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Degarelix Acetate

PubChem CID
16186010
Structure
Degarelix Acetate_small.png
Molecular Formula
Synonyms
  • Degarelix acetate
  • 934016-19-0
  • Gonax
  • ASP3550
  • UNII-EXT215F4ZU
Molecular Weight
1692.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2007-07-04
  • Modify:
    2025-01-11
Description
Degarelix Acetate is the acetate form of a long-acting, synthetic peptide with gonadotrophin-releasing hormone (GnRH) antagonistic properties. Degarelix targets and blocks GnRH receptors located on the surfaces of gonadotroph cells in the anterior pituitary, thereby reducing secretion of luteinizing hormone (LH) by pituitary gonadotroph cells and so decreasing testosterone production by interstitial (Leydig) cells in the testes.
DEGARELIX ACETATE is a Protein drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 2008 and has 3 approved and 1 investigational indication.
See also: Degarelix (has active moiety).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Degarelix Acetate.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible, mixture or salt

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Phe(4-S-dihydroorotamido)-D-Phe(4-ureido)-Leu-Lys(iPr)-Pro-D-Ala-NH2.CH3CO2H
Sequence
XXXSXXLXPA
IUPAC
N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-4-((S)-dihydroorotamido)-L-phenylalanyl-4-ureido-D-phenylalanyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide acetic acid

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(4S)-N-[4-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[4-(carbamoylamino)phenyl]-1-oxopropan-2-yl]amino]-3-oxopropyl]phenyl]-2,6-dioxo-1,3-diazinane-4-carboxamide;acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

AUTFSFUMNFDPLH-KYMMNHPFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=C(C=C2)NC(=O)N)NC(=O)[C@H](CC3=CC=C(C=C3)NC(=O)[C@@H]4CC(=O)NC(=O)N4)NC(=O)[C@H](CO)NC(=O)[C@@H](CC5=CN=CC=C5)NC(=O)[C@@H](CC6=CC=C(C=C6)Cl)NC(=O)[C@@H](CC7=CC8=CC=CC=C8C=C7)NC(=O)C.CC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C84H107ClN18O18
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

934016-19-0
934246-14-7

3.3.2 European Community (EC) Number

112-301-5

3.3.3 UNII

3.3.4 ChEMBL ID

3.3.5 DSSTox Substance ID

3.3.6 KEGG ID

3.3.7 NCI Thesaurus Code

3.3.8 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Ac-2Nal-4Cpa-3Pal-Ser-4Aph(hydroorotyl)-4Aph(carbamoyl)-Leu-ILys-pro-Ala-NH2
  • acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ILys-prolyl-alaninamide
  • degarelix
  • degarelix acetate
  • FE 200486
  • FE-200486
  • FE200486
  • Firmagon
  • Gonax
  • uglypeptide1

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
1692.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
18
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
20
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
41
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
1690.7699263 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
1690.7699263 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
550 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
121
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
3420
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
11
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Chemical Classes

4.2.1 Drugs

4.2.1.1 Human Drugs
Human drug -> Active ingredient (DEGARELIX ACETATE)
Human drug -> Prescription
Human drugs -> Other hormone antagonists and related agents -> Human pharmacotherapeutic group -> EMA Drug Category
Human drugs -> Endocrine therapy -> Human pharmacotherapeutic group -> EMA Drug Category

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Degarelix Accord is a gonadotrophin releasing hormone (GnRH) antagonist indicated: for treatment of adult male patients with advanced hormone-dependent prostate cancer . for treatment of high-risk localised and locally advanced hormone dependent prostate cancer in combination with radiotherapy. as neo-adjuvant treatment prior to radiotherapy in patients with high-risk localised or locally advanced hormone dependent prostate cancer .
FIRMAGON is a gonadotrophin releasing hormone (GnRH) antagonist indicated: - for treatment of adult male patients with advanced hormone-dependent prostate cancer . - for treatment of high-risk localised and locally advanced hormone dependent prostate cancer in combination with radiotherapy. - as neo-adjuvant treatment prior to radiotherapy in patients with high-risk localised or locally advanced hormone dependent prostate cancer .

