Goserelin

Identification

Name
Goserelin
Accession Number
DB00014
Description

Goserelin is a synthetic hormone. In men, it stops the production of the hormone testosterone, which may stimulate the growth of cancer cells. In women, goserelin decreases the production of the hormone estradiol (which may stimulate the growth of cancer cells) to levels similar to a postmenopausal state. When the medication is stopped, hormone levels return to normal.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1269.4105
Monoisotopic: 1268.641439486
Chemical Formula
C59H84N18O14
Synonyms
  • Goserelin
  • Goserelina
External IDs
  • ICI 118,630
  • ICI-118630

Pharmacology

Indication

Goserelin is indicated for:

  • Use in combination with flutamide for the management of locally confined carcinoma of the prostate
  • Palliative treatment of advanced carcinoma of the prostate
  • The management of endometriosis
  • Use as an endometrial-thinning agent prior to endometrial ablation for dysfunctional uterine bleeding
  • Use in the palliative treatment of advanced breast cancer in pre- and perimenopausal women
Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

The pharmacokinetics of goserelin have been determined in both male and female healthy volunteers and patients. In these studies, goserelin was administered as a single 250µg (aqueous solution) dose and as a single or multiple 3.6 mg depot dose by subcutaneous route.

Mechanism of action

Goserelin is a synthetic decapeptide analogue of LHRH. Goserelin acts as a potent inhibitor of pituitary gonadotropin secretion when administered in the biodegradable formulation. The result is sustained suppression of LH and serum testosterone levels.

TargetActionsOrganism
ALutropin-choriogonadotropic hormone receptor
agonist
Humans
AGonadotropin-releasing hormone receptor
agonist
Humans
Absorption

Inactive orally, rapidly absorbed following subcutaneous administration.

Volume of distribution
  • 44.1 ± 13.6 L [subcutaneous administration of 250 mcg]
Protein binding

27.3%

Metabolism

Hepatic

Route of elimination

Clearance of goserelin following subcutaneous administration of a radiolabeled solution of goserelin was very rapid and occurred via a combination of hepatic and urinary excretion. More than 90% of a subcutaneous radiolabeled solution formulation dose of goserelin was excreted in urine.

Half-life

4-5 hours

Clearance
  • 121 +/- 42.4 mL/min [prostate cancer with 10.8 mg depot]
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

No experience of overdosage from clinical trials.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirGoserelin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Goserelin.
AcebutololThe risk or severity of QTc prolongation can be increased when Goserelin is combined with Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Goserelin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Goserelin which could result in a higher serum level.
AcetaminophenGoserelin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Goserelin which could result in a lower serum level and potentially a reduction in efficacy.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Goserelin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Goserelin which could result in a higher serum level.
AclidiniumGoserelin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Goserelin acetate6YUU2PV0U8145781-92-6IKDXDQDKCZPQSZ-JHYYTBFNSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ZoladexImplant3.6 mg/1SubcutaneousAstraZeneca Pharmaceuticals LP2003-05-052020-05-31US flag
ZoladexImplant3.6 mg/1SubcutaneousA-S Medication Solutions2003-05-052019-10-31US flag
ZoladexImplant3.6 mg/1SubcutaneousTersera Therapeutics Llc2018-03-31Not applicableUS flag
ZoladexImplant3.6 mg/1SubcutaneousA-S Medication Solutions2018-03-31Not applicableUS flag
ZoladexImplant10.8 mg/1SubcutaneousAstraZeneca Pharmaceuticals LP2003-05-052020-03-31US flag
ZoladexImplant3.6 mgSubcutaneousTersera Therapeutics Llc1994-12-31Not applicableCanada flag
ZoladexImplant10.8 mg/1SubcutaneousTersera Therapeutics Llc2018-01-26Not applicableUS flag
Zoladex LAImplantSubcutaneousTersera Therapeutics Llc1996-08-28Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
L02AE03 — Goserelin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Tyrosine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Leucine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / Serine and derivatives / Alpha amino acid amides / 3-alkylindoles
show 26 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-pyrrolidone / 3-alkylindole / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Azacycle
show 51 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
0F65R8P09N
CAS number
65807-02-5
InChI Key
BLCLNMBMMGCOAS-URPVMXJPSA-N
InChI
InChI=1S/C59H84N18O14/c1-31(2)22-40(49(82)68-39(12-8-20-64-57(60)61)56(89)77-21-9-13-46(77)55(88)75-76-58(62)90)69-54(87)45(29-91-59(3,4)5)74-50(83)41(23-32-14-16-35(79)17-15-32)70-53(86)44(28-78)73-51(84)42(24-33-26-65-37-11-7-6-10-36(33)37)71-52(85)43(25-34-27-63-30-66-34)72-48(81)38-18-19-47(80)67-38/h6-7,10-11,14-17,26-27,30-31,38-46,65,78-79H,8-9,12-13,18-25,28-29H2,1-5H3,(H,63,66)(H,67,80)(H,68,82)(H,69,87)(H,70,86)(H,71,85)(H,72,81)(H,73,84)(H,74,83)(H,75,88)(H4,60,61,64)(H3,62,76,90)/t38-,39-,40-,41-,42-,43-,44-,45+,46-/m0/s1
IUPAC Name
(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanoyl]-N-(carbamoylamino)pyrrolidine-2-carboxamide
SMILES
CC(C)C[[email protected]](NC(=O)[[email protected]@H](COC(C)(C)C)NC(=O)[[email protected]](CC1=CC=C(O)C=C1)NC(=O)[[email protected]](CO)NC(=O)[[email protected]](CC1=CNC2=CC=CC=C12)NC(=O)[[email protected]](CC1=CN=CN1)NC(=O)[[email protected]@H]1CCC(=O)N1)C(=O)N[[email protected]@H](CCCN=C(N)N)C(=O)N1CCC[[email protected]]1C(=O)NNC(N)=O

References

Synthesis Reference

Kripa S. Srivastava, Matthew R. Davis, "Solid Phase Peptide for the Production of Goserelin." U.S. Patent US20100311946, issued December 09, 2010.

US20100311946
General References
Not Available
Human Metabolome Database
HMDB0014259
KEGG Drug
D00573
PubChem Compound
5311128
PubChem Substance
46507336
ChemSpider
4470656
RxNav
50610
ChEBI
5523
ChEMBL
CHEMBL1201247
Therapeutic Targets Database
DAP000023
PharmGKB
PA164747674
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Goserelin
AHFS Codes
  • 68:18.00 — Gonadotropins and Antigonadotropins
  • 92:00.00 — Miscellaneous Therapeutic Agents
FDA label
Download (992 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableLeiomyomas1
4CompletedTreatmentEndometriosis1
4CompletedTreatmentEndometriosis / Infertility1
4CompletedTreatmentKennedy's Disease / Spinobulbar Muscular Atrophy1
4CompletedTreatmentProstate Cancer1
4Not Yet RecruitingTreatmentAdvanced Prostate Cancer1
4Not Yet RecruitingTreatmentMetastatic Breast Cancer1
4RecruitingSupportive CareProstatic Neoplasms1
4TerminatedTreatmentProstate Cancer2
4TerminatedTreatmentUterine Leiomyomas1

Pharmacoeconomics

Manufacturers
  • Astrazeneca uk ltd
Packagers
  • AstraZeneca Inc.
Dosage Forms
FormRouteStrength
ImplantCutaneous; Parenteral10.8 MG
ImplantCutaneous; Parenteral3.6 MG
ImplantSubcutaneous10.8 mg/1
ImplantSubcutaneous3.6 mg/1
Injection
ImplantSubcutaneous3.6 mg
ImplantSubcutaneous10.8 mg
Implant10.8 mg
Implant3.6 mg
ImplantSubcutaneous
Prices
Unit descriptionCostUnit
Zoladex 10.8 mg implant syringe1380.65USD syringe
Zoladex 3.6 mg implant syringe451.19USD syringe
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7118552No2006-10-102022-04-13US flag
US7220247No2007-05-222022-04-09US flag
US7500964No2009-03-102021-02-26US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleNot Available
logP-2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0283 mg/mLALOGPS
logP0.3ALOGPS
logP-5.2ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)10.82ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area495.89 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity325.84 m3·mol-1ChemAxon
Polarizability131.22 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9771
Blood Brain Barrier-0.8816
Caco-2 permeable-0.7772
P-glycoprotein substrateSubstrate0.9016
P-glycoprotein inhibitor INon-inhibitor0.5834
P-glycoprotein inhibitor IINon-inhibitor0.8342
Renal organic cation transporterNon-inhibitor0.7673
CYP450 2C9 substrateNon-substrate0.7534
CYP450 2D6 substrateNon-substrate0.7806
CYP450 3A4 substrateSubstrate0.6353
CYP450 1A2 substrateNon-inhibitor0.8265
CYP450 2C9 inhibitorNon-inhibitor0.7506
CYP450 2D6 inhibitorNon-inhibitor0.8835
CYP450 2C19 inhibitorNon-inhibitor0.7254
CYP450 3A4 inhibitorNon-inhibitor0.6347
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9054
Ames testNon AMES toxic0.5851
CarcinogenicityNon-carcinogens0.6406
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6730 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8841
hERG inhibition (predictor II)Inhibitor0.5249
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Luteinizing hormone receptor activity
Specific Function
Receptor for lutropin-choriogonadotropic hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase.
Gene Name
LHCGR
Uniprot ID
P22888
Uniprot Name
Lutropin-choriogonadotropic hormone receptor
Molecular Weight
78642.01 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Kirby RS, Fitzpatrick JM, Clarke N: Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. [PubMed:20053189]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Peptide binding
Specific Function
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
Gene Name
GNRHR
Uniprot ID
P30968
Uniprot Name
Gonadotropin-releasing hormone receptor
Molecular Weight
37730.355 Da
References
  1. Kirby RS, Fitzpatrick JM, Clarke N: Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. [PubMed:20053189]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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