ABARELIX

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

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	1416.063
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41	Antagonist 2,778		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced prostate cancer 9	Palliative		Approved 8,429	Plenaxis

C_max

Value	Dose	Co-administered	Analyte	Population
43.4 ng/mL	100 mg single, intramuscular		ABARELIX plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
500 ng × h/mL	100 mg single, intramuscular		ABARELIX plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.2 h	100 mg single, intramuscular		ABARELIX plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%	100 mg single, intramuscular		ABARELIX plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
15 ug/kg 1 times / 3 weeks multiple, intramuscular	healthy, 50 - 75 years	Other AEs: Libido decreased...
15 ug/kg single, intramuscular	healthy, 50 - 75 years	Other AEs: Libido decreased...

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AEs

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AE	Significance	Dose	Population
Libido decreased	11 patient	15 ug/kg 1 times / 3 weeks multiple, intramuscular	healthy, 50 - 75 years
Libido decreased	2 patients	15 ug/kg single, intramuscular	healthy, 50 - 75 years

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Luteinizing hormone-releasing hormone antagonists in prostate cancer.	2001 Aug	11502441
New single-isomer compounds on the horizon.	2002 Apr	15131493
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Abarelix: abarelix-depot-F, abarelix-depot-M, abarelix-L, PPI 149, R 3827.	2003	12757402
Encouraging results for Plenaxis in prostate cancer trial.	2003 Apr	12722871

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Patents

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
Record UNII	W486SJ5824
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ABARELIX

Official Name

English

ABARELIX [ORANGE BOOK]

Common Name

English

ABARELIX [VANDF]

Common Name

English

R-3827

Code

English

PPI-149

Code

English

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Classification Tree

Code System

Code

Other hormone antagonists and related agents

WHO-VATC

QL02BX01

Other hormone antagonists and related agents

WHO-ATC

L02BX01

Withdrawn

EU-Orphan Drug

EU/3/10/771

Hormone Antagonist

NCI_THESAURUS

C2092

Prostate cancer

LIVERTOX

2

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Code System

Code

Type

Description

PUBCHEM

146019569

PRIMARY

EPA CompTox

DTXSID20171443

PRIMARY

RXCUI

301739

PRIMARY

RxNorm

USAN

JJ-39

PRIMARY

EVMPD

SUB07359MIG

PRIMARY

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Related Record

Type

Details


					MJK4KMT12V

GONADOTROPIN-RELEASING HORMONE RECEPTOR

TARGET -> INHIBITOR


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

[96 to 99] % (average)


					W486SJ5824

ABARELIX

EXCRETED UNCHANGED

Comments:

In humans, approximately 13% of unchanged abarelix was recovered in urine after a 15 μg/kg IM injection

Qualification:

URINE

Amount:

13 % (average)


					8XA4VN1LH4

LUTEINIZING HORMONE

TARGET -> INHIBITOR

Comments:

Saturation binding studies revealed that [125I]-abarelix has a very high affinity (KD = 0.1 nM) for the rat pituitary LHRH receptor.

Qualification:

Kd

Amount:

0.1 NANOMOLAR (average)

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Related Record

Type

Details


					W486SJ5824

ABARELIX

ACTIVE MOIETY

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	[2436 to 5649] LITERS (average)

Biological Half-life	PHARMACOKINETIC	[10 to 16.4] days (average)

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound