MedKoo Cat#: 413690 | Name: Dicetrorelix pamoate

Description:

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

Dicetrorelix pamoate is a synthetic decapeptide with gonadotropin-releasing hormone (GnRH) antagonistic activity. GnRH induces the production and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the gonadotrophic cells of the anterior pituitary. Due to a positive estradiol (E2) feedback at midcycle, GnRH liberation is enhanced resulting in an LH-surge. This LH-surge induces the ovulation of the dominant follicle, resumption of oocyte meiosis and subsequently luteinization as indicated by rising progesterone levels. Cetrorelix competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion. It competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner. Cetrorelix is marketed primarily under the brand name Cetrotide. Cetrotide (cetrorelix acetate for injection) is indicated for the inhibition of premature LH surges in women undergoing controlled ovarian stimulation.

Chemical Structure

Dicetrorelix pamoate
CAS#165186-69-6

Theoretical Analysis

MedKoo Cat#: 413690

Name: Dicetrorelix pamoate

CAS#: 165186-69-6

Chemical Formula: C163H200Cl2N34O34

Exact Mass: 3247.4343

Molecular Weight: 3250.49

Elemental Analysis: C, 60.23; H, 6.20; Cl, 2.18; N, 14.65; O, 16.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Dicetrorelix pamoate; Cetrorelix embonate; Dicetrorelix embonate
IUPAC/Chemical Name
D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-, 4,4'-methylenebis(3-hydroxy-2-naphthalenecarboxylate) (2:1) (salt)
InChi Key
UCANQOXFIYWYIX-IDEADWEOSA-N
InChi Code
InChI=1S/2C70H92ClN17O14.C23H16O6/c2*1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h2*5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102);1-10,24-25H,11H2,(H,26,27)(H,28,29)/t2*40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m11./s1
SMILES Code
C[C@H](C(N)=O)NC([C@H]1N(C([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](CCCNC(N)=O)NC([C@H](CC2=CC=C(O)C=C2)NC([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)=O)CCC1)=O.C[C@H](C(N)=O)NC([C@H]7N(C([C@H](CCCNC(N)=N)NC([C@H](CC(C)C)NC([C@@H](CCCNC(N)=O)NC([C@H](CC8=CC=C(O)C=C8)NC([C@H](CO)NC([C@@H](CC9=CC=CN=C9)NC([C@@H](CC%10=CC=C(Cl)C=C%10)NC([C@@H](CC%11=CC=C%12C=CC=CC%12=C%11)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC7)=O.O=C(C%13=C(O)C(CC%14=C%15C=CC=CC%15=CC(C(O)=O)=C%14O)=C%16C=CC=CC%16=C%13)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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 3,250.49 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
1: Tepekoy F, Uysal F, Acar N, Ustunel I, Akkoyunlu G. The effect of GnRH antagonist cetrorelix on Wnt signaling members in pubertal and adult mouse ovaries. Histochem Cell Biol. 2019 Dec;152(6):423-437. doi: 10.1007/s00418-019-01817-0. Epub 2019 Oct 19. PMID: 31630211. 2: Telegdy G, Tanaka M, Schally AV. Effects of the LHRH antagonist Cetrorelix on the brain function in mice. Neuropeptides. 2009 Jun;43(3):229-34. doi: 10.1016/j.npep.2009.03.001. Epub 2009 Apr 16. PMID: 19375162. 3: Telegdy G, Adamik A, Tanaka M, Schally AV. Effects of the LHRH antagonist Cetrorelix on affective and cognitive functions in rats. Regul Pept. 2010 Jan 8;159(1-3):142-7. doi: 10.1016/j.regpep.2009.08.005. PMID: 19706309. 4: Tur-Kaspa I, Ezcurra D. GnRH antagonist, cetrorelix, for pituitary suppression in modern, patient-friendly assisted reproductive technology. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1323-36. doi: 10.1517/17425250903279969. PMID: 19761413. 5: Debruyne F, Tzvetkov M, Altarac S, Geavlete PA. Dose-ranging study of the luteinizing hormone-releasing hormone receptor antagonist cetrorelix pamoate in the treatment of patients with symptomatic benign prostatic hyperplasia. Urology. 2010 Oct;76(4):927-33. doi: 10.1016/j.urology.2009.09.077. PMID: 20932411. 6: Bukulmez O, Carr BR, Doody KM, Doody KJ. Serum cetrorelix concentrations do not affect clinical pregnancy outcome in assisted reproduction. Fertil Steril. 2008 Jan;89(1):74-83. doi: 10.1016/j.fertnstert.2007.02.017. Epub 2007 Jul 26. PMID: 17662281. 7: Zhang J, Zhou X, Chen Y, Zhang Q, Li Y, Zhe J, Chen X, Chen S. [Effects of cetrorelix versus ganirelix in gonadotropin-releasing hormone antagonist cycles for preventing premature luteinizing hormone surges and on clinical outcomes of IVF-ET cycles]. Nan Fang Yi Ke Da Xue Xue Bao. 2019 Oct 30;39(10):1207-1212. Chinese. doi: 10.12122/j.issn.1673-4254.2019.10.12. PMID: 31801718; PMCID: PMC6867944. 8: Finas D, Hornung D, Diedrich K, Schultze-Mosgau A. Cetrorelix in the treatment of female infertility and endometriosis. Expert Opin Pharmacother. 2006 Oct;7(15):2155-68. doi: 10.1517/14656566.7.15.2155. PMID: 17020439. 9: Horvath JE, Toller GL, Schally AV, Bajo AM, Groot K. Effect of long-term treatment with low doses of the LHRH antagonist Cetrorelix on pituitary receptors for LHRH and gonadal axis in male and female rats. Proc Natl Acad Sci U S A. 2004 Apr 6;101(14):4996-5001. doi: 10.1073/pnas.0400605101. Epub 2004 Mar 24. PMID: 15044692; PMCID: PMC387362. 10: Osuga Y. [Endometriosis]. Nihon Rinsho. 2006 Apr;64 Suppl 4:112-5. Japanese. PMID: 16689294.