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

General Information of Drug (ID: DR1145)
Drug Name
Nicergoline
Synonyms
Nargoline; Nicergolin; Nicergolin [German]; Nicergolina; Nicergolina [DCIT]; Nicergoline [USAN:BAN:INN:JAN]; Nicergolinum; Nicergolinum [INN-Latin]; Nicotergoline; Nimergoline; Nimergoline base; RP 19651; Sermion; Sermion (TN); nicergoline; FI 6714; JCV8365FWN; 1-Methyl-lumilysergol 8-(5-bromonicotinate) 10-methyl ether; 10-Methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate; 27848-84-6; BRN 4828393; C24H26BrN3O3; CHEBI:31902; EINECS 248-694-6; NSC 150531; UNII-JCV8365FWN
Indication Acne vulgaris [ICD11: ED80] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 484.4 Topological Polar Surface Area 56.6
Heavy Atom Count 31 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
34040
PubChem SID
7848353 ; 8149729 ; 8173409 ; 11335299 ; 11360538 ; 11364264 ; 11366826 ; 11369388 ; 11372885 ; 11373939 ; 11377550 ; 11461510 ; 11466175 ; 11467295 ; 11485224 ; 11485929 ; 11489230 ; 11491748 ; 11492255 ; 11495184 ; 14834936 ; 14883615 ; 24897843 ; 26612185 ; 26680905 ; 26751796 ; 34675771 ; 46508741 ; 47290994 ; 47440109 ; 47588847 ; 47736318 ; 48184852 ; 48184853 ; 48259072 ; 48334339 ; 49698370 ; 49965496 ; 50104491 ; 50658085 ; 57311619 ; 57654463 ; 81092828 ; 85788051 ; 89449645 ; 92124960 ; 92125220 ; 92307617 ; 92308839 ; 93619685
ChEBI ID
CHEBI:31902
CAS Number
27848-84-6
TTD Drug ID
D0V2GH
Formula
C24H26BrN3O3
Canonical SMILES
CN1CC(CC2(C1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br
InChI
1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
InChIKey
YSEXMKHXIOCEJA-FVFQAYNVSA-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
MMDL DM002711
9796365
Hydrolysis - Hydrolysis 1 [4]
I-OHMMDL DM002712
101607606
Unclear 2 [4]
MDL DM002713
131770002
Oxidation - N-Demethylation 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001733 Nicergoline MMDL Hydrolysis - Hydrolysis Unclear [4]
MR001731 MMDL I-OHMMDL Unclear Unclear [4]
MR001732 I-OHMMDL MDL Oxidation - N-Demethylation CYP2D6 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1398 Clostridioides difficile Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1462 Salmonella enterica Not Available Not Available [3]
⏷ Show the Full List of 8  DME(s)
References
1 ClinicalTrials.gov (NCT01466673) An Efficacy and Safety Study Comparing Oral Contraceptive Containing Norgestimate or Desogestrel for Acne Treatment.
2 Involvement of CYP2D6 but not CYP2C19 in nicergoline metabolism in humans. Br J Clin Pharmacol. 1996 Dec;42(6):707-11.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Assay of nicergoline and three metabolites in human plasma and urine by high-performance liquid chromatography-atmospheric pressure ionization mass spectrometry J Chromatogr. 1991 Aug 23;568(2):375-84. doi: 10.1016/0378-4347(91)80175-c.

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