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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])(C(=N[C@@]([H])(CCCCNC(C)C)C(=O)N1CCC[C@@]1([H])C(=N[C@]([H])(C)C(=N)O)O)O)NN[C@]([H])(CC(=N)O)C(=O)C(=O)[C@]([H])(Cc2ccc(cc2)O)N(C)C(=O)[C@]([H])(CO)N=C([C@@]([H])(Cc3cccnc3)N=C([C@@]([H])(Cc4ccc(cc4)Cl)N=C([C@@]([H])(Cc5ccc6ccccc6c5)N=C(C)O)O)O)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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Plenaxis

Approved Use

For palliative treatment of advanced prostate cancer.

Launch Date

1.069632E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
43.4 ng/mL
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
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
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%
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:
healthy, 50 - 75 years
n = 15
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Population Size: 15
Sources:
Other AEs: Libido decreased...
Other AEs:
Libido decreased (11 patient)
Sources:
15 ug/kg single, intramuscular
Dose: 15 ug/kg
Route: intramuscular
Route: single
Dose: 15 ug/kg
Sources:
healthy, 50 - 75 years
n = 16
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Population Size: 16
Sources:
Other AEs: Libido decreased...
Other AEs:
Libido decreased (2 patients)
Sources:
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:
healthy, 50 - 75 years
n = 15
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Population Size: 15
Sources:
Libido decreased 2 patients
15 ug/kg single, intramuscular
Dose: 15 ug/kg
Route: intramuscular
Route: single
Dose: 15 ug/kg
Sources:
healthy, 50 - 75 years
n = 16
Health Status: healthy
Age Group: 50 - 75 years
Sex: M
Population Size: 16
Sources:
PubMed

PubMed

TitleDatePubMed
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
The gonadotropin-releasing hormone antagonist abarelix depot versus luteinizing hormone releasing hormone agonists leuprolide or goserelin: initial results of endocrinological and biochemical efficacies in patients with prostate cancer.
2001 May
New single-isomer compounds on the horizon.
2002 Apr
A phase 3, multicenter, open label, randomized study of abarelix versus leuprolide plus daily antiandrogen in men with prostate cancer.
2002 Apr
Gateways to clinical trials.
2002 May
Gateways to clinical trials.
2002 Nov
Encouraging results for Plenaxis in prostate cancer trial.
2003 Apr
Luteinizing hormone-releasing hormone agonists in the treatment of men with prostate cancer: timing, alternatives, and the 1-year implant.
2003 Dec 22
Phase II study of abarelix depot for androgen independent prostate cancer progression during gonadotropin-releasing hormone agonist therapy.
2003 May
Gateways to clinical trials.
2003 Nov
Experimental use of GnRH antagonists as second-line hormonal therapy.
2004
Gonadotropin-releasing hormone antagonist in the management of prostate cancer.
2004
Abarelix (plenaxis).
2004 Dec
Pharmacokinetics and pharmacodynamics of a novel depot formulation of abarelix, a gonadotropin-releasing hormone (GnRH) antagonist, in healthy men ages 50 to 75.
2004 May
Abarelix: the first gonadotrophin-releasing hormone antagonist for the treatment of prostate cancer.
2004 Oct
Hormone therapy in prostate cancer: LHRH antagonists versus LHRH analogues.
2004 Sep
Innovations in antineoplastic therapy.
2005 Mar
The effect of androgen deprivation therapy on fasting serum lipid and glucose parameters.
2006 Aug
Discovery of a pituitary adenoma following treatment with a gonadotropin-releasing hormone agonist in a patient with prostate cancer.
2006 Jan
Discovery of a pituitary adenoma following a gonadotropin-releasing hormone agonist in a patient with prostate cancer.
2006 Mar
Dose-escalated abarelix in androgen-independent prostate cancer: a phase I study.
2006 Oct
Proprietary Rel-Ease drug delivery technology: opportunity for sustained delivery of peptides, proteins and small molecules.
2006 Sep
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
[GnRH antagonists--a new therapy option for advanced prostate cancer].
2009 May
Retraction statement: Reconstitution of Plenaxis® (Abarelix) 100 mg for injection is more effective with a vortex-like mixer than when performed manually.
2010 Feb
Evaluation of degarelix in the management of prostate cancer.
2010 Jan 25
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 Oct
Patents

Sample Use Guides

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
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 Fri Jun 25 20:37:28 UTC 2021
Edited
by admin
on Fri Jun 25 20:37:28 UTC 2021
Record UNII
W486SJ5824
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ABARELIX
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ABARELIX [WHO-DD]
Common 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
R3827
Code English
ABARELIX [USAN]
Common Name English
PLENAXIS
Brand Name English
ABARELIX [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QL02BX01
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
WHO-ATC L02BX01
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
EU-Orphan Drug EU/3/10/771
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
NCI_THESAURUS C2092
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
LIVERTOX 2
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
Code System Code Type Description
PUBCHEM
146019569
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
EPA CompTox
183552-38-7
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
RXCUI
301739
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY RxNorm
EVMPD
SUB07359MIG
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
MERCK INDEX
M1273
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1252
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
CAS
183552-38-7
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
DRUG BANK
DB00106
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
IUPHAR
1188
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
DRUG CENTRAL
35
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
NCI_THESAURUS
C2015
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
WIKIPEDIA
ABARELIX
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
FDA UNII
W486SJ5824
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
INN
7689
Created by admin on Fri Jun 25 20:37:28 UTC 2021 , Edited by admin on Fri Jun 25 20:37:28 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
In humans, approximately 13% of unchanged abarelix was recovered in urine after a 15 ?g/kg IM injection
URINE
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
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC