Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C53H76N14O12 |
Molecular Weight | 1101.2571 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(CCC(=O)N1)C(=O)N[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCCNC(N)=N)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N6CCC[C@H]6C(=O)N7CCC[C@H]7C(O)=O
InChI
InChIKey=UUUHXMGGBIUAPW-CSCXCSGISA-N
InChI=1S/C53H76N14O12/c1-3-29(2)43(51(77)66-25-9-16-39(66)50(76)67-26-10-17-40(67)52(78)79)63-45(71)34(18-20-41(54)68)60-46(72)37-14-7-23-64(37)48(74)35(13-6-22-57-53(55)56)61-47(73)38-15-8-24-65(38)49(75)36(62-44(70)33-19-21-42(69)59-33)27-30-28-58-32-12-5-4-11-31(30)32/h4-5,11-12,28-29,33-40,43,58H,3,6-10,13-27H2,1-2H3,(H2,54,68)(H,59,69)(H,60,72)(H,61,73)(H,62,70)(H,63,71)(H,78,79)(H4,55,56,57)/t29-,33-,34-,35-,36-,37-,38-,39-,40-,43-/m0/s1
Molecular Formula | C53H76N14O12 |
Molecular Weight | 1101.2571 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Teprotide, a nonapeptide isolated from the venom of a Brazilian pit viper, Bothrops jararaca, was the first angiotensin converting enzyme (ACE) inhibitor to be discovered and tested. It was found to be an effective, non-toxic antihypertensive agent as well as an afterload-reducing agent for patients with congestive heart failure (CHF). The primary activity of teprotide resulted from blockade of the angiotensin I converting enzyme--the pivotal step in the renin-angiotensin-aldosterone system (RAAS), and consequent reductions in angiotensin II levels. There was limited clinical testing for teprotide because of: its scarcity; the need for parenteral administration; and the subsequent discovery and synthesis of captopril, the first orally active angiotensin converting enzyme inhibitor.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Antihypertensive activity in rats for SQ 14,225, an orally active inhibitor of angiotensin I-converting enzyme. | 1978 Feb |
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[Acute and chronic cardiac decompensation: is vasodilator therapy useful?]. | 1982 Jan 14 |
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Adverse reactions with angiotensin converting enzyme (ACE) inhibitors. | 1986 Mar-Apr |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6158478
An intravenous infusion of Teprotide (SQ 20,881) was given over a 3-minute period. In- creasing doses of SQ 20,881 (30,100, and 300 ug/kg;
0.024-0.240 umoles/kg) were administered over three
successive 20-minute intervals or until a 15 mm Hg drop in DBP was noted.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6167813
Inhibition of converting enzyme with teprotide (10 ug/ml) had no effect on contractile responses to angiotensin II or [Sar1]angiotensin II in field-stimulated rabbit left atria and isometrically contracting aortic strips..
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:42:20 GMT 2023
by
admin
on
Fri Dec 15 15:42:20 GMT 2023
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Record UNII |
C3E5QBF1R6
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C247
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C3E5QBF1R6
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3815
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DTXSID301029698
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CHEMBL408983
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TEPROTIDE
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35115-60-7
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443376
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100000082682
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SUB10906MIG
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C152566
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Related Record | Type | Details | ||
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ACTIVE MOIETY |