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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
Structure of TEPROTIDE

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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antihypertensive activity in rats for SQ 14,225, an orally active inhibitor of angiotensin I-converting enzyme.
1978 Feb
[Acute and chronic cardiac decompensation: is vasodilator therapy useful?].
1982 Jan 14
Adverse reactions with angiotensin converting enzyme (ACE) inhibitors.
1986 Mar-Apr
Patents

Sample Use Guides

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
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..
Name Type Language
TEPROTIDE
INN   MART.   USAN  
USAN   INN  
Official Name English
SO-20881
Code English
teprotide [INN]
Common Name English
TEPROTIDE [USAN]
Common Name English
TEPROTIDE [MART.]
Common Name English
TEPROMIDE
Common Name English
SQ-20881
Code English
SQ 20881
Code English
5-OXO-L-PROLYL-L-TRYPTOPHYL-L-PROLYL-L-ARGINYL-L-PROLYL-L-GLUTAMINYL-L-ISOLEUCYL-L-PROLYL-L-PROLINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
Code System Code Type Description
FDA UNII
C3E5QBF1R6
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
PRIMARY
INN
3815
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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EPA CompTox
DTXSID301029698
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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ChEMBL
CHEMBL408983
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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WIKIPEDIA
TEPROTIDE
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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CAS
35115-60-7
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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PUBCHEM
443376
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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SMS_ID
100000082682
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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EVMPD
SUB10906MIG
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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NCI_THESAURUS
C152566
Created by admin on Fri Dec 15 15:42:21 UTC 2023 , Edited by admin on Fri Dec 15 15:42:21 UTC 2023
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