CETRORELIX MONOACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C70H92ClN17O14.C2H4O2
Molecular Weight	1491.0927
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC2=CN=CC=C2)NC(=O)[C@@H](CC3=CC=C(Cl)C=C3)NC(=O)[C@@H](CC4=CC5=CC=CC=C5C=C4)NC(C)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N6CCC[C@H]6C(=O)N[C@H](C)C(N)=O

InChI

InChIKey=KFEFLCOCAHJBEA-ANRVCLKPSA-N

InChI=1S/C70H92ClN17O14.C2H4O2/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44;1-2(3)4/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102);1H3,(H,3,4)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C70H92ClN17O14
Molecular Weight	1431.0406
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021197s010lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00050

Cetrorelix is a synthetic decapeptide with gonadotropin-releasing hormone (GnRH) antagonistic activity. GnRH induces the production and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the gonadotrophic cells of the anterior pituitary. Due to a positive estradiol (E2) feedback at midcycle, GnRH liberation is enhanced resulting in an LH-surge. This LH-surge induces the ovulation of the dominant follicle, resumption of oocyte meiosis and subsequently luteinization as indicated by rising progesterone levels. Cetrorelix competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion. It competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix is marketed primarily under the brand name Cetrotide. Cetrotide (cetrorelix acetate for injection) is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian stimulation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021197s010lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/11462984	Antagonist 2849		1.21 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Female infertility 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021197s010lbl.pdf	Primary		Approved 8583	CETROTIDE Approved Use Cetrotide (cetrorelix acetate for injection) is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian stimulation. Launch Date 2000

C_max

Value	Dose	Analyte	Population
28.5 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
4.97 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg single, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
6.42 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg 1 times / day multiple, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
536 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
31.4 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg single, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
44.5 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg 1 times / day multiple, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
62.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg single, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
20.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	0.25 mg 1 times / day multiple, subcutaneous dose: 0.25 mg route of administration: Subcutaneous experiment type: MULTIPLE co-administered:	CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
14% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2000/21197lbl.pdf	3 mg single, subcutaneous dose: 3 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		CETRORELIX plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 mg 1 times / day multiple, subcutaneous Highest studied dose Dose: 5 mg, 1 times / day Route: subcutaneous Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26460564	unhealthy, 58.9 ± 8.3 years Health Status: unhealthy Age Group: 58.9 ± 8.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/26460564	Sources: https://pubmed.ncbi.nlm.nih.gov/26460564

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252		inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8/9 42 CYP2C19 2057 CYP2E1 1060 BSEP 550 MRP2 499 MRP3 246 MRP4 290	CYP 303

Drug as perpetrator

Target	Modality	Activity
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
CYP2C8/9 42	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2006/P200600012/53019100_21800AMY10090_W100_1.pdf#PAGE=34 Page: (PMDA_W100) 37	no
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes [IC50 1.47 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21-197_Cetrotide_biopharmr.pdf#page=9 Page: 9.0	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:59224	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59224
ChemicalBook	CB0316370	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0316370
ChemicalBook	CB9874701	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9874701
MolPort	MolPort-009-194-176	https://www.molport.com/shop/molecule-link/MolPort-009-194-176
MolPort	MolPort-042-652-596	https://www.molport.com/shop/molecule-link/MolPort-042-652-596

