MedKoo Cat#: 317147 | Name: Adjudin
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Description:

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

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

Adjudin
Adjudin
CAS#252025-52-8

Theoretical Analysis

MedKoo Cat#: 317147

Name: Adjudin

CAS#: 252025-52-8

Chemical Formula: C15H12Cl2N4O

Exact Mass: 334.0388

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
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 850.00 Ready to ship
1g USD 1,550.00 Ready to ship
2g USD 2,790.00 Ready to ship
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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
More Info
Biological target:
Adjudin is a Cl- channel blocker and a mitochondria inhibitor.
In vitro activity:
As a result, Adjudin inhibited cell proliferation in a dose dependent manner in SGC-7901 (human gastric adenocarcinoma cell), MDA-MB-231 (human breast adenocarcinoma cell), Smmc-7721 (human hepatoma cell) and MIA Paca-2 (human pancreatic adenocarcinoma cell) cells (Fig. 2A). Similar results were obtained in other human and mice cancer cell lines (Table 1). To further study the anti-cancer effect of Adjudin compared with LND, the cell growth analysis was used to determine the value of IC50 after treatment of Adjudin and LND for 24 h. In both cell lines Adjudin was shown to be a more potent drug to reduce cell proliferation than LND. These results seemed to suggest a therapeutic window for Adjudin in cancer treatment. Reference: Biochem Pharmacol. 2013 Feb 1; 85(3): 345–355. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4108200/
In vivo activity:
Twenty-four hours after tMCAO, mice were divided randomly into three groups for NSC or vehicle injection: PBS group, NSC group, and adjudin-pretreated NSC group. NSCs (1 × 106 cells suspended in PBS) that was pretreated with or without adjudin or untreated were injected into the striatum of the ipsilateral hemisphere in mice. Adjudin-pretreated NSCs greatly reduced infarct volume by as much as 50% compared to the PBS group, whereas untreated NSCs only produced ~ 30% reduction in the infarct volume compared to the PBS group (Fig. 5b). Meanwhile, adjudin preconditioning improved behavioral performance with the neuroscore plummeting by approximately 50% in comparison to the PBS group, while untreated NSCs resulted in only a 25% decrease in neuroscore (Fig. 5c). These findings illustrate that adjudin pretreatment could significantly attenuate I/R-induced cerebral injury. Moreover, compared to the untreated NSCs, PBS, and sham groups, the adjudin preconditioning group considerably increased the ratio of p-Akt/Akt both in the cortex and the striatum (Fig. 5d–g). Reference: Stem Cell Res Ther. 2017; 8: 248. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5678778/
Solvent mg/mL mM
Solubility
DMSO 34.6 103.11
DMF 30.0 89.50
DMF:PBS (pH 7.2) (1:20) 0.1 0.15
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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
Formulation protocol:
