Drug Information

General Information
Drug ID
DR00272
Drug Name
Bumetanide
Synonyms
3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid; 3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid; 3-(aminosulfonyl)-5-(butylamino)-4-(phenyloxy)benzoic acid; 3-butylamino-4-(phenoxy)-5-sulfamoylbenzoic acid; Aquazone; AstraZeneca Brand of Bumetanide; Atlantis Brand of Bumetanide; B 3023; Bumedyl; Bumetanida; Bumetanida [INN-Spanish]; Bumetanide (JP15/USP); Bumetanide (JP15/USP/INN); Bumetanide AstraZeneca Brand; Bumetanide Atlantis Brand; Bumetanide Farmacusi Brand; Bumetanide Grossmann Brand; Bumetanide Leo Brand; Bumetanide Roche Brand; Bumetanide Senosiain Brand; Bumetanide [USAN:BAN:INN:JAN]; Bumetanidum; Bumetanidum [INN-Latin]; Bumethanide; Bumex; Bumex (TN); Bumex, Bumetanide; Burine; Burinex; Butinat; Cambiex; Diurama; Drenural; Farmacusi Brand of Bumetanide; Fontego; Fordiuran; Grossmann Brand of Bumetanide; Leo Brand of Bumetanide; Lixil; Lixil-Leo; Lunetoron; Miccil; PF 1593; PF-1593; PF1593; Ro 10-6338; Ro-10-6338; Roche Brand of Bumetanide; Segurex; Senosiain Brand of Bumetanide; Yurinex
Drug Type
Small molecular drug
Indication Edema associated with congestive heart failure [ICD11:BD10] Approved [1]
Therapeutic Class
Diuretics
Structure
3D MOL 2D MOL
Formula
C17H20N2O5S
Canonical SMILES
CCCCNC1=C(C(=CC(=C1)C(=O)O)S(=O)(=O)N)OC2=CC=CC=C2
InChI
InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)
InChIKey
MAEIEVLCKWDQJH-UHFFFAOYSA-N
CAS Number
CAS 28395-03-1
Pharmaceutical Properties Molecular Weight 364.4 Topological Polar Surface Area 127
Heavy Atom Count 25 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
XLogP
2.8
PubChem CID
2471
PubChem SID
10321639 ,11110843 ,11110844 ,11120301 ,11120789 ,11121277 ,11121573 ,11122053 ,11335209 ,11360448 ,11362642 ,11364211 ,11365204 ,11366773 ,11367766 ,11369335 ,11370555 ,11370556 ,11372660 ,11373367 ,11373578 ,11375928 ,11377497 ,11461420 ,11466304 ,11467424 ,11484716 ,11486107 ,11488866 ,11491296 ,11491845 ,11495131 ,14852701 ,17404725 ,24278265 ,26612248 ,26680422 ,26746951 ,26746952 ,26751481 ,26758346 ,29221635 ,46508147 ,4652638 ,47216571 ,47440017 ,7847313 ,8149787 ,8151648 ,855675
ChEBI ID
CHEBI:3213
TTD Drug ID
D0R7HO
DT(s) Transporting This Drug MCT6 Transporter Info Monocarboxylate transporter 6 Substrate [2]
NCC Transporter Info Thiazide-sensitive sodium-chloride cotransporter Substrate [3]
OAT2 Transporter Info Organic anion transporter 2 Substrate [4]
OAT3 Transporter Info Organic anion transporter 3 Substrate [5]
OAT4 Transporter Info Organic anion transporter 4 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OAT2 Transporter Info Km =7.52 microM Oocytes-OAT2 [4]
OAT3 Transporter Info Km =1586 microM Proximal tubule (S2) cells-OAT3 [5]
OAT4 Transporter Info Km =306 microM Proximal tubule (S2) cells-OAT4 [5]
References
1 Bumetanide was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Quercetin, Morin, Luteolin, and Phloretin Are Dietary Flavonoid Inhibitors of Monocarboxylate Transporter 6. Mol Pharm. 2017 Sep 5;14(9):2930-2936.
3 Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. Clin Pharmacol Ther. 2007 Sep;82(3):300-9.
4 Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8.
5 Interactions of human organic anion transporters with diuretics. J Pharmacol Exp Ther. 2004 Mar;308(3):1021-9.

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