Cilazapril

Title: Cilazapril
CAS Registry Number: 88768-40-5
CAS Name: (1S,9S)-9-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
Additional Names: (1S,9S)-9-[[(S)-1-carboxy-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid 9-ethyl ester
Manufacturers' Codes: Ro-31-2848
Trademarks: Dynorm (Roche)
Molecular Formula: C22H31N3O5
Molecular Weight: 417.50
Percent Composition: C 63.29%, H 7.48%, N 10.06%, O 19.16%
Literature References: Angiotensin-converting enzyme (ACE) inhibitor; hydrolyzed in vivo to the active diacid metabolite. Prepn: M. R. Attwood et al., DE 3317290; eidem, US 4512924 (1983, 1985 both to Hoffmann-La Roche); eidem, J. Chem. Soc. Perkin Trans. 1 1986, 1011. HPLC determn in urine and pharmaceutical formulations: J. A. Prieto et al., J. Chromatogr. B 714, 285 (1998). Pharmacology: I. L. Natoff et al., J. Cardiovasc. Pharmacol. 7, 569 (1985). Review of clinical pharmacology: C. H. Kleinbloesem et al., Am. J. Med. 87, Suppl. 6B, 45S-49S (1989). Review of clinical experience in hypertension: T. Szucs, Drugs 41, Suppl. 1, 18-24 (1991); in chronic heart failure: L. Dössegger et al., J. Cardiovasc. Pharmacol. 24, Suppl. 3, S38-S41 (1994); in combination with hydrochlorothiazide: R. C. Pordy, Cardiology 86, 41-48 (1995).
Derivative Type: Monohydrate
CAS Registry Number: 92077-78-6
Trademarks: Inhibace (Roche); Initiss (Pharmacia); Justor (Chiesi); Vascace (Roche)
Molecular Formula: C22H31N3O5.H2O
Molecular Weight: 435.51
Percent Composition: C 60.67%, H 7.64%, N 9.65%, O 22.04%
Properties: White to off-white crystalline powder, mp 98° (dec). [a]D20 -62.51° (c = 1% in ethanol). Soly in water (25°): 0.5 g/100 ml. pKa1 3.3; pKa2 6.4. Partition coefficient (octanol/pH 7.4 buffer, 22°): 0.8.
Melting point: mp 98° (dec)
pKa: pKa1 3.3; pKa2 6.4
Optical Rotation: [a]D20 -62.51° (c = 1% in ethanol)
Log P: Partition coefficient (octanol/pH 7.4 buffer, 22°): 0.8
Derivative Type: Diacid
CAS Registry Number: 90139-06-3
Additional Names: Cilazaprilat
Manufacturers' Codes: Ro-31-3113
Molecular Formula: C20H27N3O5
Molecular Weight: 389.45
Percent Composition: C 61.68%, H 6.99%, N 10.79%, O 20.54%
Properties: Crystals from water, mp 242°. [a]D20 -74.7° (c = 0.5 in 1M NaOH).
Melting point: mp 242°
Optical Rotation: [a]D20 -74.7° (c = 0.5 in 1M NaOH)
Therap-Cat: Antihypertensive.
Keywords: ACE-Inhibitor; Antihypertensive; N-Carboxyalkyl (peptide/lactam) Derivatives.
Ciliary Neurotrophic Factor Cilnidipine Cilomilast Cimaterol Cimetropium Bromide

Cilazapril
Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-[(2S)-2-yl]amin,-1-carbox)
Identifiers
CAS number 88768-40-5 N
PubChem 56330, 40467985 (1R,9S)-(2S)-butylamino isomer
ChemSpider 50831 N
UNII 8Q9454114Q N
DrugBank DB01340
KEGG D07699 YesY
ChEMBL CHEMBL515606 N
ATC code C09AA08
Jmol-3D images Image 1
Properties
Molecular formula C22H31N3O5
Molar mass 417.50 g mol−1
log P 2.212
Acidity (pKa) 2.285
Basicity (pKb) 11.712
Pharmacology
Routes of
administration
Oral
Legal status

POM(UK)

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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure.[1][2] It is branded as Inhibace in Canada and other countries, Vascace and Dynorm in a number of European countries, among many other names. None of these are available in the United States as of May 2010.[3]

Of the eight possible stereoisomers, only the all-S form is medically viable.[citation needed]