Gamendazole | CAS#877773-32-5

MedKoo Cat#: 330113 | Name: Gamendazole

Description:

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

Gamendazole is a novel drug candidate for male contraception. It is an indazole carboxylic acid derived from lonidamine (LND). It has been shown to reduce fertility in male rats without affecting testosterone levels, but human clinical trials have not been started.

Chemical Structure

Gamendazole

CAS#877773-32-5

Theoretical Analysis

MedKoo Cat#: 330113

Name: Gamendazole

CAS#: 877773-32-5

Chemical Formula: C18H11Cl2F3N2O2

Exact Mass: 414.0150

Molecular Weight: 415.19

Elemental Analysis: C, 52.07; H, 2.67; Cl, 17.08; F, 13.73; N, 6.75; O, 7.71

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Gamendazole;

IUPAC/Chemical Name

(E)-3-[1-[(2,4-Dichlorophenyl)methyl]-6-(trifluoromethyl)indazol-3-yl]prop-2-enoic acid

InChi Key

KYYQMVUKYQCSQY-AATRIKPKSA-N

InChi Code

InChI=1S/C18H11Cl2F3N2O2/c19-12-3-1-10(14(20)8-12)9-25-16-7-11(18(21,22)23)2-4-13(16)15(24-25)5-6-17(26)27/h1-8H,9H2,(H,26,27)/b6-5+

SMILES Code

O=C(O)/C=C/C1=NN(CC2=CC=C(Cl)C=C2Cl)C3=C1C=CC(C(F)(F)F)=C3

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 415.19 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: Burglová K, Rylová G, Markos A, Prichystalova H, Soural M, Petracek M, Medvedikova M, Tejral G, Sopko B, Hradil P, Dzubak P, Hajduch M, Hlavac J. Identification of Eukaryotic Translation Elongation Factor 1-α 1 Gamendazole-Binding Site for Binding of 3-Hydroxy-4(1 H)-quinolinones as Novel Ligands with Anticancer Activity. J Med Chem. 2018 Mar 16. doi: 10.1021/acs.jmedchem.8b00078. [Epub ahead of print] PubMed PMID: 29498519. 2: Naas M, El Kazzouli S, Essassi el M, Bousmina M, Guillaumet G. Palladium-Catalyzed Oxidative Direct C3- and C7-Alkenylations of Indazoles: Application to the Synthesis of Gamendazole. Org Lett. 2015 Sep 4;17(17):4320-3. doi: 10.1021/acs.orglett.5b02136. Epub 2015 Aug 26. PubMed PMID: 26308587. 3: Olesen SH, Ingles DJ, Zhu JY, Martin MP, Betzi S, Georg GI, Tash JS, Schönbrunn E. Stability of the human Hsp90-p50Cdc37 chaperone complex against nucleotides and Hsp90 inhibitors, and the influence of phosphorylation by casein kinase 2. Molecules. 2015 Jan 19;20(1):1643-60. doi: 10.3390/molecules20011643. PubMed PMID: 25608045; PubMed Central PMCID: PMC4601640. 4: Cheng CY. Toxicants target cell junctions in the testis: Insights from the indazole-carboxylic acid model. Spermatogenesis. 2015 Jan 21;4(2):e981485. eCollection 2014 May-Aug. Review. PubMed PMID: 26413399; PubMed Central PMCID: PMC4581065. 5: Nya-Ngatchou JJ, Amory JK. New approaches to male non-hormonal contraception. Contraception. 2013 Mar;87(3):296-9. doi: 10.1016/j.contraception.2012.08.016. Epub 2012 Sep 17. Review. PubMed PMID: 22995542; PubMed Central PMCID: PMC3529759. 6: Mok KW, Mruk DD, Lie PP, Lui WY, Cheng CY. Adjudin, a potential male contraceptive, exerts its effects locally in the seminiferous epithelium of mammalian testes. Reproduction. 2011 May;141(5):571-80. doi: 10.1530/REP-10-0464. Epub 2011 Feb 9. Review. PubMed PMID: 21307270; PubMed Central PMCID: PMC4381908. 7: Matts RL, Brandt GE, Lu Y, Dixit A, Mollapour M, Wang S, Donnelly AC, Neckers L, Verkhivker G, Blagg BS. A systematic protocol for the characterization of Hsp90 modulators. Bioorg Med Chem. 2011 Jan 1;19(1):684-92. doi: 10.1016/j.bmc.2010.10.029. Epub 2010 Oct 19. PubMed PMID: 21129982; PubMed Central PMCID: PMC4618652. 8: Tash JS, Attardi B, Hild SA, Chakrasali R, Jakkaraj SR, Georg GI. A novel potent indazole carboxylic acid derivative blocks spermatogenesis and is contraceptive in rats after a single oral dose. Biol Reprod. 2008 Jun;78(6):1127-38. doi: 10.1095/biolreprod.106.057810. Epub 2008 Jan 23. PubMed PMID: 18218612. 9: Tash JS, Chakrasali R, Jakkaraj SR, Hughes J, Smith SK, Hornbaker K, Heckert LL, Ozturk SB, Hadden MK, Kinzy TG, Blagg BS, Georg GI. Gamendazole, an orally active indazole carboxylic acid male contraceptive agent, targets HSP90AB1 (HSP90BETA) and EEF1A1 (eEF1A), and stimulates Il1a transcription in rat Sertoli cells. Biol Reprod. 2008 Jun;78(6):1139-52. doi: 10.1095/biolreprod.107.062679. Epub 2008 Jan 23. PubMed PMID: 18218611.