(8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

• ChemBase ID: 1177
• Molecular Formular: C22H30N2O5S2
• Molecular Mass: 466.614
• Monoisotopic Mass: 466.15961407
• SMILES: S1C2(SCC1)C[C@H](N(C2)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCC)C)C(=O)O
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)C)CCc1ccccc1
• InChI: InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1
• InChIKey: HRWCVUIFMSZDJS-SZMVWBNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
• IUPAC Traditional name: spirapril
• Brand Name: Renormax
• Synonyms: Spirapril

Database IDs

• CAS Number: 83647-97-6
• PubChem SID: 46506126; 160964639
• PubChem CID: 5311447

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6249576
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.301563
• LogD (pH = 7.4): -0.0290567
• Log P: 1.6036346
• Molar Refractivity: 121.9396 cm^3
• Polarizability: 48.518734 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.79
• LOG S: -4.2
• Solubility (Water): 2.93e-02 g/l

DETAILS

DrugBank - DB01348

• Drug Groups: approved
• Description: Spirapril is an ACE inhibitor antihypertensive drug used to treat hypertension. Like many ACE inhibitors, this is a prodrug which is converted to the active metabolite spiraprilat following oral administration. ACE inhibitors are used primarily in treatment of hypertension and congestive heart failure.
• Indication: Spirapril is an ACE inhibitor class drug used to treat hypertension.
• Pharmacology: Spirapril is an angiotensin-converting enzyme (ACE) inhibitor. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. By blocking ACE, spirapril decreases angiotensin II which is a vasoconstrictor and inducer of aldosterone. So by inhibiting the enzymes, aldosterone secreation is decreased (so less sodium is reabsorbed) and there is a decrease in vasoconstriction. Combined, this leades to a decrease in blood pressure.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Converted to spiraprilat following oral administration.
• Absorption: Bioavailability is 50% following oral administration.
• Half Life: 30 to 35 hours
• References: Hannedouche T, Ikeni A, Marques LP, Natov S, Dechaux M, Schmitt F, Lacour B, Grunfeld JP: Renal effects of angiotensin II in normotensive subjects on short-term cilazapril treatment. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S25-7. [Pubmed] ; Noble S, Sorkin EM: Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension. Drugs. 1995 May;49(5):750-66. [Pubmed] ; Rosendorff C, Patton J, Radford HM, Kalliatakis B: Alpha-adrenergic and angiotensin II pressor sensitivity in hypertensive patients treated with an angiotensin-converting enzyme inhibitor. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S105-9. [Pubmed] ; Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G: Acute and chronic effects of spirapril, alone or in combination with isradipine on kidney function and blood pressure in patients with reduced kidney function and hypertension. Scand J Urol Nephrol. 1999 Feb;33(1):57-62. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Hannedouche T, Ikeni A, Marques LP, Natov S, Dechaux M, Schmitt F, Lacour B, Grunfeld JP: Renal effects of angiotensin II in normotensive subjects on short-term cilazapril treatment. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S25-7. Pubmed
• Noble S, Sorkin EM: Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension. Drugs. 1995 May;49(5):750-66. Pubmed
• Rosendorff C, Patton J, Radford HM, Kalliatakis B: Alpha-adrenergic and angiotensin II pressor sensitivity in hypertensive patients treated with an angiotensin-converting enzyme inhibitor. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S105-9. Pubmed
• Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G: Acute and chronic effects of spirapril, alone or in combination with isradipine on kidney function and blood pressure in patients with reduced kidney function and hypertension. Scand J Urol Nephrol. 1999 Feb;33(1):57-62. Pubmed