Identification
- Summary
Triptorelin is a GnRH agonist indicated for the palliative treatment of advanced prostate cancer.
- Brand Names
- Decapeptyl, Trelstar, Triptodur
- Generic Name
- Triptorelin
- DrugBank Accession Number
- DB06825
- Background
Triptorelin is a synthetic decapeptide agonist analog of luteinizing hormone releasing hormone (LHRH). Possessing greater potency than endogenous LHRH, triptorelin reversibly represses gonadotropin secretion. After chronic, continuous administration, this agent effects sustained decreases in LH and FSH production and testicular and ovarian steroidogenesis. Serum testosterone concentrations may fall to levels typically observed in surgically castrated men.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Triptorelin (DB06825)
- Weight
- Average: 1311.473
Monoisotopic: 1310.630874772 - Chemical Formula
- C64H82N18O13
- Synonyms
- (6-D-Tryptophan)luteinizing hormone-releasing hormone
- (D-Trp6)-GnRH
- Luteinizing hormone-releasing factor (pig), 6-D-tryptophan
- pGlu-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2
- Triptorelin
- Triptorelina
- Triptoreline
- Triptorelinum
- External IDs
- AY-25650
- CL 118,532
- CL-118532
- WY-42462
Pharmacology
- Indication
Triptorelin is indicated for the palliative treatment of advanced prostate cancer.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Advanced prostate cancer •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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The first administration of triptorelin is followed by a transient surge of follicle stimulating hormone (FSH), luteinizing hormone (LH), estradiol,and testosterone. The time, peak and decline of testosterone in the body varies depending on the dose administered. This initial surge is often responsible for worsening of prostate cancer symptoms such as urethral or bladder outlet obstruction, bone pain, spinal cord injury and hematuria in the early stages. A sustained decrease in FSH and LH, and significant reduction of testicular steroidogenesis is usually seen 2-4 weeks post-initiation of therapy. This result is a reduction of serum testosterone to levels which are typically seen in surgically castrated men. Ultimately, tissues and functions that require these hormones become inactive. The effects of triptorelin can usually be reversed once the drug is discontinued.
- Mechanism of action
Triptorelin is a synthetic agonist analog of gonadotropin releasing hormone (GnRH). Animal studies comparing triptorelin to native GnRH found that triptorelin had 13 fold higher releasing activity for luteinizing hormone, and 21-fold higher releasing activity for follicle-stimulating hormone.
Target Actions Organism AGonadotropin-releasing hormone receptor agonistHumans - Absorption
Following IV administration of triptorelin, triptorelin is completely absorbed.
- Volume of distribution
After a single IV dose of 0.5mg, the volume of distribution of triptorelin peptide in healthy males was 30 - 33L.
- Protein binding
Triptorelin does not bind to plasma proteins at clinically relevant concentrations.
- Metabolism
The metabolism of triptorelin in humans is not well understood; however, metabolism likely does not involve hepatic enzymes such as cytochrome P450. Whether or not triptorelin affects, or how it affects other metabolizing enzymes is also poorly understood. Triptorelin has no identified metabolites.
- Route of elimination
Elimination of triptorelin involves both the kidneys and the liver.
- Half-life
The pharmacokinetics of triptorelin follows a 3 compartment model. The half lives are estimated to be 6 minutes, 45 minutes, and 3 hours respectively.
- Clearance
In healthy male volunteers, total clearance of triptorelin was 211.9 mL/min.
- Adverse Effects
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Some of the most commonly reported adverse effects of triptorelin are hot flushes reported in 58.6% of patients, skeletal pain in 12.1%, impotence in 7.1%, and headache in 5.0%. Other reported adverse effects include injection site pain, general body pain, leg pain, fatigue, hypertension, dizziness, diarrhea, vomiting, insomnia, emotional lability, anemia, pruritus, urinary tract infections, and urinary retention. Triptorelin is classified as Pregnancy Category X and contraindicated in pregnant women or in women who may become pregnant. Hormonal changes caused by triptorelin increase the risk for pregnancy loss. Studies done on pregnant rats demonstrated maternal toxicity and embryo-fetal toxicities.
