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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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Acute and chronic cardiac decompensation: is vasodilator therapy useful?].
1982 Jan 14
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..
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:42:20 UTC 2023
Edited
by admin
on Fri Dec 15 15:42:20 UTC 2023
Record UNII
C3E5QBF1R6
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
ACTIVE MOIETY