DICETRORELIX PAMOATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C70H92ClN17O14.C23H16O6
Molecular Weight	3250.4517
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)C1=CC2=CC=CC=C2C(CC3=C(O)C(=CC4=CC=CC=C34)C(O)=O)=C1O.CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](CC5=CC=C(O)C=C5)NC(=O)[C@H](CO)NC(=O)[C@@H](CC6=CN=CC=C6)NC(=O)[C@@H](CC7=CC=C(Cl)C=C7)NC(=O)[C@@H](CC8=CC9=CC=CC=C9C=C8)NC(C)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N%10CCC[C@H]%10C(=O)N[C@H](C)C(N)=O.CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](CC%11=CC=C(O)C=C%11)NC(=O)[C@H](CO)NC(=O)[C@@H](CC%12=CN=CC=C%12)NC(=O)[C@@H](CC%13=CC=C(Cl)C=C%13)NC(=O)[C@@H](CC%14=CC%15=CC=CC=C%15C=C%14)NC(C)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N%16CCC[C@H]%16C(=O)N[C@H](C)C(N)=O

InChI

InChIKey=UCANQOXFIYWYIX-IDEADWEOSA-N

InChI=1S/2C70H92ClN17O14.C23H16O6/c2*1-39(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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h2*5-7,11-13,17-27,32,37,39-40,50-58,89,91H,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);1-10,24-25H,11H2,(H,26,27)(H,28,29)/t2*40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m11./s1

HIDE SMILES / InChI

Molecular Formula	C70H92ClN17O14
Molecular Weight	1431.0406
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

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

Molecular Formula	C23H16O6
Molecular Weight	388.3704
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

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 Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41	Antagonist 2,849		1.21 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Female infertility 7	Primary		Approved 8,583	CETROTIDE

C_max

Value	Dose	Analyte	Population
28.5 ng/mL	3 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
4.97 ng/mL	0.25 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
6.42 ng/mL	0.25 mg 1 times / day multiple, subcutaneous	CETRORELIX plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
536 ng × h/mL	3 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
31.4 ng × h/mL	0.25 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
44.5 ng × h/mL	0.25 mg 1 times / day multiple, subcutaneous	CETRORELIX plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
62.8 h	3 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
5 h	0.25 mg single, subcutaneous	CETRORELIX plasma	Homo sapiens
20.6 h	0.25 mg 1 times / day multiple, subcutaneous	CETRORELIX plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
14%	3 mg single, subcutaneous		CETRORELIX plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
5 mg 1 times / day multiple, subcutaneous Highest studied dose	unhealthy, 58.9 ± 8.3 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252		inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C8/9 42 CYP2C19 2,057 CYP2E1 1,060 BSEP 550 MRP2 499 MRP3 246 MRP4 290	CYP 303

Drug as perpetrator

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Target	Modality	Activity
MRP2 625	inhibitor 4,027	no [IC50 >133 uM]
MRP3 326	inhibitor 4,027	no [IC50 >133 uM]
MRP4 345	inhibitor 4,027	no [IC50 >133 uM]
CYP1A2 2,333	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4,014	no

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
[Research on synthetic peptides of biological interest].	2001	11769093
Luteinizing hormone-releasing hormone antagonists in prostate cancer.	2001 Aug	11502441
Applications for GnRH antagonists.	2001 Aug	11476072
Suppression of spermatogenesis to azoospermia by combined administration of GnRH antagonist and 19-nortestosterone cannot be maintained by this non-aromatizable androgen alone.	2001 Dec	11726576
Human ovarian steroid secretion in vivo: effects of GnRH agonist versus antagonist (cetrorelix).	2001 Dec	11726570

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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
Record UNII	DY3PDH8A8N
Record Status	`FAILED`
Record Version

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Name

Type

Language

DICETRORELIX PAMOATE

Common Name

English

CETRORELIX PAMOATE

Preferred Name

English

Cetrorelix pamoate [WHO-DD]

Common Name

English

DICETRORELIX EMBONATE

Common 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-, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (2:1) (SALT)

Systematic Name

English

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Code System

Code

Type

Description

SMS_ID

100000175146

PRIMARY

CAS

145672-82-8

NON-SPECIFIC STOICHIOMETRY

PUBCHEM

92135817

PRIMARY

FDA UNII

DY3PDH8A8N

PRIMARY

EPA CompTox

DTXSID601339371

PRIMARY

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Related Record

Type

Details


					OON1HFZ4BA

CETRORELIX

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					OON1HFZ4BA

CETRORELIX

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator