Identification
- Summary
Goserelin is a synthetic analog of luteinizing hormone-releasing hormone used to treat breast cancer and prostate cancer by reducing secretion of gonadotropins from the pituitary.
- Brand Names
- Zoladex
- Generic Name
- Goserelin
- DrugBank Accession Number
- DB00014
- Background
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
Structure for Goserelin (DB00014)
- 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
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism ALutropin-choriogonadotropic hormone receptor agonistHumans AGonadotropin-releasing hormone receptor agonistHumans - 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
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No experience of overdosage from clinical trials.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Goserelin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Goserelin. Aceclofenac Aceclofenac may decrease the excretion rate of Goserelin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Goserelin which could result in a higher serum level. Acetaminophen Goserelin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Goserelin which could result in a lower serum level and potentially a reduction in efficacy. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Goserelin. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Goserelin which could result in a higher serum level. Aclidinium Goserelin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Goserelin. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Goserelin acetate 6YUU2PV0U8 145781-92-6 IKDXDQDKCZPQSZ-JHYYTBFNSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Zoladex Implant 10.8 mg/1 Subcutaneous Tersera Therapeutics Llc 2018-01-26 Not applicable US 
Zoladex Implant 3.6 mg/1 Subcutaneous AstraZeneca Pharmaceuticals LP 2003-05-05 2020-05-31 US Zoladex Implant 3.6 mg Subcutaneous Tersera Therapeutics Llc 1994-12-31 Not applicable Canada 
Zoladex Implant 3.6 mg/1 Subcutaneous Tersera Therapeutics Llc 2018-03-31 Not applicable US Zoladex Implant 3.6 mg/1 Subcutaneous A-S Medication Solutions 2003-05-05 2019-10-31 US Zoladex Implant 10.8 mg/1 Subcutaneous AstraZeneca Pharmaceuticals LP 2003-05-05 2020-03-31 US Zoladex Implant 3.6 mg/1 Subcutaneous A-S Medication Solutions 2018-03-31 Not applicable US Zoladex LA Implant 10.8 mg Subcutaneous Tersera Therapeutics Llc 1996-08-28 Not applicable Canada
Categories
- ATC Codes
- L02AE03 — Goserelin
- Drug Categories
- Adrenal Cortex Hormones
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Antineoplastic Agents, Hormonal
- Antineoplastic and Immunomodulating Agents
- Drugs that are Mainly Renally Excreted
- Endocrine Therapy
- Gonadotropin Releasing Hormone Receptor Agonist
- Gonadotropin Releasing Hormone Receptor Agonists
- Gonadotropin-releasing hormone agonist
- Gonadotropins and Antigonadotropins
- Hormones
- Hormones and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Hypothalamic Hormones
- Miscellaneous Therapeutic Agents
- Moderate Risk QTc-Prolonging Agents
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary Hormone-Releasing Hormones
- QTc Prolonging Agents
- 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
- Affected organisms
- Humans and other mammals
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[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]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
- External Links
- Human Metabolome Database
- HMDB0014259
- KEGG Drug
- D00573
- PubChem Compound
- 5311128
- PubChem Substance
- 46507336
- ChemSpider
- 4470656
- 50610
- ChEBI
- 5523
- ChEMBL
- CHEMBL1201247
- Therapeutic Targets Database
- DAP000023
- PharmGKB
- PA164747674
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Goserelin
- FDA label
- Download (992 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Uterine Fibroids (Leiomyomas) 1 4 Completed Treatment Endometriosis 1 4 Completed Treatment Endometriosis / Infertility 1 4 Completed Treatment Kennedys Disease / Spinobulbar Muscular Atrophy 1 4 Completed Treatment Prostate Cancer 1 4 Not Yet Recruiting Other Androgen Deprivation Therapy / Disorders of the Autonomic Nervous System / Hypertension / Kidney Diseases / Prostate Cancer 1 4 Recruiting Supportive Care Neoplasms of the Prostate 1 4 Recruiting Treatment Endometriosis 1 4 Recruiting Treatment Metastatic Breast Cancer 1 4 Terminated Treatment Advanced Prostate Cancer 1
Pharmacoeconomics
- Manufacturers
- Astrazeneca uk ltd
- Packagers
- AstraZeneca Inc.
- Dosage Forms
Form Route Strength Implant Parenteral; Subcutaneous 10.8 MG Implant Parenteral; Subcutaneous 3.6 MG Implant Subcutaneous 10.8 mg/1 Implant Subcutaneous 3.6 mg/1 Implant Subcutaneous 3.6 mg Implant Injection Subcutaneous 3.6 mg Implant Subcutaneous 10.8 mg Injection Subcutaneous Injection Subcutaneous 10.8 mg Solution 3.6 mg Solution 10.8 mg - Prices
Unit description Cost Unit Zoladex 10.8 mg implant syringe 1380.65USD syringe Zoladex 3.6 mg implant syringe 451.19USD syringe DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7118552 No 2006-10-10 2022-04-13 US US7220247 No 2007-05-22 2022-04-09 US US7500964 No 2009-03-10 2021-02-26 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble Not Available logP -2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0283 mg/mL ALOGPS logP 0.3 ALOGPS logP -5.1 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 9.36 Chemaxon pKa (Strongest Basic) 10.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 17 Chemaxon Polar Surface Area 495.89 Å2 Chemaxon Rotatable Bond Count 33 Chemaxon Refractivity 325.84 m3·mol-1 Chemaxon Polarizability 130.74 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9771 Blood Brain Barrier - 0.8816 Caco-2 permeable - 0.7772 P-glycoprotein substrate Substrate 0.9016 P-glycoprotein inhibitor I Non-inhibitor 0.5834 P-glycoprotein inhibitor II Non-inhibitor 0.8342 Renal organic cation transporter Non-inhibitor 0.7673 CYP450 2C9 substrate Non-substrate 0.7534 CYP450 2D6 substrate Non-substrate 0.7806 CYP450 3A4 substrate Substrate 0.6353 CYP450 1A2 substrate Non-inhibitor 0.8265 CYP450 2C9 inhibitor Non-inhibitor 0.7506 CYP450 2D6 inhibitor Non-inhibitor 0.8835 CYP450 2C19 inhibitor Non-inhibitor 0.7254 CYP450 3A4 inhibitor Non-inhibitor 0.6347 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9054 Ames test Non AMES toxic 0.5851 Carcinogenicity Non-carcinogens 0.6406 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6730 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8841 hERG inhibition (predictor II) Inhibitor 0.5249
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 24, 2023 20:20