A synthetic GNRH peptide agonist
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Triptorelin (trifluoroacetate salt)

Item No. 28613

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-D-tryptophan-luteinizing hormone-releasing factor (swine), trifluoroacetate
CAS Number
2240176-35-4
Synonyms
  • [D-Trp6]-GnRH
  • [D-Trp6]LH-RH
  • AY 25650
  • BIM 21003
  • CL 118,53
  • Wy 42422
  • Wy 42462
Molecular Formula
C64H82N18O13 • XCF3COOH
Formula Weight
1311.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10mg/mLDMSO: 3mg/mLPBS (pH 7.2): 3mg/mL
λmax
222 nm
SMILES
O=C([C@@H]1CCC(N1)=O)N[C@@H](CC2=CN=CN2)C(N[C@@H](CC3=CNC4=CC=CC=C34)C(N[C@@H](CO)C(N[C@@H](CC5=CC=C(O)C=C5)C(N[C@H](CC6=CNC7=CC=CC=C67)C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N8CCC[C@H]8C(NCC(N)=O)=O)=O=C([C@@H]1CCC(N1)=O)N[C@@H](CC2=CN=CN2)C(N[C@@H](CC3=CNC4=CC=CC=C34)C(N[C@@H](CO)C(N[C@@H](CC5=CC=C(O)C=C5)C(N[C@H](CC6=CNC7=CC=CC=C67)C(N[C@H](C(N[C@@H](CCCNC(N)=N)C(N8CCC[C@H]8C(NCC(N)=O)=O)=O)=O)CC(C)C)=O)=O)=O)=O)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C64H82N18O13.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t44-,45-,46-,47-,48+,49-,50-,51-,52-;/m0./s1
InChi Key
KHNZXCLOURPVAS-OYLNGHKZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Triptorelin is a synthetic gonadotropin-releasing hormone (GnRH) peptide agonist that binds to the GnRH receptor (GnRHR; Ki = 0.3 nM in CHO cells expressing the human receptor).1 It inhibits the growth of DU145, LNCaP, and PC3 prostate and OVCAR-3 ovarian cancer cells (IC50s = 62.1, 73.4, 98.1, and 67.7 μM, respectively).2 Triptorelin also inhibits the growth of the triple-negative breast cancer (TNBC) cell lines HCC1806 and MDA-MB-231 (EC50s = 58.29 and 31.59 μM, respectively).3 It stimulates follicle stimulating hormone (FSH) and luteinizing hormone (LH) release from primary rat pituitary cells when used at a concentration of 50 nM.2 It also decreases tumor volume of Dunning R3327H prostate tumor flank implants and reduces prostate and testis weight in rats when administered at a dose of 1 mg/kg per day.4 Formulations containing triptorelin have been used in the palliative treatment of advanced prostate cancer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nederpelt, I., Georgi, V., Schiele, F., et al. Characterization of 12 GnRH peptide agonists - a kinetic perspective. Br. J. Pharmacol. 173(1), 128-141 (2016).

    2. Varamini, P., Rafiee, A., Giddam, A.K., et al. Development of new gonadotropin-releasing hormone-modified dendrimer platforms with direct antiproliferative and gonadotropin releasing activity. J. Med. Chem. 60(20), 8309-8320 (2017).

    3. Kwok, C.W., Treeck, O., Buchholz, S., et al. Receptors for luteinizing hormone-releasing hormone (GnRH) as therapeutic targets in triple negative breast cancers (TNBC). Target Oncol. 10(3), 365-373 (2015).

    4. Princivalle, M., Broqua, P., White, R., et al. Rapid suppression of plasma testosterone levels and tumor growth in the dunning rat model treated with degarelix, a new gonadotropin-releasing hormone antagonist. J. Pharmacol. Exp. Ther. 320(3), 1113-1118 (2007).