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Details

Stereochemistry ABSOLUTE
Molecular Formula C60H86N16O13
Molecular Weight 1239.4242
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUSERELIN

SMILES

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](CC2=CC=C(O)C=C2)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=C3C=CC=C4)NC(=O)[C@H](CC5=CNC=N5)NC(=O)[C@@H]6CCC(=O)N6

InChI

InChIKey=CUWODFFVMXJOKD-UVLQAERKSA-N
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

HIDE SMILES / InChI

Molecular Formula C60H86N16O13
Molecular Weight 1239.4242
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: http://www.netdoctor.co.uk/medicines/sexual-health/a7588/suprecur-buserelin/

Buserelin is a synthetic peptide analog of the luteinizing hormone-releasing hormone (LHRH) agonist, which stimulates the pituitary gland's gonadotrophin-releasing hormone receptor (GnRHR). Buserelin is used for palliative treatment of prostate cancer, and for treatment of endometriosis. Buserelin is also used for infertility treatment to prepare the pituitary gland before starting treatment with gonadotrophins (FSH and LH) to artificially stimulate ovulation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.12 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
SUPREFACT

Approved Use

The palliative treatment (initial and maintenance treatment) of patients with hormonedependent advanced carcinoma of the prostate gland
Primary
SUPREFACT

Approved Use

SUPREFACT® (buserelin acetate) nasal solution is indicated for the treatment of endometriosis in patients who do not require surgery as primary therapy. The duration of treatment is usually six months and should not exceed nine months.
Primary
SUPERCUR

Approved Use

This medicine is used to prepare the pituitary gland before starting treatment with gonadotrophins (FSH and LH) to artificially stimulate ovulation.
PubMed

PubMed

TitleDatePubMed
Specific binding of a potent LHRH agonist in rat testis.
1980 Nov
Specific binding of a potent LHRH agonist in rat testis.
1980 Nov
The neurochemistry of the GnRH pulse generator.
1996
Patents

Sample Use Guides

In Vivo Use Guide
Buserelin is marketed as a nasal spray or as a solution for subcutaneous injections. For palliative treatment of patients with prostate cancer, for the first seven days of treatment give 500 mcg (0.5 mL) every 8 hours should be given by subcutaneous injection. The dose of buserelin in patients with endometriosis is 400 mcg (200 mcg into each nostril) three times daily using the metered-dose pump (nebulizer) provided.
Route of Administration: Other
In Vitro Use Guide
Binding affinity of buserelin towards gonadotrophin-releasing hormone receptor was measured using rat Leydig cells and iodinated buserelin as a radioligand. The iodinated buserelin to a single class of high affinity sites at a KD value of 0.12 nM and the number of binding sites is approx. 2500 per interstitial cell. The agonistic activitt was measured as the potency of the peptides to stimulate and inhibit LHRH-induced LH release in rat anterior pituitary cells in primary culture.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:31:03 UTC 2023
Edited
by admin
on Thu Jul 06 00:31:03 UTC 2023
Record UNII
PXW8U3YXDV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUSERELIN
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
buserelin [INN]
Common Name English
LUTEINIZING HORMONE-RELEASING FACTOR (PIG), 6-(O-(1,1-DIMETHYLETHYL)-D-SERINE)-9-(N-ETHYL-L-PROLINAMIDE)-10-DEGLYCINAMIDE-
Common Name English
(DES-GLY10,D-SER(TBU)6,PRO-NHET9)-LHRH
Common Name English
Buserelin [WHO-DD]
Common Name English
5-OXO-L-PROLYL-L-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TYROSYL-O-TERT-BUTYL-D-SERYL-L-LEUCYL-L-ARGINYL-N-ETHYL-L-PROLINAMIDE
Common Name English
BUSERELIN [MART.]
Common Name English
TILORYTH
Brand Name English
BUSERELIN [MI]
Common Name English
BUSERELIN [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1910
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
WHO-ATC L02AE01
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
WHO-VATC QL02AE01
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
WHO-VATC QH01CA90
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
Code System Code Type Description
SMS_ID
100000088470
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
DAILYMED
PXW8U3YXDV
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
RXCUI
1825
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY RxNorm
FDA UNII
PXW8U3YXDV
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
IUPHAR
3860
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
CAS
57982-77-1
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110824
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID301024155
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
EVMPD
SUB05991MIG
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
DRUG BANK
DB06719
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
WIKIPEDIA
BUSERELIN
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
NCI_THESAURUS
C320
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
PUBCHEM
50225
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
261-061-9
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
MERCK INDEX
M2776
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY Merck Index
INN
4045
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
MESH
D002064
Created by admin on Thu Jul 06 00:31:03 UTC 2023 , Edited by admin on Thu Jul 06 00:31:03 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY