CAS 214766-78-6|(4R)-N-{4-[(2S)-2-{[(1R)-2-[4-(carbamoylamino)phenyl]-1-{[(1S)-1-{[(2S)-1-(2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-1-oxo-6-[(propan-2-yl)amino]hexan-2-yl]carbamoyl}-3-me...

General Information

Structure

Molecular Formula

C₈₂H₁₀₃ClN₁₈O₁₆

Molecular Mass

1632.25922

Exact Mass

1630.74879699

Charge

InChI

InChI=1S/C82H103ClN18O16/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/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)/t47-,59+,60+,61-,62-,63-,64+,65-,66-,67+,68?/m1/s1

InChIKey

MEUCPCLKGZSHTA-RHCWOGDZSA-N

Canonic Smiles

OC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCCC1C(=O)N[C@@H](C(=O)N)C)CCCCNC(C)C)CC(C)C)Cc1ccc(cc1)NC(=O)N)Cc1ccc(cc1)NC(=O)[C@H]1CC(=O)NC(=O)N1)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)NC(=O)C)Cc1ccc(cc1)Cl)Cc1cccnc1

Isomeric Smiles

Clc1ccc(C[C@@H](NC(=O)[C@H](NC(=O)C)Cc2cc3c(cc2)cccc3)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2C(CCC2)C(=O)N[C@H](C)C(=O)N)CCCCNC(C)C)CC(C)C)Cc2ccc(NC(=O)N)cc2)Cc2ccc(NC(=O)[C@@H]3NC(=O)NC(=O)C3)cc2)CO)Cc2cccnc2)cc1

Calculated Properties

JChem

Acid pKa

7.230074

H Acceptors

H Donor

LogD (pH = 5.5)

-2.5750062

LogD (pH = 7.4)

-1.6150687

Log P

-1.4164691

Molar Refractivity

431.128

Polarizability

167.52441

Polar Surface Area

512.87

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

2.66

LOG S

-5.6

Solubility (Water)

4.10e-03 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

(4R)-N-{4-[(2S)-2-{[(1R)-2-[4-(carbamoylamino)phenyl]-1-{[(1S)-1-{[(2S)-1-(2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-1-oxo-6-[(propan-2-yl)amino]hexan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]ethyl]phenyl}-2,6-dioxo-1,3-diazinane-4-carboxamide

Brand Name

Firmagon

Synonyms

Degarelix

IUPAC Traditional name

(4R)-N-{4-[(2S)-2-{[(1R)-2-[4-(carbamoylamino)phenyl]-1-{[(1S)-1-{[(2S)-1-(2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl)-6-(isopropylamino)-1-oxohexan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]ethyl]phenyl}-2,6-dioxo-1,3-diazinane-4-carboxamide

Names and Identifiers

Registration numbers

CAS Number

214766-78-6

PubChem SID

99443253160967869

PubChem CID

44151801

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB06699

Drug Groups

approved

Description

Degarelix is used for the treatment of advanced prostate cancer. Degarelix is a synthetic peptide derivative drug which binds to gonadotropin-releasing hormone(GnRH) receptors in the pituitary gland and blocks their interaction with GnRH. This antagonism reduces luteinising hormone (LH), follicle-stimulating hormone (FSH) and in turn, testosterone suppression. Reduction in testosterone is important in treating men with advanced prostate cancer.

Indication

Degaralix is used for the management of advanced prostate cancer. Its action ultimately results in a reduction in circulating androgens, which provides a therapeutic benefit by reducing the growth stimulus used by hormone-sensitive malignant prostate tissue.

Pharmacology

Degarelix is a synthetic derivative of GnRH decapeptide which normally stimulates the GnRH receptor. Gonadotropin and androgen production result from the binding of endogenous GnRH to the GnRH receptor. The ability of Degarelix to antagonize GnRH at its receptor and suppress the release of these hormones is what gives it potency in slowing advanced prostate cancer.
Degarelix antagonizes the GnRH receptor which in turn blocks the release of LH and FSH from the pituitary. The reduction in LH leads to a decrease in testosterone release from the testes and subsequently reduces the size and growth of the prostate cancer.

Affected Organisms

Humans and other mammals

Biotransformation

Degarelix is subject to peptide hydrolysis during its passage through the hepatobiliary system and is mainly excreted as peptide fragments in feces. Approximately 20-30% of a given dose of degarelix is renally eliminated, suggesting that approximately 70-80% is excreted via the hepatobiliary system.

Absorption

Degarelix forms a depot at the site of injection after subcutaneous administration from which the drug slowly released into circulation. Peak plasma concentrations of degarelix generally occur within 2 days following subcutaneous administration of a single 240-mg dose at a concentration of 40 mg/mL.

Half Life

23-61 days

Protein Binding

90% of the drug is bound to plasma proteins.

References

• Steinberg M: Degarelix: a gonadotropin-releasing hormone antagonist for the management of prostate cancer. Clin Ther. 2009;31 Pt 2:2312-31. [Pubmed]

• Persson BE, Kold Olesen T, Jensen JK: Degarelix: a new approach for the treatment of prostate cancer. Neuroendocrinology. 2009;90(3):235-44. Epub 2009 Jul 14. [Pubmed]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• Steinberg M: Degarelix: a gonadotropin-releasing hormone antagonist for the management of prostate cancer. Clin Ther. 2009;31 Pt 2:2312-31. Pubmed

• Persson BE, Kold Olesen T, Jensen JK: Degarelix: a new approach for the treatment of prostate cancer. Neuroendocrinology. 2009;90(3):235-44. Epub 2009 Jul 14. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data