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methylthioninium chloride 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	1763	61-73-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: methylthioninium benzalkonium chloride hydrate methylthioninium chloride hydrate methylenum coeruleum methylthioninium chloratum methylene blue methylthioninium chloride aizen methylene blue proveblue	A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN. Molecular weight: 284.40 Formula: C16H18N3S CLOGP: -1.87 LIPINSKI: 0 HAC: 3 HDO: 0 TPSA: 19.37 ALOGS: -2.93 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

methylthioninium benzalkonium chloride hydrate
methylthioninium chloride hydrate
methylenum coeruleum
methylthioninium chloratum
methylene blue
methylthioninium chloride
aizen methylene blue
proveblue

A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.

Molecular weight: 284.40
Formula: C16H18N3S
CLOGP: -1.87
LIPINSKI: 0
HAC: 3
HDO: 0
TPSA: 19.37
ALOGS: -2.93
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
None	FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Serotonin syndrome	1030.29	87.74	231	2069	28451	63458271
Myoglobin urine present	332.53	87.74	51	2249	721	63486001
Drug interaction	329.88	87.74	161	2139	228970	63257752
Toxic encephalopathy	278.29	87.74	61	2239	6518	63480204
Amylase increased	225.30	87.74	51	2249	6294	63480428
Troponin increased	201.62	87.74	51	2249	10070	63476652
Blood creatine phosphokinase increased	189.76	87.74	62	2238	30368	63456354
Blood potassium increased	171.68	87.74	51	2249	18258	63468464
Blood lactate dehydrogenase increased	159.96	87.74	51	2249	23065	63463657
Clonus	141.66	87.74	33	2267	4603	63482119
Hyperreflexia	128.53	87.74	32	2268	5902	63480820
Alanine aminotransferase increased	96.91	87.74	55	2245	103715	63383007
Agitation	88.05	87.74	43	2257	59714	63427008

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Serotonin syndrome	657.58	77.47	157	1467	19776	34935531
Drug interaction	166.91	77.47	112	1512	225834	34729473
Vasoplegia syndrome	105.73	77.47	23	1601	1833	34953474
Drug ineffective	93.04	77.47	109	1515	456642	34498665

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Serotonin syndrome	1512.68	65.22	362	3453	44665	79695908
Drug interaction	428.41	65.22	257	3558	414926	79325647
Myoglobin urine present	279.73	65.22	47	3768	900	79739673
Toxic encephalopathy	222.84	65.22	60	3755	11380	79729193
Amylase increased	164.07	65.22	47	3768	11162	79729411
Clonus	147.97	65.22	39	3776	6801	79733772
Troponin increased	139.02	65.22	47	3768	19208	79721365
Hyperreflexia	126.46	65.22	36	3779	8349	79732224
Blood potassium increased	123.34	65.22	48	3767	29227	79711346
Blood creatine phosphokinase increased	117.23	65.22	59	3756	66031	79674542
Vasoplegia syndrome	114.60	65.22	28	3787	3602	79736971
Blood lactate dehydrogenase increased	106.58	65.22	47	3768	39123	79701450
Coma	91.53	65.22	58	3757	100591	79639982
Encephalopathy	87.83	65.22	49	3766	67348	79673225
Nystagmus	86.79	65.22	28	3787	9876	79730697
Hypotension	71.42	65.22	96	3719	440221	79300352
Drug ineffective	69.42	65.22	156	3659	1080757	78659816
Agitation	65.53	65.22	47	3768	99668	79640905

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	V03AB17	VARIOUS ALL OTHER THERAPEUTIC PRODUCTS ALL OTHER THERAPEUTIC PRODUCTS Antidotes
ATC	V04CG05	VARIOUS DIAGNOSTIC AGENTS OTHER DIAGNOSTIC AGENTS Tests for gastric secretion
MeSH PA	D004791	Enzyme Inhibitors
CHEBI has role	CHEBI:22586	antioxidants
CHEBI has role	CHEBI:33281	antibiotics
CHEBI has role	CHEBI:35208	physical tracer
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:37733	EC 3.1.1.8 inhibitor
CHEBI has role	CHEBI:38068	antimalarials
CHEBI has role	CHEBI:38623	monoamine oxidase inhibitors
CHEBI has role	CHEBI:50407	acid-base indicator
CHEBI has role	CHEBI:51217	fluorochromes
CHEBI has role	CHEBI:63726	neuroprotective agents
CHEBI has role	CHEBI:77178	biological stain
CHEBI has role	CHEBI:77307	cardioprotective agents
CHEBI has role	CHEBI:78678	EC 4.6.1.2 inhibitor