PubMed

Title	Date	PubMed
Gonadotropin-releasing hormone receptor gene expression during pubertal development of female rats.	2004-02	14561652
Expression and function of gonadotropin-releasing hormone (GnRH) receptor in human olfactory GnRH-secreting neurons: an autocrine GnRH loop underlies neuronal migration.	2004-01-02	14565958
Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models.	2004-01	14605254
Preferential ligand selectivity of the monkey type-II gonadotropin-releasing hormone (GnRH) receptor for GnRH-2 and its analogs.	2003-11-14	14604814
[Revisiting the clomifene-gonadotropin protocol in IVF with the use of a GnRH antagonist].	2003-11	14623556
Gonadal protection from radiation by GnRH antagonist or recombinant human FSH: a controlled trial in a male nonhuman primate (Macaca fascicularis).	2003-11	14596670
GnRH-II analogs for selective activation and inhibition of non-mammalian and type-II mammalian GnRH receptors.	2003-10-31	14651258
Role of gonadotropin-releasing hormone (GnRH) in ovarian cancer.	2003-10-07	14594454
GnRH antagonist in in vitro fertilization: where we are now.	2003-10	14581880
Regulatory effects of gonadotropin-releasing hormone (GnRH) I and GnRH II on the levels of matrix metalloproteinase (MMP)-2, MMP-9, and tissue inhibitor of metalloproteinases-1 in primary cultures of human extravillous cytotrophoblasts.	2003-10	14557455
Depot GnRH agonist versus the single dose GnRH antagonist regimen (cetrorelix, 3 mg) in patients undergoing assisted reproduction treatment.	2003-09	14567887
Phase II study of cetrorelix, a luteinizing hormone-releasing hormone antagonist in patients with platinum-resistant ovarian cancer.	2003-09	13678723
The use of gonadotropin-releasing hormone antagonist in a flexible protocol: a pilot study.	2003-08	14520215
Differential effects of gonadotropin-releasing hormone I and II on the urokinase-type plasminogen activator/plasminogen activator inhibitor system in human decidual stromal cells in vitro.	2003-08	12915673
Prolactin inhibits annexin 5 expression and apoptosis in the corpus luteum of pseudopregnant rats: involvement of local gonadotropin-releasing hormone.	2003-08	12865345
The steroidogenic response and corpus luteum expression of the steroidogenic acute regulatory protein after human chorionic gonadotropin administration at different times in the human luteal phase.	2003-07	12843197
An overview of GnRH antagonists in infertility treatments. Introduction.	2003-07	12831912
Actions of GnRH antagonists on IGF-II, IGF-binding protein-2 and pregnancy-associated plasma protein-A in human granulosa-lutein cells.	2003-07	12824863
PT-141: a melanocortin agonist for the treatment of sexual dysfunction.	2003-06	12851303
Josef Rudinger Memorial Lecture 2002. Peptide related drug research.	2003-06	12846479
No influence of body weight on pregnancy rate in patients treated with cetrorelix according to the single- and multiple-dose protocols.	2003-06	12831598
Single dose application of cetrorelix in combination with clomiphene for friendly IVF: results of a feasibility study.	2003-06	12831591
Safety and efficacy of a 3 mg dose of the GnRH antagonist cetrorelix in preventing premature LH surges: report of two large multicentre, multinational, phase IIIb clinical experiences.	2003-06	12831588
The impact of LH serum concentration on the clinical outcome of IVF cycles in patients receiving two regimens of clomiphene citrate/gonadotrophin/0.25 mg cetrorelix.	2003-06	12831586
Impact of the gonadotropin-releasing hormone antagonist in oocyte donation cycles.	2003-06	12798903
GnRH antagonists in the treatment of gynecological and breast cancers.	2003-06	12790790
The administration of the GnRH antagonist, cetrorelix, to ooctye donors simplifies oocyte donation.	2003-06	12773455
Stimulation of luteinizing hormone secretion by N-methyl-D,L-aspartic acid in the adult male guinea-pig: incomplete blockade by gonadotropin-releasing hormone receptor antagonism.	2003-05	12694377
Gonadotropin-releasing hormone receptor gene expression during pubertal development of male rats.	2003-05	12606421
An evaluation of the multiple dose protocol of cetrorelix in single ovary women.	2003-03-27	12655797
Gonadotrophin-releasing hormone antagonists: will they replace the agonists?	2003-03-11	12626142
Pharmacokinetic/pharmacodynamic modeling of luteinizing hormone (LH) suppression and LH surge delay by cetrorelix after single and multiple doses in healthy premenopausal women.	2003-03	12638392
Sperm to zona pellucida binding depends on the use of a gonadotropin-releasing hormone agonist or a gonadotropin-releasing hormone antagonist.	2003-03	12620461
Signalling and anti-proliferative effects mediated by gonadotrophin-releasing hormone receptors after expression in prostate cancer cells using recombinant adenovirus.	2003-02	12553876
The use of clomiphene citrate/human menopausal gonadotrophins in conjunction with GnRH antagonist in an IVF/ICSI program is not a cost effective protocol.	2003-01	12580839
Ovarian stimulation by clomiphene citrate and hMG in combination with cetrorelix acetate for ICSI cycles.	2003-01	12525439
Use of GnRH antagonists in the treatment of endometriosis.	2002-12-10	12470539
The effects of gonadotropin-releasing hormone (GnRH) I and GnRH II on the urokinase-type plasminogen activator/plasminogen activator inhibitor system in human extravillous cytotrophoblasts in vitro.	2002-12	12466358
Clomiphene-induced LH surges and cetrorelix.	2002-11-07	12419033
Tailoring the GnRH antagonist cetrorelix acetate to individual patients' needs in ovarian stimulation for IVF: results of a prospective, randomized study.	2002-11	12407036
Comparison of the effects of two GnRH antagonists on LH and FSH secretion, follicular growth and ovulation in the mare.	2002-10-31	12405453
Effective treatment of experimental ES-2 human ovarian cancers with a cytotoxic analog of luteinizing hormone-releasing hormone AN-207.	2002-10	12394258
Effectiveness of an antagonist to gonadotrophin releasing hormone on the FSH and LH response to GnRH in perifused equine pituitary cells, and in seasonally acyclic mares.	2002-09-16	12220817
[Use of GnRH antagonists (cetrorelix) in assisted reproduction: first report in Mexican literature].	2002-09	12448050
Novel formulations of cetrorelix acetate in healthy men: pharmacodynamic effects and noncompartmental pharmacokinetics.	2002-09	12211225
Inhibition of recovery of spermatogenesis in irradiated rats by different androgens.	2002-09	12193551
Regulation of microsomal P450, redox partner proteins, and steroidogenesis in the developing testes of the neonatal pig.	2002-09	12193548
New drugs 2002, part 1.	2002-01	12352750
The place of gonadotrophin-releasing hormone antagonists in reproductive medicine.	2002	12470569
[Reproductive health--new hormonal agents to treat infertility].	2002	12412351

Patents

Sample Use Guides

In Vivo Use Guide

Ovarian stimulation therapy with gonadotropins (FSH, hMG) is started on cycle Day 2 or 3. The dose of gonadotropins should be adjusted according to individual response. Cetrotide (cetrorelix acetate for injection) may be administered subcutaneously either once daily (0.25 mg dose) or once (3 mg dose) during the early- to mid-follicular phase. In the single dose regimen, 3 mg of Cetrotide (Cetrorelix) is administered when the serum estradiol level is indicative of an appropriate stimulation response, usually on stimulation day 7 (range day 5-9). If hCG has not been administered within four days after injection of Cetrotide 3 mg, Cetrotide 0.25 mg should be administered once daily until the day of hCG administration. In the multiple dose regimen, 0.25 mg of Cetrotide is administered on either stimulation day 5 (morning or evening) or day 6 (morning) and continued daily until the day of hCG administration.

Route of Administration: Other

In Vitro Use Guide

Cetrorelix inhibited rat granulosa cell growth dose-dependently in the range of 10(-10)-10(-5) M

Substance Class	Chemical Created by `admin` on `Tue Apr 01 17:01:36 GMT 2025` Edited by `admin` on `Tue Apr 01 17:01:36 GMT 2025`
Record UNII	XPQ226310Q
Record Status	`FAILED`
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Name

Type

Language

D-ALANINAMIDE, N-ACETYL-3-(2-NAPHTHALENYL)-D-ALANYL-4-CHLORO-D-PHENYLALANYL-3-(3-PYRIDINYL)-D-ALANYL-L-SERYL-L-TYROSYL-N5-(AMINOCARBONYL)-D-ORNITHYL-L-LEUCYL-L-ARGINYL-L-PROLYL-, ACETATE (1:1)

Preferred Name

English

CETRORELIX MONOACETATE

Common Name

English

CETRORELIX MONOACETATE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m3295