Drug Information

General Information
Drug ID
DR00429
Drug Name
Losartan
Synonyms
(2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl}-1H-imidazol-5-yl)methanol; (2-butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanol; 1H-Imidazole-5-methanol, 2-butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-(9CI); 2-Butyl-4-chloro-1-((2'-(1H-etrazol-5-yl) (1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-methanol; 2-Butyl-4-chloro-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl-1H-imidazole-5-methanol; 2-butyl-4-chloro-1-[p-(o-1H-tetrazol-5ylphenyl)benzyl]imidazole-5-methanol; 2-n-butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazole; 2-n-butyl-4-chloro-5-hydroxymethyl-1-[[2'-(1H-tetrazol-5-yl)-biphenyl-4-yl]methyl]imidazole; CL23623; Cozaar; Cozaar (TN); DUP 89; DuP-753; Hyzaar; LOSARTAN POTASSIUM; Lortaan; Losartan (INN); Losartan [INN:BAN]; Losartan monopotassium salt; Losartic; Losartic (TN); MK-954; MK954; [2-butyl-5-chloro-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol
Drug Type
Small molecular drug
Indication High blood pressure [ICD11:BA00] Approved [1]
Therapeutic Class
Antihypertensive Agents
Structure
3D MOL 2D MOL
Formula
C22H23ClN6O
Canonical SMILES
CCCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)CO)Cl
InChI
InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)
InChIKey
PSIFNNKUMBGKDQ-UHFFFAOYSA-N
CAS Number
CAS 114798-26-4
Pharmaceutical Properties Molecular Weight 422.9 Topological Polar Surface Area 92.5
Heavy Atom Count 30 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
XLogP
4.3
PubChem CID
3961
PubChem SID
103546496 ,104086517 ,104305027 ,11364607 ,11367169 ,11369731 ,11372014 ,11374749 ,11377893 ,11485629 ,11489493 ,11490813 ,11492940 ,11495527 ,118212888 ,14758375 ,14880416 ,26612696 ,26680690 ,26748956 ,26748957 ,29223075 ,46506538 ,46530544 ,47773674 ,48072880 ,48221855 ,48416186 ,4964191 ,49979780 ,50107496 ,50150720 ,53789286 ,56312013 ,56314181 ,57322070 ,6595486 ,7979808 ,8152487 ,842088 ,85209145 ,85789659 ,91011664 ,92124757 ,92307932 ,9283 ,93166444 ,93617630 ,96024836 ,99375910
ChEBI ID
ChEBI:6541
TTD Drug ID
D0DD0K
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
PEPT1 Transporter Info Peptide transporter 1 Substrate [3]
Drug-Transporter Activity Data
Drug-Transporter Activity Data P-GP Transporter Info Km =100 microM Chinese hamster ovary AA8 cells-MDR1 [4]
P-GP Transporter Info Km =232 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [2]
P-GP Transporter Info Km =403.2 microM Madin-Darby canine kidney cells (MDCKII)-MDR1 [2]
References
1 Losartan was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Active transport of the angiotensin-II antagonist losartan and its main metabolite EXP 3174 across MDCK-MDR1 and caco-2 cell monolayers. Br J Pharmacol. 2000 Mar;129(6):1235-43.
3 High-affinity interaction of sartans with H+/peptide transporters. Drug Metab Dispos. 2009 Jan;37(1):143-9.
4 Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71.

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