Riboflavin

Summary

Riboflavin (CHEMBL1534) is an approved small-molecule photosensitizing agent (ATC A11HA04); indicated across 23 conditions including iron deficiency anemia and anemia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: A11HA04 (+1 more)
• Indications: 23 conditions
• Clinical trials: 80
• Chemistry: 376.4 Da · C17H20N4O6

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1534
Name	Riboflavin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	493570
ChEBI	CHEBI:17015
ATC	A11HA04, S01XA26
Molecular formula	C17H20N4O6
Molecular weight	376.4
InChIKey	AUNGANRZJHBGPY-SCRDCRAPSA-N

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

IUPAC name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione

ChEBI definition: D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.

Pharmacological roles (ChEBI): photosensitizing agent, cofactor, anti-inflammatory agent, antioxidant.

Other ChEBI roles (chemical / environmental): food colouring, Escherichia coli metabolite, mouse metabolite, plant metabolite, human urinary metabolite, fundamental metabolite.

Also known as: Bisulase, C.i. 50900, C.i. food yellow 15, E-101(iii), E-b2, E101, Freeda, INS NO. 101(I), Ins no.101(iii), Ins-101(iii), Lacto-flavin, NCI-0033298

Patent coverage: 58,444 distinct patent families (136,163 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 136,143 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 24 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Lysine-specific demethylase 4E, Ubiquitin carboxyl-terminal hydrolase 2, Fructose-bisphosphate aldolase, ATP-dependent DNA helicase Q1, Inositol monophosphatase 1, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Riboflavin-binding protein, Menin/Histone-lysine N-methyltransferase MLL, Cytochrome P450 2D6, Polyunsaturated fatty acid lipoxygenase ALOX15, Cytochrome P450 1A2, Cytochrome P450 3A4, Caspase-7, Aldehyde dehydrogenase 1A1, Cytochrome P450 2C19, Mitogen-activated protein kinase 1, 3-hydroxyacyl-CoA dehydrogenase type-2, Thiosulfate sulfurtransferase.

Bioactivity

ChEMBL activities: 20 potent at pChembl ≥ 5 of 39 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P02752	8.3	Kd	5	nM	CHEMBL_ACT_8028740
P02752	8.18	Kd	6.6	nM	CHEMBL_ACT_8028741
P02752	7.47	Kd	34	nM	CHEMBL_ACT_8028743
P02752	7.34	Kd	46	nM	CHEMBL_ACT_8028742
P02752	6.46	Ki	350	nM	CHEMBL_ACT_8028745
BRCA1	5.4	Potency	3981	nM	CHEMBL_ACT_3658856
MEN1	5.2	Potency	6310	nM	CHEMBL_ACT_3619238
CYP2C19	5.2	Potency	6310	nM	CHEMBL_ACT_4014288
CYP2C19	5.2	AC50	6310	nM	CHEMBL_ACT_6052341
KDM4E	5.15	Potency	7080	nM	CHEMBL_ACT_3706131
BRCA1	5.1	Potency	7943	nM	CHEMBL_ACT_3658817
A8B2U2	5.1	Potency	7924	nM	CHEMBL_ACT_4609064
CYP1A2	5.1	AC50	7943	nM	CHEMBL_ACT_6059710
TST	5.06	IC50	8800	nM	CHEMBL_ACT_19209150
TDP1	5.05	Potency	8912	nM	CHEMBL_ACT_3936752
ALDH1A1	5.05	Potency	8912	nM	CHEMBL_ACT_4118597
CASP7	5	Potency	10000	nM	CHEMBL_ACT_3800967
P97697	5	Potency	10000	nM	CHEMBL_ACT_4416893
USP2	5	Potency	10000	nM	CHEMBL_ACT_4747693
CASP1	5	Potency	10000	nM	CHEMBL_ACT_4867591

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

4 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
iron deficiency anemia	4	MONDO:0001356	HP:0001891
anemia	4	MONDO:0002280	EFO:0004272
chronic kidney disease	4	MONDO:0005300	EFO:0003884
eye disorder	4	MONDO:0005328	EFO:0003966

