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Details

Stereochemistry ABSOLUTE
Molecular Formula C82H103ClN18O16.C2H4O2
Molecular Weight 1692.3144
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEGARELIX ACETATE ANHYDROUS

SMILES

CC(C)C[C@@]([H])(C(=N[C@@]([H])(CCCCNC(C)C)C(=O)N1CCC[C@@]1([H])C(=N[C@]([H])(C)C(=N)O)O)O)N=C([C@@]([H])(Cc2ccc(cc2)NC(=N)O)N=C([C@]([H])(Cc3ccc(cc3)NC(=O)[C@]4([H])CC(=NC(=N4)O)O)N=C([C@]([H])(CO)N=C([C@@]([H])(Cc5cccnc5)N=C([C@@]([H])(Cc6ccc(cc6)Cl)N=C([C@@]([H])(Cc7ccc8ccccc8c7)N=C(C)O)O)O)O)O)O)O.CC(=O)O

InChI

InChIKey=AUTFSFUMNFDPLH-KYMMNHPFSA-N
InChI=1S/C82H103ClN18O16.C2H4O2/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)/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+;/m1./s1

HIDE SMILES / InChI

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

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.58 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FIRMAGON

Approved Use

FIRMAGON is a GnRH receptor antagonist indicated for treatment of patients with advanced prostate cancer.

Launch Date

1.23007677E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
66 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
635 ng × day/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
43 day
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
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%
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

Doses

DosePopulationAdverse 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: Page: p.482
unhealthy, 74.2
n = 137
Health Status: unhealthy
Condition: Advanced prostate cancer
Age Group: 74.2
Sex: M
Population Size: 137
Sources: Page: p.482
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: Page: p.482
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced prostate cancer
Sex: M
Sources: Page: p.1
Disc. AE: QT interval prolonged...
AEs leading to
discontinuation/dose reduction:
QT interval prolonged
Sources: Page: p.1
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
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:
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
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:
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
Hepatic function abnormal 1.46%
Disc. AE
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: Page: p.482
unhealthy, 74.2
n = 137
Health Status: unhealthy
Condition: Advanced prostate cancer
Age Group: 74.2
Sex: M
Population Size: 137
Sources: Page: p.482
Malaise 1.46%
Disc. AE
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: Page: p.482
unhealthy, 74.2
n = 137
Health Status: unhealthy
Condition: Advanced prostate cancer
Age Group: 74.2
Sex: M
Population Size: 137
Sources: Page: p.482
Injection site induration 2.19%
Disc. AE
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: Page: p.482
unhealthy, 74.2
n = 137
Health Status: unhealthy
Condition: Advanced prostate cancer
Age Group: 74.2
Sex: M
Population Size: 137
Sources: Page: p.482
QT interval prolonged Disc. AE
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Advanced prostate cancer
Sex: M
Sources: Page: p.1
Injection site erythema below serious, 11 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Injection site pain below serious, 2 patients
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Injection site induration below serious, 6 patients
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Nasopharyngitis below serious, 7 patients
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Abscess intestinal serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Adenosquamous cell carcinoma serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Carotid sinus syndrome serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Cerebrovascular accident serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Contusion serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Deep vein thrombosis serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Ileus serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Osteoarthritis serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Prostate cancer serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Pulmonary embolism serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Respiratory failure serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Sick sinus syndrome serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Subileus serious, 1 patient
10 mg single, subcutaneous
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy
n = 101
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 101
Sources:
Injection site pain below serious, 10 patients
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Injection site erythema below serious, 14 patients
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Hot flush below serious, 4 patients
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Injection site induration below serious, 7 patients
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Clostridium difficile colitis serious, 1 patient
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Intervertebral disc protrusion serious, 1 patient
20 mg single, subcutaneous
Dose: 20 mg
Route: subcutaneous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 100
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 100
Sources:
Injection site induration below serious, 11 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Injection site erythema below serious, 18 patients
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Injection site pain below serious, 18 patients
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Hot flush below serious, 8 patients
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Hypertension below serious, 9 patients
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Atrioventricular block complete serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Chronic obstructive pulmonary disease serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Colon cancer metastatic serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Depression serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Hypertension serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Intervertebral disc protrusion serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
Osteoarthritis serious, 1 patient
30 mg single, subcutaneous
Dose: 30 mg
Route: subcutaneous
Route: single
Dose: 30 mg
Sources:
unhealthy
n = 105
Health Status: unhealthy
Condition: Lower Urinary Tract Symptoms
Population Size: 105
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
yes [IC50 10 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

PubMed

PubMed

TitleDatePubMed
Evaluation of degarelix in the management of prostate cancer.
2010 Jan 25
Patents

Patents

Sample Use Guides

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 Fri Jun 25 20:41:39 UTC 2021
Edited
by admin
on Fri Jun 25 20:41:39 UTC 2021
Record UNII
EXT215F4ZU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEGARELIX ACETATE ANHYDROUS
Common Name English
DEGARELIX MONOACETATE ANHYDROUS
Common Name English
Code System Code Type Description
CAS
934016-19-0
Created by admin on Fri Jun 25 20:41:39 UTC 2021 , Edited by admin on Fri Jun 25 20:41:39 UTC 2021
PRIMARY
PUBCHEM
16144848
Created by admin on Fri Jun 25 20:41:39 UTC 2021 , Edited by admin on Fri Jun 25 20:41:39 UTC 2021
PRIMARY
FDA UNII
EXT215F4ZU
Created by admin on Fri Jun 25 20:41:39 UTC 2021 , Edited by admin on Fri Jun 25 20:41:39 UTC 2021
PRIMARY
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