ANTIPYRINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N2O
Molecular Weight	188.2258
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1N(C(=O)C=C1C)C2=CC=CC=C2

InChI

InChIKey=VEQOALNAAJBPNY-UHFFFAOYSA-N

InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C11H12N2O
Molecular Weight	188.2258
Charge	0
Count

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

Description
Sources: DOI: 10.1016/S1366-0071(97)80033-2 | Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ | https://mri.cts-mrp.eu/download/LV_H_0127_001_FinalSPC.pdf | Leonard, B.J. (1977) Toxicological Aspects of Food Safety, page 132, retrieved from: https://books.google.ru/books?id=563tCAAAQBAJ | https://www.sdrugs.com/?c=drug&s=anodynine

Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. It inhibits cyclooxygenases and shows little anti-inflammatory activity. Like many old and approved substances after almost 100 years of use, antipyrine has been associated with some serious side effects, namely agranulocytosis and shock reactions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: Purich, D. (2017) The Inhibitor Index, page 2037, retrieved from: https://books.google.ru/books?id=fMItDwAAQBAJ	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Otitis media 42 Sources: http://www.otipax.com/index.php/en/otipax/what-is-otipax https://www.ncbi.nlm.nih.gov/pubmed/8239401	Palliative	Approved 8583	Finoten Approved Use Antipyrine is indicated for local symptomatic treatment and relief of pain in the following diseases of the middle ear without tympanic perforation: acute, congestive otitis media; otitis in influenza, the so-called viral bullous otitis; barotraumatic otitis.
Asthma 244 Sources: https://clinicaltrials.gov/ct2/show/NCT02153541 https://www.ncbi.nlm.nih.gov/pubmed/13906947	Palliative	Phase II 1147	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6818169 https://www.sdrugs.com/?c=drug&s=anodynine	Primary	Not Provided 511	Antipyrine Approved Use Unknown

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164816/	18 mg/kg single, oral dose: 18 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ANTIPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164824/	1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered:		ANTIPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.97% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1164816/	18 mg/kg single, oral dose: 18 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		ANTIPYRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP3 246 OATP1B3 961 CYP2A6 879 MRP4 290 OATP1B1 1079 CYP2C19 2057 BSEP 550 CYP1A2 2153 CYP2E1 1060 OCT1 620 MRP2 499 CYP2J2 33 CYP19A1 429	CYP2B6 776 CYP2C8 810 CYP2E1 729 CYP2C18 149 CYP1A2 1197

Drug as perpetrator

Target	Modality	Activity
CYP2J2 36	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2206#section=Biological-Test-Results	inconclusive [IC50 50 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NDc0In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NDc0In19	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >1000 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	no [IC50 >133 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2206#section=Biological-Test-Results Page: 421.0	no
OCT1 656	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Njg1IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	weak [Inhibition 100 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzQ3NCJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/ \| https://pubmed.ncbi.nlm.nih.gov/9890159/	major
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8681486/	yes

