degarelix

Also known as FE200486, Firmagon®

Degarelix, sold under the brand name Firmagon among others, is a hormonal therapy used in the treatment of prostate cancer.

Chemical data

Formula: C82H103ClN18O16
Molecular weight: 1632.3 g/mol
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
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
InChIKey: MEUCPCLKGZSHTA-XYAYPHGZSA-N
XLogP: 3.5
Polar surface area: 513 Å²
H-bond donors: 17
H-bond acceptors: 18
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2008
Admin. routes: parenteral
Indications: neoplasm, endometriosis, prostate adenocarcinoma, benign prostatic hyperplasia

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 1630.748797
Has use: medication

Show 6 more facts

chemical formula: C₈₂H₁₀₃ClN₁₈O₁₆
route of administration: subcutaneous injection
canonical SMILES: CC(C)CC(C(=O)NC(CCCCNC(C)C)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)NC(=O)N)NC(=O)C(CC3=CC=C(C=C3)NC(=O)C4CC(=O)NC(=O)N4)NC(=O)C(CO)NC(=O)C(CC5=CN=CC=C5)NC(=O)C(CC6=CC=C(C=C6)Cl)NC(=O)C(CC7=CC8=CC=CC=C8C=C7)NC(=O)C
defined daily dose: 2.7
isomeric SMILES: CC(C)C[C@H](NC(=O)[C@@H](CC1=CC=C(NC(N)=O)C=C1)NC(=O)[C@H](CC2=CC=C(NC(=O)[C@@H]3CC(=O)NC(=O)N3)C=C2)NC(=O)[C@H](CO)NC(=O)[C@@H](CC4=CC=CN=C4)NC(=O)[C@@H](CC5=CC=C(Cl)C=C5)NC(=O)[C@@H](CC6=CC7=C(C=CC=C7)C=C6)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N8CCC[C@H]8C(=O)N[C@H](C)C(N)=O
NCI Thesaurus ID: C48385

Sources (5)

via Wikidata · CC0

~5 min read

Encyclopedic overview

7 sections

Contents

Medical uses
Side effects
Pharmacology
History
Research
See also
References

Degarelix, sold under the brand name Firmagon among others, is a hormonal therapy used in the treatment of prostate cancer.

Testosterone is a male hormone that promotes growth of many prostate tumours and therefore reducing circulating testosterone to very low (castration) levels is often the treatment goal in the management of advanced prostate cancer. Degarelix has an immediate onset of action, binding to gonadotropin-releasing hormone (GnRH) receptors in the pituitary gland and blocking their interaction with GnRH. This induces a fast and profound reduction in luteinizing hormone (LH), follicle-stimulating hormone (FSH) and in turn, testosterone suppression.

Excerpted from Wikipedia’s “degarelix” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

Available in 14 languages

via Wikidata sitelinks · CC0