Details of the Drug

General Information of Drug (ID: DM8YMWE)

Drug Name
Riboflavin
Synonyms
riboflavin; vitamin B2; Lactoflavin; Riboflavine; Vitamin G; 83-88-5; Lactoflavine; (-)-riboflavin; Beflavine; Beflavin; Riboflavina; Flavaxin; Vitaflavine; Riboflavinum; Ribocrisina; Ribovel; Lactobene; Ribotone; Flaxain; Ribosyn; Riboderm; Ribipca; Flavin BB; Vitasan B2; Fiboflavin; Dermadram; Hyflavin; HYRE; Vitamin Bi; Aqua-Flave; 7,8-Dimethyl-10-ribitylisoalloxazine; Russupteridine Yellow III; 6,7-Dimethyl-9-D-ribitylisoalloxazine; Riboflavinequinone; Riboflavinum [INN-Latin]; Riboflavine [INN-French]; Riboflavina [INN-Spanish]
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Vitamin deficiency 5B55-5B71 Approved [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 376.4
Logarithm of the Partition Coefficient (xlogp) -1.5
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
Elimination
75% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 66 - 84 minutes [4]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.32847 micromolar/kg/day [5]
Water Solubility
The ability of drug to dissolve in water is measured as 0.11 mg/mL [3]
Chemical Identifiers
Formula
C17H20N4O6
IUPAC Name
7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
Canonical SMILES
CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O
InChI
InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
InChIKey
AUNGANRZJHBGPY-SCRDCRAPSA-N
Cross-matching ID
PubChem CID
493570
ChEBI ID
CHEBI:17015
CAS Number
83-88-5
DrugBank ID
DB00140
TTD ID
D04QST
VARIDT ID
DR00079
INTEDE ID
DR1416
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Riboflavin transporter 2 (SLC52A3) DTBVQIO S52A3_HUMAN Substrate [6]
Riboflavin transporter 3 (SLC52A2) DTAVOS6 S52A2_HUMAN Substrate [6]
Riboflavin transporter 1 (SLC52A1) DT7NOKR S52A1_HUMAN Substrate [6]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [8]
Eosinophil peroxidase (EPX) DETE84Z PERE_HUMAN Substrate [9]
Tartrate-resistant acid ATPase (ACP5) DESITDW PPA5_HUMAN Substrate [9]
Xylosyl phosphatase (PXYLP1) DEGSUI0 PXYP1_HUMAN Substrate [9]
Prostatic acid phosphatase (ACP3) DEDW5H6 PPAP_HUMAN Substrate [9]
Acid phosphatase-like protein 1 (ACP6) DER6BCE PPA6_HUMAN Substrate [9]
NADPH-dependent oxidoreductase (nfrA) DE82GV7 NRFA_STAA8 Substrate [10]
NADPH-dependent nitroreductase (nfrA1) DE21PLI NFRA1_BACSU Substrate [11]
Nitroreductase (NTR) DE0K82S A0A5K1UB29_SALTM Substrate [12], [13]
Testicular acid phosphatase (ACP4) DE3OZT4 PPAT_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Abnormal spindle-like microcephaly-associated protein (ASPM) OTKXQMNA ASPM_HUMAN Gene/Protein Processing [14]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [15]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [15]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [14]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [15]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [16]
G2/mitotic-specific cyclin-B1 (CCNB1) OT19S7E5 CCNB1_HUMAN Gene/Protein Processing [14]
Glutathione reductase, mitochondrial (GSR) OTM2TUYM GSHR_HUMAN Gene/Protein Processing [16]
Kinesin-like protein KIF23 (KIF23) OTY850JC KIF23_HUMAN Gene/Protein Processing [14]
Methylenetetrahydrofolate reductase (MTHFR) OTUBJSR7 MTHR_HUMAN Drug Response [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6578).
2 Riboflavin FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 An intronic variation in SLC52A1 causes exon skipping and transient riboflavin-responsive multiple acyl-CoA dehydrogenation deficiency. Mol Genet Metab. 2017 Dec;122(4):182-188.
7 Multidrug transporter ABCG2/breast cancer resistance protein secretes riboflavin (vitamin B2) into milk. Mol Cell Biol. 2007 Feb;27(4):1247-53.
8 Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81.
9 An atlas of human metabolism. Sci Signal. 2020 Mar 24;13(624). pii: eaaz1482. (Reaction HMR_6507)
10 Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev. 2008 May;32(3):474-500.
11 Conversion of NfsA, the major Escherichia coli nitroreductase, to a flavin reductase with an activity similar to that of Frp, a flavin reductase in Vibrio harveyi, by a single amino acid substitution. J Bacteriol. 1998 Jan;180(2):422-5.
12 Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
13 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter
14 Riboflavin depletion impairs cell proliferation in adult human duodenum: identification of potential effectors. Dig Dis Sci. 2011 Apr;56(4):1007-19. doi: 10.1007/s10620-010-1374-3. Epub 2010 Sep 17.
15 [Apoptosis of human gastric cancer cell induced by photochemical riboflavin]. Ai Zheng. 2003 Mar;22(3):253-6.
16 Riboflavin deficiency causes protein and DNA damage in HepG2 cells, triggering arrest in G1 phase of the cell cycle. J Nutr Biochem. 2006 Apr;17(4):250-6. doi: 10.1016/j.jnutbio.2005.05.004. Epub 2005 Jun 13.
17 Protective association of MTHFR polymorphism on cervical intraepithelial neoplasia is modified by riboflavin status. Nutrition. 2007 Mar;23(3):229-35. doi: 10.1016/j.nut.2006.12.006. Epub 2007 Feb 14.