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

MedKoo CAT#: 202723

CAS#: 872719-49-8

Description: TAK-683 is an investigational peptide derivative of metastin that has been shown preclinically to be a potent metastin/GPR54 agonist both in vitro and in vivo. Administration of TAK-683 to male rats for 4 or 8 weeks has been shown to deplete GnRH in the hypothalamus and to reduce plasma FSH, LH and testosterone concentrations. The metastin analogue TAK-683 may be a promising candidate for further investigation in clinical trials in prostate cancer. A related metastin analogue, TAK-448, is also being evaluated in animal studies and in phase 1 clinical trials in prostate cancer

Chemical Structure

CAS# 872719-49-8

Theoretical Analysis

MedKoo Cat#: 202723
Name: TAK-683
CAS#: 872719-49-8
Chemical Formula: C64H83N17O13
Exact Mass: 1297.63563
Molecular Weight: 1298.47
Elemental Analysis: C, 59.20; H, 6.44; N, 18.34; O, 16.02

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Synonym: TAK-683, TAK 683, TAK683

IUPAC/Chemical Name: (S)-2-((R)-2-((R)-2-acetamido-3-(4-hydroxyphenyl)propanamido)-3-(1H-indol-3-yl)propanamido)-N1-((8S,11S,17S,20S,21R)-8-(((S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamoyl)-17-benzyl-21-hydroxy-3-imino-11-isobutyl-10,13,16,19-tetraoxo-2,4,9,12,14,15,18-heptaazadocosan-20-yl)succinamide


InChi Code: InChI=1S/C64H83N17O13/c1-34(2)26-48(57(88)73-46(20-13-25-69-63(67)68-5)56(87)74-47(55(66)86)29-39-32-70-44-18-11-9-16-42(39)44)78-64(94)81-80-61(92)50(27-37-14-7-6-8-15-37)77-62(93)54(35(3)82)79-60(91)52(31-53(65)85)76-59(90)51(30-40-33-71-45-19-12-10-17-43(40)45)75-58(89)49(72-36(4)83)28-38-21-23-41(84)24-22-38/h6-12,14-19,21-24,32-35,46-52,54,70-71,82,84H,13,20,25-31H2,1-5H3,(H2,65,85)(H2,66,86)(H,72,83)(H,73,88)(H,74,87)(H,75,89)(H,76,90)(H,77,93)(H,79,91)(H,80,92)(H3,67,68,69)(H2,78,81,94)/t35-,46+,47+,48+,49-,50+,51-,52+,54+/m1/s1

SMILES Code: O=C(N)[C@H](CC1=CNC2=C1C=CC=C2)NC([C@H](CCCNC(NC)=N)NC([C@H](CC(C)C)NC(NNC([C@H](CC3=CC=CC=C3)NC([C@H]([C@H](O)C)NC([C@H](CC(N)=O)NC([C@@H](CC4=CNC5=C4C=CC=C5)NC([C@@H](CC6=CC=C(O)C=C6)NC(C)=O)=O)=O)=O)=O)=O)=O)=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, not soluble 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1298.47 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.

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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

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 1: Endo N, Tamesaki C, Ohkura S, Wakabayashi Y, Matsui H, Tanaka A, Watanabe T, Okamura H, Tanaka T. Differential changes in luteinizing hormone secretion after administration of the investigational metastin/kisspeptin analog TAK-683 in goats. Anim Reprod Sci. 2015 May 29. pii: S0378-4320(15)00129-3. doi: 10.1016/j.anireprosci.2015.05.016. [Epub ahead of print] PubMed PMID: 26051610.

2: Yamamura T, Wakabayashi Y, Sakamoto K, Matsui H, Kusaka M, Tanaka T, Ohkura S, Okamura H. The effects of chronic subcutaneous administration of an investigational kisspeptin analog, TAK-683, on gonadotropin-releasing hormone pulse generator activity in goats. Neuroendocrinology. 2014;100(2-3):250-64. doi: 10.1159/000369819. Epub 2014 Nov 18. PubMed PMID: 25428554.

3: Matsui H, Masaki T, Akinaga Y, Kiba A, Takatsu Y, Nakata D, Tanaka A, Ban J, Matsumoto S, Kumano S, Suzuki A, Ikeda Y, Yamaguchi M, Watanabe T, Ohtaki T, Kusaka M. Pharmacologic profiles of investigational kisspeptin/metastin analogues, TAK-448 and TAK-683, in adult male rats in comparison to the GnRH analogue leuprolide. Eur J Pharmacol. 2014 Jul 15;735:77-85. doi: 10.1016/j.ejphar.2014.03.058. Epub 2014 Apr 18. PubMed PMID: 24747751.

4: Goto Y, Endo N, Nagai K, Ohkura S, Wakabayashi Y, Tanaka A, Matsui H, Kusaka M, Okamura H, Tanaka T. Ovarian and hormonal responses to follicular phase administration of investigational metastin/kisspeptin analog, TAK-683, in goats. Reprod Domest Anim. 2014 Apr;49(2):338-42. doi: 10.1111/rda.12283. Epub 2014 Feb 1. PubMed PMID: 24484509.

5: Tanaka T, Ohkura S, Wakabayashi Y, Kuroiwa T, Nagai K, Endo N, Tanaka A, Matsui H, Kusaka M, Okamura H. Differential effects of continuous exposure to the investigational metastin/kisspeptin analog TAK-683 on pulsatile and surge mode secretion of luteinizing hormone in ovariectomized goats. J Reprod Dev. 2013 Dec 17;59(6):563-8. Epub 2013 Sep 19. PubMed PMID: 24047956; PubMed Central PMCID: PMC3934154.

6: Asami T, Nishizawa N, Matsui H, Nishibori K, Ishibashi Y, Horikoshi Y, Nakayama M, Matsumoto S, Tarui N, Yamaguchi M, Matsumoto H, Ohtaki T, Kitada C. Design, synthesis, and biological evaluation of novel investigational nonapeptide KISS1R agonists with testosterone-suppressive activity. J Med Chem. 2013 Nov 14;56(21):8298-307. doi: 10.1021/jm401056w. Epub 2013 Oct 17. PubMed PMID: 24047141.

7: Kuze Y, Jinno F, Kondo T, Asahi S. Highly sensitive liquid chromatography-tandem mass spectrometry method for quantification of TAK-448 in human plasma. J Pharm Biomed Anal. 2013 Sep;83:75-81. doi: 10.1016/j.jpba.2013.04.023. Epub 2013 Apr 29. PubMed PMID: 23708433.

8: Scott G, Ahmad I, Howard K, MacLean D, Oliva C, Warrington S, Wilbraham D, Worthington P. Double-blind, randomized, placebo-controlled study of safety, tolerability, pharmacokinetics and pharmacodynamics of TAK-683, an investigational metastin analogue in healthy men. Br J Clin Pharmacol. 2013 Feb;75(2):381-91. doi: 10.1111/j.1365-2125.2012.04385.x. PubMed PMID: 22803642; PubMed Central PMCID: PMC3579253.

9: Yoshida N, Nishizawa N, Matsui H, Moriya Y, Kitada C, Asami T, Matsumoto H. Development and validation of sensitive sandwich ELISAs for two investigational nonapeptide metastin receptor agonists, TAK-448 and TAK-683. J Pharm Biomed Anal. 2012 Nov;70:369-77. doi: 10.1016/j.jpba.2012.05.033. Epub 2012 Jun 1. PubMed PMID: 22748666.