Home Halogens D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-[bis(ethylamino)methylene]-D-lysyl-L-leucyl-N6-[bis(ethylamino)methylene]-L-lysyl-L-prolyl-, diacetate (salt)

D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-[bis(ethylamino)methylene]-D-lysyl-L-leucyl-N6-[bis(ethylamino)methylene]-L-lysyl-L-prolyl-, diacetate (salt)

CAS No.:
129311-55-3
Catalog Number:
AG009BZZ
Molecular Formula:
C84H121ClN18O17
Molecular Weight:
1690.4229
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$255
- +
5mg
≥98%
1 week
United States
$735
- +
10mg
≥98%
1 week
United States
$1098
- +
Product Description
Catalog Number:
AG009BZZ
Chemical Name:
D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-[bis(ethylamino)methylene]-D-lysyl-L-leucyl-N6-[bis(ethylamino)methylene]-L-lysyl-L-prolyl-, diacetate (salt)
CAS Number:
129311-55-3
Molecular Formula:
C84H121ClN18O17
Molecular Weight:
1690.4229
MDL Number:
MFCD00026356
IUPAC Name:
(2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]amino]-4-methylpentanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;acetic acid
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
InChI Key:
OVBICQMTCPFEBS-SATRDZAXSA-N
SMILES:
CC(=O)O.CC(=O)O.CCNC(=NCCCC[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)N)C)CCCCN=C(NCC)NCC)CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)NC(=O)C)Cc1ccc(cc1)Cl)Cc1cccnc1)CO)Cc1ccc(cc1)O)NCC
UNII:
56U7906FQW
Properties
Complexity:
3060  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
1688.885g/mol
Formal Charge:
0
Heavy Atom Count:
120  
Hydrogen Bond Acceptor Count:
20  
Hydrogen Bond Donor Count:
18  
Isotope Atom Count:
0
Molecular Weight:
1690.451g/mol
Monoisotopic Mass:
1688.885g/mol
Rotatable Bond Count:
48  
Topological Polar Surface Area:
526A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Endometrial gene expression in the early luteal phase is impacted by mode of triggering final oocyte maturation in recFSH stimulated and GnRH antagonist co-treated IVF cycles. Human reproduction (Oxford, England) 20121101
A randomized controlled trial of the GnRH antagonist ganirelix in Chinese normal responders: high efficacy and pregnancy rates. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20121001
Dynamic testosterone responses to near-physiological LH pulses are determined by the time pattern of prior intravenous LH infusion. American journal of physiology. Endocrinology and metabolism 20120915
GnRH-agonist versus GnRH-antagonist IVF cycles: is the reproductive outcome affected by the incidence of progesterone elevation on the day of HCG triggering? A randomized prospective study. Human reproduction (Oxford, England) 20120601
The relationship of premature progesterone rise with serum estradiol levels and number of follicles in GnRH antagonist/recombinant FSH-stimulated cycles. European journal of obstetrics, gynecology, and reproductive biology 20120601
Follicular and endocrine profiles associated with different GnRH-antagonist regimens: a randomized controlled trial. Reproductive biomedicine online 20120201
Older men exhibit reduced efficacy of and heightened potency downregulation by intravenous pulses of recombinant human LH: a study in 92 healthy men. American journal of physiology. Endocrinology and metabolism 20120101
A pituitary adenoma secreting follicle-stimulating hormone with ovarian hyperstimulation: treatment using a gonadotropin-releasing hormone antagonist. Fertility and sterility 20120101
Effect of length of controlled ovarian hyperstimulation using a gonadotropin-releasing hormone antagonist on in vitro fertilization pregnancy rates. The Journal of reproductive medicine 20120101
Replacing GnRH agonists with GnRH antagonists in oocyte recipient cycle did not adversely affect the pregnancy rates. European journal of obstetrics, gynecology, and reproductive biology 20111201
No association between endogenous LH and pregnancy in a GnRH antagonist protocol: part I, corifollitropin alfa. Reproductive biomedicine online 20111001
[Use of GnRH antagonist for in vitro fertilization]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20110906
Factors that predict the probability of a successful clinical outcome after induction of oocyte maturation with a gonadotropin-releasing hormone agonist. Fertility and sterility 20110701
A randomized trial of microdose leuprolide acetate protocol versus luteal phase ganirelix protocol in predicted poor responders. Fertility and sterility 20110630
Effects of the gonadotropin-releasing hormone antagonist ganirelix on normal micturition and prostaglandin E(2)-induced detrusor overactivity in conscious female rats. European urology 20110501
Progesterone enhances adrenergic control of skin blood flow in women with high but not low orthostatic tolerance. The Journal of physiology 20110215
Effect of serum progesterone level on the day of human chorionic gonadotropin injection on outcome following in vitro fertilization-embryo transfer in women using gonadotropin releasing hormone antagonists. Clinical and experimental obstetrics & gynecology 20110101
Evidence that the main adverse effect of ganirelix on pregnancy and implantation rates is on the embryo rather than the endometrium. Clinical and experimental obstetrics & gynecology 20110101
Degarelix, a novel GnRH antagonist, causes minimal histamine release compared with cetrorelix, abarelix and ganirelix in an ex vivo model of human skin samples. British journal of clinical pharmacology 20101001
Failure of the GnRH antagonist ganirelix to block the positive feedback effect of exogenous estrogen in normal women. Fertility and sterility 20100901
Pituitary sensitizing effect of GnRH antagonists: a mechanism explaining LH escape during IVF? Human reproduction (Oxford, England) 20100601
Do GnRH analogues directly affect human endometrial epithelial cell gene expression? Molecular human reproduction 20100501
Comparison of follicular fluid and serum cytokine concentrations in women undergoing assisted reproductive treatment with GnRH agonist long and antagonist protocols. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20100301
Ovarian stimulation in women with high and low body mass index: GnRH agonist versus GnRH antagonist. Reproductive biomedicine online 20100301
A comparison of pregnancy rates following fresh and frozen embryo transfer according to the use of leuprolide acetate vs ganirelix vs cetrorelix. Clinical and experimental obstetrics & gynecology 20100101
Live births after management of severe OHSS by GnRH antagonist administration in the luteal phase. Reproductive biomedicine online 20091201
Treatment of ovarian hyperstimulation syndrome using a dopamine agonist and gonadotropin releasing hormone antagonist: a case series. Fertility and sterility 20090901
GnRH antagonist ganirelix prevents premature luteinization in IUI cycles: rationale for its use. Reproductive biomedicine online 20090801
Predictors and implications of estradiol rise after gonadotropin-releasing hormone antagonist initiation during in vitro fertilization cycles. The Journal of reproductive medicine 20090401
Altered vascular endothelial growth factor expression during GnRH antagonist protocol in women of reproductive age with normal baseline hormone profiles. Fertility and sterility 20090301
The effect of cetrorelix vs. ganirelix on pregnancy outcome using minimal gonadotropin stimulation in women with elevated day 3 serum follicle stimulating hormone levels. Clinical and experimental obstetrics & gynecology 20090101
Comparison of multiple dose GnRH antagonist and minidose long agonist protocols in poor responders undergoing in vitro fertilization: a randomized controlled trial. Archives of gynecology and obstetrics 20081101
Endometrial thickness dynamics and morphologic characteristics during pituitary downregulation with antagonists in assisted reproductive technology cycles. Journal of ultrasound in medicine : official journal of the American Institute of Ultrasound in Medicine 20081101
Predictors of ovarian response in intrauterine insemination patients and development of a dosage nomogram. Reproductive biomedicine online 20081101
Effects and clinical significance of GnRH antagonist administration for IUI timing in FSH superovulated cycles: a meta-analysis. Fertility and sterility 20080801
Oral contraceptive pretreatment and half dose of ganirelix does not excessively suppress LH and may be an excellent choice for scheduling IUI cycles. Journal of assisted reproduction and genetics 20080801
Sex hormone effects on body fluid regulation. Exercise and sport sciences reviews 20080701
Flexible GnRH antagonist versus flare-up GnRH agonist protocol in poor responders treated by IVF: a randomized controlled trial. Human reproduction (Oxford, England) 20080601
GnRH antagonists may affect endometrial receptivity. Fertility and sterility 20080501
Prospective, randomized, comparative study of leuprorelin + human menopausal gonadotropins versus ganirelix + recombinant follicle-stimulating hormone in oocyte donors and pregnancy rates among the corresponding recipients. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20080401
The impact of ovarian stimulation with recombinant FSH in combination with GnRH antagonist on the endometrial transcriptome in the window of implantation. Reproductive sciences (Thousand Oaks, Calif.) 20080401
The effect of luteal phase vaginal estradiol supplementation on the success of in vitro fertilization treatment: a prospective randomized study. Fertility and sterility 20080301
The use of gonadotropin-releasing hormone (GnRH) agonist to induce oocyte maturation after cotreatment with GnRH antagonist in high-risk patients undergoing in vitro fertilization prevents the risk of ovarian hyperstimulation syndrome: a prospective randomized controlled study. Fertility and sterility 20080101
[Ovulation induction in high risk IVF patients: GnRH-agonist, diminished dose of urinary or recombinant chorion gonadotropin]. Akusherstvo i ginekologiia 20080101
The effects of GnRH antagonist on the endometrium of normally menstruating women. Journal of assisted reproduction and genetics 20071201
Management of severe early ovarian hyperstimulation syndrome by re-initiation of GnRH antagonist. Reproductive biomedicine online 20071001
Age attenuates testosterone secretion driven by amplitude-varying pulses of recombinant human luteinizing hormone during acute gonadotrope inhibition in healthy men. The Journal of clinical endocrinology and metabolism 20070901
The luteal phase of recombinant follicle-stimulating hormone/gonadotropin-releasing hormone antagonist in vitro fertilization cycles during supplementation with progesterone or progesterone and estradiol. Fertility and sterility 20070301
Exogenous oestradiol and progesterone administration does not cause oedema in healthy young women. Clinical endocrinology 20070301
Ganirelix acetate causes a rapid reduction in estradiol levels without adversely affecting oocyte maturation in women pretreated with leuprolide acetate who are at risk of ovarian hyperstimulation syndrome. Human reproduction (Oxford, England) 20061101
GnRH-antagonists in ovarian stimulation for IVF in patients with poor response to gonadotrophins, polycystic ovary syndrome, and risk of ovarian hyperstimulation: a meta-analysis. Reproductive biomedicine online 20061101
Effect of luteal-phase support on endometrial L-selectin ligand expression after recombinant follicle-stimulating hormone and ganirelix acetate for in vitro fertilization. The Journal of clinical endocrinology and metabolism 20061001
Luteal hormonal profile of oocyte donors stimulated with a GnRH antagonist compared with natural cycles. Reproductive biomedicine online 20060901
[In vitro fertilization and embryo transfer]. Nihon rinsho. Japanese journal of clinical medicine 20060401
Treatment with the GnRH antagonist ganirelix prevents premature LH rises and luteinization in stimulated intrauterine insemination: results of a double-blind, placebo-controlled, multicentre trial. Human reproduction (Oxford, England) 20060301
The use of gonadotropin-releasing hormone antagonist in ovarian stimulation. Clinical obstetrics and gynecology 20060301
A comparative randomized trial to assess the impact of oral contraceptive pretreatment on follicular growth and hormone profiles in GnRH antagonist-treated patients. Human reproduction (Oxford, England) 20060101
Aging attenuates both the regularity and joint synchrony of LH and testosterone secretion in normal men: analyses via a model of graded GnRH receptor blockade. American journal of physiology. Endocrinology and metabolism 20060101
Treatment with gonadotropin-releasing hormone (GnRH) antagonists in women suppressed with GnRH agonist may avoid cycle cancellation in patients at risk for ovarian hyperstimulation syndrome. Fertility and sterility 20060101
Similar endometrial development in oocyte donors treated with either high- or standard-dose GnRH antagonist compared to treatment with a GnRH agonist or in natural cycles. Human reproduction (Oxford, England) 20051201
LH suppression following different low doses of the GnRH antagonist ganirelix in polycystic ovary syndrome. Journal of endocrinological investigation 20051201
Alternate day and daily administration of GnRH antagonist may prevent premature luteinization to a similar extent during FSH treatment. Human reproduction (Oxford, England) 20051101
Aging in healthy men impairs recombinant human luteinizing hormone (LH)-stimulated testosterone secretion monitored under a two-day intravenous pulsatile LH clamp. The Journal of clinical endocrinology and metabolism 20051001
Age-specific changes in the regulation of LH-dependent testosterone secretion: assessing responsiveness to varying endogenous gonadotropin output in normal men. American journal of physiology. Regulatory, integrative and comparative physiology 20050901
Prospective, randomized trial comparing cetrorelix acetate and ganirelix acetate in a programmed, flexible protocol for premature luteinizing hormone surge prevention in assisted reproductive technologies. Fertility and sterility 20050701
GnRH agonist versus GnRH antagonist in oocyte donation cycles: a prospective randomized study. Human reproduction (Oxford, England) 20050601
Clinical efficacy of the gonadotropin-releasing hormone antagonist, ganirelix, in Korean women undergoing controlled ovarian hyperstimulation for in vitro fertilization and embryo transfer with recombinant follicle-stimulating hormone. The journal of obstetrics and gynaecology research 20050601
A randomized prospective study of microdose leuprolide versus ganirelix in in vitro fertilization cycles for poor responders. Fertility and sterility 20050501
Age diminishes the testicular steroidogenic response to repeated intravenous pulses of recombinant human LH during acute GnRH-receptor blockade in healthy men. American journal of physiology. Endocrinology and metabolism 20050401
Ganirelix acetate use in normal- and poor-prognosis patients and the impact of estradiol patterns. Fertility and sterility 20050301
Use of antagonists in ovarian stimulation protocols. Reproductive biomedicine online 20050301
A randomized prospective trial comparing gonadotropin-releasing hormone (GnRH) antagonist/recombinant follicle-stimulating hormone (rFSH) versus GnRH-agonist/rFSH in women pretreated with oral contraceptives before in vitro fertilization. Fertility and sterility 20050201
Use of GNRH antagonists in reproductive medicine. Minerva ginecologica 20050201
[The programming of IVF cycles with antagonists]. Journal de gynecologie, obstetrique et biologie de la reproduction 20041001
[Introduction of the antagonist: on a determined day or depending on follicular growth?]. Journal de gynecologie, obstetrique et biologie de la reproduction 20041001
[GnRH antagonists in insemination : can we avoid weekends?]. Journal de gynecologie, obstetrique et biologie de la reproduction 20041001
Gonadotropin releasing hormone antagonists and cryopreservation outcome: a review. Archives of gynecology and obstetrics 20040901
Pulsatile intravenous infusion of recombinant human luteinizing hormone under acute gonadotropin-releasing hormone receptor blockade reconstitutes testosterone secretion in young men. The Journal of clinical endocrinology and metabolism 20040901
A randomized, multicenter study comparing the efficacy of recombinant FSH vs recombinant FSH with Ganirelix during superovulation/IUI therapy. American journal of obstetrics and gynecology 20040801
Association of inhibin B serum levels with parameters of follicular response in a randomized controlled trial comparing gnRH agonist versus antagonist protocols for ovarian hyperstimulation. Journal of assisted reproduction and genetics 20040701
Exaggerated 17-hydroxyprogesterone response to intravenous infusions of recombinant human LH in women with polycystic ovary syndrome. American journal of physiology. Endocrinology and metabolism 20040601
Effects of estrogen and progesterone administration on extracellular fluid. Journal of applied physiology (Bethesda, Md. : 1985) 20040301
A randomized, double-blind, multicentre clinical trial comparing starting doses of 150 and 200 IU of recombinant FSH in women treated with the GnRH antagonist ganirelix for assisted reproduction. Human reproduction (Oxford, England) 20040101
Gonadotropin-releasing hormone antagonists for assisted reproductive techniques: are there clinical differences between agents? Drugs 20040101
Effect of antagonists vs agonists on in vitro fertilization outcome. Clinical and experimental obstetrics & gynecology 20040101
Endometrial HOXA10 expression after controlled ovarian hyperstimulation with recombinant follicle-stimulating hormone. Fertility and sterility 20030901
Actions of GnRH antagonists on IGF-II, IGF-binding protein-2 and pregnancy-associated plasma protein-A in human granulosa-lutein cells. European journal of endocrinology 20030701
Clinical outcome of using ganirelix acetate versus a 4-day follicular phase leuprolide acetate protocol in unselected women undergoing in vitro fertilization. Fertility and sterility 20030701
Exposure to high levels of luteinizing hormone and estradiol in the early follicular phase of gonadotropin-releasing hormone antagonist cycles is associated with a reduced chance of pregnancy. Fertility and sterility 20030401
Concurrent ganirelix and follitropin beta therapy is an effective and safe regimen for ovulation induction in women with polycystic ovary syndrome. Fertility and sterility 20030301
Minimal ovarian hyperstimulation for in vitro fertilization using sequential clomiphene citrate and gonadotropin with or without the addition of a gonadotropin-releasing hormone antagonist. Fertility and sterility 20021101
Effect of in vivo GnRH agonist and GnRH antagonist on hCG and insulin-stimulated progesterone production by human granulosa-lutein cells in vitro. Journal of assisted reproduction and genetics 20020801
Endocrine profiles after triggering of final oocyte maturation with GnRH agonist after cotreatment with the GnRH antagonist ganirelix during ovarian hyperstimulation for in vitro fertilization. The Journal of clinical endocrinology and metabolism 20020201
Optimizing gonadotrophin-releasing hormone antagonist protocols. Human fertility (Cambridge, England) 20020201
Use of gonadotrophin-releasing hormone agonists to trigger ovulation. Human fertility (Cambridge, England) 20020201
The gonadotrophin-releasing hormone antagonist ganirelix--history and introductory data. Human fertility (Cambridge, England) 20020201
[GnRH antagonists]. Gynecologie, obstetrique & fertilite 20020101
Rescue IVF and coasting with the use of a GnRH antagonist after ovulation induction. Reproductive biomedicine online 20020101
The place of gonadotrophin-releasing hormone antagonists in reproductive medicine. Reproductive biomedicine online 20020101
Use of GnRH antagonists in ovarian stimulation for assisted reproductive technologies compared to the long protocol. Meta-analysis. Archives of gynecology and obstetrics 20011101
[GnRH antagonists in IVF]. Journal de gynecologie, obstetrique et biologie de la reproduction 20011101
Use of third generation gonadotropin-releasing hormone antagonists in in vitro fertilization-embryo transfer: a review. Obstetrical & gynecological survey 20010901
'You'll know it when you see it' statistics. Fertility and sterility 20010901
'You'll know it when you see it' statistics. Fertility and sterility 20010901
Gonadotropin-releasing hormone antagonists implications for oocyte quality and uterine receptivity. Annals of the New York Academy of Sciences 20010901
Applications for GnRH antagonists. Trends in endocrinology and metabolism: TEM 20010801
Actions of gonadotropin-releasing hormone antagonists on steroidogenesis in human granulosa lutein cells. European journal of endocrinology 20010601
Comparable clinical outcome using the GnRH antagonist ganirelix or a long protocol of the GnRH agonist triptorelin for the prevention of premature LH surges in women undergoing ovarian stimulation. Human reproduction (Oxford, England) 20010401
Dynamics of the development of multiple follicles during ovarian stimulation for in vitro fertilization using recombinant follicle-stimulating hormone (Puregon) and various doses of the gonadotropin-releasing hormone antagonist ganirelix (Orgalutran/Antagon). Fertility and sterility 20010401
Efficacy and safety of ganirelix acetate versus leuprolide acetate in women undergoing controlled ovarian hyperstimulation. Fertility and sterility 20010101
Pregnancy and birth after GnRH agonist treatment for induction of final oocyte maturation in a woman undergoing ovarian stimulation for ICSI, using a GnRH antagonist (Orgalutran/Antagon) to prevent a premature LH surge: a case report. Journal of assisted reproduction and genetics 20010101
Gonadotrophin-releasing hormone antagonists for assisted conception. The Cochrane database of systematic reviews 20010101
Local tolerance, pharmacokinetics, and dynamics of ganirelix (Orgalutran) administration by Medi-Jector compared to conventional needle injections. Human reproduction (Oxford, England) 20000201
Properties