Adjudin
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MedKoo CAT#: 317147

CAS#: 252025-52-8

Description: Adjudin, also known as AF-2364, is a drug which is under development as a potential non-hormonal male contraceptive drug, which acts by blocking the production of sperm in the testes, but without affecting testosterone production. It is an analogue of the chemotherapy drug lonidamine, an indazole-carboxylic acid, and further studies continue to be conducted into this family of drugs as possible contraceptives. A study in 2013 indicated that Adjudin, similar to its analogue lonidamine, has properties that inhibit cancer growth by targeting mitochondria and blocking energy metabolism in certain kinds of tumor cells in mice, indicating that it has potential as a drug for cancer therapy.


Chemical Structure

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Adjudin
CAS# 252025-52-8

Theoretical Analysis

MedKoo Cat#: 317147
Name: Adjudin
CAS#: 252025-52-8
Chemical Formula: C15H12Cl2N4O
Exact Mass: 334.03882
Molecular Weight: 335.19
Elemental Analysis: C, 53.75; H, 3.61; Cl, 21.15; N, 16.72; O, 4.77

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Same Day
100.0mg USD 250.0 Same Day
200.0mg USD 450.0 Same Day
500.0mg USD 850.0 Same Day
1.0g USD 1450.0 Same Day
2.0g USD 2450.0 Same Day
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Synonym: AF-2364; AF 2364; AF2364; Adjudin

IUPAC/Chemical Name: 1-(2,4-dichlorobenzyl)-1H-indazole-3-carbohydrazide

InChi Key: VENCPJAAXKBIJD-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12Cl2N4O/c16-10-6-5-9(12(17)7-10)8-21-13-4-2-1-3-11(13)14(20-21)15(22)19-18/h1-7H,8,18H2,(H,19,22)

SMILES Code: O=C(C1=NN(CC2=CC=C(Cl)C=C2Cl)C3=C1C=CC=C3)NN

Appearance: White to off-white 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 in water

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

Preparing Stock Solutions

The following data is based on the product molecular weight 335.19 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

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1: Cheng YH, Xia W, Wong EW, Xie BQ, Shao J, Liu T, Quan Y, Zhang T, Yang X, Geng K, Silvestrini B, Cheng CY. Adjudin - a Male Contraceptive with Other Biological Activities. Recent Pat Endocr Metab Immune Drug Discov. 2015 Oct 29. [Epub ahead of print] PubMed PMID: 26510796.

2: Quan Y, Xia L, Shao J, Yin S, Cheng CY, Xia W, Gao WQ. Adjudin protects rodent cochlear hair cells against gentamicin ototoxicity via the SIRT3-ROS pathway. Sci Rep. 2015 Feb 2;5:8181. doi: 10.1038/srep08181. PubMed PMID: 25640330; PubMed Central PMCID: PMC4313083.

3: Cheng YH, Jenardhanan P, Mathur PP, Qian X, Xia W, Silvestrini B, Cheng CY. Interaction of oligomeric breast cancer resistant protein (BCRP) with adjudin: a male contraceptive with anti-cancer activity. Curr Mol Pharmacol. 2014;7(2):147-53. Review. PubMed PMID: 25620224.

4: Liu T, Zhang T, Yu H, Shen H, Xia W. Adjudin protects against cerebral ischemia reperfusion injury by inhibition of neuroinflammation and blood-brain barrier disruption. J Neuroinflammation. 2014 Jun 14;11:107. doi: 10.1186/1742-2094-11-107. PubMed PMID: 24927761; PubMed Central PMCID: PMC4132223.

5: Qian X, Cheng YH, Jenardhanan P, Mruk DD, Mathur PP, Xia W, Silvestrini B, Cheng CY. Adjudin disrupts spermatogenesis by targeting drug transporters: Lesson from the breast cancer resistance protein (BCRP). Spermatogenesis. 2013 Apr 1;3(2):e24993. PubMed PMID: 23885306; PubMed Central PMCID: PMC3710224.

6: Su L, Jenardhanan P, Mruk DD, Mathur PP, Cheng YH, Mok KW, Bonanomi M, Silvestrini B, Cheng CY. Role of P-glycoprotein at the blood-testis barrier on adjudin distribution in the testis: a revisit of recent data. Adv Exp Med Biol. 2012;763:318-33. PubMed PMID: 23397632; PubMed Central PMCID: PMC4114387.

7: Xie QR, Liu Y, Shao J, Yang J, Liu T, Zhang T, Wang B, Mruk DD, Silvestrini B, Cheng CY, Xia W. Male contraceptive Adjudin is a potential anti-cancer drug. Biochem Pharmacol. 2013 Feb 1;85(3):345-55. doi: 10.1016/j.bcp.2012.11.008. Epub 2012 Nov 23. PubMed PMID: 23178657; PubMed Central PMCID: PMC4108200.

8: Li K, Ni Y, He Y, Chen WY, Lu JX, Cheng CY, Ge RS, Shi QX. Inhibition of sperm capacitation and fertilizing capacity by adjudin is mediated by chloride and its channels in humans. Hum Reprod. 2013 Jan;28(1):47-59. doi: 10.1093/humrep/des384. Epub 2012 Oct 31. PubMed PMID: 23117128; PubMed Central PMCID: PMC3522416.

9: Shao J, Liu T, Xie QR, Zhang T, Yu H, Wang B, Ying W, Mruk DD, Silvestrini B, Cheng CY, Xia W. Adjudin attenuates lipopolysaccharide (LPS)- and ischemia-induced microglial activation. J Neuroimmunol. 2013 Jan 15;254(1-2):83-90. doi: 10.1016/j.jneuroim.2012.09.012. Epub 2012 Oct 17. PubMed PMID: 23084372; PubMed Central PMCID: PMC4108195.

10: Cheng CY, Lie PP, Wong EW, Mruk DD, Silvestrini B. Adjudin disrupts spermatogenesis via the action of some unlikely partners: Eps8, Arp2/3 complex, drebrin E, PAR6 and 14-3-3. Spermatogenesis. 2011 Oct;1(4):291-297. Epub 2011 Oct 1. PubMed PMID: 22332112; PubMed Central PMCID: PMC3271640.

11: Mruk DD, Cheng CY. Testin and actin are key molecular targets of adjudin, an anti-spermatogenic agent, in the testis. Spermatogenesis. 2011 Apr;1(2):137-146. PubMed PMID: 22319662; PubMed Central PMCID: PMC3271656.

12: Mok KW, Mruk DD, Lee WM, Cheng CY. Spermatogonial stem cells alone are not sufficient to re-initiate spermatogenesis in the rat testis following adjudin-induced infertility. Int J Androl. 2012 Feb;35(1):86-101. doi: 10.1111/j.1365-2605.2011.01183.x. Epub 2011 Jun 22. PubMed PMID: 21696392; PubMed Central PMCID: PMC3457811.

13: 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.

14: Su L, Cheng CY, Mruk DD. Adjudin-mediated Sertoli-germ cell junction disassembly affects Sertoli cell barrier function in vitro and in vivo. Int J Biochem Cell Biol. 2010 Nov;42(11):1864-75. doi: 10.1016/j.biocel.2010.08.004. Epub 2010 Aug 14. PubMed PMID: 20713173; PubMed Central PMCID: PMC2950250.

15: Kopera IA, Su L, Bilinska B, Cheng CY, Mruk DD. An in vivo study on adjudin and blood-testis barrier dynamics. Endocrinology. 2009 Oct;150(10):4724-33. doi: 10.1210/en.2008-1779. Epub 2009 Jul 2. PubMed PMID: 19574397; PubMed Central PMCID: PMC2754679.

16: Hu GX, Hu LF, Yang DZ, Li JW, Chen GR, Chen BB, Mruk DD, Bonanomi M, Silvestrini B, Cheng CY, Ge RS. Adjudin targeting rabbit germ cell adhesion as a male contraceptive: a pharmacokinetics study. J Androl. 2009 Jan-Feb;30(1):87-93. doi: 10.2164/jandrol.108.004994. Epub 2008 Sep 18. PubMed PMID: 18802200; PubMed Central PMCID: PMC4381873.

17: Sarkar O, Mathur PP. Adjudin-mediated germ cell depletion alters the anti-oxidant status of adult rat testis. Mol Reprod Dev. 2009 Jan;76(1):31-7. doi: 10.1002/mrd.20928. PubMed PMID: 18449895.

18: Xia W, Mruk DD, Lee WM, Cheng CY. Unraveling the molecular targets pertinent to junction restructuring events during spermatogenesis using the Adjudin-induced germ cell depletion model. J Endocrinol. 2007 Mar;192(3):563-83. PubMed PMID: 17332525; PubMed Central PMCID: PMC2804028.

19: Wolski KM, Mruk DD, Cameron DF. The Sertoli-spermatid junctional complex adhesion strength is affected in vitro by adjudin. J Androl. 2006 Nov-Dec;27(6):790-4. Epub 2006 Jun 28. PubMed PMID: 16809272.

20: Sarkar O, Xia W, Mruk DD. Adjudin-mediated junction restructuring in the seminiferous epithelium leads to displacement of soluble guanylate cyclase from adherens junctions. J Cell Physiol. 2006 Jul;208(1):175-87. PubMed PMID: 16547975.

Adjudin

50.0mg / USD 150.0