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Methemoglobinemia	indication	38959009	DOID:10783
Gastritis	contraindication	4556007	DOID:4029
Hypocalcemia	contraindication	5291005
Severe chronic ulcerative colitis	contraindication	14311001
Disorder of autonomic nervous system	contraindication	15241006
Cirrhosis of liver	contraindication	19943007	DOID:5082
Hyperphosphatemia	contraindication	20165001	DOID:0050459
Glaucoma	contraindication	23986001	DOID:1686
Toxic megacolon	contraindication	28536002	DOID:1770
Atony of colon	contraindication	29479008
Hyperthyroidism	contraindication	34486009	DOID:7998
Hypertensive disorder	contraindication	38341003	DOID:10763
Hypernatremia	contraindication	39355002
Hypovolemic shock	contraindication	39419009
Gastrointestinal ulcer	contraindication	40845000
Body fluid retention	contraindication	43498006
Conduction disorder of the heart	contraindication	44808001
Achalasia of esophagus	contraindication	45564002	DOID:9164
Chronic heart failure	contraindication	48447003
Disorder of cardiovascular system	contraindication	49601007	DOID:1287
Vitamin K deficiency	contraindication	52675005	DOID:11249
Nasal polyp	contraindication	52756005
Paralytic ileus	contraindication	55525008	DOID:8442
Acute nephropathy	contraindication	58574008
Hepatic failure	contraindication	59927004
Blood coagulation disorder	contraindication	64779008	DOID:1247
Diabetes mellitus	contraindication	73211009	DOID:9351
Factor II deficiency	contraindication	73975000
Gastrointestinal hemorrhage	contraindication	74474003
Thrombotic thrombocytopenic purpura	contraindication	78129009	DOID:10772
Hiatal hernia	contraindication	84089009	DOID:12642
Kidney disease	contraindication	90708001	DOID:557
Thyrotoxicosis	contraindication	90739004	DOID:7997
Hemophilia	contraindication	90935002
Myasthenia gravis	contraindication	91637004	DOID:437
Anemia due to enzyme deficiency	contraindication	111577008
Deficiency of glucose-6-phosphate dehydrogenase	contraindication	124134002	DOID:2862
Liver function tests abnormal	contraindication	166603001
Gastroesophageal reflux disease	contraindication	235595009	DOID:8534
Disease of liver	contraindication	235856003	DOID:409
Bladder outflow obstruction	contraindication	236645006
Pyloric obstruction	contraindication	244815007
Benign prostatic hyperplasia	contraindication	266569009
Edema	contraindication	267038008
Anemia	contraindication	271737000	DOID:2355
Pregnancy, function	contraindication	289908002
Cardiovascular event risk	contraindication	395112001
Breastfeeding (mother)	contraindication	413712001
Disorder of coronary artery	contraindication	414024009
Fever greater than 100.4 Fahrenheit	contraindication	426000000
Severe dehydration	contraindication	450316000

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	4.42	Basic
pKa2	3.81	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
10MG/2ML (5MG/ML)	PROVAYBLUE	PROVEPHARM SAS	N204630	July 18, 2019	RX	SOLUTION	INTRAVENOUS	April 8, 2023	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
50MG/10ML (5MG/ML)	PROVAYBLUE	PROVEPHARM SAS	N204630	April 8, 2016	RX	SOLUTION	INTRAVENOUS	April 8, 2023	FOR TREATMENT OF PEDIATRIC AND ADULT PATIENTS WITH ACQUIRED METHEMOGLOBINEMIA.

Bioactivity Summary:

Target	Class	Pharos	UniProt	Type	Activity value (-log[M])	Bioact source
Glutathione reductase, mitochondrial	Enzyme	P00390	GSHR_HUMAN	IC50	4.80	CHEMBL
Amine oxidase [flavin-containing] B	Enzyme	P27338	AOFB_HUMAN	IC50	5.36	CHEMBL
Amine oxidase [flavin-containing] A	Enzyme	P21397	AOFA_HUMAN	IC50	7.15	CHEMBL
Thioredoxin reductase 1, cytoplasmic	Enzyme	Q16881	TRXR1_HUMAN	IC50	4.52	CHEMBL
Microtubule-associated protein tau	Structural	P10636	TAU_HUMAN	IC50	5.72	CHEMBL
Amyloid beta A4 protein	Unclassified	P05067	A4_HUMAN	IC50	6.26	CHEMBL
Glutathione reductase	Enzyme		GSHR_PLAF7	IC50	5.19	CHEMBL
Cruzipain	Enzyme		CYSP_TRYCR	IC50	4.26	CHEMBL

External reference:

ID	Source
4018579	VUID
N0000146895	NUI
D02312	KEGG_DRUG
7220-79-3	SECONDARY_CAS_RN
4018579	VANDF
C0025746	UMLSCUI
CHEBI:6872	CHEBI
MBT	PDB_CHEM_ID
CHEMBL550495	ChEMBL_ID
CHEMBL405110	ChEMBL_ID
CHEMBL191083	ChEMBL_ID
DB09241	DRUGBANK_ID
6099	PUBCHEM_CID
6878	RXNORM
1036	MMSL
5090	MMSL
d01128	MMSL
001094	NDDF
002616	NDDF
002877	NDDF
354064008	SNOMEDCT_US
6725000	SNOMEDCT_US
D008751	MESH_DESCRIPTOR_UI
T42P99266K	UNII

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
URELLE	HUMAN PRESCRIPTION DRUG LABEL	5	0037-6321	TABLET	10.80 mg	ORAL	Unapproved drug other	12 sections
URIBEL	HUMAN PRESCRIPTION DRUG LABEL	5	0076-0111	CAPSULE	10 mg	ORAL	unapproved drug other	20 sections
Hyophen	HUMAN PRESCRIPTION DRUG LABEL	5	0076-0901	TABLET	10.80 mg	ORAL	unapproved drug other	19 sections
Phosphasal	HUMAN PRESCRIPTION DRUG LABEL	5	0076-0902	TABLET	10.80 mg	ORAL	unapproved drug other	20 sections
Ustell	HUMAN PRESCRIPTION DRUG LABEL	5	0076-0903	CAPSULE	10 mg	ORAL	unapproved drug other	20 sections
Utira-C	HUMAN PRESCRIPTION DRUG LABEL	5	0178-0513	TABLET	10.80 mg	ORAL	unapproved drug other	12 sections
Utira-C	HUMAN PRESCRIPTION DRUG LABEL	5	0178-0513	TABLET	10.80 mg	ORAL	unapproved drug other	12 sections
URIBEL	HUMAN PRESCRIPTION DRUG LABEL	5	0178-0740	CAPSULE	10 mg	ORAL	unapproved drug other	21 sections
URIBEL	HUMAN PRESCRIPTION DRUG LABEL	5	0178-0740	CAPSULE	10 mg	ORAL	unapproved drug other	21 sections
UROGESIC BLUE	HUMAN PRESCRIPTION DRUG LABEL	4	0485-0151	TABLET, COATED	10.80 mg	ORAL	unapproved drug other	18 sections
UROGESIC BLUE	HUMAN PRESCRIPTION DRUG LABEL	4	0485-0151	TABLET, COATED	10.80 mg	ORAL	unapproved drug other	18 sections
UROGESIC BLUE	HUMAN PRESCRIPTION DRUG LABEL	4	0485-0151	TABLET, COATED	10.80 mg	ORAL	unapproved drug other	18 sections
UROGESIC BLUE	HUMAN PRESCRIPTION DRUG LABEL	4	0485-0151	TABLET, COATED	10.80 mg	ORAL	unapproved drug other	18 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0125	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0125	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0125	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0371	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0371	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0371	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0374	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0374	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0374	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0381	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0381	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
PROVAYBLUE	HUMAN PRESCRIPTION DRUG LABEL	1	0517-0381	INJECTION	5 mg	INTRAVENOUS	NDA	29 sections
Uretron D/S	HUMAN PRESCRIPTION DRUG LABEL	5	12539-144	TABLET	10.80 mg	ORAL	unapproved drug other	20 sections
UroAv-81	HUMAN PRESCRIPTION DRUG LABEL	5	15338-502	TABLET	10.80 mg	ORAL	unapproved drug other	18 sections
UroAv-B	HUMAN PRESCRIPTION DRUG LABEL	5	15338-503	CAPSULE	10 mg	ORAL	unapproved drug other	18 sections
Methylene Blue	HUMAN PRESCRIPTION DRUG LABEL	1	17478-504	INJECTION	10 mg	INTRAVENOUS	unapproved drug other	15 sections
URIMAR-T CAPS	HUMAN PRESCRIPTION DRUG LABEL	5	28595-224	CAPSULE	10.80 mg	ORAL	unapproved drug other	19 sections