Ganirelix acetateProduct ingredient for Ganirelix

Name
Ganirelix acetate
Drug Entry
Ganirelix

Ganirelix is an injectable competitive gonadotropin-releasing hormone antagonist (GnRH antagonist). It is utilized frequently in assisted reproduction therapy to control the occurrence of ovulation. The drug exerts its effects by inhibiting the action of GnRH in the pituitary gland, leading to fast suppression of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). Ganirelix is used in fertility treatment to prevent premature ovulation that could result in the harvesting of eggs that are too immature to be used in procedures such as in vitro fertilization. Ganirelix is marketed by Merck & Co., Inc. as Orgalutran®.

Accession Number
DBSALT001230
Structure
Thumb
Synonyms
Not Available
UNII
56U7906FQW
CAS Number
129311-55-3
Weight
Average: 1690.45
Monoisotopic: 1688.8845622
Chemical Formula
C84H121ClN18O17
InChI Key
OVBICQMTCPFEBS-SATRDZAXSA-N
InChI
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
IUPAC Name
(2R)-6-{[bis(ethylamino)methylidene]amino}-N-[(1S)-1-{[(2S)-6-{[bis(ethylamino)methylidene]amino}-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}-3-methylbutyl]-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]hexanamide; bis(acetic acid)
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](CC1=CN=CC=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC2=CC=CC=C2C=C1)NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O
External Links
ChemSpider
17290936
Wikipedia
Ganirelix
Predicted Properties
PropertyValueSource
Water Solubility0.00531 mg/mLALOGPS
logP3.42ALOGPS
logP1.62ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)12.14ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area451.49 Å2ChemAxon
Rotatable Bond Count44ChemAxon
Refractivity423.46 m3·mol-1ChemAxon
Polarizability171.91 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon