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Compound Detail

CHEMBL288470

AMINOPYRINE
💊 Approved Drug
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💊 Approved Drug
Cc1c(N(C)C)c(=O)n(-c2ccccc2)n1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL288470
Name AMINOPYRINE
Phase Approved
Structure Type MOL
InChI Key RMMXTBMQSGEXHJ-UHFFFAOYSA-N

Known Names

4-dimethylaminoantipyrine Amidazophene Amidopyrazoline Aminofenazona Aminophenazone Aminopyrine Brufaneuxol Dereuma Febron Itamidone Mamallet a Netsusarin +1 more
1
Targets
1
Activities
1
Assay Types
4
PK Parameters
20
Publications
13
Known Names
2
Indications
1
Mechanisms

Molecular Properties

231.3
MW (Da)
1.55
ALogP
4
HBA
0
HBD
30.2
PSA (Ų)
0.78
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C13H17N3O
MW 231.30
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -1.31

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Indications

Fever Pain

ATC Classification

N02BB03
aminophenazone
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BB53
aminophenazone, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BB73
aminophenazone, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Withdrawn
General Warning
Adverse effects
Country: France; United States; United Kingdom; Germany; Australia; Sweden; Philippines; Turkey; Kuwait; Denmark; Finland; Switzerland; India; Ethiopia; Venezuela; Chile; Republic of Korea; Japan; Rwanda; Mauritius   Year: 1965
Withdrawn
hematological toxicity
Bone marrow depression and fatal agranulocytosis
Country: France; United States; United Kingdom; Germany; Australia; Sweden; Philippines; Turkey; Kuwait; Denmark; Finland; Switzerland; India; Ethiopia; Venezuela; Chile; Republic of Korea; Japan; Rwanda; Mauritius   Year: 1965
Withdrawn
hematological toxicity
Agranulocytosis
Country: France; United States; United Kingdom; Germany; Australia; Sweden; Philippines; Turkey; Kuwait; Denmark; Finland; Switzerland; India; Ethiopia; Venezuela; Chile; Republic of Korea; Japan; Rwanda; Mauritius   Year: 1965
Withdrawn
carcinogenicity
Potential to produce carcinogenic nitrosamines
Country: France; United States; United Kingdom; Germany; Australia; Sweden; Philippines; Turkey; Kuwait; Denmark; Finland; Switzerland; India; Ethiopia; Venezuela; Chile; Republic of Korea; Japan; Rwanda; Mauritius   Year: 1965
Withdrawn
hematological toxicity
Serious side effects such as bone marrow depression and agranulocytosis
Country: France; United States; United Kingdom; Germany; Australia; Sweden; Philippines; Turkey; Kuwait; Denmark; Finland; Switzerland; India; Ethiopia; Venezuela; Chile; Republic of Korea; Japan; Rwanda; Mauritius   Year: 1965

Activity Summary

Ki 1 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nicotinate phosphoribosyltransferase
CHEMBL4523354
 Ki 9.0 9.0 1.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.47 uL.min-1.(10^6cells)-1 Homo sapiens
CL - - Homo sapiens
CL - - Homo sapiens
F 100.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nicotinate phosphoribosyltransferase Ki = 1.0 nM 9.0 Inhibition of NAPRT (unknown origin) -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17418579 10.1016/j.bmc.2007.03.040 ADMET 8
106119 10.1021/jm00187a014 Mus musculus 6
20879794 10.1021/jf102525e No relevant target 4
458805 10.1021/jm00191a017 Mus musculus 4
13215 10.1021/jm00211a010 No relevant target 4
106119 10.1021/jm00187a014 Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
21467212 10.1124/dmd.111.039180 Liver microsome 3
20014752 10.1021/tx900326k Hepatotoxicity 3
311385 10.1021/jm00187a013 Rattus norvegicus 3
11754587 10.1021/jm010289a No relevant target 2
17418579 10.1016/j.bmc.2007.03.040 No relevant target 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
311385 10.1021/jm00187a013 Mus musculus 2
6708056 10.1021/jm00370a020 Mus musculus 2
894678 10.1021/jm00218a017 No relevant target 2
21467212 10.1124/dmd.111.039180 ADMET 2

Data from ChEMBL 36 via Core Engine