MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 329856 | Name: Cetrorelix acetate
Featured New

Description:

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

Cetrorelix is is a gonadotropin-releasing hormone (GnRH) antagonist that is marketed primarily under the brand name Cetrotide. A synthetic decapeptide, it is used is used in assisted reproduction to inhibit premature luteinizing hormone surges. The drug works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of luteinizing hormone (LH) and follicle-stimulating hormone (FSH).

Chemical Structure

Cetrorelix acetate
Cetrorelix acetate
CAS#130143-01-0 (2 acetate)

Theoretical Analysis

MedKoo Cat#: 329856

Name: Cetrorelix acetate

CAS#: 130143-01-0 (2 acetate)

Chemical Formula: C74H100ClN17O18

Exact Mass: 0.0000

Molecular Weight: 1551.17

Elemental Analysis: C, 57.30; H, 6.50; Cl, 2.29; N, 15.35; O, 18.57

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
500mg USD 2,950.00 2 Weeks
1g USD 4,350.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
120287-85-6 (free base) 130143-01-0 (2 acetate) 130289-71-3 (3TFA) 145672-81-7 (1 acetate); 165186-69-6 (pamoate)
Synonym
NS-75A; NS75A; NS 75A; D-20761; SB-075 acetate; SB 075 acetate; SB075 acetate; Cetrorelix acetate; Cetrotide; Cetrotide acetate;
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-, diacetate (salt)
InChi Key
DTPVYWHLQLAXFT-SMCUOGPFSA-N
InChi Code
InChI=1S/C70H92ClN17O14.2C2H4O2/c1-39(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;2*1-2(3)4/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,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);2*1H3,(H,3,4)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;;/m1../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.CC(O)=O.CC(O)=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
Shelf Life
>2 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
In addition, cetrorelix can be used to treat hormone-sensitive cancers of the prostate[citation needed] and breast (in pre-/perimenopausal women)[citation needed] and some benign gynaecological disorders (endometriosis, uterine fibroids and endometrial thinning).[citation needed] It is administered as either multiple 0.25 mg daily subcutaneous injections or as a single-dose 3 mg subcutaneous injection. The duration of the 3 mg single dose is four days; if human chorionic gonadotropin (hCG) is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cetrorelix Acetate (SB-75 acetate) is a potent gonadotropin-releasing hormone (GnRH) receptor antagonist with an IC50 of 1.21 nM.
In vitro activity:
To investigate the effect of LHRH-I antagonist on myeloma cell growth, Cetrorelix was used to treat 8 MM cells lines, including the RPMI 8226–derived ATO- or BZM-resistant cells, and KAS-6/1–derived, lenalidomide-resistant myeloma cells generated in our laboratories. Cetrorelix treatment reduced cell growth after 48 hours in all cell lines. At the concentration of 1 to 2 μmol/L (a concentration comparable with the previous studies; ref. 16), a 20% to 50% decrease of cell growth as compared with the vehicle was seen and a maximal response was reached at 4 μmol/L (Fig. 2A). Importantly, although RPMI 8226-ATOR cells, RPMI 8226-BZMR, and KAS-6/R10R cells show resistance to ATO, BZM, and lenalidomide, respectively (Fig. 2A inset), they remained sensitive to Cetrorelix treatment. The growth inhibition was further confirmed by colony formation assays (Fig. 2B), showing that Cetrorelix (1 μmol/L) reduced colony-forming ability of the two MM cell lines tested. Reference: Mol Cancer Ther. 2011 Jan;10(1):148-58. http://mct.aacrjournals.org/cgi/pmidlookup?view=long&pmid=21062912
In vivo activity:
In mice, ovarian stimulation via hormone administration is an effective method for obtaining many ova simultaneously, but its effect is reduced by the influence of aging. In this study, it’s demonstrate that this problem can be improved by administering the gonadotropin-releasing hormone antagonist Cetrorelix prior to ovarian stimulation. Before 12-month-old female mice were injected with 5 IU pregnant mare serum gonadotropin and 5 IU human chorionic gonadotropin, we administered 5 µg/kg Cetrorelix for 7 consecutive days (7 times) or 3 times once every 3 days. As a result, 8.7 ± 1.9 (mean ± SEM, n=10) and 9.8 ± 1.3 (n=10) oocytes were obtained, respectively, as opposed to 4.7 ± 1.2 oocytes (n=9) in the case of no administration. Collagen staining of ovarian tissue showed that Cetrorelix administration reduced the degree of fibrosis, which improved ovarian function. In addition, equivalent fertilization and fetal development rates between control and Cetrorelix-treated aged mouse-derived oocytes were confirmed by in vitro fertilization and embryo transfer (Fertilization rate; control: 92.2% vs. 3 times: 96.9%/7 times: 88.5%, Birth rate; control: 56.4% vs. 3 times: 58.3%/7 times: 51.8%), indicating the normality of the obtained oocytes. It is concluded that Cetrorelix improved the effect of superovulation in aged mice without reducing oocyte quality. This procedure will contribute to animal welfare by extending the effective utilization of aged female breeding mice. Reference: Exp Anim. 2021 Feb 6;70(1):31-36. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/32863284/
