-L-TYROSYL-D-ASPARAGINYL-L-LEUCYL-N(SUP 6)-ISOPROPYL-L-LYSYL-L-PROLYL-D-ALANINAMIDE
Common Name English
ABARELIX [MART.]
Common Name English
Abarelix [WHO-DD]
Common Name English
R3827
Code English
ABARELIX [USAN]
Common Name English
ABARELIX [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QL02BX01
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
WHO-ATC L02BX01
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
EU-Orphan Drug EU/3/10/771
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
NCI_THESAURUS C2092
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
LIVERTOX 2
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
Code System Code Type Description
PUBCHEM
146019569
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID20171443
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
RXCUI
301739
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY RxNorm
USAN
JJ-39
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
EVMPD
SUB07359MIG
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
MERCK INDEX
m1273
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1252
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
CAS
183552-38-7
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
CHEBI
337298
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
DRUG BANK
DB00106
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
SMS_ID
100000082343
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
IUPHAR
1188
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
DRUG CENTRAL
35
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
NCI_THESAURUS
C2015
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
WIKIPEDIA
ABARELIX
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
FDA UNII
W486SJ5824
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
INN
7689
Created by admin on Mon Mar 31 18:07:21 GMT 2025 , Edited by admin on Mon Mar 31 18:07:21 GMT 2025
PRIMARY
Related Record Type Details
GONADOTROPIN-RELEASING HORMONE RECEPTOR
TARGET -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of ABARELIX
EXCRETED UNCHANGED
In humans, approximately 13% of unchanged abarelix was recovered in urine after a 15 ?g/kg IM injection
URINE
LUTEINIZING HORMONE
TARGET -> INHIBITOR
Saturation binding studies revealed that [125I]-abarelix has a very high affinity (KD = 0.1 nM) for the rat pituitary LHRH receptor.
Kd
Related Record Type Details
Structure of ABARELIX
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
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