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

General Information of Drug (ID: DR0390)
Drug Name
Cyclobenzaprine
Synonyms
Ciclobenzaprina; Ciclobenzaprina [INN-Spanish]; Cyclobenzaprine (INN); Cyclobenzaprine [INN]; Cyclobenzaprinum; Cyclobenzaprinum [INN-Latin]; Fexmid; Flexeril hydrochloride; Lisseril; MK 130; Proeptatriene; Proeptatriene [Italian]; Proheptatrien; Proheptatriene; Ro 4-1577; Yurelax; cyclobenzaprine; 10,11-Dehydroamitriptyline; 3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine; 303-53-7; 5-(3-Dimetilaminopropiliden)-5H-dibenzo-(a,d)-ciclopentene; 69O5WQQ5TI; 9715 R.P; CHEBI:3996; EINECS 206-145-8; UNII-69O5WQQ5TI
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 275.4 Topological Polar Surface Area 3.2
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
2895
PubChem SID
9148 ; 798360 ; 4253288 ; 7407325 ; 7849637 ; 8151851 ; 10320885 ; 10517820 ; 11110649 ; 11110650 ; 11335222 ; 11360461 ; 11364429 ; 11366991 ; 11369553 ; 11372671 ; 11373782 ; 11377715 ; 11446077 ; 11458991 ; 11460887 ; 11461433 ; 11466473 ; 11467593 ; 11485084 ; 11486165 ; 11489350 ; 11491381 ; 11491977 ; 11495349 ; 14872814 ; 26652854 ; 29222048 ; 46508313 ; 47290965 ; 47290966 ; 47290967 ; 47365012 ; 47365013 ; 47440075 ; 47515151 ; 47736294 ; 48110285 ; 48334305 ; 49699345 ; 49961818 ; 50108641 ; 50111010 ; 51092050 ; 57321502
ChEBI ID
CHEBI:3996
CAS Number
303-53-7
TTD Drug ID
D01KHH
Formula
C20H21N
Canonical SMILES
CN(C)CCC=C1C2=CC=CC=C2C=CC3=CC=CC=C31
InChI
1S/C20H21N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14H,7,15H2,1-2H3
InChIKey
JURKNVYFZMSNLP-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
4-Hydroxycyclophosphamide DM003738
99735
Oxidation - 4-hydroxylation 1 [2] , [5]
Chloroacetaldehyde DM003749
33
Unclear 1 [6]
Dechloroethyl cyclophosphamide DM003748
114861
Unclear 1 [6]
4-Ketocyclophosphamide DM003747
33676
Unclear 2 [6]
Aldophosphamide DM003739
107744
Unclear 2 [5]
Acrolein DM003742
7847
Unclear 3 [2]
Alcophosphamide DM003746
98612
Unclear 3 [6]
Carboxyphosphamide DM003744
31515
Unclear 3 [6]
Phosphoramide Mustard DM003740
96356
Unclear 3 [7]
Acrylic Acid DM003743
6581
Unclear 4 [7]
Nornitrogen mustard DM003745
9533
Unclear 4 [6]
Phosphoramide Aziridinium DM003741
85976655
Unclear 4 [7]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012897 Cyclobenzaprine 4-Hydroxycyclophosphamide Oxidation - 4-hydroxylation CYP2C9 ... [2], [5]
MR012907 Cyclobenzaprine Dechloroethyl cyclophosphamide Unclear CYP3A4 ... [6]
MR012908 Cyclobenzaprine Chloroacetaldehyde Unclear CYP3A7 [6]
MR012898 4-Hydroxycyclophosphamide Aldophosphamide Unclear Unclear [5]
MR012906 4-Hydroxycyclophosphamide 4-Ketocyclophosphamide Unclear Unclear [6]
MR012899 Aldophosphamide Phosphoramide Mustard Unclear Unclear [7]
MR012901 Aldophosphamide Acrolein Unclear Unclear [2]
MR012903 Aldophosphamide Carboxyphosphamide Unclear Unclear [6]
MR012905 Aldophosphamide Alcophosphamide Unclear ADH1A ... [6]
MR012902 Acrolein Acrylic Acid Unclear ALDH1A1 [7]
MR012904 Carboxyphosphamide Nornitrogen mustard Unclear Unclear [6]
MR012900 Phosphoramide Mustard Phosphoramide Aziridinium Unclear Unclear [7]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alcohol dehydrogenase class-I alpha (ADH1A) DME0127 Homo sapiens
ADH1A_HUMAN
1.1.1.1
[2]
Aldehyde dehydrogenase 1 (ALDH1) DME0286 Homo sapiens
AL1A1_HUMAN
1.2.1.36
[2]
Aldehyde dehydrogenase 7 (ALDH7) DME0294 Homo sapiens
AL3B1_HUMAN
1.2.1.5
[2]
Aldehyde dehydrogenase family 1 member A3 (ALDH1A3) DMEN146 Homo sapiens
AL1A3_HUMAN
1.2.1.36
[2]
Aldehyde dehydrogenase family 3 member B2, (ALDH3B2) DMEN147 Homo sapiens
AL3B2_HUMAN
1.2.1.3
[2]
Aldo-keto reductase 1A1 (AKR1A1) DME0098 Homo sapiens
AK1A1_HUMAN
1.1.1.2
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
⏷ Show the Full List of 11  DME(s)
References
1 Nortriptyline Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The KEGG resource for deciphering the genome
3 Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine. Drug Metab Dispos. 1996 Jul;24(7):786-91.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 U. S. FDA Label -Cyclobenzaprine
7 DrugBank(Pharmacology-Metabolism):Cyclobenzaprine

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