GANIRELIX ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C80H113ClN18O13.2C2H4O2
Molecular Weight	1690.423
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.CC(O)=O.CCNC(NCC)=NCCCC[C@@H](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](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N6CCC[C@H]6C(=O)N[C@H](C)C(N)=O

InChI

InChIKey=OVBICQMTCPFEBS-SATRDZAXSA-N

InChI=1S/C80H113ClN18O13.2C2H4O2/c1-9-84-79(85-10-2)88-38-17-15-24-60(70(104)94-62(41-49(5)6)71(105)93-61(25-16-18-39-89-80(86-11-3)87-12-4)78(112)99-40-20-26-68(99)77(111)90-50(7)69(82)103)92-73(107)64(44-53-30-35-59(102)36-31-53)97-76(110)67(48-100)98-75(109)66(46-55-21-19-37-83-47-55)96-74(108)65(43-52-28-33-58(81)34-29-52)95-72(106)63(91-51(8)101)45-54-27-32-56-22-13-14-23-57(56)42-54;2*1-2(3)4/h13-14,19,21-23,27-37,42,47,49-50,60-68,100,102H,9-12,15-18,20,24-26,38-41,43-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,107)(H,93,105)(H,94,104)(H,95,106)(H,96,108)(H,97,110)(H,98,109)(H2,84,85,88)(H2,86,87,89);2*1H3,(H,3,4)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C80H113ClN18O13
Molecular Weight	1570.319
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	5
Optical Activity	UNSPECIFIED

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021057s010lbl.pdf
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB06785 | https://clinicaltrials.gov/ct2/show/NCT02796105 | https://clinicaltrials.gov/ct2/show/NCT00298025 | https://www.ncbi.nlm.nih.gov/pubmed/11056249 | http://reference.medscape.com/drug/ganirelix-342757

Ganirelix (N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-L-tyrosyl-N9 ,N10-diethyl-D-homoarginyl-L-leucylN9 ,N10-diethyl-L-homoarginyl-L-prolyl-D-acrylamide) is a synthetic decapeptide with high antagonistic activity against naturally occurring gonadotropin-releasing hormone (GnRH). Ganirelix Acetate Injection is indicated for the inhibition of premature luteinizing hormone (LH) surges in women undergoing controlled ovarian hyperstimulation. Ganirelix is administered by a subcutaneous injection of 250 µg once per day during the mid to late follicular phase of a woman’s menstrual cycle. Treatment should start on the 5th or 6th day after the start of ovarian stimulation, and the mean duration of its use is five days. Clinical studies have shown that the most common side effect is a slight reaction at the site of injection in the form of redness, and sometimes swelling. Clinical studies have shown that, one hour after injection, the incidence of at least one moderate or severe local skin reaction per treatment cycle was 12% in 4 patients treated with Ganirelix and 25% in patients treated subcutaneously with a GnRH agonist. The local reactions generally disappear within 4 hours after administration. Other reported side effects are some that are known to be associated with ovarian hyperstimulation, including gynecological abdominal pain, headache, vaginal bleeding, nausea, and gastrointestinal abdominal pain.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11462984	Antagonist 2778		3.6 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prevent premature ovulation 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021057s010lbl.pdf	Preventing		Approved 8429	GANIRELIX ACETATE Approved Use Ganirelix Acetate Injection is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian hyperstimulation. Launch Date 9.3320643E11

C_max

Value	Dose	Co-administered	Analyte	Population
11.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg 1 times / day steady-state, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
14.8 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
77.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg 1 times / day steady-state, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
96 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg 1 times / day steady-state, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
12.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
18.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21057lbl.pdf	250 μg single, subcutaneous dose: 250 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		GANIRELIX serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.5 mg 1 times / day steady, subcutaneous Highest studied dose Dose: 0.5 mg, 1 times / day Route: subcutaneous Route: steady Dose: 0.5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10593372	healthy, 22.1 years n = 15 Health Status: healthy Age Group: 22.1 years Sex: F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/10593372	Sources: https://pubmed.ncbi.nlm.nih.gov/10593372
0.25 mg single, intravenous Dose: 0.25 mg Route: intravenous Route: single Dose: 0.25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10593371	healthy, 22.4 years (range: 19-31 years) n = 15 Health Status: healthy Age Group: 22.4 years (range: 19-31 years) Sex: F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/10593371	Other AEs: Headache, Fatigue... Other AEs: Headache (7 patients) Fatigue (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10593371
6 mg single, intranasal Dose: 6 mg Route: intranasal Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9091332	healthy, 23-43 years n = 5 Health Status: healthy Age Group: 23-43 years Sex: F Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/9091332	Sources: https://pubmed.ncbi.nlm.nih.gov/9091332

AEs

AE	Significance	Dose	Population
Fatigue	7 patients	0.25 mg single, intravenous Dose: 0.25 mg Route: intravenous Route: single Dose: 0.25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10593371	healthy, 22.4 years (range: 19-31 years) n = 15 Health Status: healthy Age Group: 22.4 years (range: 19-31 years) Sex: F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/10593371
Headache	7 patients	0.25 mg single, intravenous Dose: 0.25 mg Route: intravenous Route: single Dose: 0.25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10593371	healthy, 22.4 years (range: 19-31 years) n = 15 Health Status: healthy Age Group: 22.4 years (range: 19-31 years) Sex: F Population Size: 15 Sources: https://pubmed.ncbi.nlm.nih.gov/10593371

Sourcing

Vendor/Aggregator	ID	URL
Acorn PharmaTech	ACN-057297	http://www.acornpharmatech.com/
Ambinter	Amb19893456	http://www.ambinter.com/reference/19893456
BLD Pharm	BD131887	http://www.bldpharm.com/products/124904-93-4.html
BOC Sciences	129311-55-3	https://www.bocsci.com/ganirelix-acetate-cas-129311-55-3-item-56829.html
BOC Sciences	123246-29-7	https://www.bocsci.com/ganirelix-cas-123246-29-7-item-56282.html
BioSynth	Y-100038	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Y-100038.html
Chemenu	CM100981	http://www.chemenu.com/products/CM100981
MuseChem	M026596	https://www.musechem.com/product/M026596.html
MuseChem	M028341	https://www.musechem.com/product/M028341.html
NovoSeek	16130957
PubChem	16130957	https://pubchem.ncbi.nlm.nih.gov/compound/16130957
eNovation Chemicals	D678700	https://www.enovationchem.com/ProductDetails.asp?ProductID=D678700

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

250 mcg SC qDay during mid-to-late follicular phase after initiating follicle-stimulating hormone on day 2 and 3 of the cycle, continue therapy until day of hCG administration

Route of Administration: Other

In Vitro Use Guide

Human granulosa-lutein (GL) cells and cumulus cells (CC) were plated onto 24-well culture dishes at a density of 100,000 cells in 1 mL medium per well in triplicate. After an overnight incubation in 5% CO2 at 37°C, the incubation medium was exchanged with Hanks M-199 medium containing 100 IU/mL of penicillin, 100 mg/mL of streptomycin, 1.4 ng/mL of sodium bicarbonate, and 3 mg/mL of bovine serum albumin (Sigma). A further 48 hours of culturing of the cells was performed either with or without the addition of 1 nM ganirelix or triptorelin (Ferring). During the last 6 hours of this culturing period, the cells were stimulated with 1–5 IU of hCG with the GnRH analogs still present. The overnight incubation enabled the cells both to attach to the bottom of the culture plates and to recover from any immediate effect of in vivo exposure to the GnRH agonistic analog triptorelin and hMG during COH. The intracellular and extracellular cAMP accumulations of the cultured cells were determined by an 125I scintillation proximity assay

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:40:46 UTC 2023` Edited by `admin` on `Sat Dec 16 00:40:46 UTC 2023`
Record UNII	56U7906FQW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GANIRELIX ACETATE

Official Name

English

GANIRELIX ACETATE [MI]

Common Name

English

Ganirelix acetate [WHO-DD]

Common Name

English

RS-26306-298

Code

English

GANIRELIX ACETATE [VANDF]

Common Name

English

GANIREST

Brand Name

English

N-ACETYL-3-(2-NAPHTHYL)-D-ALANYL-P-CHLORO-D-PHENYLALANYL-3-(3-PYRIDYL)-D-ALANYL-L-SERYL-L-TYROSYL-N(SUP 6)-(N,N'-DIETHYLAMIDINO)-D-LYSYL-L-LEUCYL-N(SUP 6)-(N,N'-DIETHYLAMIDINO)-L-LYSYL-L-PROLYL-D-ALANINAMIDE DIACETATE (SALT)

Common Name

English

GANIRELIX ACETATE [JAN]

Common Name

English

GANIRELIX ACETATE [USAN]

Common Name

English

GANIRELIX ACETATE [ORANGE BOOK]

Common Name

English

GANIRELIX ACETATE [MART.]

Common Name

English

RS-26306

Code

English

GANIRELIX ACETATE INJECTION

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2092