Antipyrine

Details

• Internal ID: ca3eb552-ad45-481f-bdae-0be1b32df0ee
• Taxonomy: Organoheterocyclic compounds > Azoles > Pyrazoles > Phenylpyrazoles
• IUPAC Name: 1,5-dimethyl-2-phenylpyrazol-3-one
• InChI: InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
• InChI Key: VEQOALNAAJBPNY-UHFFFAOYSA-N
• Popularity: 11,436 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂N₂O
• Molecular Weight: 188.23 g/mol
• Exact Mass: 188.094963011 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Phenazone
• 60-80-0
• Antipyrin
• Phenazon
• Analgesine
• Anodynin
• Anodynine
• Fenazone
• Azophen
• 2,3-Dimethyl-1-phenyl-5-pyrazolone
• Antipirin
• Antipyrinum
• Phenozone
• Apirelina
• Azophene
• Methozin
• Parodyne
• Phenazonum
• Phenylone
• Pyrazophyl
• Sedatine
• Dimethyloxychinizin
• Azophenum
• Phenylon
• Sedatin
• Dimethyloxyquinazine
• Oxydimethylquinazine
• 3-Antipyrine
• Fenazona
• Fenazon [Czech]
• Fenazon
• Phenazone (pharmaceutical)
• 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-
• Fenazona [INN-Spanish]
• 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
• 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
• 1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
• 1-Phenyl-2,3-dimethyl-5-pyrazolone
• 1-Phenyl-2,3-dimethylpyrazole-5-one
• Oxydimethylquinizine
• CHEBI:31225
• NSC 7945
• CCRIS 1369
• Phenazonum [INN-Latin]
• UNII-T3CHA1B51H
• Phenazone;Phenazon
• EINECS 200-486-6
• T3CHA1B51H
• Phenazone [INN]
• DTXSID6021117
• AI3-15293
• Antipyrine [USP:JAN]
• DTXCID401117
• EC 200-486-6
• Phenazone (INN)
• NSC-7945
• 1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
• CAS-60-80-0
• NCGC00016274-04
• Antipyrine (USP:JAN)
• Fenazona (INN-Spanish)
• Phenazonum (INN-Latin)
• PHENAZONE (MART.)
• PHENAZONE [MART.]
• ANTIPYRINE (USP-RS)
• ANTIPYRINE [USP-RS]
• Antipyrine [JAN]
• PHENAZONE (EP IMPURITY)
• PHENAZONE [EP IMPURITY]
• PHENAZONE (EP MONOGRAPH)
• PHENAZONE [EP MONOGRAPH]
• ANTIPYRINE (USP IMPURITY)
• ANTIPYRINE [USP IMPURITY]
• ANTIPYRINE (USP MONOGRAPH)
• ANTIPYRINE [USP MONOGRAPH]
• SMR000238140
• PROPYPHENAZONE IMPURITY A (EP IMPURITY)
• PROPYPHENAZONE IMPURITY A [EP IMPURITY]
• SR-05000001566
• 1,5-dimethyl-2-phenylpyrazol-3-one
• Antipyrien
• 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; Phenazone
• .beta.-Antipyrine
• Prestwick_26
• MFCD00003146
• component of Auralgan
• 1,5-dimethyl-2-phenyl-pyrazol-3-one
• Spectrum_000058
• ANTIPYRINE [MI]
• Prestwick0_000029
• Prestwick1_000029
• Prestwick2_000029
• Prestwick3_000029
• Spectrum2_000088
• Spectrum3_000305
• Spectrum4_000152
• Spectrum5_000842
• ANTIPYRINE [VANDF]
• ANTIPYRINUM [HPUS]
• Antipyrine (JP17/USP)
• Epitope ID:124927
• PHENAZONE [WHO-DD]
• 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
• SCHEMBL20452
• BSPBio_000097
• BSPBio_001870
• KBioGR_000624
• KBioSS_000438
• MLS001331753
• MLS001332401
• MLS001332402
• MLS002154179
• DivK1c_000484
• SPECTRUM1500128
• SPBio_000016
• SPBio_002018
• Antipyrine, analytical standard
• BPBio1_000107
• CHEMBL277474
• HMS501I06
• KBio1_000484
• KBio2_000438
• KBio2_003006
• KBio2_005574
• KBio3_001370
• N02BB01
• NSC7945
• S02DA03
• Antipyrine, >=99.0% (RT)
• NINDS_000484
• HMS1568E19
• HMS1920E09
• HMS2091K09
• HMS2095E19
• HMS2272G04
• HMS3652C09
• HMS3712E19
• HMS3885C11
• Pharmakon1600-01500128
• WLN: T5NNVJ A1 BR& E1
• HY-B0171
• Tox21_110342
• Tox21_201600
• Tox21_303026
• Antipyrine, Sigma Reference Standard
• BDBM50103600
• CCG-38904
• NSC755874
• s3173
• 1,5-Dimethyl-2-phenyl-3-pyrazolone
• AKOS000588788
• Tox21_110342_1
• CS-2044
• DB01435
• NSC-755874
• IDI1_000484
• Phenazone 10 microg/mL in Acetonitrile
• Antipyrine, analytical reference material
• Antipyrine, tested according to Ph.Eur.
• NCGC00016274-01
• NCGC00016274-02
• NCGC00016274-03
• NCGC00016274-05
• NCGC00016274-06
• NCGC00016274-07
• NCGC00016274-09
• NCGC00016274-10
• NCGC00094591-01
• NCGC00094591-02
• NCGC00094591-03
• NCGC00178937-01
• NCGC00178937-02
• NCGC00256527-01
• NCGC00259149-01
• AS-13248
• SBI-0051287.P003
• Antipyrine, Vetec(TM) reagent grade, 98%
• D1876
• FT-0609690
• FT-0662246
• SW196343-3
• EN300-17057
• A19580
• BIM-0051287.0001
• D01776
• H11233
• 1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one
• A936893
• AF-960/00437050
• Q415578
• Q-201552
• SR-05000001566-1
• SR-05000001566-3
• BRD-K46937689-001-05-1
• BRD-K46937689-001-08-5
• Z56869297
• 2-Trideuteromethyl-3-methyl-1-phenyl-3-pyrazolin-5-one
• F2173-0728
• 1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one #
• Phenazone, European Pharmacopoeia (EP) Reference Standard
• Antipyrine, United States Pharmacopeia (USP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	+	0.9325	93.25%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9429	94.29%
Subcellular localzation	Mitochondria	0.8629	86.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9547	95.47%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7817	78.17%
P-glycoprotein inhibitior	-	0.9742	97.42%
P-glycoprotein substrate	-	0.9822	98.22%
CYP3A4 substrate	-	0.5547	55.47%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	-	0.9615	96.15%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9533	95.33%
CYP2D6 inhibition	-	0.9444	94.44%
CYP1A2 inhibition	-	0.8617	86.17%
CYP2C8 inhibition	-	0.9301	93.01%
CYP inhibitory promiscuity	-	0.7357	73.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Warning	0.5190	51.90%
Eye corrosion	-	0.9876	98.76%
Eye irritation	+	0.8282	82.82%
Skin irritation	-	0.8039	80.39%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6593	65.93%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.7982	79.82%
skin sensitisation	-	0.7657	76.57%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6866	68.66%
Acute Oral Toxicity (c)	III	0.8028	80.28%
Estrogen receptor binding	-	0.6451	64.51%
Androgen receptor binding	+	0.5192	51.92%
Thyroid receptor binding	-	0.5848	58.48%
Glucocorticoid receptor binding	-	0.5873	58.73%
Aromatase binding	-	0.6073	60.73%
PPAR gamma	-	0.8546	85.46%
Honey bee toxicity	-	0.9854	98.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	+	0.7346	73.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4523354	Q6XQN6	Nicotinate phosphoribosyltransferase	1 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.41%	95.56%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.16%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.09%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.32%	96.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.54%	96.25%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.93%	93.65%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2206
• LOTUS: LTS0179922
• wikiData: Q415578