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Bendazac

HCID 2313
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
20187-55-7
Standard SMILES
O=C(O)COc1nn(Cc2ccccc2)c2ccccc12
InChIKey
BYFMCKSPFYVMOU-UHFFFAOYSA-N
Molecular formula
C16H14N2O3
Average molar mass
282.29 g/mol
Monoisotopic mass
282.10044231

Overview

Bendazac is a monocarboxylic acid that is glycolic acid in which the hydrogen attached to the 2-hydroxy group is replaced by a 1-benzyl-1H-indazol-3-yl group. Although it has anti-inflammatory, antinecrotic, choleretic and antilipidaemic properties and has been used for the treatment of various inflammatory skin disorders, its principal effect is to inhibit the denaturation of proteins. Its lysine salt is used in the management of cataracts. It has a role as a non-steroidal anti-inflammatory drug and a radical scavenger. It is a monocarboxylic acid and a member of indazoles.

Names & identifiers

Preferred name
Bendazac
IUPAC
2-(1-benzylindazol-3-yl)oxyacetic acid
English name
Bendazac
Molecular formula
C16H14N2O3
Molecular weight
282.29

Names & synonyms

bendazac20187-55-7Bendazolic acidBindazacBendazacoIwazac2-((1-Benzyl-1H-indazol-3-yl)oxy)acetic acidBendazacum1-Benzylindazole-3-oxyacetic acid[(1-Benzyl-1H-indazol-3-yl)oxy]acetic AcidBRN 0893958((1-Benzyl-1H-indazol-3-yl)oxy)acetic acid
Show more names
[[1-(phenylmethyl)-1h-indazol-3-yl]oxy]acetic acidVersusAF 983ZildasacDogalinaZildazacAKOS 90683Bendazac >
AF-1934 LYSINEAF 1934 FREE ACIDAF-1934 FREE ACIDG4AG71204ODTXSID1048334CHEBI:312572-[(1-benzyl-1H-indazol-3-yl)oxy]acetic acidbendazac lisina

Database identifiers

CAS
20187-55-7
PubChem CID
2313
DTXSID
DTXSID1048334
ChEMBL
CHEMBL1089221
ChEBI
CHEBI:31257

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
64.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
21
Formal charge
0
Complexity
357

Physicochemical properties

Melting point
161 · 161-163°C
Boiling point
424.91 °C · 424.91°C (rough estimate)
Density
1.1658 · 1.1658 (rough estimate)
refractive index
1.624 · 1.6240 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
DMSO (Slightly), Methanol (Slightly, Heated)
form
Solid
pka
2.89 · 2.89±0.10(Predicted)
color
Crystals from ethanol
λmax
306 nm · 306nm(lit.)
Merck
14 · 14,1035
InChI
InChI=1S/C16H14N2O3/c19-15(20)11-21-16-13-8-4-5-9-14(13)18(17-16)10-12-6-2-1-3-7-12/h1-9H,10-11H2,(H,19,20)
InChIKey
BYFMCKSPFYVMOU-UHFFFAOYSA-N
SMILES
C(O)(=O)COC1C2=C(N(CC3=CC=CC=C3)N=1)C=CC=C2
CAS DataBase Reference
20187 · 20187-55-7(CAS DataBase Reference)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Bendazac

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
WGK 3
rtecs
AF5085000
hs_code
2933998090
Toxicity
LD50 in mice, rats (mg/kg): 380, 304 i.v.; 355, 388 i.p.; 440, 910 s.c.; 1105, ~1200 orally (Rx Bulletin)
Signal word
Warning
Symbol(GHS)
GHS07
Storage Class
11 - Combustible Solids
Hazard statements
H302
Precautionary statements
P264-P270-P301+P312+P330-P501

Chemistry & industry

Pharmacology

ATC Code · 4 items

S - Sensory organs

M - Musculo-skeletal system

QS - Sensory organs

QM - Musculo-skeletal system

Protein BindingBendazac is >99% highly bound to plasma albumin protein in healthy subjects.
Pharmacodynamics · 1 item

Bendazac principally demonstrates an antidenaturant action on proteins. This effect has been shown to inhibit the denaturation of various proteins like ocular lens proteins by heat, ultraviolet radiation, free radicals, and other chemicals. The medication may be administered to patients via a number of different formulations, including orally as the lysine salt, as eye drops, or even topical applications for the skin. Some preliminary studies have suggested that an apparent improvement of the blood-retinal barrier had been observed in diabetic patients using bendazac lysine 500 mg three times a day for three to six months. Moreover, the use of topical bendazac has also been shown to demonstrate anti-inflammatory effects in animal models and clinical studies to effectively treat varied dermatoses, especially those involving a necrotic component. Additionally, bendazac has also demonstrated choleretic and antilipidaemic activities that have resulted in substantial reductions in beta/alpha lipoprotein ratio, and total lipid, total cholesterol, and triglyceride levels in patients with dyslipidaemia using oral bendazac lysine 500 mg three times daily. The medication has also elicited the inhibition of phytohaemagglutinin induced lymphocyte transformation in vitro.

