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DEGARELIX

CAS No.:
214766-78-6
Catalog Number:
AG00BF6N
Molecular Formula:
C82H103ClN18O16
Molecular Weight:
1632.2592
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
2mg
99%
1 week
United States
$207
- +
5mg
99%
1 week
United States
$307
- +
10mg
99%
1 week
United States
$473
- +
50mg
99%
1 week
United States
$1473
- +
100mg
99%
1 week
United States
$2723
- +
Product Description
Catalog Number:
AG00BF6N
Chemical Name:
DEGARELIX
CAS Number:
214766-78-6
Molecular Formula:
C82H103ClN18O16
Molecular Weight:
1632.2592
MDL Number:
MFCD05860888
IUPAC Name:
(4S)-N-[4-[(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-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[4-(carbamoylamino)phenyl]-1-oxopropan-2-yl]amino]-3-oxopropyl]phenyl]-2,6-dioxo-1,3-diazinane-4-carboxamide
InChI:
InChI=1S/C82H103ClN18O16/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117)/t47-,59+,60+,61-,62-,63-,64+,65-,66+,67+,68+/m1/s1
InChI Key:
MEUCPCLKGZSHTA-XYAYPHGZSA-N
SMILES:
OC[C@@H](C(=O)N[C@H](C(=O)N[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)CCCCNC(C)C)CC(C)C)Cc1ccc(cc1)NC(=O)N)Cc1ccc(cc1)NC(=O)[C@@H]1CC(=O)NC(=O)N1)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)NC(=O)C)Cc1ccc(cc1)Cl)Cc1cccnc1
UNII:
SX0XJI3A11
Properties
Complexity:
3390  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
11  
Defined Bond Stereocenter Count:
0
Exact Mass:
1630.749g/mol
Formal Charge:
0
Heavy Atom Count:
117  
Hydrogen Bond Acceptor Count:
18  
Hydrogen Bond Donor Count:
17  
Isotope Atom Count:
0
Molecular Weight:
1632.286g/mol
Monoisotopic Mass:
1630.749g/mol
Rotatable Bond Count:
41  
Topological Polar Surface Area:
513A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5  
Literature
Title Journal
Rapid elimination kinetics of free PSA or human kallikrein-related peptidase 2 after initiation of gonadotropin-releasing hormone-antagonist treatment of prostate cancer: potential for rapid monitoring of treatment responses. Clinical chemistry and laboratory medicine 20121101
Gonadotropin-releasing hormone: an update review of the antagonists versus agonists. International journal of urology : official journal of the Japanese Urological Association 20120701
The effect of baseline testosterone on the efficacy of degarelix and leuprolide: further insights from a 12-month, comparative, phase III study in prostate cancer patients. Urology 20120701
Editorial comment. Urology 20120701
[The efficacy of degarelix on LUTS (Lower urinary tract symptoms) relief in patients with prostate cancer]. Urologia 20120701
The efficacy and safety of degarelix, a GnRH antagonist: a 12-month, multicentre, randomized, maintenance dose-finding phase II study in Japanese patients with prostate cancer. Japanese journal of clinical oncology 20120601
Androgen deprivation therapy: past, present and future. BJU international 20120601
Short-term testosterone manipulations modulate visual recognition memory and some aspects of emotional reactivity in male rhesus monkeys. Physiology & behavior 20120515
Cost-effectiveness analysis of degarelix for advanced hormone-dependent prostate cancer. BJU international 20120401
Follicular and endocrine profiles associated with different GnRH-antagonist regimens: a randomized controlled trial. Reproductive biomedicine online 20120201
Gonadotropin-releasing hormone blockers and cardiovascular disease risk: analysis of prospective clinical trials of degarelix. The Journal of urology 20111101
In vitro studies investigating the interactions between degarelix, a decapeptide gonadotropin-releasing hormone blocker, and cytochrome P450. Basic & clinical pharmacology & toxicology 20110901
A phase III extension trial with a 1-arm crossover from leuprolide to degarelix: comparison of gonadotropin-releasing hormone agonist and antagonist effect on prostate cancer. The Journal of urology 20110901
Hot flushes in prostatic cancer patients during androgen-deprivation therapy with monthly dose of degarelix or leuprolide. Prostate cancer and prostatic diseases 20110601
Efficacy and safety of androgen deprivation therapy after switching from monthly leuprolide to monthly degarelix in patients with prostate cancer. International journal of clinical practice 20110501
Response to degarelix after resistance to luteinizing hormone-releasing hormone agonist therapy for metastatic prostate cancer. Anti-cancer drugs 20110301
