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]

Affected Organisms

Humans and other mammals

ATC Code

A11HA04: Riboflavin

A11HA: Other plain vitamin preparations

A11H: OTHER PLAIN VITAMIN PREPARATIONS

A11: VITAMINS

A: ALIMENTARY TRACT AND METABOLISM

S01XA26: Riboflavin

S01XA: Other ophthalmologicals

S01X: OTHER OPHTHALMOLOGICALS

S01: OPHTHALMOLOGICALS

S: SENSORY ORGANS

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL1534
CAS Number: 83-88-5
UNII: TLM2976OFR
DrugBank ID: DB00140
TTD ID: D04QST
VARIDT ID: DR00079
INTEDE ID: DR1416

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[14]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[15]
Kinesin-like protein KIF23 (KIF23)	OTY850JC	KIF23_HUMAN	Gene/Protein Processing	[14]
Myc proto-oncogene protein (MYC)	OTPV5LUK	MYC_HUMAN	Gene/Protein Processing	[16]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A)	OTHCDQ22	PRGC1_HUMAN	Gene/Protein Processing	[17]
Zinc finger protein PLAGL1 (PLAGL1)	OTZAO900	PLAL1_HUMAN	Gene/Protein Processing	[15]

Molecular Interaction Atlas (MIA)

MIA Detail

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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	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.
16	[Apoptosis of human gastric cancer cell induced by photochemical riboflavin]. Ai Zheng. 2003 Mar;22(3):253-6.
17	A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.