AMINOPHENAZONE ASCORBATE

US Previously Marketed

First marketed in 1897

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H17N3O.C6H8O6
Molecular Weight	407.4177
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO.CN(C)C2=C(C)N(C)N(C2=O)C3=CC=CC=C3

InChI

InChIKey=ZPBURGJOLTWBJU-MGMRMFRLSA-N

InChI=1S/C13H17N3O.C6H8O6/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11;7-1-2(8)5-3(9)4(10)6(11)12-5/h5-9H,1-4H3;2,5,7-10H,1H2/t;2-,5+/m.0/s1

HIDE SMILES / InChI

Molecular Formula	C13H17N3O
Molecular Weight	231.2936
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C6H8O6
Molecular Weight	176.1241
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261 | Vaz, R.J. & Klabunde, T. (2008) Antitargets: Prediction and Prevention of Drug Side Effects, page 5, retrieved from: https://books.google.ru/books?id=oSnSk1kv0dAC | (2004) Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments: Pharmaceuticals, page 18, retrieved from: https://books.google.ru/books?id=leVCukUgNlsC | Suchy, F.J. et al. (2007) Liver Disease in Children, page 107, retrieved from: https://books.google.ru/books?id=rGxPASmZWesC

Aminophenazone is a phenyl-pyrazolone derivative with potent analgesic and antipyretic properties. Aminophenazone has been used as salt or complexes, including topically as the salicylate. It was recommended for the treatment of a fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. In 1999 the FDA suspended aminophenazone. The drug caused agranulocytosis. Some of the cases of agranulocytosis were fatal. Another reason for suspending this drug from the market was its ability to react with nitrite-containing food, thus forming carcinogenic nitrosamines. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2095157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2498559	Inhibitor 8297		3.8 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Myositis 7 Sources: http://noillen.bitballoon.com/nutritional-suppleme5/	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Arthritis 89 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Rheumatism 10 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Neuralgia 12 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.

C_max

Value	Dose	Co-administered	Analyte	Population
2.7 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
17.4 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.3 h REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.6 h REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15437290/			AMINOPHENAZONE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Co-administed with:: allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days) Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	unhealthy, 27 years n = 1 Health Status: unhealthy Condition: pain Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	Other AEs: Agranulocytosis... Other AEs: Agranulocytosis Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/
10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	healthy, 28 years n = 1 Health Status: healthy Age Group: 28 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	Other AEs: Contact urticaria... Other AEs: Contact urticaria Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/
286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	Other AEs: Tiredness, Nausea... Other AEs: Tiredness (13.1%) Nausea (10.7%) Headache (1.2%) Vomiting (1.2%) Mental confusion (5.9%) Palpitation (1.2%) Faintness (1.2%) Loss of memory (1.2%) Urticaria (1.2%) Vertigo (1.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Co-administed with:: codeine(5 mg; 2 per day) diallymal(30 mg; 2 per day) Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	unhealthy, mean age 6.4 years n = 43 Health Status: unhealthy Condition: pain Age Group: mean age 6.4 years Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	Other AEs: Vomiting... Other AEs: Vomiting (5.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/

AEs

AE	Significance	Dose	Population
Agranulocytosis		220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Co-administed with:: allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days) Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	unhealthy, 27 years n = 1 Health Status: unhealthy Condition: pain Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/
Contact urticaria		10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	healthy, 28 years n = 1 Health Status: healthy Age Group: 28 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/
Faintness	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Headache	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Loss of memory	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Palpitation	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Urticaria	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vertigo	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vomiting	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Nausea	10.7%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Tiredness	13.1%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Mental confusion	5.9%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vomiting	5.5%	220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Co-administed with:: codeine(5 mg; 2 per day) diallymal(30 mg; 2 per day) Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	unhealthy, mean age 6.4 years n = 43 Health Status: unhealthy Condition: pain Age Group: mean age 6.4 years Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349 CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C18 138 CYP2C19 991 CYP2E1 667

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C18 138	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/12124312/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:160246	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:160246
ChemicalBook	CB1476086	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1476086
MolPort	MolPort-001-783-069	https://www.molport.com/shop/molecule-link/MolPort-001-783-069
Selleck Chemicals	amidopyrine	http://www.selleckchem.com/products/amidopyrine.html
ZINC	ZINC000000057115	http://zinc15.docking.org/substances/ZINC000000057115
eMolecules	537453	https://www.emolecules.com/cgi-bin/more?vid=537453

PubMed

Title	Date	PubMed
[Bilateral renal cortical necrosis following pyrazolone treatment].	1967 Jun 9	4225848
Tumor induction in rats by feeding aminopyrine or oxytetracycline with nitrite.	1975 Aug 15	168160
Mechanism of peroxidative activation of the bladder carcinogen 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT): comparison with benzidine.	1990 Nov	2121382
Breath tests: concepts, applications and limitations.	1997 Aug	9266210
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
The influence of interferon alpha on the rat liver injured by chronic administration of carbon tetrachloride.	2002	12898905
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007 Feb 26	17324258

Patents

Sample Use Guides

In Vivo Use Guide

250-300 mg 3-4 times a day

Route of Administration: Oral

In Vitro Use Guide

Aminophenazone inhibits rat gastric mucosal 6-keto-prostaglandin F1 alpha production with IC50 3.8x10(-3) M.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:05:10 GMT 2023` Edited by `admin` on `Sat Dec 16 08:05:10 GMT 2023`
Record UNII	G46D7HK10C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOPHENAZONE ASCORBATE

Common Name

English

ANTIPYRINE, 4-(DIMETHYLAMINO)-, L-ASCORBATE

Common Name

English

L-ASCORBIC ACID, COMPD. WITH 4-(DIMETHYLAMINO)-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-3H-PYRAZOL-3-ONE

Common Name

English

VADITON

Brand Name

English

AMINOPYRINE ASCORBATE

Common Name

English

L-ASCORBIC ACID, COMPD. WITH 4-(DIMETHYLAMINO)ANTIPYRINE

Common Name

English

3H-PYRAZOL-3-ONE, 4-(DIMETHYLAMINO)-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-, COMPD. WITH L-ASCORBIC ACID

Common Name

English

Code System Code Type Description

FDA UNII

G46D7HK10C

Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023

PRIMARY

CAS

23635-43-0

Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023

PRIMARY

PUBCHEM

72710703

Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023

PRIMARY

Related Record Type Details


					01704YP3MO

AMINOPHENAZONE

ACTIVE MOIETY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Cmax

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound