U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C70H92ClN17O14.C2HF3O2
Molecular Weight 1545.061
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CETRORELIX TRIFLUOROACETATE

SMILES

OC(=O)C(F)(F)F.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=QJPSZAPHZMUGOX-ANRVCLKPSA-N
InChI=1S/C70H92ClN17O14.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m1./s1

HIDE SMILES / InChI
Molecular Formula C70H92ClN17O14
Molecular Weight 1431.038
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 3
Optical Activity UNSPECIFIED
Molecular Formula C2HF3O2
Molecular Weight 114.0233
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

2000
171
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 1.21 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
5 mg 1 times / day multiple, subcutaneous (starting)
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
n = 27
Health Status: unhealthy
Condition: Rheumatoid Arthritis
Age Group: 58.9 ± 8.3 years
Sex: M+F
Population Size: 27
Sources:
https://pubmed.ncbi.nlm.nih.gov/26460564
Sources:
https://pubmed.ncbi.nlm.nih.gov/26460564
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C8/9
44

CYP2C19
1478

CYP2E1
882

BSEP
402

MRP2
383

MRP3
157

MRP4
204
CYP
270
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MRP2
475
 no [IC50 >133 uM]
MRP3
207
 no [IC50 >133 uM]
MRP4
238
 no [IC50 >133 uM]
CYP1A2
1692
 no
CYP2C19
1553
 no
CYP2C8/9
44
 no
CYP2D6
1891
 no
CYP2E1
970
 no
CYP3A4
1925
 no
BSEP
403
 yes [IC50 1.47 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
The place of gonadotrophin-releasing hormone antagonists in reproductive medicine.
2002
[Reproductive health--new hormonal agents to treat infertility].
2002
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 Dec
New drugs 2002, part 1.
2002 Jan
Use of GnRH antagonists in the treatment of endometriosis.
2002 Jul-Aug
Comparison of the effects of two GnRH antagonists on LH and FSH secretion, follicular growth and ovulation in the mare.
2002 May-Jun
Tailoring the GnRH antagonist cetrorelix acetate to individual patients' needs in ovarian stimulation for IVF: results of a prospective, randomized study.
2002 Nov
Effective treatment of experimental ES-2 human ovarian cancers with a cytotoxic analog of luteinizing hormone-releasing hormone AN-207.
2002 Oct
[Use of GnRH antagonists (cetrorelix) in assisted reproduction: first report in Mexican literature].
2002 Sep
Novel formulations of cetrorelix acetate in healthy men: pharmacodynamic effects and noncompartmental pharmacokinetics.
2002 Sep
Inhibition of recovery of spermatogenesis in irradiated rats by different androgens.
2002 Sep
Regulation of microsomal P450, redox partner proteins, and steroidogenesis in the developing testes of the neonatal pig.
2002 Sep
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 Sep 16
Clomiphene-induced LH surges and cetrorelix.
2002 Sep-Oct
The use of gonadotropin-releasing hormone antagonist in a flexible protocol: a pilot study.
2003 Aug
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 Aug
Prolactin inhibits annexin 5 expression and apoptosis in the corpus luteum of pseudopregnant rats: involvement of local gonadotropin-releasing hormone.
2003 Aug
Signalling and anti-proliferative effects mediated by gonadotrophin-releasing hormone receptors after expression in prostate cancer cells using recombinant adenovirus.
2003 Feb
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 Jan
Ovarian stimulation by clomiphene citrate and hMG in combination with cetrorelix acetate for ICSI cycles.
2003 Jan
An evaluation of the multiple dose protocol of cetrorelix in single ovary women.
2003 Jan-Feb
Gonadotrophin-releasing hormone antagonists: will they replace the agonists?
2003 Jan-Feb
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 Jul
An overview of GnRH antagonists in infertility treatments. Introduction.
2003 Jul
Actions of GnRH antagonists on IGF-II, IGF-binding protein-2 and pregnancy-associated plasma protein-A in human granulosa-lutein cells.
2003 Jul
PT-141: a melanocortin agonist for the treatment of sexual dysfunction.
2003 Jun
Josef Rudinger Memorial Lecture 2002. Peptide related drug research.
2003 Jun
No influence of body weight on pregnancy rate in patients treated with cetrorelix according to the single- and multiple-dose protocols.
2003 Jun
Single dose application of cetrorelix in combination with clomiphene for friendly IVF: results of a feasibility study.
2003 Jun
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 Jun
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 Jun
Impact of the gonadotropin-releasing hormone antagonist in oocyte donation cycles.
2003 Jun
GnRH antagonists in the treatment of gynecological and breast cancers.
2003 Jun
The administration of the GnRH antagonist, cetrorelix, to ooctye donors simplifies oocyte donation.
2003 Jun
Pharmacokinetic/pharmacodynamic modeling of luteinizing hormone (LH) suppression and LH surge delay by cetrorelix after single and multiple doses in healthy premenopausal women.
2003 Mar
Sperm to zona pellucida binding depends on the use of a gonadotropin-releasing hormone agonist or a gonadotropin-releasing hormone antagonist.
2003 Mar
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 May
Gonadotropin-releasing hormone receptor gene expression during pubertal development of male rats.
2003 May
[Revisiting the clomifene-gonadotropin protocol in IVF with the use of a GnRH antagonist].
2003 Nov
Gonadal protection from radiation by GnRH antagonist or recombinant human FSH: a controlled trial in a male nonhuman primate (Macaca fascicularis).
2003 Nov
Preferential ligand selectivity of the monkey type-II gonadotropin-releasing hormone (GnRH) receptor for GnRH-2 and its analogs.
2003 Nov 14
GnRH antagonist in in vitro fertilization: where we are now.
2003 Oct
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 Oct
GnRH-II analogs for selective activation and inhibition of non-mammalian and type-II mammalian GnRH receptors.
2003 Oct 31
Role of gonadotropin-releasing hormone (GnRH) in ovarian cancer.
2003 Oct 7
Depot GnRH agonist versus the single dose GnRH antagonist regimen (cetrorelix, 3 mg) in patients undergoing assisted reproduction treatment.
2003 Sep
Phase II study of cetrorelix, a luteinizing hormone-releasing hormone antagonist in patients with platinum-resistant ovarian cancer.
2003 Sep
Gonadotropin-releasing hormone receptor gene expression during pubertal development of female rats.
2004 Feb
Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models.
2004 Jan
Expression and function of gonadotropin-releasing hormone (GnRH) receptor in human olfactory GnRH-secreting neurons: an autocrine GnRH loop underlies neuronal migration.
2004 Jan 2
Patents

