Abarelix acetate | CAS# 785804-17-3 | GnRHR Antagonist

MedKoo Cat#: 574014 | Name: Abarelix acetate

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Description:

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

Abarelix acetate is a synthetic third generation gonadotropin-releasing hormone receptor (GnRHR) antagonist. It increases histamine release from rat peritoneal mast cells in vitro and from a human skin model ex vivo. In vivo, abarelix decreases plasma luteinizing hormone (LH) levels six hours post-treatment in castrated rats, with levels returning to baseline within 24 hours.3 Abarelix (2 mg/kg) also transiently decreases plasma testosterone levels in intact rats, with levels returning to baseline within seven days post-treatment. Formulations containing abarelix have previously been used in the treatment of advanced prostate cancer.

Chemical Structure

Abarelix acetate

CAS#785804-17-3 (acetate)

Theoretical Analysis

MedKoo Cat#: 574014

Name: Abarelix acetate

CAS#: 785804-17-3 (acetate)

Chemical Formula: C74H99ClN14O16

Exact Mass: 1474.7052

Molecular Weight: 1476.14

Elemental Analysis: C, 60.21; H, 6.76; Cl, 2.40; N, 13.28; O, 17.34

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks
25mg	USD 1,050.00	2 Weeks

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Related CAS #

785804-17-3 (acetate) 183552-38-7 (free base)

Synonym

Abarelix acetate

IUPAC/Chemical Name

N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-N-methyl-L-tyrosyl-D-asparaginyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-D-alaninamide, acetate salt

InChi Key

ZRHCGBCCWJPSQF-JOOIWXSYSA-N

InChi Code

InChI=1S/C72H95ClN14O14.C2H4O2/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47;1-2(3)4/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96);1H3,(H,3,4)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+;/m1./s1

SMILES Code

CC(N[C@H](CC1=CC(C=CC=C2)=C2C=C1)C(N[C@H](CC3=CC=C(Cl)C=C3)C(N[C@H](CC4=CC=CN=C4)C(N[C@@H](CO)C(N(C)[C@@H](CC5=CC=C(O)C=C5)C(N[C@H](CC(N)=O)C(N[C@@H](CC(C)C)C(N[C@@H](CCCCNC(C)C)C(N6CCC[C@H]6C(N[C@H](C)C(N)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O.OC(C)=O

Appearance

A crystalline solid

Purity

>95% (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

>3 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

λmax: 226 nm

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,476.14 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.

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: Debruyne F, Bhat G, Garnick MB. Abarelix for injectable suspension: first-in- class gonadotropin-releasing hormone antagonist for prostate cancer. Future Oncol. 2006 Dec;2(6):677-96. doi: 10.2217/14796694.2.6.677. PMID: 17155895. 2: Hogle WP. Abarelix (plenaxis). Clin J Oncol Nurs. 2004 Dec;8(6):663-5. doi: 10.1188/04.CJON.663-669. PMID: 15637961. 3: Abarelix: abarelix-depot-F, abarelix-depot-M, abarelix-L, PPI 149, R 3827. Drugs R D. 2003;4(3):161-6. doi: 10.2165/00126839-200304030-00004. PMID: 12757402. 4: Kirby RS, Fitzpatrick JM, Clarke N. Abarelix and other gonadotrophin- releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. PMID: 20053189. 5: Mongiat-Artus P, Teillac P. Abarelix: the first gonadotrophin-releasing hormone antagonist for the treatment of prostate cancer. Expert Opin Pharmacother. 2004 Oct;5(10):2171-9. doi: 10.1517/14656566.5.10.2171. PMID: 15461552. 6: Reddy GK. Abarelix (Plenaxis): a gonadotropin-releasing hormone antagonist for medical castration in patients with advanced prostate cancer. Clin Prostate Cancer. 2004 Mar;2(4):209-11. doi: 10.1016/s1540-0352(11)70046-4. PMID: 15072602. 7: Doehn C, Jocham D. Technology evaluation: Abarelix, Praecis pharmaceuticals. Curr Opin Mol Ther. 2000 Oct;2(5):579-85. PMID: 11249760. 8: Retraction statement: Reconstitution of Plenaxis® (Abarelix) 100 mg for injection is more effective with a vortex-like mixer than when performed manually. J Pharm Pract. 2010 Feb;23(1):78. doi: 10.1177/0897190009360369. PMID: 21507797. 9: Beer TM, Ryan C, Bhat G, Garnick M; Abarelix Study Group. Dose-escalated abarelix in androgen-independent prostate cancer: a phase I study. Anticancer Drugs. 2006 Oct;17(9):1075-9. doi: 10.1097/01.cad.0000231476.84782.55. PMID: 17001181. 10: Abarelix (Plenaxis) for advanced prostate cancer. Med Lett Drugs Ther. 2004 Mar 15;46(1178):22-3. PMID: 15037857. 11: Tomera K, Gleason D, Gittelman M, Moseley W, Zinner N, Murdoch M, Menon M, Campion M, Garnick MB. The gonadotropin-releasing hormone antagonist abarelix depot versus luteinizing hormone releasing hormone agonists leuprolide or goserelin: initial results of endocrinological and biochemical efficacies in patients with prostate cancer. J Urol. 2001 May;165(5):1585-9. PMID: 11342922. 12: Wong SL, Lau DT, Baughman SA, Menchaca D, Garnick MB. Pharmacokinetics and pharmacodynamics of abarelix, a gonadotropin-releasing hormone antagonist, after subcutaneous continuous infusion in patients with prostate cancer. Clin Pharmacol Ther. 2003 Apr;73(4):304-11. doi: 10.1016/s0009-9236(02)17637-5. PMID: 12709720. 13: Koch M, Steidle C, Brosman S, Centeno A, Gaylis F, Campion M, Garnick MB; Abarelix Study Group. An open-label study of abarelix in men with symptomatic prostate cancer at risk of treatment with LHRH agonists. Urology. 2003 Nov;62(5):877-82. doi: 10.1016/s0090-4295(03)00656-3. PMID: 14624912. 14: Garnick MB, Mottet N. New treatment paradigm for prostate cancer: abarelix initiation therapy for immediate testosterone suppression followed by a luteinizing hormone-releasing hormone agonist. BJU Int. 2012 Aug;110(4):499-504. doi: 10.1111/j.1464-410X.2011.10708.x. Epub 2011 Nov 16. PMID: 22093775. 15: Wong SL, Lau DT, Baughman SA, Fotheringham N, Menchaca D, Garnick MB. Pharmacokinetics and pharmacodynamics of a novel depot formulation of abarelix, a gonadotropin-releasing hormone (GnRH) antagonist, in healthy men ages 50 to 75. J Clin Pharmacol. 2004 May;44(5):495-502. doi: 10.1177/0091270004264920. PMID: 15102870. 16: McLeod D, Zinner N, Tomera K, Gleason D, Fotheringham N, Campion M, Garnick MB; Abarelix Study Group. A phase 3, multicenter, open-label, randomized study of abarelix versus leuprolide acetate in men with prostate cancer. Urology. 2001 Nov;58(5):756-61. doi: 10.1016/s0090-4295(01)01342-5. PMID: 11711355. 17: Beer TM, Garzotto M, Eilers KM, Lemmon D. Phase II study of abarelix depot for androgen independent prostate cancer progression during gonadotropin- releasing hormone agonist therapy. J Urol. 2003 May;169(5):1738-41. doi: 10.1097/01.ju.0000059584.47272.9d. PMID: 12686821. 18: Beer TM, Garzotto M, Eilers KM, Lemmon D, Wersinger EM. Targeting FSH in androgen-independent prostate cancer: abarelix for prostate cancer progressing after orchiectomy. Urology. 2004 Feb;63(2):342-7. doi: 10.1016/j.urology.2003.09.045. PMID: 14972486. 19: Garnick MB, Campion M. Abarelix Depot, a GnRH antagonist, v LHRH superagonists in prostate cancer: differential effects on follicle-stimulating hormone. Abarelix Depot study group. Mol Urol. 2000 Fall;4(3):275-7. PMID: 11062384. 20: Trachtenberg J, Gittleman M, Steidle C, Barzell W, Friedel W, Pessis D, Fotheringham N, Campion M, Garnick MB; Abarelix Study Group. A phase 3, multicenter, open label, randomized study of abarelix versus leuprolide plus daily antiandrogen in men with prostate cancer. J Urol. 2002 Apr;167(4):1670-4. doi: 10.1097/00005392-200204000-00021. PMID: 11912385.