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Details

Stereochemistry ABSOLUTE
Molecular Formula C70H92ClN17O14
Molecular Weight 1431.038
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CETRORELIX

SMILES

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=SBNPWPIBESPSIF-MHWMIDJBSA-N
InChI=1S/C70H92ClN17O14/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/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)/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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 3
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
1.21 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CETROTIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
6.42 ng/mL
0.25 mg 1 times / day multiple, subcutaneous
CETRORELIX plasma
Homo sapiens
4.97 ng/mL
0.25 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens
28.5 ng/mL
3 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
44.5 ng × h/mL
0.25 mg 1 times / day multiple, subcutaneous
CETRORELIX plasma
Homo sapiens
31.4 ng × h/mL
0.25 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens
536 ng × h/mL
3 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20.6 h
0.25 mg 1 times / day multiple, subcutaneous
CETRORELIX plasma
Homo sapiens
5 h
0.25 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens
62.8 h
3 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
14%
3 mg single, subcutaneous
CETRORELIX plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
OON1HFZ4BA
Record Status Validated (UNII)
Record Version