GOSERELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C59H84N18O14
Molecular Weight	1269.4128
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

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

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	Agonist 2,752
LNCaP 3	Inhibitor 8,504	0.82 nM [IC50]
Gonadotropin-releasing hormone receptor 41	Agonist 2,752	1.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Locally confined carcinoma of the prostate 2	Primary		Approved 8,583	ZOLADEX
Advanced carcinoma of the prostate 2	Palliative		Approved 8,583	ZOLADEX

C_max

Value	Dose	Analyte	Population
7.79 μg/L	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
13.9 μg/L	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
7.5 μg/L	250 μg single, subcutaneous	GOSERELIN plasma	Homo sapiens
9.5 μg/L	250 μg 1 times / day multiple, subcutaneous	GOSERELIN plasma	Homo sapiens
2.84 ng/mL	3.6 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens
1.46 ng/mL	3.6 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens
8.85 ng/mL	10.8 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens
3 ng/mL	3.6 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
36.9 μg × h/L	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
41.3 μg × h/L	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
44.5 μg × h/L	250 μg single, subcutaneous	GOSERELIN plasma	Homo sapiens
44 μg × h/L	250 μg 1 times / day multiple, subcutaneous	GOSERELIN plasma	Homo sapiens
27.8 ng × day/mL	3.6 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens
18.5 ng × day/mL	3.6 mg single, subcutaneous	GOSERELIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.2 h	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
2.3 h	250 μg single, subcutaneous	GOSERELIN serum	Homo sapiens
4.6 h	250 μg single, subcutaneous	GOSERELIN plasma	Homo sapiens
5 h	250 μg 1 times / day multiple, subcutaneous	GOSERELIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
73%	10.8 mg single, subcutaneous		GOSERELIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years	Other AEs: Fatigue, Hot flashes...
10.8 mg 1 times / day steady, subcutaneous Recommended	unhealthy, adult	Other AEs: Gastrointestinal disorder (NOS), Bladder disorder NOS...
10.8 mg 1 times / day steady, subcutaneous Recommended	unhealthy, adult	Other AEs: Diarrhea, Cystitis...

Showing 1 to 3 of 3 entries

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AEs

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AE	Significance	Dose	Population
Muscle pain	grade 2, 1 patient	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years
Sweating	grade 2, 10 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years
Dryness vaginal	grade 2, 12 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years
Headache	grade 2, 12 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years
Fatigue	grade 2, 2 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years

Showing 1 to 5 of 23 entries

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0290	http://www.3bsc.com/index/pro_info.php?id=19646
abcr GmbH	AB477773	http://www.abcr.de/shop/en/AB477773
Achemtek	0104-042050	http://www.achemtek.com/65807-02-5
Acorn PharmaTech	ACN-057301	http://www.acornpharmatech.com/
AHH Chemical co.,ltd	API-1276	http://www.ahhchemical.com/product/API-1276.html

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PubMed

Show entries

Title	Date	PubMed
[Severe toxic hepatitis during flutamide (Eulexin) treatment].	1989 Jan 16	2911917
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
Randomized trial of adjuvant tamoxifen and/or goserelin in premenopausal breast cancer--self-rated physiological effects and symptoms.	2000	11207003
Gonadotrophin-releasing hormone agonist treatment of aggression in Alzheimer's disease: a case report.	2005 Jun	16050439

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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.

Show entries

Name

Type

Language

ICI 118,630

Preferred Name

English

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

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Classification Tree

Code System

Code

Therapeutic Hormone

NCI_THESAURUS

C1910

Prostate cancer

LIVERTOX

NBK548740

Established Pharmacologic Class

NDF-RT

N0000175655

Gonadotropin releasing hormone analogues

WHO-VATC

QL02AE03

Gonadotropin releasing hormone analogues

WHO-ATC

L02AE03

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Code System

Code

Type

Description

DRUG BANK

DB00014

PRIMARY

ChEMBL

CHEMBL1201247

PRIMARY

EPA CompTox

DTXSID7048297

PRIMARY

CAS

65807-02-5

PRIMARY

HSDB

7606

PRIMARY

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ACTIVE MOIETY


					0F65R8P09N

GOSERELIN

SALT/SOLVATE (PARENT)


					6YUU2PV0U8

GOSERELIN ACETATE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound