Goserelin

Source: Wikipedia, the free encyclopedia.
Goserelin
GnRH agonist; Antigonadotropin
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding27.3%
Elimination half-life4–5 hours
Identifiers
  • N-(21-((1H-indol-3-yl)methyl)-1,1-diamino-12-(tert-butoxymethyl)-6-(2-(2-carbamoylhydrazinecarbonyl)cyclopentanecarbonyl)-15-(4-hydroxybenzyl)-18-(hydroxymethyl)-25-(1H-imidazol-5-yl)-9-isobutyl-8,11,14,17,20,23-hexaoxo-2,7,10,13,16,19,22-heptaazapentacos-1-en-24-yl)-5-oxopyrrolidine-2-carboxamide
JSmol)
  • CC(C)C[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NNC(N)=O
  • InChI=1S/C59H84N18O14/c1-31(2)22-40(49(82)68-39(12-8-20-64-57(60)61)56(89)77-21-9-13-46(77)55(88)75-76-58(62)90)69-54(87)45(29-91-59(3,4)5)74-50(83)41(23-32-14-16-35(79)17-15-32)70-53(86)44(28-78)73-51(84)42(24-33-26-65-37-11-7-6-10-36(33)37)71-52(85)43(25-34-27-63-30-66-34)72-48(81)38-18-19-47(80)67-38/h6-7,10-11,14-17,26-27,30-31,38-46,65,78-79H,8-9,12-13,18-25,28-29H2,1-5H3,(H,63,66)(H,67,80)(H,68,82)(H,69,87)(H,70,86)(H,71,85)(H,72,81)(H,73,84)(H,74,83)(H,75,88)(H4,60,61,64)(H3,62,76,90)/t38-,39-,40-,41-,42-,43-,44-,45+,46-/m0/s1 checkY
  • Key:BLCLNMBMMGCOAS-URPVMXJPSA-N checkY
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Goserelin, sold under the brand name Zoladex among others, is a

gonadotropin releasing hormone agonist
(GnRH agonist).

Structurally, it is a

decapeptide. It is the natural GnRH decapeptide with two substitutions
to inhibit rapid degradation.

Goserelin stimulates the production of the sex hormones testosterone and estrogen in a non-pulsatile (non-physiological) manner. This causes the disruption of the endogenous hormonal feedback systems, resulting in the down-regulation of testosterone and estrogen production.

It was patented in 1976 and approved for medical use in 1987.[4] It is on the World Health Organization's List of Essential Medicines.[5]

Medical uses

10.8mg implant syringe

Goserelin is used to treat hormone-sensitive cancers of the

assisted reproduction and in the treatment of precocious puberty. It may also be used in the treatment of male-to-female transgender people.[6]

Side effects

Goserelin may cause

swelling and tenderness of breasts (infrequent), decreased erections and reduced sexual desire. Bone pain can be managed symptomatically, and erectile dysfunction can be treated by vardenafil (Levitra) or other similar oral therapies, although they will not treat the reduced sexual desire. The rates of gynecomastia with goserelin have been found to range from 1 to 5%.[7]

Short-term memory impairment has also been reported in women and may in some cases be severe, but this effect disappears gradually once treatment is discontinued.[8]<[9]

Pharmacology

Goserelin is a synthetic analogue of a naturally occurring

downregulation, and sex hormones are generally reduced to castrate levels.[10]

Chemistry

Goserelin is a

decapeptide. It is provided as the acetate salt
.

Society and culture

Names

Goserelin is the

INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BAN
Tooltip British Approved Name.

References

  1. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  2. ISBN 978-0-412-54090-5
    .
  3. ISBN 978-94-011-4439-1
    .
  4. ISBN 9783527607495
    .
  5. hdl:10665/345533
    . WHO/MHP/HPS/EML/2021.02.
  6. PMID 16320157
    .
  7. PMID 16321765
    .
  8. ^ Newton CR, Yuzpe AA, Timmon IS, Slota MD (October 1993). Memory complaints: a side effect of continued exposure to gonadotropin-releasing hormone agonists (GnRHa). Conjoint Annual Meetings of the American Fertility Society and the Canadian Fertility and Andrology Society. Montreal, Canada.
  9. PMID 8425646
    .
  10. PMID 10678560
    .
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