- 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 softwareAcarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Triptorelin. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Triptorelin. Acrivastine The risk or severity of QTc prolongation can be increased when Triptorelin is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Triptorelin is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Triptorelin. - Food Interactions
- 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 Triptorelin acetate 43OFW291R9 140194-24-7 HPPONSCISKROOD-OYLNGHKZSA-N Triptorelin pamoate 08AN7WA2G0 124508-66-3 ZBVJFYPGLGEMIN-OYLNGHKZSA-N - International/Other Brands
- Diphereline (Ferring Pharmaceuticals) / Gonapeptyl (Ferring Pharmaceuticals) / Variopeptyl (Varian Darou Pajooh)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Decapeptyl Solution 0.1 mg / mL Subcutaneous Ferring Pharmaceuticals 2012-08-09 Not applicable Canada 
Trelstar Kit 11.25 mg/2mL Intramuscular Actavis Pharma Company 2001-06-29 2018-10-31 US 
Trelstar Injection, powder, lyophilized, for suspension 11.25 mg/2mL Intramuscular Actavis Pharma Company 2001-06-29 2018-10-31 US Trelstar Injection, powder, for suspension, extended release 22.5 mg / vial Intramuscular Knight Therapeutics Inc. 2013-10-16 Not applicable Canada Trelstar Injection, powder, lyophilized, for suspension; Kit 11.25 mg/2mL Intramuscular Verity Pharmaceuticals Inc. 2001-06-29 Not applicable US
Categories
- ATC Codes
- L02AE04 — Triptorelin
- Drug Categories
- Adrenal Cortex Hormones
- Amino Acids, Peptides, and Proteins
- Antineoplastic Agents
- Antineoplastic Agents, Hormonal
- Antineoplastic and Immunomodulating Agents
- Contraceptive Agents, Hormonal
- Endocrine Therapy
- Gonadotropin Releasing Hormone Receptor Agonist
- Gonadotropin Releasing Hormone Receptor Agonists
- Gonadotropin-releasing hormone agonist
- Hormones
- Hormones and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Hypothalamic Hormones
- Luteolytic Agents
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary Hormone-Releasing Hormones
- Potential QTc-Prolonging Agents
- Proteins
- QTc Prolonging Agents
- Reproductive Control Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Peptides / Tyrosine and derivatives / Phenylalanine and derivatives / Histidine and derivatives / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Proline and derivatives / Tryptamines and derivatives / Serine and derivatives / Alpha amino acid amides show 23 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 2-pyrrolidone / 3-alkylindole / Alcohol / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Azacycle show 48 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- oligopeptide (CHEBI:63633)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9081Y98W2V
- CAS number
- 57773-63-4
- InChI Key
- VXKHXGOKWPXYNA-PGBVPBMZSA-N
- InChI
- InChI=1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1
- IUPAC Name
- (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamide
- SMILES
- CC(C)C[C@H](NC(=O)[C@@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)NCC(N)=O
References
- General References
- Lahlou N, Carel JC, Chaussain JL, Roger M: Pharmacokinetics and pharmacodynamics of GnRH agonists: clinical implications in pediatrics. J Pediatr Endocrinol Metab. 2000 Jul;13 Suppl 1:723-37. [Article]
- Padula AM: GnRH analogues--agonists and antagonists. Anim Reprod Sci. 2005 Aug;88(1-2):115-26. [Article]
- External Links
- KEGG Drug
- D06247
- PubChem Compound
- 25074470
- PubChem Substance
- 310264898
- ChemSpider
- 17290424
- 38782
- ChEBI
- 63633
- ChEMBL
- CHEMBL1201334
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Triptorelin
- FDA label
