DEGARELIX ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C82H103ClN18O16.C2H4O2.H2O
Molecular Weight	1710.326
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.CC(O)=O.[H][C@]1(CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=C(NC(N)=O)C=C2)NC(=O)[C@H](CC3=CC=C(NC(=O)[C@@H]4CC(=O)NC(=O)N4)C=C3)NC(=O)[C@H](CO)NC(=O)[C@@H](CC5=CN=CC=C5)NC(=O)[C@@H](CC6=CC=C(Cl)C=C6)NC(=O)[C@@H](CC7=CC=C8C=CC=CC8=C7)NC(C)=O)C(=O)N[C@H](C)C(N)=O

InChI

InChIKey=QMBXFMRFTMPFEY-YECCWIQASA-N

InChI=1S/C82H103ClN18O16.C2H4O2.H2O/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52;1-2(3)4;/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117);1H3,(H,3,4);1H2/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C82H103ClN18O16
Molecular Weight	1632.259
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

DEGARELIX (FIRMAGON®) is a synthetic linear decapeptide amide containing seven unnatural amino acids, five of which are D-amino acids. It is a GnRH receptor antagonist. It binds reversibly to the pituitary GnRH receptors, thereby reducing the release of gonadotropins and consequently testosterone. DEGARELIX (FIRMAGON®) is effective in achieving and maintaining testosterone suppression below the castration level of 50 ng/dL and is indicated for the treatment of patients with advanced prostate cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41	Antagonist 2,778		0.58 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced prostate cancer 9	Primary		Approved 8,429	FIRMAGON

C_max

Value	Dose	Co-administered	Analyte	Population
66 ng/mL	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens
26.2 ng/mL	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
635 ng × day/mL	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens
1054 ng × day/mL	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
43 day	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens
53 day	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens
10%	240 mg single, subcutaneous		DEGARELIX plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy, 74.2	Disc. AE: Injection site induration, Malaise...
240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy	Disc. AE: QT interval prolonged...
10 mg single, subcutaneous	unhealthy	Other AEs: Sick sinus syndrome, Ileus...
20 mg single, subcutaneous	unhealthy	Other AEs: Clostridium difficile colitis, Intervertebral disc protrusion...
30 mg single, subcutaneous	unhealthy	Other AEs: Atrioventricular block complete, Intervertebral disc protrusion...

Showing 1 to 5 of 5 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Hepatic function abnormal	1.46% Disc. AE	240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy, 74.2
Malaise	1.46% Disc. AE	240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy, 74.2
Injection site induration	2.19% Disc. AE	240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy, 74.2
QT interval prolonged	Disc. AE	240 mg 1 times / 4 weeks multiple, subcutaneous Recommended	unhealthy
Injection site erythema	below serious, 11 patient	10 mg single, subcutaneous	unhealthy

Showing 1 to 5 of 39 entries

Previous1 2 3 4 5…8Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781	inducer 389 inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP3A4/5 278 CYP2C19 1,478 CYP2E1 882 P-gp 1,461 OATP1B3 706 BCRP 699 MRP2 383 BSEP 402 OATP1B1 788 OATP2B1 123	CYP450 65 P-gp 1,537 BCRP 561 MRP2 205 BSEP 52 OATP1B1 406 OATP2B1 104	CYP1A2 701 CYP2C8 168 CYP2C19 293 BCRP 75 MRP2 111 BSEP 6 OATP1B1 26 OATP2B1 6

Drug as perpetrator

Show entries

Target	Modality	Activity
BCRP 773	inducer 1,573	no
BCRP 773	inhibitor 3,277	no
BSEP 403	inducer 1,573	no
BSEP 403	inhibitor 3,277	no
CYP1A2 1,692	inducer 1,573	no

Showing 1 to 5 of 23 entries

Previous1 2 3 4 5Next

Drug as victim

Show entries

Target	Modality	Activity
BCRP 561	substrate 3,367	no
BSEP 52	substrate 3,367	no
MRP2 205	substrate 3,367	no
OATP1B1 406	substrate 3,367	no
OATP2B1 104	substrate 3,367	no

Showing 1 to 5 of 7 entries

Previous1 2Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
AA Blocks	AA00BF3V	https://www.aablocks.com/goods/Goods/detail?id=AA00BF3V
Achemtek	0102-014289	http://www.achemtek.com/214766-78-6
Adooq BioScience	A12840	https://www.adooq.com/degarelix-acetate.html
Alsachim	2920	http://www.alsachim.com/product-C3990-glo.bal-view.html
Aurum Pharmatech LLC	Z-3147	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_3147

Showing 1 to 5 of 20 entries

Previous1 2 3 4Next

PubMed

Title	Date	PubMed
Evaluation of degarelix in the management of prostate cancer.	2010 Jan 25	21188095

Patents

Sample Use Guides

In Vivo Use Guide

FIRMAGON® is for subcutaneous administration only: Treatment is started with a dose of 240 mg given as two injections of 120 mg each. The starting dose is followed by maintenance doses of 80 mg administered as a single injection every 28 days.

Route of Administration: Other

Substance Class	Chemical
Record UNII	I18S89P20R
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

DEGARELIX ACETATE

Official Name

English

DEGARELIX ACETATE [USAN]

Common Name

English

FIRMAGON

Brand Name

English

DEGARELIX (AS ACETATE)

Common Name

English

Degarelix acetate [WHO-DD]

Common Name

English

Showing 1 to 5 of 12 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

GENITAL NEOPLASMS, MALE

EMA ASSESSMENT REPORTS

FIRMAGON (AUTHORIZED: PROSTATIC, NEOPLASMS)

Hormone Antagonist

NCI_THESAURUS

C2092

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Code System

Code

Type

Description

RXCUI

835863

PRIMARY

NCI_THESAURUS

C80443

PRIMARY

MERCK INDEX

m4136

PRIMARY

Merck Index

USAN

TT-111

PRIMARY

PUBCHEM

118984466

PRIMARY

Showing 1 to 5 of 10 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					SX0XJI3A11

DEGARELIX

PARENT -> SALT/SOLVATE

Amount:


					SX0XJI3A11

DEGARELIX

PARENT -> SALT/SOLVATE

Amount:


					EXT215F4ZU

DEGARELIX ACETATE ANHYDROUS

ANHYDROUS->SOLVATE

Showing 1 to 3 of 3 entries

Previous1Next

Show entries

Related Record

Type

Details


					SX0XJI3A11

DEGARELIX

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator