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

Details

Stereochemistry ABSOLUTE
Molecular Formula C80H113ClN18O13
Molecular Weight 1570.319
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GANIRELIX

SMILES

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=GJNXBNATEDXMAK-PFLSVRRQSA-N
InChI=1S/C80H113ClN18O13/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/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)/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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.6 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
GANIRELIX ACETATE

Approved Use

Ganirelix Acetate Injection is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian hyperstimulation.

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11.2 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
77.1 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.2 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
18.1%
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

Doses

DosePopulationAdverse 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:
healthy, 22.1 years
n = 15
Health Status: healthy
Age Group: 22.1 years
Sex: F
Population Size: 15
Sources:
0.25 mg single, intravenous
Dose: 0.25 mg
Route: intravenous
Route: single
Dose: 0.25 mg
Sources:
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:
Other AEs: Headache, Fatigue...
Other AEs:
Headache (7 patients)
Fatigue (7 patients)
Sources:
6 mg single, intranasal
Dose: 6 mg
Route: intranasal
Route: single
Dose: 6 mg
Sources:
healthy, 23-43 years
n = 5
Health Status: healthy
Age Group: 23-43 years
Sex: F
Population Size: 5
Sources:
AEs

AEs

AESignificanceDosePopulation
Fatigue 7 patients
0.25 mg single, intravenous
Dose: 0.25 mg
Route: intravenous
Route: single
Dose: 0.25 mg
Sources:
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:
Headache 7 patients
0.25 mg single, intravenous
Dose: 0.25 mg
Route: intravenous
Route: single
Dose: 0.25 mg
Sources:
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:
PubMed

PubMed

TitleDatePubMed
Local tolerance, pharmacokinetics, and dynamics of ganirelix (Orgalutran) administration by Medi-Jector compared to conventional needle injections.
2000 Feb
Patents

Patents

Sample Use Guides

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
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 17:34:25 GMT 2023
Edited
by admin
on Sat Dec 16 17:34:25 GMT 2023
Record UNII
IX503L9WN0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GANIRELIX
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
GANIRELIX [VANDF]
Common Name English
Ganirelix [WHO-DD]
Common Name English
GANIRELIX [MI]
Common Name English
GANIRELIX [EMA EPAR]
Common Name English
ORGALUTRAN
Brand Name English
ganirelix [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QH01CC01
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
NDF-RT N0000008638
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
NDF-RT N0000175084
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
NDF-RT N0000175839
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
EMA ASSESSMENT REPORTS ORGALUTRAN (AUTHORIZED: REPRODUCTIVE TECHNIQUES, ASSISTED)
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
NCI_THESAURUS C2092
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
WHO-ATC H01CC01
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
EMA ASSESSMENT REPORTS ORGALUTRAN (AUTHORIZED: OVULATION INDUCTION)
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID401027283
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
PUBCHEM
16130957
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
MESH
C061018
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
SMS_ID
100000085437
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
RXCUI
35825
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY RxNorm
DAILYMED
IX503L9WN0
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
WIKIPEDIA
GANIRELIX
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL1251
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
DRUG BANK
DB06785
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
DRUG CENTRAL
1279
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
CAS
124904-93-4
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
MERCK INDEX
m5665
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY Merck Index
INN
6830
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
CAS
123246-29-7
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
SUPERSEDED
FDA UNII
IX503L9WN0
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
EVMPD
SUB07883MIG
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
NCI_THESAURUS
C77423
Created by admin on Sat Dec 16 17:34:26 GMT 2023 , Edited by admin on Sat Dec 16 17:34:26 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
MAJOR
FECAL
Related Record Type Details
ACTIVE MOIETY