Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H26N2O5S2 |
Molecular Weight | 438.561 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N2CC3(C[C@H]2C(O)=O)SCCS3
InChI
InChIKey=FMMDBLMCSDRUPA-BPUTZDHNSA-N
InChI=1S/C20H26N2O5S2/c1-13(21-15(18(24)25)8-7-14-5-3-2-4-6-14)17(23)22-12-20(28-9-10-29-20)11-16(22)19(26)27/h2-6,13,15-16,21H,7-12H2,1H3,(H,24,25)(H,26,27)/t13-,15-,16-/m0/s1
Molecular Formula | C20H26N2O5S2 |
Molecular Weight | 438.561 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugs.com/international/spirapril.htmlCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01348 | https://www.ncbi.nlm.nih.gov/pubmed/18154140 | https://www.ncbi.nlm.nih.gov/pubmed/15490771 | https://www.ncbi.nlm.nih.gov/pubmed/15752941
Sources: https://www.drugs.com/international/spirapril.html
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB01348 | https://www.ncbi.nlm.nih.gov/pubmed/18154140 | https://www.ncbi.nlm.nih.gov/pubmed/15490771 | https://www.ncbi.nlm.nih.gov/pubmed/15752941
Spirapril (Renormax) is an ACE inhibitor antihypertensive drug used to treat hypertension. Spiraprilat, the active metabolite of spirapril, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion. Spiraprilat may also act on kininase II, an enzyme identical to ACE that degrades the vasodilator bradykinin.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2544729 |
67.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | RENORMAX Approved UseUnknown Launch Date7.8865918E11 |
|||
Primary | RENORMAX Approved UseUnknown Launch Date7.8865918E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81.6 μg/L |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SPIRAPRILAT plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
37.85 μg/L |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SPIRAPRILAT plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
846.75 μg × h/L |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SPIRAPRILAT plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
152.5 μg × h/L |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SPIRAPRILAT plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.85 h |
6 mg 1 times / day multiple, oral dose: 6 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SPIRAPRILAT plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
Other AEs: Cough, Dizziness... Other AEs: Cough (3.8%) Sources: Dizziness (5.3%) Fatigue (6%) Headache (9%) Oedema (3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Oedema | 3% | 24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
Cough | 3.8% | 24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
Dizziness | 5.3% | 24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
Fatigue | 6% | 24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
Headache | 9% | 24 mg 1 times / day steady, oral (max) Recommended Dose: 24 mg, 1 times / day Route: oral Route: steady Dose: 24 mg, 1 times / day Sources: |
unhealthy, adult n = 133 Health Status: unhealthy Condition: hypertension Age Group: adult Sex: M+F Population Size: 133 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Alpha-adrenergic and angiotensin II pressor sensitivity in hypertensive patients treated with an angiotensin-converting enzyme inhibitor. | 1992 |
|
Efficacy and safety of spirapril, a new ace-inhibitor, in elderly hypertensive patients. | 1996 |
|
Mechanism and pressor relevance of the short-term cardiovascular and renin excitatory actions of the selective A2A-adenosine receptor agonists. | 1997 Sep |
|
[Blood pressure control must be effective until the next tablet. Infarct is most frequent in the morning]. | 2002 Jan 24 |
|
Drug interaction of spirapril hydrochloride monohydrate and hydrochlorothiazide. A clinical study to compare the pharmacokinetics after administration of spirapril hydrochloride monohydrate tablets, hydrochlorothiazide tablets and fixed combination bi-layer tablets. | 2003 |
|
[Effect of spirapril on remodeling of the heart in patients with mild and moderate arterial hypertension]. | 2007 |
|
The Lipid lowering and Onset of Renal Disease (LORD) Trial: a randomized double blind placebo controlled trial assessing the effect of atorvastatin on the progression of kidney disease. | 2008 Mar 18 |
|
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. | 2008 Nov |
Sample Use Guides
The daily dose is 6 mg, the frequency of application is 1 time / day. After 4-6 weeks, in the absence of a satisfactory therapeutic effect, the dose can be increased.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22197392
Pooled human liver microsomes were obtained from Pfizer Global Supply and the tested compounds were acquired from Pfizer Global Material Management. Each incubation contained tested compounds (Spirapril) (1 mkM), microsomes (0.25 lM protein), NADPH regenerating system (1 mM NADP+, 5 mM isocitric acid and 1 unit/ mL isocitric dehydrogenase), MgCl2 (1 mM) and potassium phosphate buffer (100 mM at pH 7.4). This mixture was incubated at 37 _C for 0, 5, 10, 20, 30 and 60 min before quenching with acetonitrile. Control incubations were prepared using the same procedure without adding the catalytic cofactor NADPH. Individual samples were then analyzed in a ‘trap-and-elute’ mode using LC/MS
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:50:14 UTC 2023
by
admin
on
Fri Dec 15 15:50:14 UTC 2023
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Record UNII |
QS56V5Y7EC
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Record Status |
Validated (UNII)
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Record Version |
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C247
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100000083804
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C076884
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AA-32
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83602-05-5
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CHEMBL579
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C152419
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Spiraprilat
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m10150
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QS56V5Y7EC
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |