Structure via PubChem · Public domain (PubChem)
leuprolide
Sign in to saveAlso known as ABBOTT-43818, Lupron®, TAP-144, Leuprorelin, L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamide, pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt, (D-Leu(6),des-Gly-NH2(10),Pro-ethylamide(9))-gonadotropin-releasing hormone, pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5
Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, for early puberty, as part of transgender hormone therapy, or to perform chemical castration of violent sex offenders. It is given by injection into a muscle or under the skin.
Chemical data
- Formula
- C59H84N16O12
- Molecular weight
- 1209.4 g/mol
- IUPAC name
- (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-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]-4-methyl-1-oxopentan-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](CC(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6
- InChIKey
- GFIJNRVAKGFPGQ-LIJARHBVSA-N
- XLogP
- 0.7
- Polar surface area
- 432 Ų
- H-bond donors
- 15
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
Research
3,959 papersvia PubMed
Wikidata facts
- Mass
- 1208.645462
Show 6 more facts
- defined daily dose
- 0.134
- chemical formula
- C₅₉H₈₄N₁₆O₁₂
- World Health Organisation international non-proprietary name
- leuprorelin
- canonical SMILES
- CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
- 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](CC(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6
- Commons category
- Leuprorelin
via Wikidata · CC0
~11 min read
Article
17 sectionsContents
- Medical uses
- Side effects
- Lupron "flare"
- Pharmacology
- Mechanism of action
- Available forms
- Chemistry
- History
- Approvals
- Society and culture
- Legal status
- Names
- Legal history
- Research
- Veterinary use
- References
- Further reading
Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, for early puberty, as part of transgender hormone therapy, or to perform chemical castration of violent sex offenders. It is given by injection into a muscle or under the skin.
Leuprorelin is in the gonadotropin-releasing hormone (GnRH) analogue family of medications. It works by decreasing gonadotropins, thereby decreasing testosterone and estradiol. Common side effects include hot flashes, unstable mood, trouble sleeping, headaches, and pain at the site of injection. Other side effects may include high blood sugar, allergic reactions, and problems with the pituitary gland. Use during pregnancy may harm foetal development.