Buserelin

Buserelin
Clinical data
Trade namesSuprefact, others
Other namesEtilamide; HOE-766; HOE-766A; ICI-123215; S-746766; D-Ser(tBu)6EA10-LHRH; 6-[O-(1,1-Dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)-10-deglycinamide-LHRH (pig)
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • X
Routes of
administration		Nasal spray, subcutaneous injection, subcutaneous implant[1][2]
Drug classGnRH analogue; GnRH agonist; Antigonadotropin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: ineffective[1]
Intranasal: 2.5–3.3%[3]
Subcutaneous: 70%[1]
Protein binding15%[1]
MetabolismLiver, kidneys, gastrointestinal tract (pyroglutamyl peptidase, chymotrypsin-like endopeptidase)[1]
MetabolitesBuserelin (1–5)[4]
Elimination half-lifeIntravenous: 50–80 min[5]
Subcutaneous: 80 min[5]
Intranasal: 1–2 hours[5]
ExcretionUrine, bile[3][5]
Identifiers
  • (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]-3-[(2-methylpropan-2-yl)oxy]-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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.493 Edit this at Wikidata
Chemical and physical data
FormulaC60H86N16O13
Molar mass1239.447 g·mol−1
3D model (JSmol)
  • CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4c3cccc4)NC(=O)[C@H](Cc5cnc[nH]5)NC(=O)[C@@H]6CCC(=O)N6
  • InChI=1S/C60H86N16O13/c1-7-64-57(87)48-15-11-23-76(48)58(88)41(14-10-22-65-59(61)62)69-51(81)42(24-33(2)3)70-56(86)47(31-89-60(4,5)6)75-52(82)43(25-34-16-18-37(78)19-17-34)71-55(85)46(30-77)74-53(83)44(26-35-28-66-39-13-9-8-12-38(35)39)72-54(84)45(27-36-29-63-32-67-36)73-50(80)40-20-21-49(79)68-40/h8-9,12-13,16-19,28-29,32-33,40-48,66,77-78H,7,10-11,14-15,20-27,30-31H2,1-6H3,(H,63,67)(H,64,87)(H,68,79)(H,69,81)(H,70,86)(H,71,85)(H,72,84)(H,73,80)(H,74,83)(H,75,82)(H4,61,62,65)/t40-,41-,42-,43-,44-,45-,46-,47+,48-/m0/s1 checkY
  • Key:CUWODFFVMXJOKD-UVLQAERKSA-N checkY
  (verify)

Buserelin, sold under the brand name Suprefact among others, is a medication which is used primarily in the treatment of prostate cancer and endometriosis.[3][1][2] It is also used for other indications such as the treatment of premenopausal breast cancer, uterine fibroids, and early puberty, in assisted reproduction for female infertility, and as a part of transgender hormone therapy.[6][3][7] In addition, buserelin is used in veterinary medicine.[8] The medication is typically used as a nasal spray three times per day, but is also available for use as a solution or implant for injection into fat.[1][2]

Side effects of buserelin are related to sex hormone deprivation and include symptoms of low testosterone levels and low estrogen levels such as hot flashes, sexual dysfunction, vaginal atrophy, and osteoporosis.[3][1] Buserelin is a gonadotropin-releasing hormone agonist (GnRH agonist) and works by preventing the production of sex hormones by the gonads.[3][1] It can lower sex hormone levels by about 95% in both sexes.[9][10][11] Buserelin is a peptide and an analogue of GnRHTooltip gonadotropin-releasing hormone.[12]

Buserelin was first patented in 1974 and approved for medical use in 1985.[13] It is not available in the United States, but is marketed widely elsewhere in the world, including in the United Kingdom, Canada, and many other countries.[14][8][15] The medication is one of only two medically used GnRH analogues that are available as nasal sprays, the other being nafarelin.[16] Buserelin is available as a generic medication.[17][18]

  1. ^ a b c d e f g h i "Suprefact - Buserelin Acetate (Product Monograph)" (PDF). Sanofi Aventis. August 10, 2015. Archived (PDF) from the original on April 23, 2018. Retrieved December 17, 2017.
  2. ^ a b c "Suprefact Depot 2 months and Suprefact Depot 3 months (Product Monograph)" (PDF). Sanofi Aventis. August 10, 2015. Archived (PDF) from the original on June 19, 2018. Retrieved December 17, 2017.
  3. ^ a b c d e f Brogden RN, Buckley MM, Ward A (March 1990). "Buserelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical profile". Drugs. 39 (3): 399–437. doi:10.2165/00003495-199039030-00007. PMID 2109679. S2CID 195691965.
  4. ^ Höffken K (6 December 2012). Peptides in Oncology I: LH-RH Agonists and Antagonists. Springer Science & Business Media. pp. 77–. ISBN 978-88-470-2186-0. Archived from the original on 11 February 2022. Retrieved 17 December 2017.
  5. ^ a b c d "Buserelin". Archived from the original on 2018-03-12. Retrieved 2017-12-17.
  6. ^ "Buserelin - Pharm-Sintez - AdisInsight". Archived from the original on 2017-12-24. Retrieved 2017-12-17.
  7. ^ Wilczynski C, Emanuele MA (November 2014). "Treating a transgender patient: overview of the guidelines". Postgraduate Medicine. 126 (7): 121–128. doi:10.3810/pgm.2014.11.2840. PMID 25387220. S2CID 22639336.
  8. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Hemat2003 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Becker2001 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference CorsonDerman1995 was invoked but never defined (see the help page).
  12. ^ Srivastava V (26 June 2017). Peptide-based Drug Discovery: Challenges and New Therapeutics. Royal Society of Chemistry. pp. 182–. ISBN 978-1-78262-732-6. Archived from the original on 28 October 2021. Retrieved 6 January 2018.
  13. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 978-3-527-60749-5. Archived from the original on 2021-06-20. Retrieved 2020-09-19.
  14. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference DPD@HealthCanada was invoked but never defined (see the help page).
  16. ^ Önerci TM (17 August 2013). Nasal Physiology and Pathophysiology of Nasal Disorders. Springer Science & Business Media. pp. 208–. ISBN 978-3-642-37250-6. Archived from the original on 28 October 2021. Retrieved 6 January 2018.
  17. ^ Farkas E, Ryadnov M (31 August 2013). Amino Acids, Peptide and Proteins. Royal Society of Chemistry. pp. 227–. ISBN 978-1-84973-585-8. Archived from the original on 11 February 2022. Retrieved 17 December 2017.
  18. ^ "CinnaGen: CinnaFact". Archived from the original on 2018-01-06. Retrieved 2017-12-17.