- Download (691 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Idiopathic Short Stature (ISS) 1 4 Completed Not Available Prostate Cancer 1 4 Completed Treatment Assisted Reproduction 1 4 Completed Treatment Endometriosis 1 4 Completed Treatment Endometriosis / Infertility 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Parenteral Injection, powder, for solution Intramuscular; Subcutaneous 0.1 MG/ML Injection, powder, for suspension Intramuscular 3.75 mg Injection, powder, for suspension Parenteral 3.75 MG/2ML Injection, powder, for suspension, extended release 11.25 MG/2ML Injection, powder, for suspension, extended release 22.5 MG/2ML Solution Subcutaneous 0.1 mg / mL Injection Parenteral 0.1 mg Injection; solution Subcutaneous Injection, solution Subcutaneous Powder 3.75 mg Injection, powder, for solution Intramuscular; Subcutaneous 3.75 mg/syringe Injection, suspension, extended release Intramuscular; Subcutaneous Capsule, extended release Intramuscular; Subcutaneous 4.12 mg Suspension Subcutaneous 3.75 mg Injection Subcutaneous 100 mcg/ml Injection, powder, for suspension Injection, powder, for suspension, extended release Intramuscular; Subcutaneous 3.75 mg Injection, powder, for suspension Intramuscular 11.25 mg Injection, powder, for suspension, extended release Intramuscular; Subcutaneous 11.25 mg Injection, powder, for suspension, extended release Intramuscular 3.75 mg Injection, solution Injection, solution 0.1 MG/1ML Injection, solution 0.1 mg/ml Solution Subcutaneous 0.09560 mg Solution Subcutaneous 95.6 mcg Injection, powder, for suspension, extended release Intramuscular; Subcutaneous 3.75 mg/ml Suspension Other 4.1200 mg Injection, powder, lyophilized, for solution 11.25 mg Injection, powder, lyophilized, for solution 22.5 mg Injection, powder, lyophilized, for solution 3.75 mg Suspension Parenteral 3.750 MG Injection, powder, for suspension Parenteral 11.25 mg Injection, powder, for suspension Parenteral 22.5 mg Injection, powder, for suspension Parenteral 3.75 mg Injection, powder, lyophilized, for suspension Intramuscular 11.25 mg Injection, powder, lyophilized, for suspension Intramuscular 22.5 mg Injection, powder, for suspension Intramuscular Injection, powder, lyophilized, for suspension Intramuscular 3.75 mg Injection, powder, for suspension, extended release Intramuscular 11.25 mg / vial Injection, powder, for suspension, extended release Intramuscular 22.5 mg / vial Injection, powder, for suspension, extended release Intramuscular 3.75 mg / vial Injection, powder, lyophilized, for suspension Intramuscular 11.25 mg/2mL Injection, powder, lyophilized, for suspension Intramuscular 22.5 mg/2mL Injection, powder, lyophilized, for suspension Intramuscular 3.75 mg/2mL Injection, powder, lyophilized, for suspension; kit Intramuscular 11.25 mg/2mL Injection, powder, lyophilized, for suspension; kit Intramuscular 3.75 mg/2mL Kit Intramuscular 11.25 mg/2mL Kit Intramuscular 22.5 mg/2mL Kit Intramuscular 3.75 mg/2mL Injection, powder, lyophilized, for suspension; kit Intramuscular 22.5 mg/2mL Injection, solution Parenteral 0.1 mg/ml Solution Subcutaneous 0.1 mg/1ml Injection, powder, for solution Intramuscular; Subcutaneous 3.75 mg/1vial Injection, powder, for solution Intramuscular; Subcutaneous 0.1 mg/1vial - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5776885 No 1998-07-07 2015-07-07 US US10166181 No 2019-01-01 2029-02-10 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0305 mg/mL ALOGPS logP 1.07 ALOGPS logP -3.6 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 9.49 Chemaxon pKa (Strongest Basic) 11.54 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 17 Chemaxon Hydrogen Donor Count 18 Chemaxon Polar Surface Area 487.92 Å2 Chemaxon Rotatable Bond Count 33 Chemaxon Refractivity 352.43 m3·mol-1 Chemaxon Polarizability 135.23 Å3 Chemaxon Number of Rings 8 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 339.73056 predictedDeepCCS 1.0 (2019) [M+H]+ 341.3838 predictedDeepCCS 1.0 (2019) [M+Na]+ 347.54062 predictedDeepCCS 1.0 (2019)
Targets
- 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
Drug created at September 14, 2010 16:21 / Updated at April 18, 2024 09:15