Solvent mg/mL mM
Solubility
DMSO 50.0 33.53
Water 2.0 1.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,551.17 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:
1. Wen J, Feng Y, Bjorklund CC, Wang M, Orlowski RZ, Shi ZZ, Liao B, O'Hare J, Zu Y, Schally AV, Chang CC. Luteinizing Hormone-Releasing Hormone (LHRH)-I antagonist cetrorelix inhibits myeloma cell growth in vitro and in vivo. Mol Cancer Ther. 2011 Jan;10(1):148-58. doi: 10.1158/1535-7163.MCT-10-0829. Epub 2010 Nov 9. PMID: 21062912. 2. Gründker C, Emons G. Role of gonadotropin-releasing hormone (GnRH) in ovarian cancer. Reprod Biol Endocrinol. 2003 Oct 7;1:65. doi: 10.1186/1477-7827-1-65. PMID: 14594454; PMCID: PMC239893.
In vivo protocol:
1. Kanda A, Nobukiyo A, Sotomaru Y. Effect of Cetrorelix administration on ovarian stimulation in aged mice. Exp Anim. 2021 Feb 6;70(1):31-36. doi: 10.1538/expanim.20-0058. Epub 2020 Aug 31. PMID: 32863284; PMCID: PMC7887618.
1: 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. Review. PubMed PMID: 19761413. 2: 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. Review. PubMed PMID: 17020439. 3: Reissmann T, Schally AV, Bouchard P, Riethmiiller H, Engel J. The LHRH antagonist cetrorelix: a review. Hum Reprod Update. 2000 Jul-Aug;6(4):322-31. Review. PubMed PMID: 10972520. 4: Griesinger G, Felberbaum RE, Schultze-Mosgau A, Diedrich K. Gonadotropin-releasing hormone antagonists for assisted reproductive techniques: are there clinical differences between agents? Drugs. 2004;64(6):563-75. Review. PubMed PMID: 15018588. 5: Depalo R, Jayakrishan K, Garruti G, Totaro I, Panzarino M, Giorgino F, Selvaggi LE. GnRH agonist versus GnRH antagonist in in vitro fertilization and embryo transfer (IVF/ET). Reprod Biol Endocrinol. 2012 Apr 13;10:26. doi: 10.1186/1477-7827-10-26. Review. PubMed PMID: 22500852; PubMed Central PMCID: PMC3442989. 6: Ludwig M, Katalinic A, Felberbaum RE, Diedrich K. Safety aspects of gonadotrophin-releasing hormone antagonists in ovarian stimulation procedures: ovarian hyperstimulation syndrome and health of children born. Reprod Biomed Online. 2002;5 Suppl 1:61-7. Review. PubMed PMID: 12537784. 7: Felberbaum R, Diedrich K. Ovarian stimulation for in-vitro fertilization/intracytoplasmic sperm injection with gonadotrophins and gonadotrophin-releasing hormone analogues: agonists and antagonists. Hum Reprod. 1999 Sep;14 Suppl 1:207-21. Review. PubMed PMID: 10573035. 8: Osuga Y. [Endometriosis]. Nihon Rinsho. 2006 Apr;64 Suppl 4:112-5. Review. Japanese. PubMed PMID: 16689294. 9: Yano T, Taketani Y. [GnRH antagonist]. Nihon Rinsho. 2001 Jan;59 Suppl 1:133-8. Review. Japanese. PubMed PMID: 11235152. 10: Dal Prato L, Borini A. Use of antagonists in ovarian stimulation protocols. Reprod Biomed Online. 2005 Mar;10(3):330-8. Review. PubMed PMID: 15820038. 11: Engel JB, Riethmüller-Winzen H, Diedrich K. Extrapituitary effects of GnRH antagonists in assisted reproduction: a review. Reprod Biomed Online. 2005 Feb;10(2):230-4. Review. PubMed PMID: 15823230. 12: Howles CM. The place of gonadotrophin-releasing hormone antagonists in reproductive medicine. Reprod Biomed Online. 2002;4 Suppl 3:64-71. Review. PubMed PMID: 12470569. 13: Hugues JN. [The programming of IVF cycles with antagonists]. J Gynecol Obstet Biol Reprod (Paris). 2004 Oct;33(6 Pt 2):3S19-20. Review. French. PubMed PMID: 15643680. 14: Merviel P, Najas S, Campy H, Floret S, Brasseur F. Use of GNRH antagonists in reproductive medicine. Minerva Ginecol. 2005 Feb;57(1):29-43. Review. PubMed PMID: 15758864. 15: Barri PN, Martinez F, Coroleu B, Tur R. The role of GnRH antagonists in assisted reproduction. Reprod Biomed Online. 2002;5 Suppl 1:14-9. Review. PubMed PMID: 12537777. 16: Felberbaum RE, Küpker W, Diedrich K. Will GnRH antagonists assist in the treatment of benign gynaecological diseases? Reprod Biomed Online. 2002;5 Suppl 1:68-72. Review. PubMed PMID: 12537785. 17: Diedrich K, Ludwig M, Felberbaum RE. The role of gonadotropin-releasing hormone antagonists in in vitro fertilization. Semin Reprod Med. 2001 Sep;19(3):213-20. Review. PubMed PMID: 11679902. 18: Haviv F, Bush EN, Knittle J, Greer J. LHRH antagonists. Pharm Biotechnol. 1998;11:131-49. Review. PubMed PMID: 9760679. 19: Ekerhovd E. [Use of GnRH antagonist for in vitro fertilization]. Tidsskr Nor Laegeforen. 2011 Sep 6;131(17):1649-52. doi: 10.4045/tidsskr.10.0489. Review. Norwegian. PubMed PMID: 21901037. 20: Schally AV, Comaru-Schally AM, Gonzalez-Barcena D. Present status of agonistic and antagonistic analogs of LH-RH in the treatment of advanced prostate cancer. Biomed Pharmacother. 1992;46(10):465-71. Review. PubMed PMID: 1363977.