X8Z

L-CAPTOPRIL

Created: 2010-03-14
Last modified:  2011-06-04

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Chemical Details

Formal Charge0
Atom Count29
Chiral Atom Count2
Bond Count29
Aromatic Bond Count0
2D diagram of X8Z

Chemical Component Summary

NameL-CAPTOPRIL
Systematic Name (OpenEye OEToolkits)(2S)-1-[(2S)-2-methyl-3-sulfanyl-propanoyl]pyrrolidine-2-carboxylic acid
FormulaC9 H15 N O3 S
Molecular Weight217.285
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)C1N(C(=O)C(C)CS)CCC1
SMILESCACTVS3.352C[CH](CS)C(=O)N1CCC[CH]1C(O)=O
SMILESOpenEye OEToolkits1.6.1CC(CS)C(=O)N1CCCC1C(=O)O
Canonical SMILESCACTVS3.352 C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
Canonical SMILESOpenEye OEToolkits1.6.1 C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O
InChIInChI1.03 InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
InChIKeyInChI1.03 FAKRSMQSSFJEIM-RQJHMYQMSA-N

Drug Info: DrugBank

DrugBank IDDB01197 
NameCaptopril
Groups approved
DescriptionCaptopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Captopril may be used in the treatment of hypertension.
Synonyms
  • D-3-mercapto-2-methylpropanoyl-L-proline
  • L-Captopril
  • (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
  • Captopryl
  • CP
Brand Names
  • Captopril
  • Tria-captopril 12.5mg Tablet
  • Capoten Tab 12.5mg
  • Med Captopril - Tab 25mg
  • Bci Captopril Tablets
IndicationFor the treatment of essential or renovascular hypertension (usually administered with other drugs, particularly thiazide diuretics). May be used to treat congestive heart failure in combination with other drugs (e.g. cardiac glycosides, diuretics, β-adrenergic blockers). May improve survival in patients with left ventricular dysfunction following myocardial infarction. May be used to treat nephropathy, including diabetic nephropathy.
Categories
  • ACE Inhibitors and Diuretics
  • Agents Acting on the Renin-Angiotensin System
  • Agents causing angioedema
  • Agents causing hyperkalemia
  • Agents Causing Muscle Toxicity
ATC-Code
  • C09AA01
  • C09BA01
CAS number62571-86-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Angiotensin-converting enzymeMGAASGRRGPGLLLPLPLLLLLPPQPALALDPGLQPGNFSADEAGAQLFA...unknowninhibitor
72 kDa type IV collagenaseMEALMARGALTGPLRALCLLGCLLSHAAAAPSPIIKFPGDVAPKTDKELA...unknowninhibitor
Matrix metalloproteinase-9MSLWQPLVLVLLVLGCCFAAPRQRQSTLVLFPGDLRTNLTDRQLAEEYLY...unknowninhibitor
Leukotriene A-4 hydrolaseMPEIVDTCSLASPASVCRTKHLHLRCSVDFTRRTLTGTAALTVQSQEDNL...unknowninhibitor
B1 bradykinin receptorMASSWPPLELQSSNQSQLFPQNATACDNAPEAWDLLHRVLPTFIISICFF...unknown
View More
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

Related Resource References

Resource NameReference
Pharos CHEMBL1560
PubChem 12851888, 44093
ChEMBL CHEMBL1560
ChEBI CHEBI:3380
CCDC/CSD MCPRPL01, MCPRPL02, MCPRPL03
COD 2019870