Structure via PubChem · Public domain (PubChem)
histrelin
Sign in to saveAlso known as ORF 17070, RWJ 17070, Vantas®, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-N(tau)-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide, L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-N(im)-benzyl-histidyl-L-leucyl-L-arginyl-L-proline ethylamide, [(im-Bzl)-D-His(6),Pro(9)-NEt]-gonadotropin releasing hormone
Histrelin acetate, sold under the brand name Supprelin among others, is a nonapeptide analogue of gonadotropin-releasing hormone (GnRH) with added potency. When present in the bloodstream, it acts on particular cells of the pituitary gland called gonadotropes. Histrelin stimulates these cells to release luteinizing hormone and follicle-stimulating hormone. Thus it is considered a gonadotropin-releasing hormone agonist or GnRH agonist.
Chemical data
- Formula
- C66H86N18O12
- Molecular weight
- 1323.5 g/mol
- IUPAC name
- (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-3-(1-benzylimidazol-4-yl)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-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
- CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CN(C=N2)CC3=CC=CC=C3)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
- HHXHVIJIIXKSOE-QILQGKCVSA-N
- XLogP
- 0.7
- Polar surface area
- 449 Ų
- H-bond donors
- 15
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 1991
- Admin. routes
- parenteral
- Indications
- neoplasm, prostate adenocarcinoma, Central precocious puberty, metastatic prostate cancer
via ChEMBL · EBI
Wikidata facts
- Mass
- 1322.66726
- Has use
- medication
Show 4 more facts
- canonical SMILES
- CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC2=CN(C=N2)CC3=CC=CC=C3)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
- chemical formula
- C₆₆H₈₆N₁₈O₁₂
- isomeric SMILES
- CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CN(C=N2)CC3=CC=CC=C3)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
- World Health Organisation international non-proprietary name
- histrelin
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Society and culture
- Economics
- References
Histrelin acetate, sold under the brand name Supprelin among others, is a nonapeptide analogue of gonadotropin-releasing hormone (GnRH) with added potency. When present in the bloodstream, it acts on particular cells of the pituitary gland called gonadotropes. Histrelin stimulates these cells to release luteinizing hormone and follicle-stimulating hormone. Thus it is considered a gonadotropin-releasing hormone agonist or GnRH agonist.
==Medical uses== Histrelin is used to treat hormone-sensitive cancers of the prostate in men and uterine fibroids in women. In addition, histrelin has been proven to be highly effective in treating central precocious puberty in children.
Excerpted from Wikipedia’s “histrelin” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0