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

General Information of Drug (ID: DR1513)
Drug Name
Sulfasalazine
Prodrug Info Sulfasalazine is the prodrug of Mesalazine
Synonyms
Salazopiridazin; Salazopyridin; Salazopyrin; Salazosulfapiridina; Salazosulfapyridin; Salazosulfapyridine; Salazosulfapyridinum; Salicylazosulfapyridine; Salisulf; Sas-500; Sulcolon; Sulfasalazin; Sulfasalazina; Sulfasalazinum; Sulfazalazine; Sulphasalazine; Asulfidine; Azopyrin; Azopyrine; Azosulfidin; Azulfidine; Azulfidine EN; Azulfidine EN-tabs; Benzosulfa; Colo-Pleon; Reupirin; S.A.S.-500; Salazo-sulfapyridinum; sulfasalazine; w-t Sasp oral; 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid; 599-79-1; Accucol; SASP
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 398.4 Topological Polar Surface Area 150
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
5339
PubChem SID
9524 ; 452205 ; 7847514 ; 7890377 ; 10321791 ; 11112423 ; 17389737 ; 26747277 ; 26747278 ; 39383787 ; 46391376 ; 46505451 ; 48414442 ; 48416584 ; 48424062 ; 48425604 ; 49698537 ; 50105482 ; 50105483 ; 53789773 ; 57361929 ; 78341122 ; 85147460 ; 85164696 ; 85174423 ; 85787939 ; 87560165 ; 92125445 ; 93166319 ; 103914276 ; 103994509 ; 104134816 ; 114147521 ; 117607242 ; 124890162 ; 124890163 ; 134337474 ; 134339436 ; 134976371 ; 135692179 ; 139618183 ; 144204588 ; 144208437 ; 144210859 ; 160964137 ; 164788662 ; 170464716 ; 172386498 ; 175267319 ; 179038496
ChEBI ID
CHEBI:9334
CAS Number
599-79-1
TTD Drug ID
D02ZTJ
Formula
C18H14N4O5S
Canonical SMILES
C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O
InChI
1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)
InChIKey
NCEXYHBECQHGNR-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
Mesalazine DM000380
4075
Unclear 1 [8]
Sulfapyridine DM003083
5336
Unclear 1 [8]
N-acetyl mesalazine DM000381
65512
Conjugation - Acetylation 2 [8]
N-acetylsufapyridine DM000376 N. A. Conjugation - Acetylation 2 [8]
OH-sulfapyridine DM000378 N. A. Oxidation - Hydroxylation 2 [8]
Sulfapyridine glucuronide DM000379 N. A. Conjugation - Glucuronidation 2 [9]
Acetylated sulfapyridine glucuronide DM000377 N. A. Conjugation - Glucuronidation 3 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002290 Sulfasalazine 5-aminosalicylic acid Unclear azoR [8]
MR002291 Sulfasalazine Sulfapyridine Unclear Unclear [8]
MR002289 5-aminosalicylic acid N-acetyl-5-aminosalicylic acid Conjugation - Acetylation NAT1 [8]
MR002292 Sulfapyridine N-acetylsufapyridine Conjugation - Acetylation NAT2 [8]
MR002293 Sulfapyridine OH-sulfapyridine Oxidation - Hydroxylation Unclear [8]
MR002294 Sulfapyridine Sulfapyridine glucuronide Conjugation - Glucuronidation Unclear [9]
MR002288 N-acetylsufapyridine Acetylated sulfapyridine glucuronide Conjugation - Glucuronidation Unclear [9]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Azoreductase (azoR) DME1345 Enterococcus faecium
A0A132Z973_ENTFC
1.7.1.6
[2] , [3]
Azoreductase (azoR) DME1081 Enterococcus casseliflavus
T0VG26_9ENTE
1.7.1.6
[4]
Azoreductase (azoR) DME1083 Bifidobacterium dentium
A0A0P0ETC6_BACT4
1.7.1.6
[4]
Azoreductase (azoR) DME1315 Enterococcus faecalis
AZOR_ENTFA
1.7.1.6
[2] , [3]
Azoreductase (azoR) DME1316 Clostridium perfringens
AZOR_CLOP1
1.7.1.6
[2] , [3]
Azoreductase (azoR) DME1322 Lactobacillus buchneri
A0A349MYB4_9LACO
1.7.1.6
[4]
Azoreductase (azoR) DME1473 Bacteroides fragilis
A0A0P0ETC6_BACT4
1.7.1.6
[5]
Azoreductase (azoR) DME1474 Bifidobacterium animalis
A0A0P0ETC6_BACT4
1.7.1.6
[2] , [3]
Azoreductase (azoR) DME1475 Lactobacillus acidophilus
A0A349MYB4_9LACO
1.7.1.6
[2] , [3]
Azoreductase (azoR) DME1080 Streptococcus salivarius
A0A074IU04_STRSL
1.7.1.6
[2]
Azoreductase (azoR) DME1082 Bacteroides thetaiotaomicron
A0A0P0ETC6_BACT4
1.7.1.6
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[7]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[7]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [5]
⏷ Show the Full List of 67  DME(s)
References
1 Sulfasalazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The influence of probiotic treatment on sulfasalazine metabolism in rat. Xenobiotica. 2012 Aug;42(8):791-7.
3 Developing a metagenomic view of xenobiotic metabolism. Pharmacol Res. 2013 Mar;69(1):21-31.
4 The role of intestinal bacteria in the metabolism of salicylazosulfapyridine. J Pharmacol Exp Ther. 1972 Jun;181(3):555-62.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
7 Effects of NAT2 polymorphism on SASP pharmacokinetics in Chinese population Clin Chim Acta. 2009 Sep;407(1-2):30-5. doi: 10.1016/j.cca.2009.06.025.
8 Effects of NAT2 polymorphism on SASP pharmacokinetics in Chinese population. Clin Chim Acta. 2009 Sep;407(1-2):30-5.
9 Small bowel absorption of sulfasalazine and its hepatic metabolism in human beings, cats, and rats Gastroenterology. 1979 Aug;77(2):280-4.

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