Mechanism of Action · 1 item

Bendazac seems to elicit an anticataract action by inhibiting the denaturation of ocular lens proteins, although the precise mechanisms by which this action occurs has not yet been formally elucidated - despite there being many proposed mechanisms. In particular, the denaturation of lens proteins may in part be prevented by inhibiting the binding of certain chemicals like cyanates or sugars and 5-hydroxybendazac - the major metabolite of bendazac - has been shown to be capable of inhibiting the glycosylation of lens proteins by sugars like galactose or glucose-6-phosphate in a dose-dependent manner. Moreover, the apparent ability for administered bendazac to elicit free radical scavenger activities due to interactions with protein molecules suggests that the medication may also be able to prevent the oxidation of lens proteins by free radicals in the development of cataracts. Furthermore, bendazac may also be capable of reducing the sulfhydryl group oxidation of lens proteins by the saliva, serum, or urine from patients with cataracts following single dose administration and reduce biological liquid oxidant activity (BLOA) in doing so. Otherwise, it is believed that bendazac also possesses non-steroidal anti-inflammatory actions, as well as analgesic, antipyretic, and platelet-inhibitory effects These effects may be accounted for in part by the substance's capability to inhibit prostaglandin synthesis by inhibiting cyclooxygenase activity in converting arachidonic acid to cyclic endoperoxides - the precursors of prostaglandins.

Related reactions

2 records
New reaction record
HRID 1414162 reaction equation
HRID 1414162As reactantuspto-grants-1977_01
HRID 1538537 reaction equation
HRID 1538537As reactantTraining data from https://doi.org/10.1039/C8SC04228D (1/10)

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
G4AG71204O
EC Number
243-569-2
Nikkaji
J3.148H
FDA UNII
4 AG71204O · G4AG71204O
ATC code
2 AA11,S01BC07 · M02AA11,S01BC07
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312+P330-P501
WGK Germany
3 · WGK 3
RTECS
5085000 · AF5085000
HS Code
2933998090 · 2933998090
Storage Class
11 · 11 - Combustible Solids
Toxicity
50 in · LD50 in mice, rats (mg/kg): 380, 304 i.v.; 355, 388 i.p.; 440, 910 s.c.; 1105, ~1200 orally (Rx Bulletin)
Biological Half-LifeThe plasma elimination half-life recorded for bendazac is given as 1.7 to 5.2 hours, with a mean of 3.5 hours.
Metabolism/Metabolites · 1 item

Bendazac is largely eliminated by metabolism, where more than 60% of an administered dose is excreted in the urine as the hydroxylated primary metabolite 5-hydroxybendazac and its glucuronide while up to approximately 15% of a bendazac dose is also excreted in the urine unchanged and as a glucuronide. Unfortunately, there is little data available regarding the specific enzymes responsible for bendazac's metabolism.

MeSH Pharmacological Classification · 1 item

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Absorption, Distribution and Excretion · 4 items

Administered as its lysine salt, a 500 mg oral tablet of bendazac is well absorbed into the human body with maximum plasma concentrations Cmax ranging from 35 to 55 mg/L being attained within 0.5 to 1 hour in healthy volunteers after oral administration of a single 500 mg dose.

About 60% of a dose of bendazac is eliminated via the urine as its primary metabolite, 5-hydroxybendazac. Approximately 15% of a dose is eliminated as unchanged drug and bendazac glucuronide in the urine as well.

The volume of distribution documented for bendazac is 0.16 L/kg.

The plasma clearance recorded for bendazac is given as 0.018 to 0.054 L/h/kg with a mean of 0.033 L/h/kg.

Applications · 1 item

UsesBendazac is a non-steroidal anti-inflammatory drug (NSAID). Bendazac is often used for joint and muscular pain. Bendazac has potential as an anti-denaturant drug for cataract and other condensation di seases as it protects proteins from denaturation induced by different agents.

Upstream & downstream products

Upstream raw materials

Hydrochloric acidChloroacetonitrile

Downstream products

1-Benzyl-3-methoxy-1H-indazole

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
合肥瑞洛新材料科技有限公司19567218739 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
湖北海克斯生化有限公司18696113233 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
湖北辰心化工有限公司18696113233 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
常州科化生物科技有限公司0519-68985668 13685222090 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
西安泽邦生物科技有限公司[email protected]
InvivoChem中国13549236410 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
郑州研德生物科技有限公司0371-63682289 15538176268 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
美岚实业(上海)有限公司021-58958189 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
广拓化学(上海)有限公司021-60899189-8001 18918189673 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
济南鲁欣化工科技有限公司0531-0531-82929600 18615510361 · [email protected]
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
上海有朋化工有限公司021-69005955 13701776567 · [email protected]
北京海力扬化学科技有限公司13718199399 · [email protected]
北京欣赛维化学科技有限公司010-56218822 13717722232 · [email protected]
四川海诺威科技有限公司13708085536 13708085536 · [email protected]
上海凯赛化工有限公司021-33516722 13701817869 · [email protected]
上海彤源化工有限公司021-021-69182866 13701855675 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
北京华扬致成科技有限公司13716033033 · [email protected]
上海蓝润化学有限公司021-69515658 ; 69515628 13701998368 · [email protected]
上海容立化学科技有限公司021-69992220 13701886816 · [email protected]
上海康拓化工有限公司021-69185552 13701777608 · [email protected]
AN PharmaTech Co Ltd86(21)68097365 · [email protected]
Accela ChemBio Inc.+1(858) 699-3322 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A monocarboxylic acid that is glycolic acid in which the hydrogen attached to the 2-hydroxy group is replaced by a 1-benzyl-1H-indazol-3-yl group. Although it has anti-inflammatory, antinecrotic, choleretic and antilipidaemic properties nd has been used for the treatment of various inflammatory skin disorders, its principal effect is to inhibit the denaturation of proteins. Its lysine salt is used in the management of cataracts.