BUSERELIN

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 Search

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
Sources: http://products.sanofi.ca/en/suprefact.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6777213	Agonist 2678		0.12 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: http://products.sanofi.ca/en/suprefact.pdf	Palliative	Approved 8429	SUPREFACT Approved Use The palliative treatment (initial and maintenance treatment) of patients with hormonedependent advanced carcinoma of the prostate gland
Endometriosis 32 Sources: http://products.sanofi.ca/en/suprefact.pdf	Primary	Approved 8429	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.
Infertility 14 Sources: http://www.netdoctor.co.uk/medicines/sexual-health/a7588/suprecur-buserelin/	Primary	Approved 8429	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

Title	Date	PubMed
Specific binding of a potent LHRH agonist in rat testis.	1980 Nov	6777213
Specific binding of a potent LHRH agonist in rat testis.	1980 Nov	6777213
The neurochemistry of the GnRH pulse generator.	1996	8917899

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 `Fri Dec 15 17:08:51 GMT 2023` Edited by `admin` on `Fri Dec 15 17:08:51 GMT 2023`
Record UNII	PXW8U3YXDV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUSERELIN

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