Identification
- Generic Name
- Aniline
- DrugBank Accession Number
- DB06728
- Background
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of an amine attached to a benzene ring, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish. Aniline is colorless, but it slowly oxidizes and resinifies in air, giving a red-brown tint to aged samples.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Aniline (DB06728)
- Weight
- Average: 93.1265
Monoisotopic: 93.057849229 - Chemical Formula
- C6H7N
- Synonyms
- Aminobenzene
- Aminophen
- Anilin
- Anilina
- Aniline
- Aniline oil
- Anilinum
- Benzenamine
- Benzeneamine
- Fentanyl impurity F
- Huile d'aniline
- Kyanol
- Phenylamine
- Trimethoprim specified impurity K
- External IDs
- Caswell No. 051C
- RCRA waste no. U012
- RCRA waste number U012
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UKallikrein-1 Not Available Humans USerum albumin Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Aniline can be increased when combined with Abatacept. Acetaminophen Aniline may increase the hepatotoxic activities of Acetaminophen. Adalimumab The metabolism of Aniline can be increased when combined with Adalimumab. Ademetionine The metabolism of Aniline can be decreased when combined with Ademetionine. Aldesleukin The metabolism of Aniline can be decreased when combined with Aldesleukin. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Aniline acetate 9K3OS48D34 542-14-3 FHSWXOCOMAVQKE-UHFFFAOYSA-N Aniline hydrobromide 01XK3D1SXO 542-11-0 KBPWECBBZZNAIE-UHFFFAOYSA-N Aniline hydrochloride 576R1193YL 142-04-1 MMCPOSDMTGQNKG-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Aniline and substituted anilines
- Direct Parent
- Aniline and substituted anilines
- Alternative Parents
- Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aniline or substituted anilines / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Primary amine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- primary arylamine, anilines (CHEBI:17296) / an arylamine (ANILINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- SIR7XX2F1K
- CAS number
- 62-53-3
- InChI Key
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
- IUPAC Name
- aniline
- SMILES
- NC1=CC=CC=C1
References
- Synthesis Reference
Michel Dury, "Method for preparing 2-trifluoro-methoxy-aniline." U.S. Patent US6121492, issued 0000.
US6121492- General References
- Not Available
- External Links
- PDB Entries
- 1aee / 1hj9 / 1ppa / 2ov4 / 5cie / 5mna / 5mnc / 7bs0 / 7bs7
- MSDS
- Download (49.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Recruiting Treatment Multiple Myeloma (MM) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) -6 °C PhysProp boiling point (°C) 184.1 °C PhysProp water solubility 3.6E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.90 HANSCH,C ET AL. (1995) pKa 4.6 (at 25 °C; aniline conjugate acid) PERRIN,DD (1972) - Predicted Properties
Property Value Source Water Solubility 18.0 mg/mL ALOGPS logP 0.89 ALOGPS logP 1.14 Chemaxon logS -0.71 ALOGPS pKa (Strongest Basic) 4.64 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 26.02 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 30.76 m3·mol-1 Chemaxon Polarizability 10.29 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9849 Blood Brain Barrier + 0.9546 Caco-2 permeable + 0.8816 P-glycoprotein substrate Non-substrate 0.8908 P-glycoprotein inhibitor I Non-inhibitor 0.9864 P-glycoprotein inhibitor II Non-inhibitor 0.9856 Renal organic cation transporter Non-inhibitor 0.8716 CYP450 2C9 substrate Non-substrate 0.8594 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.8107 CYP450 1A2 substrate Non-inhibitor 0.5372 CYP450 2C9 inhibitor Non-inhibitor 0.7538 CYP450 2D6 inhibitor Non-inhibitor 0.889 CYP450 2C19 inhibitor Non-inhibitor 0.615 CYP450 3A4 inhibitor Non-inhibitor 0.9558 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7944 Ames test Non AMES toxic 0.7047 Carcinogenicity Carcinogens 0.5 Biodegradation Not ready biodegradable 0.5917 Rat acute toxicity 2.5399 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9567 hERG inhibition (predictor II) Non-inhibitor 0.9589
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 110.5141461 predictedDarkChem Lite v0.1.0 [M-H]- 110.4472461 predictedDarkChem Lite v0.1.0 [M-H]- 116.698 predictedDeepCCS 1.0 (2019) [M-H]- 110.5141461 predictedDarkChem Lite v0.1.0 [M-H]- 110.4472461 predictedDarkChem Lite v0.1.0 [M-H]- 116.698 predictedDeepCCS 1.0 (2019) [M+H]+ 111.4192461 predictedDarkChem Lite v0.1.0 [M+H]+ 111.5330461 predictedDarkChem Lite v0.1.0 [M+H]+ 119.03933 predictedDeepCCS 1.0 (2019) [M+H]+ 111.4192461 predictedDarkChem Lite v0.1.0 [M+H]+ 111.5330461 predictedDarkChem Lite v0.1.0 [M+H]+ 119.03933 predictedDeepCCS 1.0 (2019) [M+Na]+ 110.7501461 predictedDarkChem Lite v0.1.0 [M+Na]+ 110.6722461 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.422325 predictedDeepCCS 1.0 (2019) [M+Na]+ 110.7501461 predictedDarkChem Lite v0.1.0 [M+Na]+ 110.6722461 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.422325 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine-type endopeptidase activity
- Specific Function
- Glandular kallikreins cleave Met-Lys and Arg-Ser bonds in kininogen to release Lys-bradykinin.
- Gene Name
- KLK1
- Uniprot ID
- P06870
- Uniprot Name
- Kallikrein-1
- Molecular Weight
- 28889.425 Da
References
- Sousa MO, Miranda TL, Costa EB, Bittar ER, Santoro MM, Figueiredo AF: Linear competitive inhibition of human tissue kallikrein by 4-aminobenzamidine and benzamidine and linear mixed inhibition by 4-nitroaniline and aniline. Braz J Med Biol Res. 2001 Jan;34(1):35-44. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Thier R, Lewalter J, Selinski S, Bolt HM: Biological monitoring in workers in a nitrobenzene reduction plant: haemoglobin versus serum albumin adducts. Int Arch Occup Environ Health. 2001 Sep;74(7):483-8. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Flockhart Table of Drug Interactions [Link]
Drug created at August 18, 2010 20:11 / Updated at February 21, 2021 18:52