Abarelix

Identification

Generic Name
Abarelix
DrugBank Accession Number
DB00106
Background

Synthetic decapeptide antagonist to gonadotropin releasing hormone (GnRH). It is marketed by Praecis Pharmaceuticals as Plenaxis. Praecis announced in June 2006 that it was voluntarily withdrawing the drug from the market.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Thumb
Weight
Average: 1416.09
Monoisotopic: 1414.6840715
Chemical Formula
C72H95ClN14O14
Synonyms
  • Abarelix

Pharmacology

Indication

For palliative treatment of advanced prostate cancer.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Used in the palliative treatment of advanced prostate cancer. Abarelix is a luteinizing hormone agonist that results in suppression of testicular or follicular steroidogenesis.

Mechanism of action

Abarelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion.

TargetActionsOrganism
AGonadotropin-releasing hormone receptor
antagonist
Humans
Absorption

Following IM administration of 100 mg, abarelix is absorbed slowly with a mean peak concentration of 43.4 ng/mL observed approximately 3 days after the injection.

Volume of distribution

Not Available

Protein binding

96-99%

Metabolism

In vitro hepatocyte (rat, monkey, human) studies and in vivo studies in rats and monkeys showed that the major metabolites of abarelix were formed via hydrolysis of peptide bonds. No significant oxidative or conjugated metabolites of abarelix were found either in vitro or in vivo. There is no evidence of cytochrome P-450 involvement in the metabolism of abarelix.

Route of elimination

Not Available

Half-life

13.2 ± 3.2 days

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

The maximum tolerated dose of abarelix has not been determined. The maximum dose used in clinical studies was 150 mg. There have been no reports of accidental overdose with abarelix.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

Products
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International/Other Brands
Plenaxis (Praecis Pharmaceuticals)

Categories

ATC Codes
L02BX01 — Abarelix
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Tyrosine and derivatives / Phenylalanine and derivatives / Asparagine and derivatives / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Proline and derivatives / Serine and derivatives / Alpha amino acid amides / Alanine and derivatives / Amphetamines and derivatives
show 21 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Acetamide / Alanine or derivatives / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Amphetamine or derivatives
show 45 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
polypeptide (CHEBI:337298)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
W486SJ5824
CAS number
183552-38-7
InChI Key
AIWRTTMUVOZGPW-HSPKUQOVSA-N
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
IUPAC Name
(2R)-N-[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-6-[(propan-2-yl)amino]hexan-2-yl]carbamoyl}-3-methylbutyl]-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxy-N-methylpropanamido]-3-(4-hydroxyphenyl)propanamido]butanediamide
SMILES
CC(C)C[C@H](NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC1=CN=CC=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC2=C(C=CC=C2)C=C1)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O

References

General References
Not Available
KEGG Drug
D02738
PubChem Compound
16131215
PubChem Substance
46508237
ChemSpider
10482301
BindingDB
50102442
RxNav
301739
ChEBI
337298
ChEMBL
CHEMBL1252
Therapeutic Targets Database
DAP000094
PharmGKB
PA164754915
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Abarelix
FDA label
Download (121 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4SuspendedTreatmentProstate Cancer1
3CompletedTreatmentProstate Cancer1
2CompletedTreatmentProstate Cancer1

Pharmacoeconomics

Manufacturers
  • Speciality european pharma ltd
Packagers
  • Baxter International Inc.
  • Fisher Clinical Services Inc.
Dosage Forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6423686No2002-07-232015-06-07US flag
US6180608No2001-01-302016-12-11US flag
US5968895No1999-10-192016-12-11US flag
US5843901No1998-12-012015-12-01US flag
US6699833No2004-03-022016-12-11US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00371 mg/mLALOGPS
logP2.84ALOGPS
logP-0.46ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)10.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area424.98 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity373.91 m3·mol-1ChemAxon
Polarizability149.31 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Peptide binding
Specific Function
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
Molecular Weight
37730.355 Da
References
  1. Debruyne FM: Gonadotropin-releasing hormone antagonist in the management of prostate cancer. Rev Urol. 2004;6 Suppl 7:S25-32. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 03, 2021 08:56