Gamendazole

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

MedKoo CAT#: 330113

CAS#: 877773-32-5

Description: 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

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Gamendazole
CAS# 877773-32-5
Instruction

Theoretical Analysis

MedKoo Cat#: 330113
Name: Gamendazole
CAS#: 877773-32-5
Chemical Formula: C18H11Cl2F3N2O2
Exact Mass: 414.02
Molecular Weight: 415.193
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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vivo protocol:

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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.