U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C72H95ClN14O14
Molecular Weight 1416.063
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

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
Hormonal therapy of prostate cancer.
2002 Aug
Gateways to Clinical Trials. June 2002.
2002 Jun
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
Gateways to clinical trials.
2003 Nov
Abarelix (plenaxis).
2004 Dec
Targeting FSH in androgen-independent prostate cancer: abarelix for prostate cancer progressing after orchiectomy.
2004 Feb
Abarelix (Plenaxis): a gonadotropin-releasing hormone antagonist for medical castration in patients with advanced prostate cancer.
2004 Mar
Abarelix (Plenaxis) for advanced prostate cancer.
2004 Mar 15
Abarelix for injectable suspension: first-in-class gonadotropin-releasing hormone antagonist for prostate cancer.
2006 Dec
Discovery of a pituitary adenoma following a gonadotropin-releasing hormone agonist in a patient with prostate cancer.
2006 Mar
Pharmacological characterization of a novel nonpeptide antagonist of the human gonadotropin-releasing hormone receptor, NBI-42902.
2007 Feb
Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer.
2009 Dec
Evaluation of degarelix in the management of prostate cancer.
2010 Jan 25
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.
Name Type Language
ABARELIX
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official 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
PLENAXIS
Brand Name English
ABARELIX [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QL02BX01
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
WHO-ATC L02BX01
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
EU-Orphan Drug EU/3/10/771
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
NCI_THESAURUS C2092
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
LIVERTOX 2
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
Code System Code Type Description
PUBCHEM
146019569
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PRIMARY
EPA CompTox
DTXSID20171443
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PRIMARY
RXCUI
301739
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PRIMARY RxNorm
USAN
JJ-39
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PRIMARY
EVMPD
SUB07359MIG
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PRIMARY
MERCK INDEX
m1273
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PRIMARY Merck Index
ChEMBL
CHEMBL1252
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PRIMARY
CAS
183552-38-7
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PRIMARY
CHEBI
337298
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PRIMARY
DRUG BANK
DB00106
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PRIMARY
SMS_ID
100000082343
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PRIMARY
IUPHAR
1188
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PRIMARY
DRUG CENTRAL
35
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PRIMARY
NCI_THESAURUS
C2015
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
PRIMARY
WIKIPEDIA
ABARELIX
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
PRIMARY
FDA UNII
W486SJ5824
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
PRIMARY
INN
7689
Created by admin on Fri Dec 15 15:45:01 UTC 2023 , Edited by admin on Fri Dec 15 15:45:01 UTC 2023
PRIMARY