13 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
hematologic disorder	3	MONDO:0005570	HP:0001871
diabetic neuropathy	3	MONDO:0006626	EFO:1000783
keratoconus	3	MONDO:0015486	MONDO:0015486
stroke disorder	3	MONDO:0005098	EFO:0000712
psoriasis	2	MONDO:0005083	EFO:0000676
myocardial infarction	2	MONDO:0005068	EFO:0000612
heart failure	2	MONDO:0005252	EFO:0003144
refractive error	2	MONDO:0004892	HP:0000483
myopia	2	MONDO:0001384	HP:0000545
lactic acidosis	2	MONDO:0006040	EFO:1000036
hyperopia	1	MONDO:0004891	HP:0000540
multiple sclerosis	1	MONDO:0005301	MONDO:0005301
corneal ulcer	1	MONDO:0004577	MONDO:0004577

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 80.

Phase distribution

Phase	Trials
Not specified	25
PHASE3	21
PHASE2	13
PHASE2/PHASE3	8
PHASE4	4
PHASE1/PHASE2	3
PHASE1	3
EARLY_PHASE1	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00202228	PHASE4	COMPLETED	Lactate Metabolism Study in HIV Infected Persons
NCT02415777	PHASE4	COMPLETED	Clinical Trial to Evaluate the Efficacy and Safety of ‘URSA SOFT CAP. (UDCA-003)’ in Fatigue Patients With Liver Dysfunction
NCT03012529	PHASE4	COMPLETED	Investigation of Rifampin to Reduce Pedal Amputations for Osteomyelitis in Diabetics
NCT04427956	PHASE4	COMPLETED	Corneal Crosslinking Treatment Study
NCT03922542	PHASE2/PHASE3	RECRUITING	Comparison of Standard vs. Accelerated Corneal Crosslinking
NCT06100939	PHASE3	ACTIVE_NOT_RECRUITING	Epithelium-On Corneal Cross-linking in Subjects 8 to 45 Years of Age With Keratoconus
NCT06100952	PHASE3	ACTIVE_NOT_RECRUITING	Epithelium-On Corneal Cross-linking in Subjects 8 to 45 Years of Age with Keratoconus
NCT00143702	PHASE2/PHASE3	COMPLETED	D4T or Abacavir Plus Vitamin Enhancement in HIV-Infected Patients (DAVE)
NCT00435799	PHASE2/PHASE3	UNKNOWN	Evaluating Collagen Cross-Linking (CCL) Treatment in Norway
NCT00626717	PHASE2/PHASE3	COMPLETED	Riboflavin Mediated Corneal Crosslinking for Stabilizing Progression of Keratoconus
NCT00679666	PHASE2/PHASE3	WITHDRAWN	Corneal Crosslinking in Keratoconus and Corneal Ectasia
NCT01081561	PHASE2/PHASE3	UNKNOWN	Collagen Cross-Linking for Keratoconus/Ectasia With and Without Intacs
NCT01112072	PHASE3	UNKNOWN	Corneal Collagen Crosslinking and Intacs for Keratoconus and Ectasia
NCT01152541	PHASE3	UNKNOWN	Corneal Collagen Crosslinking for Progressive Keratoconus and Ectasia Using Riboflavin/Dextran and Hypotonic Riboflavin
NCT01190306	PHASE3	TERMINATED	Safety Study of the VEGA UV-A System to Treat Keratoconus
NCT01344187	PHASE3	COMPLETED	Safety and Efficacy Study of Corneal Collagen Cross-Linking in Eyes With Keratoconus
NCT01398839	PHASE3	TERMINATED	Safety Study of the VEGA UV-A System to Treat Ectasia
NCT01398852	PHASE3	TERMINATED	Safety and Effectiveness Study of the VEGA UV-A System for Cross-linking in Eyes With Keratoconus and Ectasia
NCT01464268	PHASE3	UNKNOWN	Transepithelial Corneal Collagen Crosslinking for Keratoconus and Corneal Ectasia
NCT01643226	PHASE3	COMPLETED	Safety and Efficacy Study of Corneal Collagen Cross-Linking in Eyes With Keratoconus
NCT01972854	PHASE3	TERMINATED	Safety and Efficacy of Corneal Collagen Cross-Linking in Eyes With Keratoconus
NCT02095730	PHASE3	UNKNOWN	Corneal Cross-Linking Comparing Variables
NCT02769494	PHASE3	WITHDRAWN	The Efficacy of Topical Mesalazine Sustained-Release Tablets in Crohn’s Disease Patients With Oral Ulcer
