LPR/PRD_000560

Lisinopril

Created:	2002-11-25
Last modified:	2020-06-05

LPR/PRD_000560 is described in the Biologically Interesting Molecule Reference Dictionary (BIRD).

The representative PDB ID is 1J36.

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Chemical Details
Formal Charge	0
Atom Count	60
Chiral Atom Count	3
Bond Count	61
Aromatic Bond Count	6

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Chemical Component Summary
Name	Lisinopril
Synonyms	LISINOPRIL
Systematic Name (OpenEye OEToolkits)	(2S)-1-[(2S)-6-amino-2-[[(2S)-1-hydroxy-1-oxo-4-phenyl-butan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
Formula	C₂₁ H₃₁ N₃ O₅
Molecular Weight	405.488
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)C2N(C(=O)C(NC(C(=O)O)CCc1ccccc1)CCCCN)CCC2
SMILES	CACTVS	3.341	NCCCC[CH](N[CH](CCc1ccccc1)C(O)=O)C(=O)N2CCC[CH]2C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	c1ccc(cc1)CCC(C(=O)O)NC(CCCCN)C(=O)N2CCCC2C(=O)O
Canonical SMILES	CACTVS	3.341	NCCCC[C@H](N[C@@H](CCc1ccccc1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1ccc(cc1)CC[C@@H](C(=O)O)N[C@@H](CCCCN)C(=O)N2CCC[C@H]2C(=O)O
InChI	InChI	1.03	InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
InChIKey	InChI	1.03	RLAWWYSOJDYHDC-BZSNNMDCSA-N

Drug Info: DrugBank

DrugBank ID	DB00722
Name	Lisinopril
Groups	approved investigational
Description	Lisinopril is an angiotensin converting enzyme inhibitor (ACEI) used to treat hypertension, heart failure, and myocardial infarction.[L8384,L8387,L8390] Lisinopril and [captopril] are the only ACEIs that are not prodrugs.[A184853] It functions by inhibition of angiotensin converting enzyme as well as the renin angiotensin aldosterone system.[A184781,A184808,A184817] ACEIs are commonly used as a first line therapy in the treatment of hypertension, along with thiazide diuretics or beta blockers.[A184844] Lisinopril was granted FDA approval on 29 December 1987.[L8384]
Synonyms	Lisinopril Lisinopril anhydrous Lisinopril dihydrate Lisinoprilum (S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline [N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline
Brand Names	Teva-lisinopril (type P) Nu-lisinopril Ran-lisinopril Auro-lisinopril Lisnopril/hctz (type P) Lisinopril 40mg Apo-lisinopril Tablet 40 mg Ava-lisinopril HCT Ntp-lisinopril/hctz (type P) Lisinopril/hctz (type Z) Dom-lisinopril Lisinopril and Hydrochlorothiazide Pro-lisinopril - 10 Lisinopril/HCTZ Mylan-lisinopril Qbrelis Apo-lisinopril/hctz Lisinopril and HCTZ Lytensopril-90 Lisinopril Tablets USP Apo-lisinopril Tablet (type P) - 5mg Sandoz Lisinopril HCT Riva-lisinopril Mar-lisinopril Zestril Ntp-lisinopril/hctz (type Z) PMS-lisinopril Sandoz Lisinopril Apo-lisinopril Tablet (type P) - 10mg Prinzide Apo-lisinopril Tablet (type P) - 20mg Lisinopril 20mg Teva-lisinopril/hctz (type P) Zestoretic Teva-lisinopril/hctz (type Z) Teva-lisinopril (type Z) Prinivil Ratio-lisinopril Z Lisinoril Apo-lisinopril Ipg-lisinopril Lisinopril 10mg Lisinopril Lisinopril and Hydrochlorthiazide Mint-lisinopril Lisinopril 5mg Pro-lisinopril - 5 Lisinopril 2.5mg Act Lisinopril Lisinopril Tablets Ratio-lisinopril P Jamp-lisinopril Lytensopril Lisinopril with Hydrochlorothiazide Nu-lisinopril/hctz Lisinopril and hydrochlorothiazide Mylan-lisinopril Hctz Apo-lisinopril Tablet (type P) - 40mg Pro-lisinopril - 20
Indication	Lisinopril is indicated for the treatment of acute myocardial infarction, hypertension in patients ≥6 years, and as an adjunct therapy for heart failure.[L8384,L8387] A combination product with hydrochlorothiazide is indicated for the treatment of hypertension.[L8390]
Categories	ACE Inhibitors and Calcium Channel Blockers ACE Inhibitors and Diuretics Agents Acting on the Renin-Angiotensin System Agents causing angioedema Agents causing hyperkalemia Amino Acids, Peptides, and Proteins Angiotensin-Converting Enzyme Inhibitors Antihypertensive Agents Antihypertensive Agents Indicated for Hypertension Cardiotonic Agents Cardiovascular Agents Compounds used in a research, industrial, or household setting Dipeptides Drugs causing inadvertant photosensitivity Drugs that are Mainly Renally Excreted Enzyme Inhibitors Hypotensive Agents Lipid Modifying Agents Oligopeptides Peptides Photosensitizing Agents Protease Inhibitors Protective Agents
ATC-Code	C09BA03 C10BX07 C09AA03 C09BB03
CAS number	76547-98-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Angiotensin-converting enzyme	MGAASGRRGPGLLLPLPLLLLLPPQPALALDPGLQPGNFSADEAGAQLFA...	unknown	inhibitor
Renin	MDGWRRMPRWGLLLLLWGSCTFGLPTDTTTFKRIFLKRMPSIRESLKERG...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown	substrate,inhibitor
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown	substrate

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682