Ozarelix

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202110

CAS#: 295350-45-7 (free base)

Description: Ozarelix is a fourth generation GnRH antagonist, induces apoptosis in hormone refractory androgen receptor negative prostate cancer cells modulating expression and activity of death receptors. Mechanistically, LHRH antagonists exert rapid inhibition of luteinizing hormone and follicle stimulating hormone with an accompanying rapid decrease in sex hormones and would therefore be expected to be effective in a variety of hormonally dependent disease states including ovarian cancer, prostate cancer, BPH, infertility, uterine myoma and endometriosis. BPH is a non-cancerous enlargement of the prostate that is caused by testosterone. Unlike LHRH agonists, ozarelix has the potential to reduce testosterone just enough to reduce both prostate size and symptoms without the severe side effects associated with a reduction in testosterone.

Chemical Structure

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Ozarelix
CAS# 295350-45-7 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 202110
Name: Ozarelix
CAS#: 295350-45-7 (free base)
Chemical Formula: C72H96ClN17O14
Exact Mass: 1,457.70
Molecular Weight: 1,459.090
Elemental Analysis: C, 59.27; H, 6.63; Cl, 2.43; N, 16.32; O, 15.35

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 896710-46-6 (acetate)   295350-45-7 (free base)  

Synonym: Ozarelix; D 63153; D-63153; D-63 153;

IUPAC/Chemical Name: (2S)-N-((R)-1-amino-1-oxopropan-2-yl)-1-((2S,5R,8S,11S,14R,17R,20R)-3-(2-aminohexanoyl)-17-(4-chlorobenzyl)-2-(3-guanidinopropyl)-8-(4-hydroxybenzyl)-11-(hydroxymethyl)-9-methyl-20-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22-heptaoxo-14-(pyridin-3-ylmethyl)-5-(4-ureidobutyl)-3,6,9,12,15,18,21-heptaazatricosan-1-oyl)pyrrolidine-2-carboxamide

InChi Key: AFPLCEKVZYMXHQ-CZGJKCRTSA-N

InChi Code: InChI=1S/C72H96ClN17O14/c1-5-6-17-52(74)67(100)90(59(19-12-33-80-71(76)77)70(103)89-34-13-20-58(89)65(98)82-42(2)61(75)94)69(102)53(18-9-10-32-81-72(78)104)84-66(99)60(39-45-24-29-51(93)30-25-45)88(4)68(101)57(41-91)87-64(97)56(38-47-14-11-31-79-40-47)86-63(96)55(36-44-22-27-50(73)28-23-44)85-62(95)54(83-43(3)92)37-46-21-26-48-15-7-8-16-49(48)35-46/h7-8,11,14-16,21-31,35,40,42,52-60,91,93H,5-6,9-10,12-13,17-20,32-34,36-39,41,74H2,1-4H3,(H2,75,94)(H,82,98)(H,83,92)(H,84,99)(H,85,95)(H,86,96)(H,87,97)(H4,76,77,80)(H3,78,81,104)/t42-,52?,53-,54-,55-,56-,57+,58+,59+,60+/m1/s1

SMILES Code: O=C([C@H]1N(C([C@H](CCCNC(N)=N)N(C(C(N)CCCC)=O)C([C@@H](CCCCNC(N)=O)NC([C@H](CC2=CC=C(O)C=C2)N(C)C([C@H](CO)NC([C@@H](CC3=CC=CN=C3)NC([C@@H](CC4=CC=C(Cl)C=C4)NC([C@@H](CC5=CC=C6C=CC=CC6=C5)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)CCC1)N[C@H](C)C(N)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Current therapies for BPH either address its symptoms but not the underlying condition, or block growth of new prostate cells and reduce prostate size with only moderate relief of symptoms. There are two classes of drugs to treat BPH. The first, alpha-adrenergic receptor blockers, are believed to work by relaxing the smooth muscle in the urethra and bladder without addressing the underlying condition of the enlarged prostate. Drugs in the second category, 5-alpha reductase inhibitors, work by blocking production of the hormones that stimulate the growth of new prostate cells thereby stopping and eventually reversing enlargement of the prostate. This class of drugs has a slow onset of action, typically requiring daily treatment for many months before improving patient symptoms. Drugs in both classes can have significant side effects, including decreased libido, impotence, abnormal ejaculation, rhinitis, and cardiovascular effects such as dizziness, fainting and lightheadedness. See: http://www.spectrumpharm.com/ozarelix_SPI153.html .   According to news published in 27. January 2010,  Spectrum Pharmaceuticals  announced that it is discontinuing development of ozarelix in benign prostatic hypertrophy (BPH). “While ozarelix is a potent GnRH antagonist, low-dose intermittent therapy has been disappointing in the treatment of lower urinary tract symptoms in men with BPH. As a result, Spectrum Pharmaceuticals has made the strategic decision to discontinue the ozarelix BPH program”  said Rajesh C. Shrotriya, MD, Chairman, Chief Executive Officer, and President of Spectrum Pharmaceuticals.      

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,459.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Festuccia C, Dondi D, Piccolella M, Locatelli A, Gravina GL, Tombolini V, Motta M. Ozarelix, a fourth generation GnRH antagonist, induces apoptosis in hormone refractory androgen receptor negative prostate cancer cells modulating expression and activity of death receptors. Prostate. 2010 Apr 5;70(12):1340-1349. [Epub ahead of print] PubMed PMID: 20623634.

2: Schneider A, Lang A, Naumann W. Fluorescence Spectroscopic Determination of the Critical Aggregation Concentration of the GnRH Antagonists Cetrorelix, Teverelix and Ozarelix. J Fluoresc. 2010 Jun 1. [Epub ahead of print] PubMed PMID: 20514551.

3: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Dec;29(10):697-735. PubMed PMID: 18200333.

4: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Oct;29(8):547-83. PubMed PMID: 18040531.