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Details

Stereochemistry ACHIRAL
Molecular Formula C15H12Cl2N4O
Molecular Weight 335.188
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADJUDIN

SMILES

NNC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C3=CC=CC=C13

InChI

InChIKey=VENCPJAAXKBIJD-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H12Cl2N4O
Molecular Weight 335.188
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Adjudin (known as AF-2364) was developed as a male contraceptive drug, which induces reversible germ cell loss from the seminiferous epithelium by disrupting cell adhesion function between Sertoli and germ cells, in particular, elongating/elongate/round spermatids and spermatocytes but not spermatogonia. This drug was in phase II clinical trial for human. In addition was discovered, that adjudin could trigger mitochondrial dysfunction in cancer cells, apparently affecting the mitochondrial mass, inducing the loss of mitochondrial membrane potential and reducing cellular ATP levels and thus could be a potential drug for cancer therapy.

Originator

Curator's Comment: Cheng CY et al from Population Council, The Rockefeller University

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Adjudin disrupts spermatogenesis by targeting drug transporters: Lesson from the breast cancer resistance protein (BCRP).
2013 Apr 1
Adjudin protects against cerebral ischemia reperfusion injury by inhibition of neuroinflammation and blood-brain barrier disruption.
2014 Jun 14
Adjudin--A Male Contraceptive with Other Biological Activities.
2015

Sample Use Guides

in rabbits: Animals were treated intravenously or orally with 25 mg/kg per week adjudin (1 injection each week) for 4 consecutive weeks.
Route of Administration: Other
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. The IC50 of Adjudin was determined to be 58.0 µM, 13.8 µM, 72.3 µM and 52.7 µM against SGC-7901, MDA-MB-231, Smmc-7721 and MIA Paca-2 cells, respectively, after treatment for 24 h.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:41:11 GMT 2023
Edited
by admin
on Sat Dec 16 17:41:11 GMT 2023
Record UNII
VZT8V72829
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADJUDIN
Common Name English
1-(2,4-DICHLOROBENZYL)-1H-INDAZOLE-3-CARBOHYDRAZIDE
Common Name English
1H-INDAZOLE-3-CARBOXYLIC ACID, 1-((2,4-DICHLOROPHENYL)METHYL)-, HYDRAZIDE
Systematic Name English
1-((2,4-DICHLOROPHENYL)METHYL)INDAZOLE-3-CARBOHYDRAZIDE
Systematic Name English
1-((2,4-DICHLOROPHENYL)METHYL)-1H-INDAZOLE-3-CARBOXYLIC ACID HYDRAZIDE
Systematic Name English
AF-2364
Code English
Code System Code Type Description
CAS
252025-52-8
Created by admin on Sat Dec 16 17:41:11 GMT 2023 , Edited by admin on Sat Dec 16 17:41:11 GMT 2023
PRIMARY
PUBCHEM
9819086
Created by admin on Sat Dec 16 17:41:11 GMT 2023 , Edited by admin on Sat Dec 16 17:41:11 GMT 2023
PRIMARY
FDA UNII
VZT8V72829
Created by admin on Sat Dec 16 17:41:11 GMT 2023 , Edited by admin on Sat Dec 16 17:41:11 GMT 2023
PRIMARY
WIKIPEDIA
Adjudin
Created by admin on Sat Dec 16 17:41:11 GMT 2023 , Edited by admin on Sat Dec 16 17:41:11 GMT 2023
PRIMARY