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

General Information of Drug (ID: DR1021)
Drug Name
Melphalan
Synonyms
Melfalan; Melfalano; Melfalano [INN-Spanish]; Melphalanum; Melphalanum [INN-Latin]; Phenylalanine mustard; Phenylalanine nitrogen mustard; Alanine Nitrogen Mustard; Alkeran; L-Phenylalanine mustard; L-Sarcolysin; L-Sarcolysine; L-Sarkolysin; Levofalan; Levofolan; Levopholan; melphalan; p-L-Sarcolysin; 148-82-3; 3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine; 4-[Bis(2-chloroethyl)amino]-L-phenylalanine; L-PAM; p-Bis(beta-chloroethyl)aminophenylalanine; p-Di-(2-chloroethyl)amino-L-phenylalanine
Indication Multiple myeloma [ICD11: 2A83] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 305.2 Topological Polar Surface Area 66.6
Heavy Atom Count 19 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
460612
PubChem SID
9332 ; 611396 ; 7847435 ; 7979898 ; 8149411 ; 10303302 ; 10321915 ; 11335828 ; 11361067 ; 11363291 ; 11365853 ; 11368415 ; 11371727 ; 11374423 ; 11376577 ; 11462039 ; 11484023 ; 11487890 ; 11490500 ; 11492697 ; 11494211 ; 14874007 ; 14898602 ; 17389837 ; 24278538 ; 26611805 ; 26680129 ; 26752787 ; 46509130 ; 47588994 ; 47662283 ; 47736480 ; 47959741 ; 48413968 ; 48416205 ; 48423637 ; 48425272 ; 49831062 ; 49855032 ; 49865835 ; 50105436 ; 50989121 ; 53790153 ; 56463160 ; 57288513 ; 57288721 ; 57405528 ; 85789225 ; 91010646 ; 92307226
ChEBI ID
CHEBI:28876
CAS Number
148-82-3
TTD Drug ID
D00FGO
Formula
C13H18Cl2N2O2
Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)N(CCCl)CCCl
InChI
1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
InChIKey
SGDBTWWWUNNDEQ-LBPRGKRZSA-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
Dihydroxy-melphalan DM001102
155704
Oxidation - Degradation 1 [4]
Monohydroxy-melphalan DM001101
11219908
Oxidation - Degradation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001638 Melphalan Monohydroxymelphalan Oxidation - Degradation Non-ME [4]
MR001639 Melphalan Dihydroxymelphalan Oxidation - Degradation Non-ME [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1360 Anaerostipes hadrus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1394 Blautia luti Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1404 Clostridium sporogenes Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1418 Enterococcus faecalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1420 Erysipelatoclostridium ramosum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1425 Eubacterium rectale Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1427 Eubacterium ventriosum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1439 Marvinbryantia formatexigens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1452 Providencia alcalifaciens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1453 Providencia rettgeri Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1454 Providencia stuartii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1467 Subdoligranulum variabile Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [3]
⏷ Show the Full List of 67  DME(s)
References
1 Melphalan was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of melphalan by rat liver microsomal glutathione S-transferase. Chem Biol Interact. 2005 Apr 15;152(2-3):101-6.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Kinetics of intravenous melphalan Clin Pharmacol Ther. 1979 Jul;26(1):73-80. doi: 10.1002/cpt197926173.

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