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 Cancer Drugs

Drug Name
Degarelix
Brand Name(s)
Firmagon
FDA Approved
Yes
Drug Use

Degarelix is approved to treat:

• Prostate cancer that is advanced.

7.5 Clinical Trials

7.5.1 ClinicalTrials.gov

7.5.2 EU Clinical Trials Register

7.6 EMA Drug Information

1 of 2
Category
Human drugs
Therapeutic area
Prostatic Neoplasms
Active Substance
degarelix acetate
INN/Common name
degarelix
Pharmacotherapeutic Classes
Other hormone antagonists and related agents
Status
This medicine is authorized for use in the European Union
Company
Accord Healthcare S.L.U.
Market Date
2023-09-29
2 of 2
Medicine
Category
Human drugs
Therapeutic area
Prostatic Neoplasms
Active Substance
degarelix
INN/Common name
degarelix
Pharmacotherapeutic Classes
Endocrine therapy
Status
This medicine is authorized for use in the European Union
Company
Ferring Pharmaceuticals A/S
Market Date
2009-02-17

8 Pharmacology and Biochemistry

8.1 ATC Code

L02BX02

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Human drugs -> Other hormone antagonists and related agents -> Human pharmacotherapeutic group -> EMA Drug Category
Human drugs -> Endocrine therapy -> Human pharmacotherapeutic group -> EMA Drug Category
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Precautionary Statement Codes

P203, P261, P264, P270, P271, P280, P301+P317, P304+P340, P318, P319, P330, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

STOT SE 3 (100%)

Repr. 1B (100%)

Repr. 1B (100%)

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 FDA Orange Book Patents

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 EPA DSSTox Classification

15.6 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (4S)-N-{4-[(2S,5S,8R,11R,14R)-2-({(2R)-1-{[(2S)-1-{[(2S)-1-[(2S)-2-{[(2R)-1-Amino-1-oxo-2-propanyl]carbamoyl}-1-pyrrolidinyl]-6-(isopropylamino)-1-oxo-2-hexanyl]amino}-4-methyl-1-oxo-2-pentanyl]amino} -3-[4-(carbamoylamino)phenyl]-1-oxo-2-propanyl}carbamoyl)-11-(4-chlorobenzyl)-5-(hydroxymethyl)-14-(2-naphthylmethyl)-4,7,10,13,16-pentaoxo-8-(3-pyridinylmethyl)-3,6,9,12,15-pentaazaheptadec-1-yl]phen yl}-2,6-dioxohexahydro-4-pyrimidinecarboxami
    https://echa.europa.eu
    (4S)-N-{4-[(2S,5S,8R,11R,14R)-2-({(2R)-1-{[(2S)-1-{[(2S)-1-[(2S)-2-{[(2R)-1-Amino-1-oxo-2-propanyl]carbamoyl}-1-pyrrolidinyl]-6-(isopropylamino)-1-oxo-2-hexanyl]amino}-4-methyl-1-oxo-2-pentanyl]amino} -3-[4-(carbamoylamino)phenyl]-1-oxo-2-propanyl}carbamoyl)-11-(4-chlorobenzyl)-5-(hydroxymethyl)-14-(2-naphthylmethyl)-4,7,10,13,16-pentaoxo-8-(3-pyridinylmethyl)-3,6,9,12,15-pentaazaheptadec-1-yl]phen yl}-2,6-dioxohexahydro-4-pyrimidinecarboxami (EC: 112-301-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/398271
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  7. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  9. EU Clinical Trials Register
  10. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  12. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  13. NCI Cancer Drugs
  14. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  15. Therapeutic Target Database (TTD)
  16. Wikidata
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    acetyl-2-naphthylalanyl-3-chlorophenylalanyl-1-oxohexadecyl-seryl-4-aminophenylalanyl(hydroorotyl)-4-aminophenylalanyl(carbamoyl)-leucyl-ILys-prolyl-alaninamide
    https://www.ncbi.nlm.nih.gov/mesh/67431566
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. NCBI
CONTENTS