Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C50H75N9O8 |
Molecular Weight | 930.186 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H](C)[C@H](NC(=O)[C@@H](C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](CC1=CN=CN1)N(C)C(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H]3CCCN3C(=O)OC(C)(C)C)C(C)C)C(=O)NCC4=CC=CC=N4
InChI
InChIKey=SASWSEQJAITMKS-JJNNLWIXSA-N
InChI=1S/C50H75N9O8/c1-11-33(6)43(47(64)53-29-35-20-15-16-22-52-35)57-44(61)37(32(4)5)27-42(60)38(24-31(2)3)55-46(63)41(26-36-28-51-30-54-36)58(10)48(65)39(25-34-18-13-12-14-19-34)56-45(62)40-21-17-23-59(40)49(66)67-50(7,8)9/h12-16,18-20,22,28,30-33,37-43,60H,11,17,21,23-27,29H2,1-10H3,(H,51,54)(H,53,64)(H,55,63)(H,56,62)(H,57,61)/t33-,37-,38-,39-,40-,41-,42-,43-/m0/s1
Molecular Formula | C50H75N9O8 |
Molecular Weight | 930.186 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Ditekiren is a relatively large renin inhibitor incorporating the hydroxyethylene isostere as well as both the P4 proline and P2’ isoleucine of angiotensinogen. Methylation of the P2-site histidine backbone nitrogen stabilizes the P2-P3 peptide bond towards degradation by chymotrypsin. Even though oral bioavailability was low, serum ditekiren levels were equivalent to 4–8 times the in vitro IC50 for renin inhibition for this peptide throughout the 2.5 h after oral administration that blood levels were monitored. In Na-depleted cynomolgus monkeys, oral dose elicited a hypotensive response that had not returned to baseline by 5 h. Ditekiren had been in phase II clinical trials for the treatment of heart failure and hypertension. However, these studies were discontinued.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
An orally active inhibitor of renin. | 1986 Dec |
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Systemic and renal haemodynamic effects of renin or angiotensin converting enzyme inhibition in non-human primates. | 1989 Apr |
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Disposition, metabolism, and excretion of U-71038, a novel renin inhibitor peptide, in the rat. | 1989 Sep-Oct |
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Additive combination studies of captopril and ditekiren, a renin inhibitor, in nonhuman primates. | 1991 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:58:47 GMT 2023
by
admin
on
Fri Dec 15 15:58:47 GMT 2023
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Record UNII |
5355S3W1IS
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C270
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CHEMBL1790497
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103336-05-6
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DTXSID40145787
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100000081837
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SUB06329MIG
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C95291
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5355S3W1IS
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6543
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ACTIVE MOIETY |