GOSERELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C59H84N18O14
Molecular Weight	1269.4105
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC2=CNC3=C2C=CC=C3)NC(=O)[C@H](CC4=CNC=N4)NC(=O)[C@@H]5CCC(=O)N5)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N6CCC[C@H]6C(=O)NNC(N)=O

InChI

InChIKey=BLCLNMBMMGCOAS-URPVMXJPSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00014
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/zoladex.html

Goserelin is a synthetic decapeptide analogue of LHRH. Goserelin acts as a potent inhibitor of pituitary gonadotropin secretion when administered in the biodegradable formulation. The result is sustained suppression of LH and serum testosterone levels. Goserelin is used to treat hormone-sensitive cancers of the breast (in pre- and peri- menopausal women) and prostate, and some benign gynaecological disorders (endometriosis, uterine fibroids and endometrial thinning). In addition, goserelin is used in assisted reproduction and in the treatment of precocious puberty. Goserelin is marketed under the brand names Zoladex, by AstraZeneca, or goserelin acetate.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Luteinizing hormone/Choriogonadotropin receptor 2 Target ID: CHEMBL1854 Sources: http://www.drugbank.ca/drugs/DB00014	Agonist 2678
LNCaP 3 Target ID: CHEMBL612518 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1320049	Inhibitor 8297	0.82 nM [IC50]
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: http://www.drugbank.ca/drugs/DB00014	Agonist 2678	1.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Locally confined carcinoma of the prostate 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	Primary		Approved 8429	ZOLADEX Approved Use ZOLADEX is a Gonadotropin Releasing Hormone (GnRH) agonist indicated for: Use in combination with flutamide for the management of locally confined carcinoma of the prostate Use as palliative treatment of advanced carcinoma of the prostate Launch Date 1997
Advanced carcinoma of the prostate 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	Palliative		Approved 8429	ZOLADEX Approved Use ZOLADEX is a Gonadotropin Releasing Hormone (GnRH) agonist indicated for: Use in combination with flutamide for the management of locally confined carcinoma of the prostate Use as palliative treatment of advanced carcinoma of the prostate Launch Date 1997

C_max

Value	Dose	Analyte	Population
1.46 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019726s050s051s052lbl.pdf	3.6 mg single, subcutaneous dose: 3.6 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2.84 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019726s050s051s052lbl.pdf	3.6 mg single, subcutaneous dose: 3.6 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.79 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.9 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
9.5 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg 1 times / day multiple, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.5 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
3 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019726s059,020578s037lbl.pdf	3.6 mg single, subcutaneous dose: 3.6 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.85 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019726s059,020578s037lbl.pdf	10.8 mg single, subcutaneous dose: 10.8 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
18.5 ng × day/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019726s050s051s052lbl.pdf	3.6 mg single, subcutaneous dose: 3.6 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
27.8 ng × day/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019726s050s051s052lbl.pdf	3.6 mg single, subcutaneous dose: 3.6 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
36.9 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
41.3 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
44 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg 1 times / day multiple, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
44.5 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4.2 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.3 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
5 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg 1 times / day multiple, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.6 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10926349	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:	GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
73% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019726s059,020578s037lbl.pdf	10.8 mg single, subcutaneous dose: 10.8 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		GOSERELIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.6 mg 1 times / day steady, subcutaneous Recommended Dose: 3.6 mg, 1 times / day Route: subcutaneous Route: steady Dose: 3.6 mg, 1 times / day Co-administed with:: Chemotherapy Sources: https://pubmed.ncbi.nlm.nih.gov/25738668/	unhealthy, 18 - 49 years n = 103 Health Status: unhealthy Condition: breast cancer Age Group: 18 - 49 years Sex: F Population Size: 103 Sources: https://pubmed.ncbi.nlm.nih.gov/25738668/	Other AEs: Fatigue, Hot flashes... Other AEs: Fatigue (grade 2, 2 patients) Hot flashes (grade 2, 29 patients) Menses irregular (grade 2, 5 patients) Libido decreased (grade 2, 9 patients) Agitation (grade 2, 6 patients) Anxiety (grade 2, 9 patients) Depression (grade 2, 8 patients) Muscle pain (grade 2, 1 patient) Headache (grade 2, 12 patients) Sweating (grade 2, 10 patients) Thromboembolism (grade 4, 1 patient) Dryness vaginal (grade 2, 12 patients) Hot flashes (grade 3, 4 patients) Menses irregular (grade 3, 2 patients) Depression (grade 3, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25738668/
10.8 mg 1 times / day steady, subcutaneous Recommended Dose: 10.8 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10.8 mg, 1 times / day Co-administed with:: flutamide after 90 days of radiation therapy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	unhealthy, adult n = 231 Health Status: unhealthy Condition: Prostatic Carcinoma Age Group: adult Sex: M Population Size: 231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	Other AEs: Diarrhea, Cystitis... Other AEs: Diarrhea (36%) Cystitis (16%) Bleeding rectal (14%) Proctitis (8%) Hematuria (7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf
10.8 mg 1 times / day steady, subcutaneous Recommended Dose: 10.8 mg, 1 times / day Route: subcutaneous Route: steady Dose: 10.8 mg, 1 times / day Co-administed with:: flutamide radiation therapy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	unhealthy, adult n = 231 Health Status: unhealthy Condition: Prostatic Carcinoma Age Group: adult Sex: M Population Size: 231 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf	Other AEs: Gastrointestinal disorder (NOS), Bladder disorder NOS... Other AEs: Gastrointestinal disorder (NOS) (80%) Bladder disorder NOS (58%) Skin and subcutaneous conditions NEC (37%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020578s034,020578s035lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0290	http://www.3bsc.com/index/pro_info.php?id=19646
AHH Chemical co.,ltd	API-1276	http://www.ahhchemical.com/product/API-1276.html
Achemtek	0104-042050	http://www.achemtek.com/65807-02-5
Acorn PharmaTech	ACN-057301	http://www.acornpharmatech.com/
Alfa Chemistry	AP145781926	https://reagents.alfa-chemistry.com/product/goserelin-acetate-cas-145781-92-6-5107.html
Alfa Chemistry	145781-92-6	https://www.alfa-chemistry.com/goserelin-acetate-cas-145781-92-6-item-290306.htm
ApexBio Technology	B3723	http://www.apexbt.com/goserelin-acetate.html
AvaChem Scientific	2222	http://www.avachem.com/productSearch.asp?2222
BOC Sciences	145781-92-6	https://www.bocsci.com/goserelin-acetate-cas-145781-92-6-item-58990.html
Chem Scene	CS-3114	http://www.chemscene.com/65807-02-5.html
Chemspace	CSSB02125551064	https://chem-space.com/CSSB02125551064
Glentham Life Sciences	GK2378	http://www.glentham.com/products/product/GK2378/
Lab Network	LN01254447	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01254447
MedChem Express	HY-13673	https://www.medchemexpress.com/Goserelin.html
MolPort	MolPort-006-823-831	https://www.molport.com/shop/molecule-link/MolPort-006-823-831
MuseChem	I004480	https://www.musechem.com/product/I004480.html
OChem	20403	http://www.ocheminc.com/index.php?act=psearch&pid=807G025
OChem	7371	http://www.ocheminc.com/index.php?act=psearch&pid=81G926
Smolecule	S529156	http://www.smolecule.com/products/s529156
THE BioTek	bt-269569	https://www.thebiotek.com/product/inhibitors/bt-269569
Yuhao Chemical	JZ0501	http://www.chemyuhao.com/145781-92-6.html
abcr GmbH	AB477773	http://www.abcr.de/shop/en/AB477773
iChemical	EBD22503	http://www.ichemical.com/chemicals/cas-65807-02-5

