CAS 83647-97-6|spirapril|(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|Renormax|Spirapril

General Information

Structure

Molecular Formula

C₂₂H₃₀N₂O₅S₂

Molecular Mass

466.614

Exact Mass

466.15961407

Charge

0

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

Canonic Smiles

CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)C)CCc1ccccc1

Isomeric Smiles

S1C2(SCC1)C[C@H](N(C2)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCC)C)C(=O)O

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

Polarizability

48.518734

Polar Surface Area

95.94

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

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

spirapril

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

Brand Name

Renormax

Synonyms

Spirapril

Names and Identifiers

Registration numbers

PubChem CID

5311447

PubChem SID

16096463946506126

CAS Number

83647-97-6

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:1177