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Triptorelin

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An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-tryptophyl, leucyl, arginyl, prolyl and glycinamide residues joined in sequence. It is an agonist anal ogue of gonadotropin-releasing hormone.

Category

Peptide Inhibitors

Catalog number

BAT-010064

CAS number

57773-63-4

Molecular Formula

C64H82N18O13

Molecular Weight

1311.47

Specification
Reference Reading

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

Synonyms

Triptoreline; Decapeptyl; Arvekap; (D-Trp6)-GnRH; Triptorelina; Triptorelinum; Trelstar; (6-D-Tryptophan)luteinizing hormone-releasing hormone; CL 118532; CL-118532; pGlu-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2

Related CAS

140194-24-7 (Acetate) 124508-66-3 (pamoate)

Appearance

White to Off-White Solid

Purity

>98%

Density

1.52±0.1 g/cm3(Predicted)

Melting Point

>180°C (dec.)

Sequence

XHWSYWLRPG

Storage

Store at -20°C

Solubility

Soluble in DMSO

Application

Antineoplastic Agents, Hormonal

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

InChI Key

VXKHXGOKWPXYNA-PGBVPBMZSA-N

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

1.Does lower dose of long-acting triptorelin maintain pituitary suppression and produce good live birth rate in long down-regulation protocol for in-vitro fertilization?

Chen X1, Feng SX1, Guo PP1, He YX1, Liu YD1, Ye DS1, Chen SL2. J Huazhong Univ Sci Technolog Med Sci. 2016 Apr;36(2):215-20. doi: 10.1007/s11596-016-1569-8. Epub 2016 Apr 13.

The effects of pituitary suppression with one-third depot of long-acting gonadotropin-releasing hormone (GnRH) agonist in GnRH agonist long protocol for in vitro fertilization (IVF)/intracytoplasmic sperm injection (ICSI) were investigated. A retrospective cohort study was performed on 3186 cycles undergoing IVF/ICSI with GnRH agonist long protocol in a university-affiliated infertility center. The pituitary was suppressed with depot triptorelin of 1.25 mg or 1.875 mg. There was no significant difference in live birth rate between 1.25 mg triptorelin group and 1.875 mg triptorelin group (41.2% vs. 43.7%). The mean luteinizing hormone (LH) level on follicle-stimulating hormone (FSH) starting day was significantly higher in 1.25 mg triptorelin group. The mean LH level on the day of human chorionic gonadotrophin (hCG) administration was slightly but statistically higher in 1.25 mg triptorelin group. There was no significant difference in the total FSH dose between the two groups.

2.Efficacy and safety of triptorelin 6-month formulation in patients with central precocious puberty.

Klein K, Yang J, Aisenberg J, Wright N, Kaplowitz P, Lahlou N, Linares J, Lundström E, Purcea D, Cassorla F. J Pediatr Endocrinol Metab. 2016 Feb 17. pii: /j/jpem.ahead-of-print/jpem-2015-0376/jpem-2015-0376.xml. doi: 10.1515/jpem-2015-0376. [Epub ahead of print]

BACKGROUND: Triptorelin is an established treatment for central precocious puberty (CPP) as 1- and 3-month formulations. The current triptorelin 22.5 mg 6-month formulation is approved for prostate cancer therapy. This is the first study in patients with CPP.

3.Triptorelin and cetrorelix induce immune responses and affect uterine development and expressions of genes and proteins of ESR1, LHR, and FSHR of mice.

Wei S1,2, Guo H3, Gong Z4, Zhang F2, Ma Z1. Immunopharmacol Immunotoxicol. 2016 Apr 14:1-8. [Epub ahead of print]

CONTEXT: GnRH immunity can reduce the expression of pituitary GnRH levels, and cause the changes in reproductive behaviors. It is unclear whether triptorelin (TRI) and cetrorelix (CET) immunity influences uterine development and expression of follicle-stimulating hormone receptor (FSHR), luteinizing hormone receptor (LHR), and estradiol receptor 1 (ERS1) in the uterus.

4.Impact of age on cytotoxic-induced ovarian failure in breast cancer treated with adjuvant chemotherapy and triptorelin.

Meattini I1, Saieva C2, Meacci F1, Scotti V1, De Luca Cardillo C1, Desideri I1, Baldazzi V1, Mangoni M1, Scoccianti S1, Detti B1, Simontacchi G1, Nori J3, Orzalesi L4, Sanchez L4, Casella D4, Bernini M4, Fambrini M5, Bianchi S6, Livi L1. Future Oncol. 2016 Mar;12(5):625-35. doi: 10.2217/fon.15.357. Epub 2016 Feb 3.

AIM: This study analyzes our single-center, retrospective experience on 63 premenopausal breast cancer patients treated with monthly triptorelin and concomitant chemotherapy.