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leuprolide

CHEBI:CHEBI_6427

Definition

An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the acetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.

Chemical Information

Molecular Formula
C59H84N16O12
Molecular Mass
1209.39830
Charge
0
SMILES
CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(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](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1
InChI
InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1
InChIKey
GFIJNRVAKGFPGQ-LIJARHBVSA-N

Alternative Names

  • (D-Leu(6),des-Gly-NH2(10),Pro-ethylamide(9))-gonadotropin-releasing hormone
  • 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
  • L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamide
  • Leuprorelin
  • leuprorelina
  • leuproreline
  • leuprorelinum
  • pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5
  • pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

core#notation
CHEBI:6427
DRON_00010000
42375
oboInOwl#hasDbXref
Reaxys:741818

Additional References

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

dosage_form
INJECTION, SUSPENSION, EXTENDED RELEASE
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
listing_expiration_date
20241231
marketing_start_date
19901022
labeler_name
CIPLA USA INC.
application_number
NDA021731
spl_id
e7a0a17e-c072-4cde-b7ae-8662dcbc079b
product_ndc
55150-478
package_description
1 BOTTLE in 1 BOTTLE (41701-013-54) / 111 g in 1 BOTTLE (41701-013-53)
package_ndc
54127-9002-1
route
SUBCUTANEOUS
rxcui
2371773
package_marketing_start_date
15-JAN-21
manufacturer_name
CIPLA USA INC.
core#notation
CHEBI:6427
spl_set_id
b78d1919-9dee-44fa-90f9-e0a26d32481d
active_ingredient_strength
111 g/111g
active_ingredient_name
LEUPROLIDE
unii
37JNS02E7V
pharm_class
Gonadotropin Releasing Hormone Receptor Agonists [MoA]
upc
0355150338016
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
42375
oboInOwl#hasDbXref
Reaxys:741818
oboInOwl#id
CHEBI:6427
generic_name
LEUPROLIDE
brand_name
ELIGARD
brand_name_base
ELIGARD
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_63533
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
has_treatment
http://purl.obolibrary.org/obo/DOID_2510
owl#annotatedSource
t266344
owl#someValuesFrom
t3898364