NCT03187912	PHASE3	COMPLETED	Accelerated Corneal Cross-linking With Different Riboflavin Solutions
NCT03426553	PHASE3	COMPLETED	Clinical Use of Pathogen Reduced Red Blood Cell Suspension
NCT04097730	PHASE3	COMPLETED	Steroids and Cross-linking for Ulcer Treatment
NCT04631484	PHASE3	COMPLETED	International Trial of Efficacy of Cytoflavin in Head Trauma
NCT04649203	PHASE3	COMPLETED	Cytoflavin in the Treatment of Patients With Diabetic Polyneuropathy
NCT04897503	PHASE3	UNKNOWN	Corneal Collagen Crosslinking for Keratoconus and Ectasia Using Riboflavin/Dextran or Riboflavin/Methylcellulose
NCT04905108	PHASE3	UNKNOWN	Transepithelial (Epi-on) Corneal Collagen Crosslinking to Treat Keratoconus and Corneal Ectasia
NCT05255016	PHASE2/PHASE3	UNKNOWN	Safety and Effectiveness of the PXL Platinum 330 System With Riboflavin Solution for Refractory Corneal Ulcers
NCT05255107	PHASE2/PHASE3	UNKNOWN	Safety and Effectiveness of the PXL Platinum 330 System With Riboflavin Solution for Previously Untreated Corneal Ulcers
NCT05935787	PHASE3	COMPLETED	Cytoflavin in the Complex Rehabilitation of Stroke Patients
NCT01143389	PHASE2	COMPLETED	Corneal Crosslinking in Patients With Keratoconus and Post-Refractive Ectasia
NCT01325298	PHASE2	UNKNOWN	UVA-Riboflavin Crosslinking Treatment of Corneal Ectasia
NCT01582880	PHASE1/PHASE2	COMPLETED	Use of Cross-linked Donor Corneas as Carriers for the Boston Keratoprosthesis
NCT01741558	PHASE2	UNKNOWN	The Effects of mETHotrexate Therapy on ST Segment Elevation MYocardial InfarctionS (TETHYS Trial)
NCT01956474	PHASE2	TERMINATED	CXL-04 A Study of Collagen Crosslinking With Ultraviolet-A in Asymmetric Corneas
NCT02276989	PHASE2	WITHDRAWN	Evaluation of a Compliance Marker in Prescription Opioid Abusers With Chronic Pain
NCT02324153	PHASE2	COMPLETED	Ramelteon in the Prevention of Post-operative Delirium
NCT02507362	PHASE1/PHASE2	UNKNOWN	Adapted Fluence Settings for Corneal Collagen Cross-linking in Mild to Moderate Progressive Keratoconus
NCT02514200	PHASE2	UNKNOWN	Treatment of Keratoconus With Advanced CXL-II
NCT02622386	PHASE2	COMPLETED	The Effect of Riboflavin on Moderate to Severe Plaque Type Psoriasis
NCT02762253	PHASE2	TERMINATED	Study of the Safety and Effectiveness of Photochemically Induced Collagen Cross-Linking in Eyes With Keratoconus.
NCT02772237	PHASE2	UNKNOWN	The Impact of Riboflavin on Sports-related Concussion
NCT02863809	PHASE1/PHASE2	COMPLETED	Vision Restoration With a Collagen Crosslinked Boston Keratoprosthesis Unit
NCT03552016	PHASE2	SUSPENDED	Evaluation of Progression of Myopia in Children Treated With Vitamin B2 and Outdoor Sunlight Exposure
NCT04213885	PHASE2	COMPLETED	Safety and Effectiveness of the PXL Platinum 330 System for Corneal Collagen Cross-Linking in Eyes With Corneal Thinning Position
NCT04232800	PHASE2	UNKNOWN	Riboflavin for Glutamate Reduction in Alcohol Withdrawal
NCT01381354	PHASE1	COMPLETED	Nutrition, Neuromuscular Electrical Stimulation (NMES) and Secondary Progressive Multiple Sclerosis (SPMS)
NCT02009709	PHASE1	UNKNOWN	Study of the Safety and Effectiveness of Collagen Cross-Linking at an Irradiance of 9 mW/cm2 and 18 mW/cm2
NCT02068430	PHASE1	COMPLETED	Safety and Effectiveness of the UV-X System for Corneal Collagen Cross-Linking in Eyes With Refractory Corneal Infection
