anakinra (CED0002156)

Record Information

Version

1.0

Creation Date

2016-06-03 11:01:36 UTC

Update Date

2026-04-13 20:26:21 UTC

Accession Number

CHEM043537

Identification

Common Name

anakinra

Class

Small Molecule

Description

anakinra is an organic compound with the formula C20H23N5O7S2. anakinra belongs to the beta lactams, a subclass of lactams within the organic compounds. With an average molecular weight of 509.55 g/mol, anakinra is a heavy molecule. This compound acts as an antagonist of the Interleukin-1 receptor type 1 (IL1R1). It is found in healthcare, pharmaceuticals, and veterinary products as an immunosuppressant. The recorded route of exposure for this substance is subcutaneous.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-[2-({[(2,2-dimethylpropanoyl)oxy]methoxy}imino)-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	Generator

Chemical Formula

C₂₀H₂₃N₅O₇S₂

Average Molecular Mass

509.550 g/mol

Monoisotopic Mass

509.104 g/mol

CAS Registry Number

143090-92-0

IUPAC Name

7-[2-({[(2,2-dimethylpropanoyl)oxy]methoxy}imino)-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

7-[2-({[(2,2-dimethylpropanoyl)oxy]methoxy}imino)-2-(2-imino-3H-1,3-thiazol-4-yl)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

CC(C)(C)C(=O)OCON=C(C(=O)NC1C2SCC(C=C)=C(N2C1=O)C(O)=O)C1=CSC(=N)N1

InChI Identifier

InChI=1S/C20H23N5O7S2/c1-5-9-6-33-16-12(15(27)25(16)13(9)17(28)29)23-14(26)11(10-7-34-19(21)22-10)24-32-8-31-18(30)20(2,3)4/h5,7,12,16H,1,6,8H2,2-4H3,(H2,21,22)(H,23,26)(H,28,29)

InChI Key

HMLGSIZOMSVISS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Meta-thiazine
Heteroaromatic compound
Thiazole
Tertiary carboxylic acid amide
Azole
Secondary carboxylic acid amide
Isothiourea
Carboxylic acid ester
Carboxamide group
Azetidine
Azacycle
Dialkylthioether
Hemithioaminal
Thioether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.067 g/L	ALOGPS
logP	1	ALOGPS
logP	1.93	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	0.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.48 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	135.57 m³·mol⁻¹	ChemAxon
Polarizability	49.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uki-4901100000-6a5a766d27389acde8ab	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0079-9832000000-54ca417ee47b4f79c811	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4r-9501000000-eccac3f3c4f862edd153	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0169300000-bef93d2ccb2cefa08bd3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-0935000000-4a5d1201889fd71a343c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9311000000-3234b3c2cf34694654b1	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
7658.0	Log mg/kg	[4300:14000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
362	Immunosuppressants	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Speckle-type POZ protein	O43791	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	20.1629
Click to view 3D structure	Solute carrier family 22 member 6	Q4U2R8	Humans	Predicted (SEA)	1.55698
Click to view 3D structure	Organic anion transporter 3	Q8TCC7	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Solute carrier family 22 member 11	Q9NSA0	Humans	Predicted (SEA)	0.856341
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	13.6236
Click to view 3D structure	Beta-lactamase	B2ZTR6	Acinetobacter baumannii	Predicted (SEA)	0.467095
Click to view 3D structure	ADC-11	D6NSM8	Acinetobacter baumannii	Predicted (SEA)	0.467095
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	877.439
Click to view 3D structure	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Q9GZU7	Humans	Predicted (SEA)	331.093
Click to view 3D structure	26S proteasome non-ATPase regulatory subunit 14	O00487	Humans	Predicted (SEA)	45.4639
Click to view 3D structure	AmpC	Q83TT7	Escherichia coli	Predicted (SEA)	0.311397
Click to view 3D structure	Peptidoglycan D,D-transpeptidase FtsI	Q51504	Pseudomonas aeruginosa	Predicted (SEA)	0.311397
Click to view 3D structure	Penicillin-binding protein 1A	Q07806	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)	Predicted (SEA)	0.311397
Click to view 3D structure	Small ubiquitin-related modifier 1	P63165	Humans	Predicted (SEA)	838.514
Click to view 3D structure	Probable nicotinate-nucleotide adenylyltransferase	P65502	Staphylococcus aureus (strain N315)	Predicted (SEA)	443.04
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	949.138
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	1420.98
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	2.41333
Click to view 3D structure	SHV-5 extended spectrum beta-lactamase	Q6REX6	Escherichia coli	Predicted (SEA)	5.3716
Click to view 3D structure	1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1	P19174	Humans	Predicted (SEA)	26.9358
Click to view 3D structure	Dual specificity protein phosphatase 3	P51452	Humans	Predicted (SEA)	2257.94
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	2.17978
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	2.95827
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	2.95827