PubMed

Title	Date	PubMed
An implantable bolus infusion pump for use in freely moving, nontethered rats.	2002-10	12234827
Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys.	2002-10	12228180
Myocardial protection of MCI-186 in rabbit ischemia-reperfusion.	2002-09-27	12215372
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.	2002-09-13	12231392
Direct analysis of nine pharmaceuticals in culture media by use of cartridge separation with electrospray mass spectrometric detection.	2002-09	12207243
Effect of the free radical scavenger, 3-methyl-1-phenyl-2-pyrazolin-5-one (MCI-186), on hypoxia-ischemia-induced brain injury in neonatal rats.	2002-08-23	12161256
The concordance of early antipyrine and thiopental distribution kinetics.	2002-08	12130720
Prediction of hepatic clearance and availability by cryopreserved human hepatocytes: an application of serum incubation method.	2002-08	12124306
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium acetate acetone hemisolvate.	2002-07	12094065
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.	2002-07	12070748
Estimation of intradermal disposition kinetics of drugs: II. Factors determining penetration of drugs from viable skin to muscular layer.	2002-06-04	12052698
Sequential morphological and permeability changes in the rete capillaries during hyperglycaemia.	2002-06-01	12112446
A study of immunoglobulin G glycosylation in monoclonal and polyclonal species by electrospray and matrix-assisted laser desorption/ionization mass spectrometry.	2002-06-01	12018942
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.	2002-05-17	12014681
Combined argatroban and edaravone caused additive neuroprotection against 15 min of forebrain ischemia in gerbils.	2002-05	12074843
[Pharmacological and clinical profile of the free radical scavenger edaravone as a neuroprotective agent].	2002-05	12061142
Absence of placental transfer of pentasaccharide (Fondaparinux, Arixtra) in the dually perfused human cotyledon in vitro.	2002-05	12038785
Next generation of everyday analgesics.	2002-04-10	11941381
Synthesis of syn and anti isomers of trans-cyclopropyl arginine.	2002-04-05	11925253
Migraine, Midrin, and Imitrex.	2002-04	12010397
Enzyme and plasma protein induction by multiple oral administrations of phenobarbital at a therapeutic dosage regimen in dogs.	2002-04	12000532
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.	2002-04	11999127
Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans.	2002-04	11956503
The effect of amiloride on the in vivo effective permeability of amoxicillin in human jejunum: experience from a regional perfusion technique.	2002-04	11923059
Evaluation of the anti-vascular effects of combretastatin in rodent tumours by dynamic contrast enhanced MRI.	2002-04	11870904
Auto-protective redox buffering systems in stimulated macrophages.	2002-03-12	11914132
[Optimal conditions for extraction of "caffetin" and "saridon" tablet components from aqueous solutions].	2002-03-02	11871327
Diabetes and elimination of antipyrine in man: an analysis of 298 patients classified by type of diabetes, age, sex, duration of disease and liver involvement.	2002-03	12071338
Influence of albumin supplementation on tacrolimus and cyclosporine therapy early after liver transplantation.	2002-03	11910567
Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men.	2002-03	11907490
Exercise-induced oxidative stress in older adults as a function of habitual activity level.	2002-02	12028219
Albendazole metabolism in patients with neurocysticercosis: antipyrine as a multifunctional marker drug of cytochrome P450.	2002-02	11847531
Induction of hepatic and presystemic metabolism of antipyrine in the mice: rifampicin versus rifabutin.	2002-01-26	11808861
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.	2002-01-12	11785906
Rational determination of transfer free energies of small drugs across the water-oil interface.	2002-01-03	11754587
Effects of prenatal exposure to combination of acetaminophen, isopropylantipyrine and caffeine on intrauterine development in rats.	2002-01	12046720
Imaging of ischemic but viable myocardium using a new 18F-labeled 2-nitroimidazole analog, 18F-FRP170.	2002-01	11801713
Transplacental transfer and metabolism of buprenorphine.	2002-01	11752093
Automated structural assignment of derivatized complex N-linked oligosaccharides from tandem mass spectra.	2002	12207362
Formation of the knee joint after prenatal propyphenazone (isopropylantipyrine) administration.	2002	12097837
[Absorption function of the large intestine in patients with nonspecific ulcerative colitis].	2002	12046397
A new method for measuring oxidative stress in claudicants during strenuous exercise using free radical derivatives of antipyrine as indicators: a pilot study.	2002	12017201
The onset of action and the analgesic efficacy of Saridon (a propyphenazone/paracetamol/ caffeine combination) in comparison with paracetamol, ibuprofen, aspirin and placebo (pooled statistical analysis).	2002	11999141
A female with asymptomatic primary biliary cirrhosis associated with pernicious anemia.	2001-12	11851845
Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells.	2001-12	11802005
Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter.	2001-12	11767111
Combined effects of acetaminophen, isopropylantipyrine and caffeine on pregnant and nonpregnant liver.	2001-11	11926611
Schedule of controlled substances: placement of dichloralphenazone into Schedule IV. Final rule.	2001-08-16	11794309
[Insidious drug eruption].	2001	12116489
The radiological diagnosis of analgesic nephropathy.	1975-07	1201638

Patents

Sample Use Guides

In Vivo Use Guide

54 mg apply drops along the wall of the ear canal until filled and repeating every 3 hours for 24 hours unless the subject is sleeping.

Route of Administration: Otic (auricular)

In Vitro Use Guide

The influence of phenazone on the production of prostacyclin and thromboxane in human umbilical arteries was investigated by in vitro perfusion. With perfusate concentrations ranging from 10(-7) to 10(-4) M a decrease in the formation of both prostanoids was observed. The inhibitory effect of phenazone on prostanoid formation was found to be equal to that of indomethacin.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:13 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:13 GMT 2025`
Record UNII	T3CHA1B51H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANTIPYRINE

Common Name

English

PHENAZONE

Preferred Name

English

ANTIPYRINE [USP-RS]

Common Name

English

ANTIPYRINE [VANDF]

Common Name

English

PHENAZONE [EP IMPURITY]

Common Name

English

PHENAZONE [MART.]

Common Name

English

PHENAZONE [EP MONOGRAPH]

Common Name

English

Phenazone [WHO-DD]

Common Name

English

ANTIPYRINUM

Common Name

English

2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one

Systematic Name

English

ANTIPYRINE [USP IMPURITY]

Common Name

English

ANTIPYRINUM [HPUS]

Common Name

English

phenazone [INN]

Common Name

English

PROPYPHENAZONE IMPURITY A [EP IMPURITY]

Common Name

English

ANTIPYRINE [JAN]

Common Name

English

ANTIPYRINE [USP MONOGRAPH]

Common Name

English

ANTIPYRINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

S02DA03