Drug Information

General Information
Drug ID
DR00148
Drug Name
Digoxin
Synonyms
(3beta,5beta,12beta)-3-{[2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide; 12beta-Hydroxydigitoxin; 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}; Digitek (TN); Digoxin (JP15/USP); Lanoxicaps (TN); Lanoxin (TN)
Drug Type
Small molecular drug
Indication Arrhythmias [ICD11:BC60-BC9Z] Approved [1]
Heart failure [ICD11:BD1Z] Approved [1]
Therapeutic Class
Antiarrhythmic Agents
Structure
3D MOL 2D MOL
Formula
C41H64O14
Canonical SMILES
CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)O)O
InChI
InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
InChIKey
LTMHDMANZUZIPE-PUGKRICDSA-N
CAS Number
CAS 20830-75-5
Pharmaceutical Properties Molecular Weight 780.9 Topological Polar Surface Area 203
Heavy Atom Count 55 Rotatable Bond Count 7
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 14
XLogP
1.3
PubChem CID
2724385
PubChem SID
10321270 ,103707689 ,103913751 ,111366106 ,11466465 ,11467585 ,11486129 ,11533002 ,117393920 ,121363091 ,14840467 ,16531631 ,17389540 ,24893992 ,24894045 ,25664046 ,26752810 ,29204039 ,30082596 ,3139699 ,46508524 ,47277036 ,47350829 ,47500941 ,47871144 ,48415894 ,48425070 ,48493824 ,49698492 ,49718191 ,50105460 ,50105461 ,56313674 ,56422204 ,57287890 ,57409429 ,57654114 ,7847364 ,79412392 ,7979083 ,85788562 ,87568294 ,8787891 ,90481132 ,9171 ,92125420 ,92298240 ,92729949 ,93167166 ,99431517
ChEBI ID
ChEBI:4551
TTD Drug ID
D02OZE
DT(s) Transporting This Drug MDR3 Transporter Info Multidrug resistance protein 3 Substrate [2]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [3]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [4]
OATP4C1 Transporter Info Organic anion transporting polypeptide 4C1 Substrate [5]
OSTalpha Transporter Info Organic solute transporter subunit alpha Substrate [6]
OSTbeta Transporter Info Organic solute transporter subunit beta Substrate [6]
OSTbeta Transporter Info Organic solute transporter subunit beta Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OATP4C1 Transporter Info Km =7.8 microM Madin-Darby canine kidney (MDCK) cells-OATP4C1 [5]
P-GP Transporter Info Km =25.9 microM High five cells-MDR1 [8]
P-GP Transporter Info Km =73 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [9]
P-GP Transporter Info Km =177 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [10]
P-GP Transporter Info Km =181 microM Spodoptera frugiperda (Sf9) cells-MDR1 [11]
References
1 Digoxin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 MDR3 P-glycoprotein, a phosphatidylcholine translocase, transports several cytotoxic drugs and directly interacts with drugs as judged by interference with nucleotide trapping. J Biol Chem. 2000 Aug 4;275(31):23530-9.
3 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.
4 Drug Interactions in Infectious Diseases.
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 Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82.
7 MDR1 function is sensitive to the phosphorylation state of myosin regulatory light chain. Biochem Biophys Res Commun. 2010 Jul 16;398(1):7-12.
8 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
9 Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26.
10 Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers. Pharm Res. 2003 Aug;20(8):1200-9.
11 Modulation of drug-stimulated ATPase activity of human MDR1/P-glycoprotein by cholesterol. Biochem J. 2007 Jan 15;401(2):597-605.

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