Drug Information

General Information
Drug ID
DR00155
Drug Name
Ouabain
Synonyms
3-((6-deoxyhexopyranosyl)oxy)-1,5,11,14,19-pentahydroxycard-20(22)-enolide; 3-[(6-Deoxyhexopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide; Acocantherin; Acocantherine; Acolongifloroside K; Astrobain; G-Strophanthin; G-Strophanthin (JAN); G-Strophicor; Gratibain; Gratus strophanthin; Kombetin; O 3125; OBN; Ouabagenin L-Rhamnoside; Ouabagenin-L-rhamnosid; Ouabagenin-L-rhamnosid [German]; Ouabain (anhydrous); Ouabain anhydrous; Ouabain octahydrate; Ouabain, Octahydrate; Ouabaine; Oubain; Purostrophan; Quabain; Rectobaina; Solufantina; Strodival; Strophalen; Strophanthin G; Strophanthin-G; Strophoperm; Strophosan; Uabaina; Uabanin
Drug Type
Small molecular drug
Indication Atrial fibrillation [ICD11:BC81.3] Approved [1]
Heart failure [ICD11:BD1Z] Approved [1]
Therapeutic Class
Cardiotonic Agents
Structure
3D MOL 2D MOL
Formula
C29H44O12
Canonical SMILES
CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
InChI
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey
LPMXVESGRSUGHW-HBYQJFLCSA-N
CAS Number
CAS 630-60-4
Pharmaceutical Properties Molecular Weight 584.7 Topological Polar Surface Area 207
Heavy Atom Count 41 Rotatable Bond Count 4
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 12
XLogP
-1.7
PubChem CID
439501
PubChem SID
10298350 ,103511767 ,104038270 ,104128310 ,104620666 ,11466499 ,11467619 ,11486277 ,11533037 ,121361712 ,121404260 ,14838096 ,15981102 ,17405501 ,24278610 ,26746568 ,29204593 ,36883713 ,4621 ,46392206 ,46505479 ,47291380 ,47736758 ,48035407 ,48035408 ,48185244 ,48334784 ,49698509 ,49834233 ,53778049 ,53787305 ,57287889 ,57403052 ,598376 ,75081902 ,7847180 ,7889527 ,7980210 ,8011283 ,85182289 ,85231346 ,85788049 ,87351514 ,87575707 ,90340653 ,92092794 ,92304198 ,92308875 ,95614231 ,99431516
ChEBI ID
ChEBI:7805
TTD Drug ID
D0AR3J
DT(s) Transporting This Drug OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [2]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [3]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [4]
OATP4C1 Transporter Info Organic anion transporting polypeptide 4C1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP1A2 Transporter Info Km =5500 microM Oocytes-OATP1A2 [6]
OATP4C1 Transporter Info Km =0.38 microM Madin-Darby canine kidney (MDCK) cells-OATP4C1 [5]
References
1 Ouabain - the insulin of the heart. Int J Clin Pract. 2010 Nov;64(12):1591-4.
2 Molecular cloning and functional characterization of the mouse organic-anion-transporting polypeptide 1 (Oatp1) and mapping of the gene to chromosome X. Biochem J. 2000 Jan 1;345 Pt 1:115-20.
3 Regulation of Organic Anion Transporting Polypeptides (OATP) 1B1- and OATP1B3-Mediated Transport: An Updated Review in the Context of OATP-Mediated Drug-Drug Interactions. Int J Mol Sci. 2018 Mar 14;19(3). pii: E855.
4 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
5 Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74.
6 Multispecific amphipathic substrate transport by an organic anion transporter of human liver. J Hepatol. 1996 Nov;25(5):733-8.

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