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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H56N10O15
Molecular Weight 856.8771
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAPTA

SMILES

C[C@@H](O)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H](C)N)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(N)=O

InChI

InChIKey=AKWRNBWMGFUAMF-ZESMOPTKSA-N
InChI=1S/C35H56N10O15/c1-13(36)29(54)41-22(12-46)32(57)43-26(16(4)49)34(59)45-27(17(5)50)35(60)44-25(15(3)48)33(58)40-21(11-23(37)52)30(55)39-20(10-18-6-8-19(51)9-7-18)31(56)42-24(14(2)47)28(38)53/h6-9,13-17,20-22,24-27,46-51H,10-12,36H2,1-5H3,(H2,37,52)(H2,38,53)(H,39,55)(H,40,58)(H,41,54)(H,42,56)(H,43,57)(H,44,60)(H,45,59)/t13-,14-,15-,16-,17-,20+,21+,22+,24+,25+,26+,27+/m1/s1

HIDE SMILES / InChI

Molecular Formula C35H56N10O15
Molecular Weight 856.8771
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

DAPTA (D-ala-peptide T-amide) is a synthetic peptide that prevents HIV entry by blocking binding of HIV gp120 protein with CCR5 receptor. In a small clinical study of internasal formulation of DAPTA in long-term infected HIV patients, administration of DAPTA led to decrease in the amount of virus isolated from white blood cells, an increase in gamma-interferon secreting T-cells in the absense of drug-related toxicity. In another clinical study DAPTA in combination with antiretroviral therapy reduced the peripheral (plasma and serum) viral load, but did not reduce the CSF viral load.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
55.0 pM [IC50]
PubMed

PubMed

TitleDatePubMed
Octapeptides deduced from the neuropeptide receptor-like pattern of antigen T4 in brain potently inhibit human immunodeficiency virus receptor binding and T-cell infectivity.
1986 Dec
Peptide T inhibits HIV-1 infection mediated by the chemokine receptor-5 (CCR5).
2001 Oct
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:38:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:45 GMT 2023
Record UNII
J208V4ZMP2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DAPTA
Common Name English
ADAPTAVIR
Common Name English
L-THREONINAMIDE, D-ALANYL-L-SERYL-L-THREONYL-L-THREONYL-L-THREONYL-L-ASPARAGINYL-L-TYROSYL-
Common Name English
D-ALA-SER-THR-THR-THR-ASN-TYR-THR-NH2
Common Name English
PEPTIDE T AMIDE, 1(D-ALA)
Common Name English
Code System Code Type Description
CAS
106362-34-9
Created by admin on Fri Dec 15 15:38:45 GMT 2023 , Edited by admin on Fri Dec 15 15:38:45 GMT 2023
PRIMARY
FDA UNII
J208V4ZMP2
Created by admin on Fri Dec 15 15:38:45 GMT 2023 , Edited by admin on Fri Dec 15 15:38:45 GMT 2023
PRIMARY
PUBCHEM
184644
Created by admin on Fri Dec 15 15:38:45 GMT 2023 , Edited by admin on Fri Dec 15 15:38:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> DERIVATIVE
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY