DEGARELIX ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C82H103ClN18O16.C2H4O2.H2O
Molecular Weight	1710.3296
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

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

Molecular Formula	C82H103ClN18O16
Molecular Weight	1632.2623
Charge	0
Count

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

Description
Sources: https://firmagon.com | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022201s011lbl.pdf

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 Target ID: CHEMBL1855 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16759096	Antagonist 2849		0.58 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced prostate cancer 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022201s011lbl.pdf	Primary		Approved 8583	FIRMAGON Approved Use FIRMAGON is a GnRH receptor antagonist indicated for treatment of patients with advanced prostate cancer. Launch Date 2008

C_max

Value	Dose	Co-administered	Analyte	Population
66 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26513436/	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
26.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022201s016lbl.pdf	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
635 ng × day/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26513436/	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1054 ng × day/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022201s016lbl.pdf	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
43 day REVIEW https://pubmed.ncbi.nlm.nih.gov/26513436/	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
53 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022201s016lbl.pdf	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% REVIEW https://pubmed.ncbi.nlm.nih.gov/26513436/	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022201s016lbl.pdf	240 mg single, subcutaneous dose: 240 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		DEGARELIX plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
240 mg 1 times / 4 weeks multiple, subcutaneous Recommended Dose: 240 mg, 1 times / 4 weeks Route: subcutaneous Route: multiple Dose: 240 mg, 1 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/22457321	unhealthy, 74.2 Health Status: unhealthy Age Group: 74.2 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/22457321	Disc. AE: Injection site induration, Malaise... AEs leading to discontinuation/dose reduction: Injection site induration (2.19%) Malaise (1.46%) Hepatic function abnormal (1.46%) Sources: https://pubmed.ncbi.nlm.nih.gov/22457321
240 mg 1 times / 4 weeks multiple, subcutaneous Recommended Dose: 240 mg, 1 times / 4 weeks Route: subcutaneous Route: multiple Dose: 240 mg, 1 times / 4 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022201lbl.pdf	unhealthy Health Status: unhealthy Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022201lbl.pdf	Disc. AE: QT interval prolonged... AEs leading to discontinuation/dose reduction: QT interval prolonged Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022201lbl.pdf
10 mg single, subcutaneous Dose: 10 mg Route: subcutaneous Route: single Dose: 10 mg Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	Other AEs: Sick sinus syndrome, Ileus... Other AEs: Sick sinus syndrome (serious, 1 patient) Ileus (serious, 1 patient) Subileus (serious, 1 patient) Abscess intestinal (serious, 1 patient) Contusion (serious, 1 patient) Osteoarthritis (serious, 1 patient) Adenosquamous cell carcinoma (serious, 1 patient) Prostate cancer (serious, 1 patient) Carotid sinus syndrome (serious, 1 patient) Cerebrovascular accident (serious, 1 patient) Pulmonary embolism (serious, 1 patient) Respiratory failure (serious, 1 patient) Deep vein thrombosis (serious, 1 patient) Injection site erythema (below serious, 11 patient) Injection site pain (below serious, 2 patients) Injection site induration (below serious, 6 patients) Nasopharyngitis (below serious, 7 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00947882
20 mg single, subcutaneous Dose: 20 mg Route: subcutaneous Route: single Dose: 20 mg Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	Other AEs: Clostridium difficile colitis, Intervertebral disc protrusion... Other AEs: Clostridium difficile colitis (serious, 1 patient) Intervertebral disc protrusion (serious, 1 patient) Injection site erythema (below serious, 14 patients) Injection site pain (below serious, 10 patients) Injection site induration (below serious, 7 patients) Hot flush (below serious, 4 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00947882
30 mg single, subcutaneous Dose: 30 mg Route: subcutaneous Route: single Dose: 30 mg Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	unhealthy Health Status: unhealthy Sources: https://clinicaltrials.gov/ct2/show/NCT00947882	Other AEs: Atrioventricular block complete, Intervertebral disc protrusion... Other AEs: Atrioventricular block complete (serious, 1 patient) Intervertebral disc protrusion (serious, 1 patient) Osteoarthritis (serious, 1 patient) Colon cancer metastatic (serious, 1 patient) Depression (serious, 1 patient) Chronic obstructive pulmonary disease (serious, 1 patient) Hypertension (serious, 1 patient) Injection site erythema (below serious, 18 patients) Injection site pain (below serious, 18 patients) Injection site induration (below serious, 11 patient) Hypertension (below serious, 9 patients) Hot flush (below serious, 8 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00947882

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inducer 440 inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP3A4/5 296 CYP2C19 2057 CYP2E1 1060 P-gp 1741 OATP1B3 961 BCRP 910 MRP2 499 BSEP 550 OATP1B1 1079 OATP2B1 157	CYP450 59 P-gp 2052 BCRP 697 MRP2 252 BSEP 63 OATP1B1 503 OATP2B1 122	CYP1A2 832 CYP2C8 198 CYP2C19 329 BCRP 101 MRP2 146 BSEP 8 OATP1B1 29 OATP2B1 6

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
BSEP 554	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	no
CYP2C8 1117	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	no
MRP2 625	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
MRP2 625	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP1B1 1095	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP2B1 162	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP2B1 162	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	unlikely
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	yes [IC50 10 uM]

Drug as victim

Target	Modality	Activity
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
BSEP 63	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
MRP2 252	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
OATP2B1 122	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=34 Page: 34.0	no
CYP450 59	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_ClinPharmR.pdf#page=33 Page: 33.0	poor

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022201s000_PharmR_P1.pdf#page=38 Page: 38.0

Sourcing

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
BOC Sciences	214766-78-6	https://www.bocsci.com/degarelix-acetate-cas-214766-78-6-item-465293.html
Chem Scene	CS-5350	http://www.chemscene.com/214766-78-6.html
Chemenu	CM100964	http://www.chemenu.com/products/CM100964
ChemMol	49400009	http://www.chemmol.com/chemmol/49400009.html
Chemspace	CSSB00161189522	https://chem-space.com/CSSB00161189522
CSNpharm	CSN18109	https://www.csnpharm.com/products/degarelix.html
eNovation Chemicals	D320201	https://www.enovationchem.com/ProductDetails.asp?ProductID=D320201
Glentham Life Sciences	GP2084	http://www.glentham.com/products/product/GP2084/
iChemical	EBD29766	http://www.ichemical.com/chemicals/cas-214766-78-6
Lab Network	LN01345459	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01345459
MedChem Express	HY-16168A	https://www.medchemexpress.com/Degarelix.html
MolPort	MolPort-046-417-128	https://www.molport.com/shop/molecule-link/MolPort-046-417-128
MuseChem	I002648	https://www.musechem.com/product/I002648.html
OChem	25795	http://www.ocheminc.com/index.php?act=psearch&pid=766D786
Renno Tech	RL02641	http://www.rennotech.com/product_show.asp?id=2890

PubMed

Title	Date	PubMed
Evaluation of degarelix in the management of prostate cancer.	2010-01-25	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 Created by `admin` on `Mon Mar 31 18:24:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:13 GMT 2025`
Record UNII	I18S89P20R
Record Status	`FAILED`
Record Version

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Name

Type

Language

DEGARELIX ACETATE HYDRATE

Preferred Name

English

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

N-ACETYL-3-(NAPHTHALEN-2-YL)-D-ALANYL-4-CHLORO-D-PHENYLALANYL-3-(PYRIDIN-3-YL)-D-ALANYL-L-SERYL-4-((((4S)-2,6-DIOXOHEXAHYDROPYRIMIDIN-4-YL)CARBONYL)AMINO)-L-PHENYLALANYL-4-(CARBAMOYLAMINO)-D-PHENYLALANYL-L-LEUCYL-N6-(1-METHYLETHYL)-L-LYSYL-L-PROLYL-D-ALA

Systematic Name

English

FE-200486

Code

English

DEGARELIX ACETATE [ORANGE BOOK]

Common Name

English

FE200486

Code

English

DEGARELIX ACETATE [MART.]

Common Name

English

DEGARELIX ACETATE HYDRATE [MI]

Common Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

FIRMAGON (AUTHORIZED: PROSTATIC, NEOPLASMS)