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

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

Molecular Formula	C59H84N18O14
Molecular Weight	1269.4105
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	4
Optical Activity	UNSPECIFIED

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 2,678
LNCaP 3	Inhibitor 8,297	0.82 nM [IC50]
Gonadotropin-releasing hormone receptor 41	Agonist 2,678	1.6 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Locally confined carcinoma of the prostate 2	Primary		Approved 8,429	ZOLADEX
Advanced carcinoma of the prostate 2	Palliative		Approved 8,429	ZOLADEX

C_max

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

AUC

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

T_1/2

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

F_unbound

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

Doses

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Dose	Population	Adverse events
3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years n = 103	Other AEs: Fatigue, Hot flashes...
10.8 mg 1 times / day steady, subcutaneous Recommended	unhealthy, adult n = 231	Other AEs: Diarrhea, Cystitis...
10.8 mg 1 times / day steady, subcutaneous Recommended	unhealthy, adult n = 231	Other AEs: Gastrointestinal disorder (NOS), Bladder disorder NOS...

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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 n = 103
Sweating	grade 2, 10 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years n = 103
Dryness vaginal	grade 2, 12 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years n = 103
Headache	grade 2, 12 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years n = 103
Fatigue	grade 2, 2 patients	3.6 mg 1 times / day steady, subcutaneous Recommended	unhealthy, 18 - 49 years n = 103

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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
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

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PubMed

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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
Frequency of flutamide induced hepatotoxicity in patients with prostate carcinoma.	1999 Mar	10215102
Randomized trial of adjuvant tamoxifen and/or goserelin in premenopausal breast cancer--self-rated physiological effects and symptoms.	2000	11207003

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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.