Cardiovascular safety of degarelix: results from a 12-month, comparative, randomized, open label, parallel group phase III trial in patients with prostate cancer. The Journal of urology 20101201
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
Changes in alkaline phosphatase levels in patients with prostate cancer receiving degarelix or leuprolide: results from a 12-month, comparative, phase III study. BJU international 20100701
Degarelix. More rapid medical castration, nothing more. Prescrire international 20100601
Additional analysis of the secondary end point of biochemical recurrence rate in a phase 3 trial (CS21) comparing degarelix 80 mg versus leuprolide in prostate cancer patients segmented by baseline characteristics. European urology 20100501
New Drugs2010, PART 1. Nursing 20100201
Evaluation of degarelix in the management of prostate cancer. Cancer management and research 20100101
Degarelix 240/80 mg: a new treatment option for patients with advanced prostate cancer. Expert review of anticancer therapy 20091201
Degarelix (firmagon) for prostate cancer. The Medical letter on drugs and therapeutics 20091019
Degarelix. Drugs 20091001
Degarelix acetate for the treatment of prostate cancer. Drugs of today (Barcelona, Spain : 1998) 20091001
Degarelix for prostate cancer. Expert opinion on investigational drugs 20090601
[GnRH antagonists--a new therapy option for advanced prostate cancer]. Aktuelle Urologie 20090501
Degarelix: a novel gonadotropin-releasing hormone blocker for the treatment of prostate cancer. Future oncology (London, England) 20090501
Twenty-five year evolution of medical hormonal therapy for prostate cancer. BJU international 20090101
Degarelix and its therapeutic potential in the treatment of prostate cancer. Clinical interventions in aging 20090101
Degarelix: a new approach for the treatment of prostate cancer. Neuroendocrinology 20090101
Degarelix: a gonadotropin-releasing hormone antagonist for the management of prostate cancer. Clinical therapeutics 20090101
The efficacy and safety of degarelix: a 12-month, comparative, randomized, open-label, parallel-group phase III study in patients with prostate cancer. BJU international 20081201
A 1-year, open label, randomized phase II dose finding study of degarelix for the treatment of prostate cancer in North America. The Journal of urology 20081101
Management of advanced prostate cancer: gonadotropin-releasing hormone blockers might improve prognosis. European urology 20081001
Degarelix: a novel gonadotropin-releasing hormone (GnRH) receptor blocker--results from a 1-yr, multicentre, randomised, phase 2 dosage-finding study in the treatment of prostate cancer. European urology 20081001
Management of advanced prostate cancer: can we improve on androgen deprivation therapy? BJU international 20080601
Testosterone surge: rationale for gonadotropin-releasing hormone blockers? Urology 20080601
A new model of patient tumor-derived breast cancer xenografts for preclinical assays. Clinical cancer research : an official journal of the American Association for Cancer Research 20070701
Population pharmacokinetic/pharmacodynamic (PK/PD) modelling of the hypothalamic-pituitary-gonadal axis following treatment with GnRH analogues. British journal of clinical pharmacology 20070601
Rapid suppression of plasma testosterone levels and tumor growth in the dunning rat model treated with degarelix, a new gonadotropin-releasing hormone antagonist. The Journal of pharmacology and experimental therapeutics 20070301
Semi-mechanistic pharmacodynamic modeling for degarelix, a novel gonadotropin releasing hormone (GnRH) blocker. Journal of pharmacokinetics and pharmacodynamics 20061001
Novel analogues of degarelix incorporating hydroxy-, methoxy-, and pegylated-urea moieties at positions 3, 5, 6 and the N-terminus. Part III. Journal of medicinal chemistry 20060615
Iterative approach to the discovery of novel degarelix analogues: substitutions at positions 3, 7, and 8. Part II. Journal of medicinal chemistry 20050728
Synthesis and biological activity of GnRH antagonists modified at position 3 with 3-(2-methoxy-5-pyridyl)-alanine. The journal of peptide research : official journal of the American Peptide Society 20050201
Pharmacological profile of a new, potent, and long-acting gonadotropin-releasing hormone antagonist: degarelix. The Journal of pharmacology and experimental therapeutics 20020401
GnRH antagonists: a new generation of long acting analogues incorporating p-ureido-phenylalanines at positions 5 and 6. Journal of medicinal chemistry 20010201
Properties