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

General Information of Drug (ID: DR1047)
Drug Name
Methoxsalen
Synonyms
Meladinin; Meladinin (VAN); Meladinine; Meladoxen; Meloxine; Methoxa-Dome; Methoxalen; Methoxaten; Methoxsalene; New-Meladinin; Oxoralen; Oxsoralen; Oxsoralen Ultra; Oxsoralen lotion; Oxsoralen-ultra; Oxypsoralen; Proralone-mop; Psoralon-MOP; Puvalen; Ammodin; Ammoidin; Dltasoralen; Geroxalen; Puvamet; Uvadex; XANTHOTOXIN; Xanthotoxine; Zanthotoxin; methoxsalen; 298-81-7; 8-MOP; 8-MP; 8-Methoxyfuranocoumarin; 8-Methoxypsoralen; 8-Methoxypsoralene; 9-Methoxy-7H-furo[3,2-g]chromen-7-one; 9-Methoxypsoralen; 9-methoxyfuro[3,2-g]chromen-7-one
Indication Psoriasis vulgaris [ICD11: EA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 216.19 Topological Polar Surface Area 48.7
Heavy Atom Count 16 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4114
PubChem SID
4978 ; 99459 ; 597343 ; 2465957 ; 3139055 ; 3496877 ; 4255217 ; 7666801 ; 7847207 ; 7884115 ; 7885536 ; 7979935 ; 8025195 ; 8138256 ; 8145159 ; 8149421 ; 8152581 ; 10321621 ; 10517620 ; 11112313 ; 11335938 ; 11361177 ; 11363917 ; 11366479 ; 11369041 ; 11371597 ; 11373682 ; 11377203 ; 11408476 ; 11462149 ; 11466507 ; 11467627 ; 11484740 ; 11486293 ; 11488868 ; 11490315 ; 11491867 ; 11494837 ; 11534753 ; 14822550 ; 17389831 ; 24896845 ; 26611816 ; 26679584 ; 26747188 ; 26747189 ; 26752292 ; 29204678 ; 29223222 ; 46506275
ChEBI ID
ChEBI:18358
CAS Number
298-81-7
TTD Drug ID
D08SKH
Formula
C12H8O4
Canonical SMILES
COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2
InChI
1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChIKey
QXKHYNVANLEOEG-UHFFFAOYSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Formaldehyde DM001748
712
Oxidation - O-Dealkylation from CyProduct 1 Human
Methoxsalen M1 PDM007264
65090
Oxidation - O-Dealkylation AndFromCyProduct 1 Human
Methoxsalen M2 PDM007265 N. A. Oxidation - Hydroxylation from CyProduct 1 Human
Methoxsalen M5 PDM007267 N. A. Oxidation - Epoxidation of alkene 1 Human
Methoxsalen M4 PDM007266 N. A. Conjugation - Aromatic OH-glucuronidation 2 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [4]
⏷ Show the Full List of 14  DME(s)
References
1 Methoxsalen was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of the human cytochrome P450 enzymes involved in the in vitro metabolism of artemisinin. Br J Clin Pharmacol. 1999 Oct;48(4):528-35.
3 Photochemotherapeutic agent 8-methoxypsoralen induces cytochrome P450 3A4 and carboxylesterase HCE2: evidence on an involvement of the pregnane X receptor. Toxicol Sci. 2007 Jan;95(1):13-22.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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