Patents

JP2005526546A
32
JP2007504265A
10
JP2011525180A
180
JP2011528275A
455
JP3011770B2
9
JP4653399B2
50
JP4708327B2
47
JPH07194670A
5
JPH09227404A
5

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 Sat Dec 16 09:26:48 GMT 2023
Edited
by admin
on Sat Dec 16 09:26:48 GMT 2023
Record UNII
26089221C6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CETRORELIX TRIFLUOROACETATE
Common Name English
SB-75
Code English
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-, MONO(TRIFLUOROACETATE) (SALT)
Systematic Name English
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-, 2,2,2-TRIFLUOROACETATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
130289-71-3
Created by admin on Sat Dec 16 09:26:48 GMT 2023 , Edited by admin on Sat Dec 16 09:26:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID80156438
Created by admin on Sat Dec 16 09:26:48 GMT 2023 , Edited by admin on Sat Dec 16 09:26:48 GMT 2023
PRIMARY
PUBCHEM
25074886
Created by admin on Sat Dec 16 09:26:48 GMT 2023 , Edited by admin on Sat Dec 16 09:26:48 GMT 2023
PRIMARY
FDA UNII
26089221C6
Created by admin on Sat Dec 16 09:26:48 GMT 2023 , Edited by admin on Sat Dec 16 09:26:48 GMT 2023
PRIMARY
Related Record Type Details
Structure of CETRORELIX
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CETRORELIX
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966