曲普瑞林

Also known as CL 118532, CL-118532, Decapeptyl®, (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, triptoreline

Triptorelin, sold under the brand name Decapeptyl among others, is a medication that acts as an agonist analog of gonadotropin-releasing hormone, repressing expression of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). It was patented in 1975 and approved for medical use in 1986. Triptorelin is a therapeutic alternative on the World Health Organization's List of Essential Medicines.

Chemical data

Formula: C64H82N18O13
Molecular weight: 1311.4 g/mol
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
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
InChIKey: VXKHXGOKWPXYNA-PGBVPBMZSA-N
XLogP: -0.3
Polar surface area: 490 Å²
H-bond donors: 17
H-bond acceptors: 15
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2000
Admin. routes: parenteral
Indications: neoplasm, infertility, endometriosis, breast carcinoma

via ChEMBL · EBI

Research

2,460 papers

Triptorelin for the treatment of endometriosis.Expert opinion on pharmacotherapy · 2014
Triptorelin embonate (6-month formulation).Drugs · 2010
Triptorelin depot for the treatment of children 2 years and older with central precocious puberty.Expert review of clinical pharmacology · 2018
Triptorelin in the management of prostate cancer.Future oncology (London, England) · 2013
Triptorelin: A Review of its Use as an Adjuvant Anticancer Therapy in Early Breast Cancer.Drugs · 2017

via PubMed

Wikidata facts

Mass: 1310.630875
Has use: medication

Show 5 more facts

chemical formula: C₆₄H₈₂N₁₈O₁₃
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
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
World Health Organisation international non-proprietary name: triptorelin
defined daily dose: 0.134

Sources (6)

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