Stereochemistry | ABSOLUTE |
Molecular Formula | C80H113ClN18O13 |
Molecular Weight | 1570.322 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
Molecular Formula | C80H113ClN18O13 |
Molecular Weight | 1570.322 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Doses
AEs
Sourcing
PubMed
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