PubMed

Title	Date	PubMed
Anxiety and mood disorders associated with gonadotropin-releasing hormone agonist therapy.	1997	9230649
[A case of fulminant hepatitis caused by antiandrogen, flutamide in a patient with prostate cancer].	1997 Jul	9267134
Quality of life compared during pharmacological treatments and clinical monitoring for non-localized prostate cancer: a randomized controlled trial.	2004 May	15142146
Gonadotrophin-releasing hormone agonist treatment of aggression in Alzheimer's disease: a case report.	2005 Jun	16050439
Prostate specific antigen expression does not necessarily correlate with prostate cancer cell growth.	2006 Jul	16753443
A comparative study of the effect of raloxifene and gosereline on uterine leiomyoma volume changes and estrogen receptor, progesterone receptor, bcl-2 and p53 expression immunohistochemically in premenopausal women.	2007 Nov	16973256
Death due to liver failure during endocrine therapy for premenopausal breast cancer.	2010 Aug	20482225

Patents

Sample Use Guides

In Vivo Use Guide

ZOLADEX (Goserelin), at a dose of 3.6 mg, should be administered subcutaneously every 28 days into the anterior abdominal wall below the navel line using an aseptic technique under the supervision of a physician

Route of Administration: Other

In Vitro Use Guide

Goserelin significantly inhibited LNCaP cell proliferation at doses between 10(-9)-10(-6) M.

Name

Type

Language

GOSERELIN

Official Name

English

GOSERELIN [HSDB]

Common Name

English

Goserelin [WHO-DD]

Common Name

English

1-(5-OXO-L-PROLYL-L-HISTIDYL-L-TRYPTOPHYL-L-SERYL-L-TYROSYL-O-TERT-BUTYL-D-SERYL-L-LEUCYL-L-ARGINYL-L-PROLYL)SEMICARBAZIDE

Common Name

English

ICI 118,630

Code

English

GOSERELIN [EP MONOGRAPH]

Common Name

English

LUTEINIZING HORMONE-RELEASING FACTOR (PIG), 6-(O-(1,1-DIMETHYLETHYL)-D-SERINE)-10-DEGLYCINAMIDE-, 2-(AMINOCARBONYL)HYDRAZIDE

Common Name

English

goserelin [INN]

Common Name

English

GOSERELIN [USAN]

Common Name

English

GOSERELIN [MART.]

Common Name

English

ICI-118630

Code

English

GOSERELIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1910