Drug

D0199 | Methylene Blue

Molecular Formula C16H18ClN3S
Molecular Weight 319.9
Structure
State solid
Clearance 3.0 ± 0.7 L/min.
Volume of distribution 10 mg/kg (in rats).
Route of elimination Excreted in urine and bile. About 75% of an oral dose excreted in urine, primarily as stabilized colorless leukomethylene blue.
Protein binding Methylene blue was reported to bind strongly to rabbit plasma (71–77% of bound drug).
Half life 5–6.5 hours (after IV dose).

V

V04CG05 Methylthioninium chloride


[V04CG] Tests for gastric secretion


[V04C] OTHER DIAGNOSTIC AGENTS


[V04] DIAGNOSTIC AGENTS


[V] Various ATC structures


V03AB17 Methylthioninium chloride


[V03AB] Antidotes


[V03A] ALL OTHER THERAPEUTIC PRODUCTS


[V03] ALL OTHER THERAPEUTIC PRODUCTS


[V] Various ATC structures


Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL 2.88±1.33 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 2.75 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL rat hepatocytes MMP assay Negative IC50 163

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 262 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 19 of 262 companies. For more detailed information, please visit ECHA C&L website


Of the 11 notification(s) provided by 243 of 262 companies with hazard statement code(s):


H302 (99.59%): Harmful if swallowed [Warning Acute toxicity, oral]


H318 (27.98%): Causes serious eye damage [Danger Serious eye damage/eye irritation]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]


H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard]


H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


P201, P202, P260, P264, P270, P273, P281, P301+P312, P307+P311, P308+P313, P314, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
guinea pig LDLo subcutaneous 300mg/kg (300mg/kg) "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
dog LDLo intravenous 50mg/kg (50mg/kg) "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
domestic animals - goat/sheep LD50 intravenous 42300ug/kg (42.3mg/kg) Journal of Veterinary Pharmacology and Therapeutics. Vol. 7, Pg. 225, 1984.
dog LDLo oral 500mg/kg (500mg/kg) "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
infant TDLo unreported 15mg/kg (15mg/kg) "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 390, 1969.
monkey LDLo intravenous 10mg/kg (10mg/kg) "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
rabbit LDLo oral 1gm/kg (1000mg/kg) "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1366, 1935.
man TDLo subcutaneous 28uL/kg (0.028mL/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" British Journal of Clinical Practice. Vol. 28, Pg. 289, 1974.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg) National Technical Information Service. Vol. AD691-490,
rat LD50 intravenous 1250mg/kg (1250mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 676, 1968.
mouse LD50 intravenous 77mg/kg (77mg/kg) Cesko-Slovenska Farmacie. Vol. 12, Pg. 94, 1963.
rat LD50 oral 1180mg/kg (1180mg/kg) "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1334, 1986.
rat LD50 subcutaneous 190mg/kg (190mg/kg) Drugs in Japan Vol. -, Pg. 1185, 1990.
cat LDLo intravenous 41mg/kg (41mg/kg) Annals of Internal Medicine. Vol. 7, Pg. 738, 1933.
mouse LD50 oral 3500mg/kg (3500mg/kg) Cesko-Slovenska Farmacie. Vol. 12, Pg. 94, 1963.
rat LD50 intraperitoneal 180mg/kg (180mg/kg) Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 204, Pg. 288, 1947.


