Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2301)
Drug Name
Phenazopyridine
Synonyms
Phenazopyridine [INN:BAN]; Phenazopyridinum; Phenazopyridinum [INN-Latin]; Pyrazofen; Pyridacil; Pyridiate; Urogesic; Viridium; Baridium; Eridium; Fenazopiridina; Fenazopiridina [INN-Spanish]; Gastracid; Gastrotest; Geridium; phenazopyridine; 2,6-Diamino-3-(phenylazo)pyridine; 2,6-Diamino-3-phenylazopyridine; 2,6-Pyridinediamine, 3-(phenylazo)-; 3-(Phenylazo)-2,6-pyridinediamine; 3-(phenyldiazenyl)pyridine-2,6-diamine; 94-78-0; BRN 0184497; EINECS 202-363-2; HSDB 3153; NSC 145895; Pyridine, 2,6-diamino-3-(phenylazo)-; UNII-K2J09EMJ52
Indication Infectious cystitis [ICD11: GC00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 213.24 Topological Polar Surface Area 89.6
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4756
PubChem SID
9633 ; 429038 ; 631294 ; 7348356 ; 10538554 ; 10986134 ; 11112296 ; 11335986 ; 11361225 ; 11363907 ; 11366469 ; 11369031 ; 11371787 ; 11374087 ; 11377193 ; 11462197 ; 11466780 ; 11467900 ; 11483789 ; 11486439 ; 11487833 ; 11490360 ; 11492289 ; 11494827 ; 14748951 ; 29223840 ; 46507962 ; 47211772 ; 47216813 ; 47216814 ; 47440304 ; 47515353 ; 47810793 ; 47959790 ; 48416404 ; 49698630 ; 50032107 ; 50100844 ; 57322430 ; 60914066 ; 80675658 ; 85788784 ; 92712625 ; 92763268 ; 96025033 ; 103378408 ; 104171363 ; 104307334 ; 107890263 ; 117528062
ChEBI ID
CHEBI:71416
CAS Number
136-40-3
TTD Drug ID
D00VUL
Formula
C11H11N5
Canonical SMILES
C1=CC=C(C=C1)N=NC2=C(N=C(C=C2)N)N
InChI
1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)
InChIKey
QPFYXYFORQJZEC-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2'-OH PAP DM004790
148934
Oxidation - Hydrolyzationn 1 [3] , [4]
2,3,6 Triaminopyridine DM004793
78015
Unclear 1 [3] , [5] , [4]
4'-OH PAP DM004791
72705
Oxidation - Hydrolyzationn 1 [3] , [4]
5,4'-di-OH-PAP DM004792
136395751
Oxidation - Hydrolyzationn 1 [3] , [4]
5-OH PAP DM004789
135173
Oxidation - Hydrolyzationn 1 [3] , [4]
Aniline DM004785
6115
Unclear 1 [3] , [5] , [4]
2-aminophenol DM004788
5801
Oxidation - Hydrolyzationn 2 [3] , [5] , [4]
4-aminophenol DM003816
403
Oxidation - Hydrolyzationn 2 [3] , [5] , [4]
N-acetyl-4-Aminophenol DM004787
1983
Conjugation - Acetylation 3 [3] , [5] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005145 Phenazopyridine Aniline Unclear Unclear [3], [5], [4]
MR005149 Phenazopyridine 5-OH PAP Oxidation - Hydrolyzationn Unclear [3], [4]
MR005150 Phenazopyridine 2'-OH PAP Oxidation - Hydrolyzationn Unclear [3], [4]
MR005151 Phenazopyridine 4'-OH PAP Oxidation - Hydrolyzationn Unclear [3], [4]
MR005152 Phenazopyridine 5,4'-di-OH-PAP Oxidation - Hydrolyzationn Unclear [3], [4]
MR005153 Phenazopyridine 2,3,6 Triaminopyridine Unclear Unclear [3], [5], [4]
MR005146 Aniline 4-aminophenol Oxidation - Hydrolyzationn Unclear [3], [5], [4]
MR005148 Aniline 2-aminophenol Oxidation - Hydrolyzationn Unclear [3], [5], [4]
MR005147 4-aminophenol N-acetyl-4-Aminophenol Conjugation - Acetylation Unclear [3], [5], [4]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1427 Eubacterium ventriosum Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [2]
⏷ Show the Full List of 50  DME(s)
References
1 ClinicalTrials.gov (NCT03302936) Assessing Pyridium for Post-Sling Urinary Retention
2 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
3 Metabolism and disposition of phenazopyridine in rat
4 Excretion of phenazopyridine and its metabolites in the urine of humans, rats, mice, and guinea pigs
5 The metabolism and excretion of phenazopyridine hydrochloride in animals and man

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