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

General Information of Drug (ID: DR2471)
Drug Name
CB-3304
Synonyms
Capval; Coscopin; Coscopin (VAN); Coscotabs; D01036; DB06174; DSSTox_CID_3385; DSSTox_GSID_23385; DSSTox_RID_77007; DTXSID4023385; EINECS 204-899-2; GTPL10212; Gnoscopine; H2069; HMS1569B08; HMS2096B08; HMS2269P05; HSDB 3372; HY-13716; Hederix (free base); Key-tusscapine; L-.alpha.-Narcotine; L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline; L-alpha-Narcotine; L-alpha-Noscapine; Longactin; Longatin; Lopac0_000840; Lyobex; MCULE-5334942206; MLS000069475; MLS001060855; Methoxyhydrastine; NARCOTINE; NCGC00016388-01; NCGC00023230-02; NCGC00023230-04; NCGC00023230-05; NCGC00023230-07; NCGC00023230-08; NCGC00023230-10; NCI60_004322; NSC 5366; NSC 96350; NSC-121869; NSC-5366; NSC121869; NSC5366; Narcompren; Narcosine; Narcotin; Narcotine (8CI); Narcotine alkaloid; Narcotine, (+-)-; Narcotussin; Narkotin; Nectadon; Nicolane; Nipaxon; Noscapal; Noscapalin; Noscapin; Noscapina; Noscapina [INN-Spanish]; Noscapine (JP15/USP/INN); Noscapine (JP17/USP/INN); Noscapine (TN); Noscapine 1.0 mg/ml in Acetonitrile; Noscapine [USP:INN:BAN:JAN]; Noscapine dl-form; Noscapine, European Pharmacopoeia (EP) Reference Standard; Noscapine, United States Pharmacopeia (USP) Reference Standard; Noscapinum; Noscapinum [INN-Latin]; Noscopine; Noskapin; (+-)-Noscapine; (+-)-alpha-Narcotine; (-)-.alpha.-Narcotine; (-)-.alpha.-Norcotine; 8-Methoxyhydrastin; 8V32U4AOQU; A805851; AC-20272; AKNNEGZIBPJZJG-MSOLQXFVSA-N; AKOS000278036; API0003636; ARONIS24067; BBC/205; BBL012344; BDBM50424716; BIM-0048054.P001; BPBio1_000382; BRD-K89237706-001-03-8; BRN 0099933; BSPBio_000346; C-21952; C09592; CAS-128-62-1; CBMicro_048259; CC-33083; CCG-204096; CCRIS 9304; CHEBI:73237; CHEMBL364713; CS-5115
Indication Chronic lymphocytic leukaemia [ICD11: 2A82] Phase 1/2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 413.4 Topological Polar Surface Area 75.7
Heavy Atom Count 30 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
275196
PubChem SID
11783 ; 71491 ; 415752 ; 605271 ; 855860 ; 7848099 ; 7980174 ; 8065369 ; 9413073 ; 10321868 ; 11113349 ; 11193550 ; 11408713 ; 11466591 ; 11467711 ; 11486301 ; 14831210 ; 14904386 ; 17439397 ; 24862408 ; 41295460 ; 47216689 ; 47216690 ; 47365103 ; 48184909 ; 48184910 ; 48416344 ; 49645498 ; 49698554 ; 50104123 ; 50104124 ; 50104125 ; 53788781 ; 57400976 ; 57705206 ; 61055762 ; 75471156 ; 85787957 ; 87544097 ; 87982965 ; 90341457 ; 92125312 ; 92718085 ; 103462008 ; 103914348 ; 104826459 ; 113483048 ; 115354111 ; 118055360 ; 121362983
ChEBI ID
ChEBI:73237
CAS Number
128-62-1
TTD Drug ID
D0Y8AW
Formula
C22H23NO7
Canonical SMILES
CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
InChI
1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1
InChIKey
AKNNEGZIBPJZJG-MSOLQXFVSA-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
CB-3304 Metabolite II DM005708
196528
Oxidation - Demethylation; cleavage 1 [2]
CB-3304 Metabolite VI DM005710 N. A. Oxidation - Oxidationn 1 [2]
CB-3304 Metabolite X DM005709 N. A. Oxidation - Bis-demethylation 1 [2]
Glucuronic acid conjugates DM005711 N. A. Conjugation - Conjugation 1 [2]
Hydroxylated metabolite DM005706
11372950
Oxidation - Hydrolyzationn 1 [2]
Hydroxylated metabolite DM005705
60060179
Oxidation - Hydrolyzationn 1 [2]
N-demethylated metabolite DM005707
15720261
Oxidation - N-demethylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006088 CB-3304 Hydroxylated metabolite Oxidation - Hydrolyzationn CYP1A1 ... [2]
MR006089 CB-3304 Hydroxylated metabolite Oxidation - Hydrolyzationn CYP1A1 ... [2]
MR006090 CB-3304 N-demethylated metabolite Oxidation - N-demethylation Unclear [2]
MR006091 CB-3304 CB-3304 Metabolite II Oxidation - Demethylation; cleavage CYP2C9 [2]
MR006092 CB-3304 CB-3304 Metabolite X Oxidation - Bis-demethylation CYP3A4 ... [2]
MR006093 CB-3304 CB-3304 Metabolite VI Oxidation - Oxidationn FMO1 [2]
MR006094 CB-3304 Glucuronic acid conjugates Conjugation - Conjugation UGT1A1 ... [2]
⏷ 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
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Dimethylaniline oxidase 1 (FMO1) DME0059 Homo sapiens
FMO1_HUMAN
1.14.13.8
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis 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) DME1460 Ruminococcus torques Not Available Not Available [3]
⏷ Show the Full List of 17  DME(s)
References
1 ClinicalTrials.gov (NCT00183950) Study of Noscapine for Patients With Low Grade Non Hodgkin's Lymphoma or Chronic Lymphocytic Leukemia Refractory to Chemotherapy
2 Metabolic map and bioactivation of the anti-tumour drug noscapine
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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