  • 105504-42-5 12262-49-6 1341-90-8
    152071-32-4 3,7-Bis(dimethylamino)-5-phenothiazinium Chloride 3,7-Bis(dimethylamino)phenazathionium chloride
    3,7-Bis(dimethylamino)phenothiazin-5-ium chloride 3,7-bis(dimethylamino)-phenothiazin-5-ium chloride salt 3H-Phenothiazine, 3-methochloride
    3H-Phenothiazine, 7-(dimethylamino)-3-(methylimino)-, 3-methochloride 61-73-4 6476-03-5
    8NAP7826UB 97130-83-1 A0574
    AC-15225 AK326199 AKOS000486124
    AKOS015916406 AS-35256 Aizen Methylene Blue BH
    Aizen Methylene Blue FZ BIA4084 Basic Blue 9;Tetramethylthionine chloride
    Basic blue 9 Bleu de methylene C.I. 52 015
    C.I. 52015 C.I. Basic Blue 9 C.I. Basic Blue 9 (8CI)
    C00220 C16H20N3S.HCl CAS-61-73-4
    CCRIS 833 CHEBI:6872 CHEMBL405110
    CI 52015 CI Basic Blue 9 CI NO 52015
    CI-52015 CS-2959 CXKWCBBOMKCUKX-UHFFFAOYSA-M
    Calcozine Blue ZF Caswell No. 567 Ceruleum methylenum
    Chlorure de methylthioninium Chlorure de methylthioninium [INN-French] Chromosmon
    Cloruro de metiltioninio Cloruro de metiltioninio [INN-Spanish] D And C Blue Number 1
    D and C Blue No. 1 DB09241 DOG (COUCH) GRASS Powder
    DSSTox_CID_3296 DSSTox_GSID_23296 DSSTox_RID_76963
    DTXSID0023296 EINECS 200-515-2 EPA Pesticide Chemical Code 039505
    Ehrlichs reagent III Ext D and C Blue No. 1 External Blue 1
    FT-0622580 HMS2598O03 HSDB 1405
    HY-14536 Hidaco Methylene Blue Salt Free KS-000013GW
    KS-00004B65 LS-268 Leather Pure Blue HB
    Loefflers Methylene Blue Lowacryl blue 9 M-B Tabs
    M0501 MCULE-7744087830 METHYLENE BLUE (METHYLENE BLUE, CHLORIDE:HYDRATE (7220-79-3))
    MFCD00012111 MLS000719838 Methylenblau
    Methylenblau [German] Methylene Azure II Methylene Blue (C.I. 52015)
    Methylene Blue (Inhibitor) Methylene Blue (Medicinal) Methylene Blue (anhydrous)
    Methylene Blue 2B Methylene Blue 2BF Methylene Blue 2BN
    Methylene Blue 2BP Methylene Blue A Methylene Blue B
    Methylene Blue BB Methylene Blue BB (Zinc Free) Methylene Blue BBA
    Methylene Blue BD Methylene Blue BP Methylene Blue BPC
    Methylene Blue BX Methylene Blue BZ Methylene Blue Chloride (Biological stain)
    Methylene Blue D Methylene Blue FZ Methylene Blue G
    Methylene Blue GZ Methylene Blue HGG Methylene Blue I (Medicinal)
    Methylene Blue IAD Methylene Blue JFA Methylene Blue N
    Methylene Blue NF (Medicinal) Methylene Blue NZ Methylene Blue SG
    Methylene Blue SP Methylene Blue USP (Medicinal) Methylene Blue USP XII (Medicinal)
    Methylene Blue ZF Methylene Blue ZX Methylene Blue Zinc Free
    Methylene Blue anhydrous Methylene Blue chloride Methylene Blue polychrome
    Methylene Blue, pure, certified, residual water MethyleneBlueHydrate Methylenium ceruleum
    Methylenum coeruleum Methylthionine chloride Methylthionini chloridum
    Methylthioninii chloridum Methylthioninii chloridum [INN-Latin] Methylthioninium chloride
    Methylthioninium chloride [INN] Methylthionium chloride Metiltioninio cloruro
    Metiltioninio cloruro [DCIT] Mitsui Methylene Blue Modr Methylenova [Czech]
    Modr Rozpoustedlova 8 [Czech] Modr Zasadita 9 [Czech] Modr methylenova
    Modr rozpoustedlova 8 Modr zasadita 9 N-(7-(dimethylamino)-3H-phenothiazin-3-ylidene)-N-methylmethanaminium chloride
    N-[7-(dimethylamino)-3H-phenothiazin-3-ylidene]-N-methylmethanaminium chloride NCGC00167496-01 NCGC00167496-03
    NCGC00255351-01 NSC 215213 NSC-215213
    NSC-3089 NSC-617593 NSC-759135
    NSC215213 NSC3089 NSC617593
    NSC759135 Pharmakon1600-01505444 Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride
    Phenothiazin-5-ium, 3,7-bis(dimethylamino)-, chloride (1:1) Phenothiazin-5-ium,7-bis(dimethylamino)-, chloride Prestwick_326
    Provayblue Q422134 Rember
    SBB060907 SCHEMBL1351 SMR000304367
    ST093058 ST50406802 STK018918
    Sandocryl Blue BRL Schultz No. 1038 Solvent blue 8
    Swiss Blue Tetramethylene Blue Tetramethylthionine chloride
    Tox21_112497 Tox21_112497_1 Tox21_302087
    UNII-8NAP7826UB Urolene blue WLN: T C666 BS EY INJ EUK1&1 MN1&1 &G &421
    X 138 Yamamoto Methylene Blue B Yamamoto Methylene Blue ZF
    [7-(dimethylamino)dibenzo[b,e]1,4-thiazin-3-yl]dimethylamine, chloride [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride [7-(dimethylamino)phenothiazin-3-ylidene]dimethylamine, chloride
    azul de metileno methylene blue methylene-blue
    s4535

    DrugBank Name Methylene blue
    DrugBank DB09241
    CAS Number 105504-42-5, 12262-49-6, 1341-90-8, 152071-32-4, 37247-10-2, 61-73-4, 6476-03-5, 7220-79-3, 97130-83-1
    PubChem Compound 6099
    KEGG Compound ID C00220
    KEGG Drug D10537
    PubChem.Substance 310265144
    ChEBI 6872
    PharmGKB PA450457
    ChemSpider 5874
    Wikipedia Methylene blue

    1. Anson et al., 1998