1. 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. PMID: 23178657; PMCID: PMC4108200. 2. 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. PMID: 23084372; PMCID: PMC4108195. 3. Zhang T, Yang X, Liu T, Shao J, Fu N, Yan A, Geng K, Xia W. Adjudin-preconditioned neural stem cells enhance neuroprotection after ischemia reperfusion in mice. Stem Cell Res Ther. 2017 Nov 7;8(1):248. doi: 10.1186/s13287-017-0677-0. PMID: 29115993; PMCID: PMC5678778. 4. 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. PMID: 25640330; PMCID: PMC4313083.
In vitro protocol:
1. 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. PMID: 23178657; PMCID: PMC4108200. 2. 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. PMID: 23084372; PMCID: PMC4108195.
In vivo protocol:
1. Zhang T, Yang X, Liu T, Shao J, Fu N, Yan A, Geng K, Xia W. Adjudin-preconditioned neural stem cells enhance neuroprotection after ischemia reperfusion in mice. Stem Cell Res Ther. 2017 Nov 7;8(1):248. doi: 10.1186/s13287-017-0677-0. PMID: 29115993; PMCID: PMC5678778. 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. PMID: 25640330; PMCID: PMC4313083.
1: Su Q, Su C, Zhang Y, Guo Y, Liu Y, Liu Y, Yong VW, Xue M. Adjudin protects blood-brain barrier integrity and attenuates neuroinflammation following intracerebral hemorrhage in mice. Int Immunopharmacol. 2024 May 10;132:111962. doi: 10.1016/j.intimp.2024.111962. Epub 2024 Apr 1. PMID: 38565042. 2: Zhu J, Park S, Kim SH, Kim CH, Jeong KH, Kim WJ. Sirtuin 3 regulates astrocyte activation by reducing Notch1 signaling after status epilepticus. Glia. 2024 Jun;72(6):1136-1149. doi: 10.1002/glia.24520. Epub 2024 Feb 26. PMID: 38406970. 3: Ren L, Charbord J, Chu L, Kemas AM, Bertuzzi M, Mi J, Xing C, Lauschke VM, Andersson O. Adjudin improves beta cell maturation, hepatic glucose uptake and glucose homeostasis. Diabetologia. 2024 Jan;67(1):137-155. doi: 10.1007/s00125-023-06020-4. Epub 2023 Oct 16. PMID: 37843554; PMCID: PMC10709271. 4: Gong S, Zhu S, Zhou P, Cheng CY, Li W, Yao W, Sun F. Discovering a Reversible Male Contraceptive Agent Derived from Lonidamine. ACS Omega. 2023 May 12;8(20):18245-18254. doi: 10.1021/acsomega.3c01840. PMID: 37251173; PMCID: PMC10210193. 5: Zou C, Tang Y, Zeng P, Cui D, Amili MA, Chang Y, Jin Z, Shen Y, Tan S, Guo S. cRGD-modified nanoparticles of multi-bioactive agent conjugate with pH-sensitive linkers and PD-L1 antagonist for integrative collaborative treatment of breast cancer. Nanoscale Horiz. 2023 Jun 26;8(7):870-886. doi: 10.1039/d2nh00590e. PMID: 36987679. 6: Wu D, Pandupuspitasari NS, Zhang K, Tang Y, Khan FA, Li H, Huang C, Sun F. Cytoskeletal orchestration of glucose uptake in Sertoli cell to support efferocytosis of apoptotic germ cells. Biochim Biophys Acta Mol Cell Res. 2023 Apr;1870(4):119434. doi: 10.1016/j.bbamcr.2023.119434. Epub 2023 Jan 27. PMID: 36716822. 7: Wang L, Bu T, Wu X, Gao S, Li X, De Jesus AB, Wong CKC, Chen H, Chung NPY, Sun F, Cheng CY. Cell-Cell Interaction-Mediated Signaling in the Testis Induces Reproductive Dysfunction-Lesson from the Toxicant/Pharmaceutical Models. Cells. 2022 Feb 9;11(4):591. doi: 10.3390/cells11040591. PMID: 35203242; PMCID: PMC8869896. 8: Park S, Zhu J, Jeong KH, Kim WJ. Adjudin prevents neuronal damage and neuroinflammation via inhibiting mTOR activation against pilocarpine-induced status epilepticus. Brain Res Bull. 2022 May;182:80-89. doi: 10.1016/j.brainresbull.2022.02.009. Epub 2022 Feb 16. PMID: 35182690. 