NCT04731727	EARLY_PHASE1	NOT_YET_RECRUITING	Treating Corneal Thinning Conditions With CCL Vario Riboflavin (CXL)
NCT03432572	EARLY_PHASE1	COMPLETED	Investigating Oral Agents for Urine Staining to Facilitate Intraoperative Observation of Ureteral Jets
NCT05907850	EARLY_PHASE1	COMPLETED	Effects of Riboflavin in Mitigating Muscle Soreness in Ultra-marathon Athletes
NCT04584125	Not specified	NOT_YET_RECRUITING	A Randomized Clinical Trial of Ex Vivo Corneal Cross-Linking of Donor Keratoplasty Tissue for Keratoconus Used for Keratoplasty in Keratoconus Patients
NCT04723836	Not specified	ACTIVE_NOT_RECRUITING	Optimal Nutrition for Prevention of Hypertension in Pregnancy
NCT07093463	Not specified	RECRUITING	Colon-delivered Riboflavin and Gut Microbiota Composition
NCT00031057	Not specified	COMPLETED	Vitamin B Therapy for Hyperlactatemia
NCT00037063	Not specified	WITHDRAWN	A Study to See if Certain Antioxidants and Vitamins Will Keep Lactate Levels Down in Patients Taking Anti-HIV Drugs
NCT00912509	Not specified	TERMINATED	Cross Linking for Treatment of Corneal Infection
NCT01307527	Not specified	UNKNOWN	Riboflavin Corneal Crosslinking for Brittle Cornea Syndrome and Ehlers-Danlos Syndrome Type VI
NCT01384773	Not specified	NO_LONGER_AVAILABLE	Progressive Keratoconus or Ectasia Treatment Plan
NCT01726283	Not specified	COMPLETED	Combined CXL//UV and PRK or LASIK in Forme Fruste Keratoconus or Eyes With Potential Risk of Ectasia
NCT01739673	Not specified	COMPLETED	Ultraviolet-A and Riboflavin Treatment for Infectious Keratitis
NCT01789333	Not specified	WITHDRAWN	Higher Irradiance in Keratoconus Ectasia
NCT02344238	Not specified	COMPLETED	Smart Capsule for Automatic Adherence Monitoring
NCT02349165	Not specified	COMPLETED	Standard Versus Transepithelial Corneal Crosslinking
NCT02456961	Not specified	COMPLETED	Standard Corneal Collagen Crosslinking Versus Transepithelial Corneal Crosslinking by Iontophoresis of Riboflavin
NCT02475343	Not specified	UNKNOWN	A Novel Method to Assess the Cornea Biomechanical Properties With Schiotz Tonometer
NCT02538354	Not specified	COMPLETED	The Effect of Riboflavin in Crohn’s Disease
NCT03095235	Not specified	TERMINATED	Dietary Riboflavin (Vitamin B-2) and Cornea Cross-Linking
NCT03151096	Not specified	TERMINATED	Pilot Evaluation of the Effect of Riboflavin Supplementation on Blood Pressure and Possible Effect Modification by the MTHFR C677T Genotype
NCT03668964	Not specified	COMPLETED	Effect of Nutrition Ingredients on Microbiota Modulation
NCT04278378	Not specified	COMPLETED	Blood Pressure Lowering Effect of B-vitamins in Adults With a Genetic Pre-disposition to Elevated Blood Pressure.
NCT04880499	Not specified	COMPLETED	Iron and Vitamin Supplementation in Hip/Knee Surgery
NCT05457647	Not specified	COMPLETED	Theranostic Guided Riboflavin/UV-A Corneal Cross-linking
NCT05488106	Not specified	UNKNOWN	Intervention With Riboflavin to Improve Vascular Health and ENdothelial Functioning in Genetically at- Risk Adults
NCT05803811	Not specified	COMPLETED	Effect of Colon Delivered Vitamin B2 on Gut Microbiota and Related Health Biomarkers in Healthy Older Adults
NCT05881187	Not specified	UNKNOWN	Pack Cross Linking for Infectious Keratitis

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).