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Compound Detail

CHEMBL734

ACETOHYDROXAMIC ACID
💊 Approved Drug
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💊 Approved Drug

Basic Information

ChEMBL ID CHEMBL734
Name ACETOHYDROXAMIC ACID
Phase Approved
Structure Type MOL
InChI Key RRUDCFGSUDOHDG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acetohydroxamic acid Acide acetohydroxamique Acido acetohidroxamico Lithostat NSC-176136
7
Targets
56
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names
6
Indications
1
Mechanisms

Molecular Properties

75.1
MW (Da)
-0.49
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.30
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1983
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1984

Extended Properties

Molecular Formula C2H5NO2
MW 75.07
Aromatic Rings 0
Heavy Atoms 5
NP-Likeness 0.02

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial urease inhibitor INHIBITOR Bacterial urease ✓ ✓

Indications

Urinary Tract Infections Argininosuccinic Aciduria Carbamoyl-Phosphate Synthase I Deficiency Disease Citrullinemia Ornithine Carbamoyltransferase Deficiency Disease Urea Cycle Disorders, Inborn

ATC Classification

G04BX03
acetohydroxamic acid
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: UROLOGICALS

Activity Summary

IC50 43 meas. best 4.96
Ki 9 meas. best 5.58
Kd 4 meas. best 2.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 5.58 5.475 2600.0 8
Urease subunit alpha/Urease subunit beta
CHEMBL3885651
 IC50 4.96 4.6212 11000.0 17
Unchecked
CHEMBL612545
 IC50 4.84 4.4025 14310.0 4
Urease
CHEMBL4161
 IC50 4.76 4.5067 17300.0 3
Urease
CHEMBL5325
 IC50 4.76 4.76 17200.0 1
Bacterial urease
CHEMBL2364683
 IC50 4.54 4.54 29200.0 1
Carbonic anhydrase 2
CHEMBL205
 IC50 4.33 4.33 47000.0 3
Urease subunit alpha/Urease subunit beta
CHEMBL3885651
 Ki 4.02 4.02 96000.0 1
Macrophage metalloelastase
CHEMBL4393
 Kd 2.21 2.21 6180000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 2600.0 nM 5.58 Inhibition of Klebsiella aerogenes urease 18717581
Unchecked Ki = 2600.0 nM 5.58 Inhibition of Klebsiella aerogenes urease 20684601
Unchecked Ki = 3300.0 nM 5.48 Inhibition of urease from Sporosarcina pasteurii CCM 2056 using urea as substrat... 25699141
Unchecked Ki = 3300.0 nM 5.48 Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in am... 28236590
Unchecked Ki = 3300.0 nM 5.48 Reversible inhibition of purified Sporosarcinia pasteurii urease by phenol red b... 30850166
Unchecked Ki = 3300.0 nM 5.48 Steady state inhibition of Sporosarcina pasteurii CCM 2056 urease using urea as ... 27524377
Unchecked Ki = 3300.0 nM 5.48 Inhibition of Sporosarcina pasteurii CCM 2056 native urease using urea as substr... 37290184
Unchecked Ki = 5700.0 nM 5.24 Inhibition of urease from Proteus mirabilis CCM 1944 using urea as substrate by ... 25699141
Urease subunit alpha/Urease subunit beta IC50 = 11000.0 nM 4.96 Inhibition of Helicobacter pylori ATCC 43504 urease assessed as ammonia producti... 18625539
Unchecked IC50 = 14310.0 nM 4.84 Reversible inhibition of purified Sporosarcinia pasteurii urease by phenol red b... 30850166
Urease subunit alpha/Urease subunit beta IC50 = 17000.0 nM 4.77 Inhibition of Helicobacter pylori ATCC 43504 urease after 3 hrs pre-incubation 17400458
Urease subunit alpha/Urease subunit beta IC50 = 17000.0 nM 4.77 Inhibition of Helicobacter pylori ATCC 43504 urease assessed as ammonia producti... 19804978
Urease IC50 = 17300.0 nM 4.76 Inhibition of jack bean urease 17190464
Urease subunit alpha/Urease subunit beta IC50 = 17200.0 nM 4.76 Inhibition of cell free Helicobacter pylori ATCC 43504 urease assessed as reduct... 20801557
Urease IC50 = 17200.0 nM 4.76 Inhibition of Helicobacter pylori urease after 50 mins by indophenol method 30170940
Urease subunit alpha/Urease subunit beta IC50 = 18000.0 nM 4.75 Inhibition of Helicobacter pylori ATCC 43504 urease in presence of 0.4 mM dithio... 17400458
Urease subunit alpha/Urease subunit beta IC50 = 18400.0 nM 4.74 Inhibition of urease isolated from Helicobacter pylori ATCC 43504 assessed as am... 26113187
Urease subunit alpha/Urease subunit beta IC50 = 18200.0 nM 4.74 Inhibition of Helicobacter pylori ATCC 43504 urease-mediated ammonia production ... 23567958
Urease subunit alpha/Urease subunit beta IC50 = 19000.0 nM 4.72 Inhibition of Helicobacter pylori ATCC 43504 urease in presence of 0.4 mM 2-merc... 17400458
Urease subunit alpha/Urease subunit beta IC50 = 23800.0 nM 4.62 Inhibition of Helicobacter pylori urease using urea as substrate assessed as amm... 27492194

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
27524377 10.1021/acs.jmedchem.6b00986 Urease subunit alpha/Urease subunit beta 5
28236590 10.1016/j.bmcl.2017.02.022 Unchecked 4
19791805 10.1021/jm900775q Unchecked 3
17400458 10.1016/j.bmc.2007.03.045 Urease subunit alpha/Urease subunit beta 3
27524377 10.1021/acs.jmedchem.6b00986 Unchecked 3
20014752 10.1021/tx900326k Hepatotoxicity 3
30006158 10.1016/j.ejmech.2018.06.065 Urease subunit alpha/Urease subunit beta 3
25699141 10.1021/ml500380f Unchecked 2
8355246 10.1021/jm00069a002 No relevant target 2
29983280 10.1016/j.bmc.2018.07.003 Urease subunit alpha/Urease subunit beta 2
30006158 10.1016/j.ejmech.2018.06.065 Helicobacter pylori 2
26113187 10.1016/j.bmc.2015.06.014 Urease subunit alpha/Urease subunit beta 2
20801557 10.1016/j.ejmech.2010.08.015 Urease subunit alpha/Urease subunit beta 2
23974021 10.1016/j.ejmech.2013.07.047 Urease subunit alpha/Urease subunit beta 2
22824761 10.1016/j.bmc.2012.07.002 Urease subunit alpha/Urease subunit beta 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
18625539 10.1016/j.ejmech.2008.06.001 Urease subunit alpha/Urease subunit beta 2
19804978 10.1016/j.bmc.2009.09.018 Urease subunit alpha/Urease subunit beta 2
21189019 10.1021/jm101266s 72 kDa type IV collagenase 2

Data from ChEMBL 36 via Core Engine