9: Dadgostar E, Rahimi S, Nikmanzar S, Nazemi S, Naderi Taheri M, Alibolandi Z, Aschner M, Mirzaei H, Tamtaji OR. Aquaporin 4 in Traumatic Brain Injury: From Molecular Pathways to Therapeutic Target. Neurochem Res. 2022 Apr;47(4):860-871. doi: 10.1007/s11064-021-03512-w. Epub 2022 Jan 28. PMID: 35088218. 10: Gao S, Wu X, Wang L, Bu T, Perrotta A, Guaglianone G, Silvestrini B, Sun F, Cheng CY. Signaling Proteins That Regulate Spermatogenesis Are the Emerging Target of Toxicant-Induced Male Reproductive Dysfunction. Front Endocrinol (Lausanne). 2021 Dec 24;12:800327. doi: 10.3389/fendo.2021.800327. PMID: 35002976; PMCID: PMC8739942. 11: Wu S, Li L, Wu X, Wong CKC, Sun F, Cheng CY. AKAP9 supports spermatogenesis through its effects on microtubule and actin cytoskeletons in the rat testis. FASEB J. 2021 Oct;35(10):e21925. doi: 10.1096/fj.202100960R. PMID: 34569663. 12: Chen H, Jiang Y, Mruk DD, Cheng CY. Spermiation: Insights from Studies on the Adjudin Model. Adv Exp Med Biol. 2021;1288:241-254. doi: 10.1007/978-3-030-77779-1_12. PMID: 34453740. 13: Wang L, Li L, Wu X, Wong CKC, Perrotta A, Silvestrini B, Sun F, Cheng CY. mTORC1/rpS6 and p-FAK-Y407 signaling regulate spermatogenesis: Insights from studies of the adjudin pharmaceutical/toxicant model. Semin Cell Dev Biol. 2022 Jan;121:53-62. doi: 10.1016/j.semcdb.2021.03.024. Epub 2021 Apr 15. PMID: 33867214. 14: Govindarajulu M, Ramesh S, Neel L, Fabbrini M, Buabeid M, Fujihashi A, Dwyer D, Lynd T, Shah K, Mohanakumar KP, Smith F, Moore T, Dhanasekaran M. Nutraceutical based SIRT3 activators as therapeutic targets in Alzheimer's disease. Neurochem Int. 2021 Mar;144:104958. doi: 10.1016/j.neuint.2021.104958. Epub 2021 Jan 12. PMID: 33444675. 15: Othman FA, Tan SC. Preconditioning Strategies to Enhance Neural Stem Cell- Based Therapy for Ischemic Stroke. Brain Sci. 2020 Nov 23;10(11):893. doi: 10.3390/brainsci10110893. PMID: 33238363; PMCID: PMC7700351. 16: Huang Y, Sun G, Sun X, Li F, Zhao L, Zhong R, Peng Y. The Potential of Lonidamine in Combination with Chemotherapy and Physical Therapy in Cancer Treatment. Cancers (Basel). 2020 Nov 11;12(11):3332. doi: 10.3390/cancers12113332. PMID: 33187214; PMCID: PMC7696079. 17: Wang L, Yan M, Li H, Wu S, Ge R, Wong CKC, Silvestrini B, Sun F, Cheng CY. The Non-hormonal Male Contraceptive Adjudin Exerts its Effects via MAPs and Signaling Proteins mTORC1/rpS6 and FAK-Y407. Endocrinology. 2021 Jan 1;162(1):bqaa196. doi: 10.1210/endocr/bqaa196. PMID: 33094326; PMCID: PMC8244566. 18: Mao B, Bu T, Mruk D, Li C, Sun F, Cheng CY. Modulating the Blood-Testis Barrier Towards Increasing Drug Delivery. Trends Pharmacol Sci. 2020 Oct;41(10):690-700. doi: 10.1016/j.tips.2020.07.002. Epub 2020 Aug 10. PMID: 32792159. 19: Chen D, Ge S, Zuo L, Wang S, Liu M, Li S. Adjudin-loaded redox-sensitive paclitaxel-prodrug micelles for overcoming multidrug resistance with efficient targeted Colon cancer therapy. Drug Deliv. 2020 Dec;27(1):1094-1105. doi: 10.1080/10717544.2020.1797245. PMID: 32706289; PMCID: PMC7470106. 20: Yang C, Tu K, Gao H, Zhang L, Sun Y, Yang T, Kong L, Ouyang D, Zhang Z. The novel platinum(IV) prodrug with self-assembly property and structure- transformable character against triple-negative breast cancer. Biomaterials. 2020 Feb;232:119751. doi: 10.1016/j.biomaterials.2019.119751. Epub 2019 Dec 31. PMID: 31918218.