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    Chemistry

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    Also known as: 57773-63-4, Triptoreline, Arvekap, (d-trp6)-gnrh, Decapeptyl, Triptorelina
    Molecular Formula
    C64H82N18O13
    Molecular Weight
    1311.4  g/mol
    InChI Key
    VXKHXGOKWPXYNA-PGBVPBMZSA-N
    Triptorelin Pamoate
    A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE with D-tryptophan substitution at residue 6.
    1 2D Structure

    Triptorelin Pamoate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
    2.1.2 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
    2.1.3 InChI Key
    VXKHXGOKWPXYNA-PGBVPBMZSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8
    2.1.5 Isomeric SMILES
    CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 6-d-tryptophan-luteinizing Hormone-releasing Factor (pig)

    2. Ay 25650

    3. Ay-25650

    4. Ay25650

    5. Cl 118532

    6. Cl-118532

    7. Cl118532

    8. D-trp-6-lh-rh

    9. Decapeptyl

    10. Decapeptyl Depot

    11. Decapeptyl Lp

    12. Decapeptyl Trimestral

    13. Embonate, Triptorelin

    14. Gnrh, Trp(6)-

    15. Lhrh, Trp(6)-

    16. Lhrh, Tryptophyl(6)-

    17. Pamoate, Triptorelin

    18. Trelstar

    19. Trimestral, Decapeptyl

    20. Triptorelin Embonate

    21. Triptorelin Pamoate

    22. Wy 42462

    23. Wy-42462

    24. Wy42462

    2.2.2 Depositor-Supplied Synonyms

    1. 57773-63-4

    2. Triptoreline

    3. Arvekap

    4. (d-trp6)-gnrh

    5. Decapeptyl

    6. Triptorelina

    7. Triptorelinum

    8. Trelstar

    9. Triptodur

    10. Diphereline

    11. (6-d-tryptophan)luteinizing Hormone-releasing Hormone

    12. Cl 118532

    13. Cl-118532

    14. Pglu-his-trp-ser-tyr-d-trp-leu-arg-pro-gly-nh2

    15. Ay-25650

    16. Luteinizing Hormone-releasing Factor (pig), 6-d-tryptophan

    17. Cl 118,532

    18. Chebi:63633

    19. Wy 42462

    20. Ay 25650

    21. Pamorelin

    22. Salvacyl

    23. Trelstar Depot

    24. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-tryptophyl-l-leucyl-l-arginyl-l-prolylglycinamide

    25. Trelstar La

    26. Luteinizing Hormone-releasing Factor (swine), 6-d-tryptophan-

    27. Bim 21003

    28. Wy 42422

    29. Tryptorelin

    30. Diferelin

    31. D-tryptophan-lh-rh

    32. Triptoreline [inn-french]

    33. Triptorelinum [inn-latin]

    34. Triptorelina [inn-spanish]

    35. Trellasar

    36. Moapar

    37. Triptorelin [usan:inn:ban]

    38. Decapeptyl Sr

    39. Pamorelin La

    40. Unii-9081y98w2v

    41. Triptorelin (swine)

    42. Wy-42462

    43. D-trp6-lhrh

    44. Debio-8206

    45. Triptorelin (usan/inn)

    46. (d-trp6)-lh-rh

    47. Gtpl1177

    48. Schembl5079698

    49. Chembl1201334

    50. Dtxsid2048375

    51. Schembl22289009

    52. Hms2090c17

    53. Ex-a3857

    54. Bim-21003

    55. Akos030213249

    56. 9081y98w2v

    57. Cs-5745

    58. Db06825

    59. Ncgc00167301-01

    60. Ncgc00167301-02

    61. As-71149

    62. Bn-52014

    63. Hy-12551

    64. 73t634

    65. C75704

    66. D06247

    67. [d-trp6]-lh-rh, >=97% (hplc), Powder

    68. Ab01275488-01

    69. A936467

    70. Pglu-his-trp-ser-tyr-d-trp-leu-arg-pro-glynh2

    71. Q1992452

    72. (s)-1-((3s,6s,9s,12s,15r,18s,21s)-3-((1h-imidazol-5-yl)methyl)-6,15-bis((1h-indol-3-yl)methyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-18-isobutyl-1,4,7,10,13,16,19-heptaoxo-1-((s)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-n-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide

    73. Glycinamide, 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-tryptophyl-l-leucyl-l-arginyl-l-prolyl-

    2.3 Create Date
    2008-12-10
    3 Chemical and Physical Properties
    Molecular Weight 1311.4 g/mol
    Molecular Formula C64H82N18O13
    XLogP3-0.3
    Hydrogen Bond Donor Count17
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count33
    Exact Mass1310.63087474 g/mol
    Monoisotopic Mass1310.63087474 g/mol
    Topological Polar Surface Area490 Ų
    Heavy Atom Count95
    Formal Charge0
    Complexity2710
    Isotope Atom Count0
    Defined Atom Stereocenter Count9
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameTrelstar
    PubMed HealthTriptorelin (Injection)
    Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
    Drug LabelTRELSTAR is a white to slightly yellow lyophilized cake. When reconstituted, TRELSTAR has a milky appearance. It contains a pamoate salt of triptorelin, a synthetic decapeptide agonist analog of gonadotropin releasing hormone (GnRH). The chemical...
    Active IngredientTriptorelin pamoate
    Dosage FormInjectable
    RouteIntramuscular
    Strengtheq 11.25mg base/vial; eq 3.75mg base/vial; eq 22.5mg base/vial
    Market StatusPrescription
    CompanyWatson Labs

    2 of 2  
    Drug NameTrelstar
    PubMed HealthTriptorelin (Injection)
    Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
    Drug LabelTRELSTAR is a white to slightly yellow lyophilized cake. When reconstituted, TRELSTAR has a milky appearance. It contains a pamoate salt of triptorelin, a synthetic decapeptide agonist analog of gonadotropin releasing hormone (GnRH). The chemical...
    Active IngredientTriptorelin pamoate
    Dosage FormInjectable
    RouteIntramuscular
    Strengtheq 11.25mg base/vial; eq 3.75mg base/vial; eq 22.5mg base/vial
    Market StatusPrescription
    CompanyWatson Labs

    4.2 Drug Indication

    Triptorelin is indicated for the palliative treatment of advanced prostate cancer.

    FDA Label

    For the synchronisation of ovulation in weaned sows to enable a single fixed-time artificial insemination.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents, Hormonal

    Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

    Luteolytic Agents

    Chemical compounds that cause LUTEOLYSIS or degeneration of the CORPUS LUTEUM. (See all compounds classified as Luteolytic Agents.)

    5.3 ATC Code

    QH01CA97

    L - Antineoplastic and immunomodulating agents

    L02 - Endocrine therapy

    L02A - Hormones and related agents

    L02AE - Gonadotropin releasing hormone analogues

    L02AE04 - Triptorelin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Following IV administration of triptorelin, triptorelin is completely absorbed.

    Route of Elimination

    Elimination of triptorelin involves both the kidneys and the liver.

    Volume of Distribution

    After a single IV dose of 0.5mg, the volume of distribution of triptorelin peptide in healthy males was 30 - 33L.

    Clearance

    In healthy male volunteers, total clearance of triptorelin was 211.9 mL/min.

    5.5 Metabolism/Metabolites

    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.

    5.6 Biological 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.

    5.7 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.

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